54 best things to do in Chicago with teenagers

Sweet home Chicago, one of the great American ceities is a major destination altogether, but it is also one of the best teenage vacation destinations for family travel. Chicago is one of the most popular cities in the USA.

With all the museums, sporting events, restaurants, theatre and outdoor activities you will not run out of fun things to do with teens in this Midwest metropolis.

Many consider Chicago to be a cleaner, easier version of New York City and for good reason. Whether you have an adventure teen or a more subdued teen, visitors will have no trouble finding fun activities in Chicago for teenagers. 

As a massive U.S. city, Chicago offers the standard entertainment found at places like movie theatres, bowling alleys, concert venues, arcades, and more. Below is a must-do Chicago list of things to do with teenagers.

Know before you go. Our top Chicago travel tips

Before we get to the nitty-gritty of unique Chicago teenager activities, we want to give you some simple tips for this specific family travel destination. Travelling to Chicago with teenagers can be such an enriching experience for the whole family.

There are so many things to do for teens in Chicago, and having the best place to stay in Chicago to explore is extremely important. Here we’ve got some information to get you planning a family vacation to Chicago for teens to make it completely hassle-free.

Where to Stay in Chicago with Teens

For those visiting Chicago with teenagers who love travel, there are numerous hotel options in Chicago, so you will need to decide how much you want to spend and which part of the city you want to base yourself in.

You can find everything from Uber budget to super-luxury, so it might be best to narrow it down by location and proximity to public transportation.

Not surprisingly many hotels will have a pool for extra fun after the day’s activities and plenty will offer free breakfast if that’s important to you. Here are a few that are particularly great for travel families with teenagers.

For luxury family-friendly hotels in Chicago, we recommend The Peninsula- 5-star luxury, Hotel Chicago Downtown Autograph Collection puts you very near the river walk and Michigan Avenue as well. The DoubleTree Magnificent Mile gives great deals to families and has a fabulous pool.

For more midprice and budget-friendly options in Chicago, we recommend Freehand Chicago, Holiday Inn Express Chicago Midway and HI Chicago, and The J.Ira & Nicki Harris Family Hostel.

If you’re not keen on any of our picks or have specific needs, we recommend using Trip Advisor and Expedia to find the best prices for Chicago accommodation.

Chicago apartment alternative for your stay

If you prefer a home away from home-style accommodation when on your USA trip with teenagers in Chicago, then an apartment is the best choice for you on your family vacation. There are so many options for singles, families, and budget-friendly options in Chicago as well.

You can search VRBO or if you’re looking for a luxury apartment with maybe a great view, or a spa then Plum Guide will help you find the perfect apartment in Chicago for teens on your United States trip with family.

How to get to Chicago with teenagers

• There are two main airports available to fly into one of the most popular cities in the USA. O’Hare is the major international airport, and Midway is the smaller international airport and a base for Southwest Airlines. Both airports offer a train into the Loop (the official downtown area) and are near a station that will likely be within walking distance of your accommodations. Book your flights to Chicago with Kiwi Flights. From Midway, you would use the Orange train line and from O’Hare you would use the Blue line. Both lines turn into an elevated track once inside the Loop, giving them the affectionate name the L.
  •  Book an airport transfer to your hotel
    • If your flights have a long stopover, or you just want to relax before your trip you should consider getting a lounge pass with Priority Pass. Priority Pass has access to airport lounges all over the world. Search now for your lounge pass

• If you choose to rent a car, your drive time will vary considerably depending on traffic and time of day. O’Hare Airport is about 18 miles from the downtown Loop and Midway is about 13 miles away. Honestly, you won’t need a car if you plan to keep your Chicago activities with teenagers within the city. Keep in mind that parking can cost up to $30 per night at your Chicago hotel. If you do plan to road trip with teenagers in Chicago then you can pick up a rental car at the airport.

• Chicago has several train stations and an extensive train network leading into the city, making train travel an easy alternative to flying. Once in the city, the public transportation options are not difficult to navigate. Book your trains to Chicago with Omio

Getting around Chicago with teens

Chicago has an extensive public transportation system and many of your daily activities can be bundled into certain neighbourhoods for simple walking routes. Plus, it’s fun for teens to figure out public transport if it’s new to them and you are teaching them a life skill. Consider a CTA unlimited ride pass for 1,3, or 7 days (each person must have their own).

Weather in Chicago

Chicago is known for its biting cold winters and mild summers. Rug up in January when Chicago’s coldest month only averages 14.3°F overnight. In July, the warmest month, the average daytime temperature rises to 83.5°F.

In weather records dating from 1871, Chicago’s hottest month is July, with an average temperature of 73.9 degrees. That is followed by August, whose average temperature is 72.5 degrees; and then by June, with an average temperature of 67.8 degrees.

Despite being known for cold winters, Chicago doesn’t get a lot of snowfall compared to other places like Pennsylvania and upstate New York. This makes Chicago a top spot for family vacations with teens.

Seasonal essentials for travel to Chicago

Chicago for international visitors

International travel to the United States requires a bit more thought. You will absolutely need travel insurance as the United States is one of the most expensive countries in the world for medical care.

If you use your bank account from home, you will be stung with high transaction fees, while your mobile phone calls will all be charged at an international rate. These are just some of the things you need to think about when travelling to Chicago with teenagers.

• For international travellers, travel insurance is a must get a quote through Insurance Masters and don’t go home with a huge bill for medical expenses
• Do you need a visa to visit Chicago? The United States of America may require you to have a visa or an ETA (Electronic travel authorization) to enter the country. You can check and buy these documents at iVisa
• Load a Revolut Travel Money card with US dollars for your visit and save on transaction fees
• Make phone calls with an international sim card or buy a virtual e-sim for a newer mobile phone
• A 4G pocket Wi-Fi modem is essential for accessing the internet. You can rent a pocket modem that you can pick up at the airport or your hotel, alternatively, buy a pocket modem for future travels.

Travel accessories for teenagers

For teenagers, travelling to this amazing city can be a fun and exciting experience. However, there are a few things that they need to take into account in order to make the trip as comfortable and safe as possible. One of these is ensuring that they have the necessary travel accessories.

The best things to do in Chicago with teenagers

There are so many teenage activities in Chicago to choose from. These are a few of the best things to do in Chicago with teenagers and build memories with your travelling teens.

Shedd Aquarium

Not only is the Shedd Aquarium one of the top things to do in Chicago for teens, but it is also a place of rescue and conservation for sea life.

Some of the highlights include beluga whales and bluegills, rockhopper penguins, rockfish and alligators. It was opened in 1930 and has been open ever since. The Shedd Aquarium is the second-largest aquarium in the United States, and it houses more than 32,000 animals from 600 different species.

Entertaining things to do in Chicago for teens – Ghost tour

Ghost story tours are a popular tourist attraction in many parts of the world. They are usually conducted by a guide who tells stories about the ghosts and legends of the area.

The tour guides often dress up in period costumes to add to the atmosphere. To make the experience more authentic, the tours usually take place at night, when it is dark and spooky.

You will find a number of different tours in Chicago including, The Chicago Hauntings Original Ghost Bus Tour, Windy City Ghosts, Lincoln Park Hauntings and more.

Stand-up paddle boarding in Chicago

If you’re looking for a new way to enjoy the water and get some exercise, stand-up paddleboarding (SUP) might be just the thing. SUP is a relatively new sport that involves standing on a large, surfboard-like paddleboard and using a long paddle to move through the water.

Chicago is an ideal location for a teen to try stand-up paddleboarding, with access to the river and the lake. It’s also a great way to explore new areas and see things from a different perspective. In Chicago, there are a number of options to try this activity, with Chicago SUP offering lessons and stand-up paddleboard rentals on Lake Michigan.

Hidden gems in Chicago for teenagers – Torture Museum

At the Medieval Torture Museum, you and your teenage kids can immerse yourselves in an educational and interactive journey, discovering the tools and devices used in ancient times. The museum provides audio guides to enhance your understanding of the exhibits, making it both informative and engaging. Book your tickets today.

Canoeing in Chicago

Chicago is a city that has many attractions and activities to offer. One of these activities is canoeing. It is an activity that can be enjoyed by people of all ages, and it is a great way to spend time with family and friends.

Canoeing in Chicago can be done on the Chicago River or Lake Michigan. The Chicago River offers a more urban experience with the Chicago skyline as a backdrop while Lake Michigan offers a more natural experience. Canoeing in Chicago can be done at any time of the year, but it is best enjoyed during the summer months when the weather is warmer.

Take a scenic helicopter flight over Chicago

Soaring over Chicago and taking in the best views of the Chicago River, Lake Michigan and the city skyline is a once-in-a-lifetime experience.

Going up high on a panoramic helicopter flight and seeing everything from Navy Pier to Lincoln Park can be one of the most exciting things to do in Chicago with teens and tweens. Book a helicopter tour today it really is one of the must-dos in Chicago.

Jetboating on Lake Michigan Chicago

If you’re looking for an adrenaline rush and a unique sightseeing experience, jet boating is the perfect activity for you. Climb aboard your 2,000-horsepower speed boat at Navy Pier and prepare for the fastest way to see sights while visiting Chicago with teenagers.

Whether you’re a first-time adventurer or an experienced thrill seeker, jet boating is sure to give you an experience you’ll never forget. Book your 30-minute high-speed Navy Pier Seadog cruise on Lake Michigan today

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The Blue Men Group

The Blue Man Group was founded in 1987 by three friends who wanted to create an art form that was unlike anything else they had seen before. They wanted to combine music, comedy, and theatrics into one show and they succeeded in creating a show like nothing you have ever seen before.

The Blue Man Group shows are one of the highest-rated fun things to do with teens in Chicago. Secure your seats for the Chicago Blue Men Group show.

Things to do in Chicago with teenage girls – High Tea/ Afternoon tea

High Tea started out as a quintessentially British thing. This afternoon tea tradition involves savoury sandwiches, cakes, pastries, and of course, tea. For mothers and daughters, it’s a cherished ritual that often brings them closer together.

High tea first became popular in the early 1800s, when aristocrats would gather in the late afternoon for a light meal. The spread would typically include cakes, tea, and sandwiches. These days, high tea is still enjoyed by many Britons and people the world over as a special treat, it is a great indoor activity in Chicago.

If you’re looking to experience high tea firsthand, there are plenty of places in Chicago to have a High Tea. But be warned – it can be quite addictive! Once you’ve had a taste of those delicious treats, you’ll likely want to indulge again and again. Some of the best Chicago High Tea venues are:

• Pavilion at the Langham Hotel – 330 N Wabash Ave Chicago 60611

• London House Chicago – 85 East Wacker Drive Chicago 60601

Medieval times dinner & tournament Chicago

Chicago is a city of culture, history, and entertainment. It has a lot of attractions that are fun for all ages. The Medieval Times Dinner & Tournament is a show that will make your trip to Chicago with teens worth it.

The Medieval Times Dinner & Tournament is an immersive show that takes you back to medieval times. You will be served the best food with authentic dishes from the Middle Ages and you can enjoy the show with your family or friends.

This dinner experience will take you through 12th-century England, where knights compete in games of skill and jousting on horseback in front of an audience of cheering spectators.

The jousting tournament features teams comprised of two fearless Knights who put their lives on the line in the name of entertainment in Chicago. This is one of the best attractions in Chicago for teenagers, book your seat at the Medieval Dinner and Tournament today.

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Chicago fun places for teenagers -Indoor Skydiving

Indoor skydiving is a new trend that is catching on with teenagers.

It is a safe way to experience the thrill of skydiving without having to go through all the hassle of getting on an aeroplane and going to a place that is outside the city centre that may require transportation.

The indoor skydiving facility in Chicago has been attracting many teens who are looking for something a little different and exciting on their vacation to Chicago. Book your session at iFLY Indoor Skydiving in Chicago.

Lincoln Park Zoo – things to do with kids in Chicago

If you are looking for cheap things to do in Chicago for teenagers, you can’t get any better than free!

This 35-acre zoo has all the soaring skyscrapers in the background but still finds a way to connect guests to nature. When the weather is nice, and you want to be outside, but still in the city environment, the zoo is a great choice.

Chicago teenage activities – Visit Millennium Park/Cloud Gate

Millennium Park is a public park located in the Loop community area of Chicago, Illinois.

It is a popular tourist destination, known for its iconic outdoor sculptures, including the Cloud Gate sculpture, also known as The Bean, and the Crown Fountain.

The park also features the Jay Pritzker Pavilion, a state-of-the-art outdoor concert venue, and the Lurie Garden, a 2.5-acre garden with a variety of plants and flowers.

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What to do in Chicago with a teenager – Navy Pier

Take your teens on a 15-story Ferris Wheel to get an epic view of the city and Lake Michigan! From this location.

You can hop on an evening lake cruise, put up your feet at an outdoor restaurant, play arcade games, or catch a movie at the IMAX. This has to be one of the best places to go with teens in Chicago.

Views from above in Chicago

If you want a bit of a thrill, head to the top of the Willis Tower or John Hancock building. Both of these skyscrapers offer their version of a top-level thrill.

Willis Tower

On the 103rd floor of the Willis Tower, you will find the Skydeck Chicago observation deck. The 103 floor features a viewing platform where you see the city below you.

For those with no fear, you can experience The Ledge, an enclosed glass balcony extending four feet (1.2 meters) outside the 103rd floor that provides the best views.

There is an interesting interactive exhibition on Chicago architecture and culture that you will find on the ground floor. Admission tickets for adults, which include access to the lower-level museum, Skydeck, and The Ledge, will set you back $35 USD.

John Hancock Building

The 360 Chicago Tilt Experience at the top of the John Hancock Building for teen thrill-seekers will be a memory forever!

Visitors to the Chicago observation deck can TILT outward over 1000 feet above downtown Chicago in this thrilling experience.! You will never forget this visit to the Chicago observation deck at the John Hancock building.

>> Book your Chicago 360 experience tickets here

Things for teenagers to do in Chicago – Aqua Water Trike

How does riding on water sound to you? In the warmer months, you can hire a water bike on Lake Michigan in Chicago and go for a spin.

After you put on your life jacket, sign a waiver, and receive a safety briefing and instructions, it’s time to hop onto your Aqua Water Trikes and get busy in the water for 30 minutes with this unique experience.

One Aqua Water Trike fits up to two people, so you may need more than one bike if there are a few of you who want to do this fun Chicago activity.

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Head to the theatre in Chicago

Chicago’s downtown boasts a fabulous theatre district with annual shows such as The Nutcracker but also hosting Broadway shows and the very sought-after Blue Man Group show. There are large theatre productions and small ones, giving you and your teens fun options. 

Best museums in Chicago for teenagers

It’s hard to choose just one museum as the best. There are several to choose from that may appeal to your travelling teens more than others. However, some that stand out are the Museum of Science & Industry, the Chicago History Museum and the Art Institute.

Museum of Science

The Museum of Science and Industry in Chicago is one of the largest and most interactive science museums in the world. Located in Chicago’s Hyde Park neighbourhood, the museum features more than 35,000 artifacts and exhibits, as well as live demonstrations and a range of hands-on activities.

Some of the museum’s most popular attractions include the U-505 submarine, a model of a coal mine, and a working model of the Chicago World’s Fair. The museum also has a number of special exhibits and events throughout the year.

Things to do in Chicago with kids – Scavenger hunt

If you are looking for great vacations with teens’ ideas, then look no further than a family scavenger hunt. There are quite a few different scavenger hunts to do in Chicago for families. Instead of a traditional sightseeing tour, get to know Chicago in a unique way with a scavenger hunt.

On your hunt, you will discover both popular and lesser-known sights of the city as you solve clues and tackle challenges to complete the adventure.

Scavenger hunts are completely unique things to do in Chicago with teenyboppers. How about a Chicago Chocolate Scavenger Hunt or a Lincoln Park Zoo Scavenger Hunt.

The Art Institute of Chicago

The Art Institute of Chicago is a world-renowned art museum located in Chicago, Illinois. It was founded in 1879 and is known for its extensive collection of artworks from around the world, spanning from ancient times to the present day.

Some of the museum’s most famous pieces include Georges Seurat’s A Sunday on La Grande Jatte, Edward Hopper’s Nighthawks, and Vincent van Gogh’s The Bedroom. The museum also offers a variety of educational programs, including classes, lectures, and workshops, as well as special exhibitions and events

Chicago History Museum

For families wanting a fun and educational holiday in Chicago with teens, you should start at the Chicago History Museum. The Chicago History Museum was founded in 1856 and is dedicated to collecting, interpreting, and presenting the history of Chicago and its surrounding areas.

The museum’s permanent exhibitions include displays of the city’s founding, its growth and development, and its role in national and international events. The museum also has a variety of temporary exhibitions that focus on specific aspects of Chicago’s history

These museums, although not unique, provide great entertainment and education that can be fun for teenagers in Chicago. Honourable mentions go to the Peggy Notebaert Nature Museum Shedd Aquarium and the Field Museum where you can meet Sue, the famous resident T-Rex. Get your tickets for Chicago Museums today

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Segway tours in Chicago with teenagers

There is nothing more fun than zipping around a city on a Segway and for teens, this has to be one of the best things to do in Chicago. A Chicago Segway tour is a great opportunity to have outdoor fun and learn about the city.

Segway tours are for the whole family, you will be given instructions and a short amount of practice time before you set off on your adventures in Chicago.

Chicago with kids – Oz Park

Located in the Lincoln Park neighbourhood is a park dedicated to the Wizard of Oz. The author L. Frank Baum lived in this Chicago neighbourhood in the 1890s. The main attractions in the park, are the statues of the famous characters that stand throughout the park.

Take a walk through the park, and you’ll spot the Tin Man, Scarecrow, Cowardly Lion, Dorothy and Toto. Each character was created by local artist John Kearney. A walk through Lincoln Park is one of the best activities for teenagers in Chicago.

TopGolf suite at the game room in the Chicago Athletic Association hotel

The Game Room in the Chicago Athletic Association Hotel is getting a new suite that allows players to enjoy Top Golf, which opened its first Chicago land venue this year.

The Top Golf Suite will offer guests access to an indoor driving range with golf balls and targets, as well as lounge areas with food, drinks, and TVs. A Chicago teenager will love this for the food and drink options alone.

Plan like a pro:

Riverwalk on the Chicago River

One of the best things to do at night in Chicago is to stroll along the Riverwalk of the Chicago River. This part of the city is bustling lively and fun for teenagers to experience.

During the day, you can do a kayak tour along the river and admire the Chicago architecture. It’s a special treat to visit after St. Patrick’s Day when the river is dyed green every year to celebrate!

Book a walking tour in Chicago today!

See the Architecture

There are many things to see in Chicago, hands down, the best tour in Chicago is the architectural boat tour, only offered in the summer months. It is pricey but completely worth it.

The focus of this architecture river cruise tour on the First Lady down the Chicago River is on the history of Chicago and its architectural development.

This is a perspective of the city you can’t get any other way. If you can swing it, try to get the last tour of the day so the light is gorgeous on the buildings and you finish the tour with the city lights sparkling.

Fun places for teenagers -6 Flags Great America

If your family is looking for thrills and excitement on your visit to the amazing city of Chicago, 6 Flags Great America Theme Park is the right place for you.

The park features nine themed areas, over 45 rides and attractions, including high, fast rollercoasters and captivating children’s rides for families with young children, live entertainment, dining options, and special events.

In the summer months, you can visit the adjacent Hurricane Harbor water park, a cool thing to do in Chicago with teenagers.

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The 606 for Chicago teenage activities

2.7 miles of multi-use recreational trail and park developed on an abandoned rail line as a living work of art and green space for all to enjoy.

Great for biking, running, walking, and special events this Wicker Park neighbourhood attraction can be accessed via the Blue Line at the Damen stop, or the Logan Square stop and walking a mile through Chicago’s Centennial Monument and other shop areas. The 606 is open every day from 6 am-11 pm. 

Ice skating in the Chicago winter

Chicago is a great place for ice skating! There are several popular ice skating rinks in the city, making it one of the best outdoor activities for teenagers in Chicago.

You can find ice skating in Chicago at the McCormick Tribune Ice Rink in Millennium Park Chicago, the Maggie Daley Park Skating Ribbon, and the Sky Rink at the Peninsula Hotel.

All of these rinks offer public skating sessions, so you can lace up your skates and enjoy the thrill of gliding across the ice.

Teenage Activities in Chicago – Gangsters and Ghosts tour

Experience the dark side of Chicago history with this Gangsters and Ghosts Tour. A local historian will guide you back to the roaring ’20s when Chicago was a hotspot for bootleggers and gangsters like the infamous Al Capone.

Visit historic locations such as gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley. This one is one of the fun things to do in Chicago with teenagers, both entertaining and educational.

What to do in Chicago for teens – Paintball

Paintball is a fast-paced game that involves running around, shooting opponents with paintballs, and trying to avoid being hit.

Most courses have obstacles, abandoned huts, vehicles, and the like scattered across the course. In Chicago, you can experience paintball on an indoor and outdoor course at the following locations.

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Cheer on a Chicago team at a sporting event

No matter what season you visit Chicago, you can find a live sporting event to enjoy. American football, soccer, ice hockey, basketball and baseball all have home teams in Chicago.

Teenagers tend to love big crowds and wild cheering and many will enjoy the history of the team/stadium you are visiting.

The iconic Wrigley Field, home of the Chicago Cubs is a must even if you can only do a tour in the off-season, but to catch a ballgame there is one great Chicago experience never to be forgotten.

Things for teens to do in Chicago – Big Bus Night tour

See Chicago’s dazzling skyscrapers lit up for the night during this 75-minute Big Bus tour.

The entire dazzling trip takes passengers from the Magnificent Mile to Michigan Avenue, through the Museum Campus and around the architectural gems on the Loop skyline. Audio commentary in English will explain the sights and the history of the windy city. Book the big bus tour here!

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Fun things to do in Chicago for teens – Adler Planetarium

For teens in Chicago looking skyward, the Adler Planetarium is a great place to visit in Chicago. This local Chicago Museum is home to the largest telescope in the region.

For those wanting to see starts, this is the best place to visit in Chicago. The Adler telescope helps unlock the 4500 stars that are viewable in the Chicago skies.

Having fun at Maggie Daley Park

The Maggie Daley Park is very enjoyable for all ages, from toddlers to teenagers. The park provides a wide range of activities that cater to a variety of interests. For example, rock climbing is great for people who enjoy being active.

The rock climbing wall caters for all abilities, with sections for first-timers through to challenging experienced climbers.

Rollerblading and riding electric scooters are fun things to do in Chicago for young adults. There is a special section called the Ribbon that weaves its way through the park. If you’re looking to do something a little less adventurous then, Mini golf is available for all ages.

Chicago things to do – Grant Park

Grant Park is a large public park located in the Loop community area of Chicago, Illinois. It is situated along the Lake Michigan shoreline, and it stretches for 319 acres from Randolph Street to Roosevelt Road and from Michigan Avenue to Lake Shore Drive.

The park is home to many popular attractions, including the Art Institute of Chicago, the Field Museum of Natural History, and the Shedd Aquarium. A visit is a perfect family activity in Chicago.

It also features numerous playgrounds, sports fields, and green spaces. Grant Park is a great place to spend a day outdoors, enjoying the sights and sounds of the city. In the winter, there is ice skating and plenty of snow.

What is there to do in Chicago for teenagers – Footgolf

A relatively new sport, footgolf is gaining popularity worldwide. This game combines the skills of football and golf, the objective is to kick the ball into the hole in as few kicks as possible.

Footgolf is played with soccer balls instead of clubs and uses your feet instead of your hands to kick the ball into the hole. You play footgolf in Chicago at Salt Creek Golf Club and Meadowlark Reserve.

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Teen-approved things to do in Chicago – Eat Pizza

Chicago pizza is famous for its deep-dish goodness and unique style that sets it apart from other pizzas. The main reason Chicago Pizza is so renowned is its thick, buttery crust that forms a deep dish, creating a perfect vessel for generous toppings.

You’ll find layers of gooey cheese, chunky tomato sauce, and your favourite toppings piled high. Each slice is like a hearty meal!

The indulgent flavours and the sheer size of a Chicago pizza make it a memorable and satisfying experience. It’s not just a meal; it’s an event! Locals and visitors alike love to indulge in this deep-dish delight, making it an iconic part of Chicago’s food culture.

So, when you’re in Chicago, be sure to try a slice or two of this mouthwatering pizza! You won’t be disappointed.

Have a food experience with a local

Some teens cook and some teens get served! So why not take a cooking class or eat with a local family on your vacation? Food plays a huge part in the local culture in the places you visit.

Maybe experience what the locals eat or take any number of different cooking classes in your city of choice. Food plays a big part in local cultures, whether it be cooking it, or eating it. Search and book your Chicago food experience.

The most Instagrammable places in Chicago

The Bean features in almost all photographs of Chicago. This large shiny bean-like sculpture made to resemble a drop of Mercury has become synonymous with Chicago.

The light and reflections from the surrounding buildings provide some unique images that are ever-changing with the weather. Alternatively, book yourself, an Instagram tour with a guide who will take you to all the hotspots in the city. Check prices on the best Instagram tours in Chicago.

Professional photo shoot in Chicago for families

As our kids get older, we spend less and less time with them making family memories when travelling. One excellent way to capture some of these important family vacation moments is to hire a professional photographer for a few hours to make some lifelong memories for you.

The photographer will supply everything your family just needs to provide the smiles for your Chicago photoshoot. Enquire today about making memories in Chicago.

Chicago Tiktok inspiration

If you’re in need of some inspiration, look no further than TikTok. TikTok is today’s app of choice for teens around the globe. This app is full of creative content and talented people from Chicago from fashion to travel to food, there’s something for everyone on TikTok.

Here are just a few of our favourite Chicago TikTok accounts to help inspire you and plan for your vacation.

Street Art – things to do with teenagers in Chicago

Street art is found throughout the world, but it is especially prevalent in major cities. Cities are home to a wealth of street art, from graffiti on building walls to pieces painted on lanes and bridges.

Street art provides a unique aesthetic for these places, with topics including current events, pop culture, portraits and more. Street art is a very popular free thing to do in Chicago and attracts tourists and teenagers alike.

Street Art in Chicago is found around Wabash Arts Corridor, Pilsen, Logan Square and Wicker Park.

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Escape rooms in Chicago for teens

For those new to Escape rooms, this is a quick run down. An escape room, also known as an escape game, is a physical adventure game in which players solve a series of puzzles and riddles using clues, hints, and strategies to complete the objectives at hand.

Escape rooms may consist of a large, single room, or span multiple rooms, it’s quite a unique experience. Players are given a set time limit to unveil the secret plot which is hidden within the rooms. If your teen likes this stuff it is definitely one of the fun things to do in Chicago for teens.

The Escape Game Chicago

Entertainment spot featuring 5 themed escape rooms with 60-minute challenges, hosting large groups.

Address: 42 E Ontario St, Chicago, IL 60611, United States

Focus Time Escape

Players must communicate efficiently while working together to find new keys. Uncovering clues moves you one step closer to achieving the ultimate goal of unlocking the door to freedom!

Address: 9856 Derby Ln, Westchester, IL 60154, United States

Watching a movie in Chicago for teens

Watching a movie is popular with teenagers anywhere in the world. Going to the cinema in Chicago with teenagers is a great evening activity.

You will find state-of-the-art screens and sound at Should Cinemas. Movie theatres in Chicago come in all shapes and sizes from multiple.

Pin Bowling in Chicago with teenagers

Nothing like a good bit of family competition to get everyone going on your holidays with teenagers. 10-pin bowling in Chicago is a great family activity for all. You will find bowling alleys all over the city for your family to have some fun.

Most bowling alleys these days are more entertainment centres featuring amusement, food and drink options. You will find some of the best bowling locations in Chicago below.

Diversey River Bowl: This location is known for its amazing sound and light features. The lanes can be hired by the hour or per game, with a Pizza restaurant onsite for food.

Waveland Bowl: Waveland Bowl has 40 lanes and an arcade with over 30 games along with air hockey, classic pinball and more. The always fun Cosmic Bowling sessions operate 8 times a week, with disco features such as a fog machine, dance music and black lights. Grab something to eat at Alley Dogs or play some pool in the billiard room.

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Chicago with older kids – Axe Throwing

Axe Throwing is a new phenomenon that is sweeping around the world. Chicago is home to Bad Axe Throwing. No experience is required, and Bad Axe boasts “Our axe-throwing coaches will teach you how to throw an axe while helping you improve your axe-throwing technique and make you into an axe-throwing pro in no time”.

If you are looking for unique experiences for teenagers in Chicago there are 2 locations in Chicago for Bad Axe Throwing and walk-in sessions start from $25 hours. Axe Throwing is one of the awesome things to do in Chicago on your family vacation. For more information click through to the Bad Axe website

Going to the gym in Chicago

Fitness is very important to a lot of teenagers these days and being on a family vacation in Chicago is no reason to miss a session. Working out is a big part of a healthy lifestyle. Just because one is travelling does not mean one needs to stop working out.

In Chicago, you can go to a number of Gyms that sell passes ranging from a day to a week and a month. Day passes start at $9 a day. You can find a list of Gyms in Chicago on the Trainaway fit website

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Bike riding in Chicago

Chicago bike riding is a popular family activity when travelling with teenagers. Bike riding allows you to experience your location, either in town or out in the surrounding areas.

You will find bike tours are the best way to go if you want to get an up-close and personal experience of the city. You will either have a guide to point out all the important attractions in Chicago or a map to follow.

The bike tours will take you on a Chicago family vacation 2-wheeled adventure. Alternatively, you can find locations that hire bikes and let you explore on your own. Plan a Chicago bike tour today.

Shopping in Chicago

The Magnificent Mile district extends a full square mile along North Michigan Avenue. With more than 460 stores, 275 restaurants, and 60 hotels all along its length. The Magnificent Mile is a shopping haven for teens and one of the fun trips with teenagers in Chicago.

If you happen to look for fun stuff for teens in Chicago around the holidays, there is a Christkindl Market in Daley Plaza downtown. Modelled on an authentic German Christmas market, stalls will be selling artisan crafts, gifts, food, and of course, mulled wine! (Or hot chocolate for the teens!)

Free things to do in Chicago with teens

Chicago offers, some of the best free things to do with your teenage family members. These free City of Chicago activities are perfect for keeping everyone happy and entertained without having to spend any money.

There are plenty of places to visit in Chicago including affordable restaurants and shops where you can shop for souvenirs without breaking the bank. Some of our recommendations for free activities in Chicago for families are as follows.

Things to do in Chicago this weekend with teens

There are countless things to do in Chicago this weekend, including visiting popular attractions like Millennium Park and the Art Institute and exploring the vibrant neighbourhoods such as Wicker Park and Lincoln Park.

On any given weekend in Chicago, you will find any number of events and sporting activities to see. Search the Choose Chicago website for things to do in Chicago today.

Annual events in Chicago that teens will love

Chicago is a city with a rich culture and history. There are many annual events that take place that can be enjoyed by families and teens visiting Chicago. Some of these events include The Chicago Air and Water Show, the Chicago Summer Dance and the Chicago House Music Festival.

These teenage holiday activities in Chicago help to make it a vibrant and exciting city to visit on your next family travel vacation.

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Day trips from Chicago for families

While staying in the city with teenagers may be the easiest option on your family vacation to Chicago, there are some fun trips for teenagers to make out of the city too. The best vacations for teenagers usually include at least one day trip.

Below we have a couple of day trip recommendations for families travelling with teenagers. There are also so many more things to do on your vacation with teenagers when you add a day trip from Chicago.

Holland Michigan

Holland, Michigan has a population of 34,832 people. Holland is popular for its yearly Tulip Festival and its Dutch heritage. The town is located at the junction of Lake Michigan and the Grand River.

You can explore Dutch Bakeries, tulip Gardens and Windmill Island. This is your family’s chance to explore a little bit of Holland near Chicago. Grab yourself a rental car and head off on a 2.5-hour journey to Holland.

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Fun Chicago restaurants for teenagers

If you are looking for quintessential Chicago eateries, your teens will love Portillo’s Italian beef sandwiches and Lou Malnati’s Chicago-style deep-dish pizza. Both have affordable prices and are easy to find with several locations in the city.

Of course, if you make it to Wrigley, you’ll need to have a Chicago dog-the hot dog is topped with yellow mustard, chopped white onions, bright green sweet pickle relish, a dill pickle spear, tomato slices or wedges, pickled sport peppers and a dash of celery salt. 

Speaking of Wrigley Field, Harry Caray’s Italian steakhouse is chock full of Chicago memorabilia and HOLY COW their steaks are marvellous. 

The Purple Pig is a James Beard award-winning chef restaurant located on the Magnificent Mile. If you have teens who are into the foodie scene this would be a great option. A Mediterranean menu with a  focus on pork, but a healthy selection of dishes.

If you have teens who love Mexican food, you will want to try Frontera Grill, the authentic Rick Bayliss restaurant utilizing midwestern farmers to source ingredients. You will recognize the flavours, but you will still be wowed by this food.

Au Cheval-the BEST burger in Chicago! And what teenybopper doesn’t love a great burger? This spot is outside the Loop, but you can still get there with public transit. They do not take reservations and the lines can be extremely long, but if you want a burger to remember, give it a shot.

Garrett Popcorn Shops is a Chicago-based gourmet popcorn company with several locations in the Chicago area. Some of their most popular flavours include Cheese Corn, Caramel Crisp, and The Chicago Mix, which is a combination of Cheese Corn and Caramel Crisp.

The high-quality ingredients and unique flavour combinations are what Garrett popcorn shops are known for

Portillo’s is a Chicago-based restaurant chain known for their Chicago-style hot dogs and other Chicago-style food. Portillo’s hot dogs are made with 100% Vienna beef and are served on a steamed poppyseed bun.

They refer to their toppings as dragged through-the-garden toppings including mustard, onion, sweet pickle relish, a dill pickle spear, tomato slices, pickled sport peppers, and celery salt.

Revival Food Hall, located in the heart of the city’s downtown area, is set to open its doors this fall. The hall will provide locals and visitors alike with an array of delicious meals from Chicago’s best local chefs and restaurateurs.

Revival Food Hall will feature stalls serving a variety of cuisines ranging from Mediterranean to Mexican and beyond. Visitors can expect an ever-changing selection of dishes that are sure to tantalize their taste buds.

Local vendors will be featured, as well as offerings from some of the city’s hottest restaurants like Au Cheval and Bang Bang Pie & Biscuits. There will also be a full bar with craft beer and cocktails.

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Street food in Chicago

Street food is a popular way to eat in many parts of the world. It’s a quick and easy way to get some delicious local food without having to go to a full restaurant. Street food can be found in many different styles and options.

Some of the most well-known street foods include tacos in Mexico, Zapiekanka in Poland, Dan noodles in China, and Shawarma in Middle Eastern countries.

Street food in Chicago often has its origins in the cultural history of people who have immigrated to The United States in the past. Some of the most popular Chicago street foods include Pizza, Polish sausages, Tamales and Jibaritos

Frequently asked questions about Chicago

Chicago is one of the best family city breaks in The United States of America and one of the best places to vacation with teenagers. There are so many things to consider when you are planning your family vacation to Chicago.

Here is a list of some of the most frequently asked questions about the city to help you make your family vacation to Chicago easy and hassle-free.

Where to Stay in Chicago with Teenagers

At the top of the article, we suggest some accommodation choices for your family holidays with teenagers. If you are looking for a wider variety of choices please find below an interactive map from Booking.com for you to find your perfect stay in Chicago on your family vacations with teens.

Booking.com

Are you looking to book flights, hotels, apartments, tours, airport transfers, travel insurance and more? Are you just not sure what companies you can trust to book your travel online? We have a resource page that is full of companies that we personally use and book through for all trips from a weekend away to long term travel around the world. Click here to search our travel resources page.

We hope this article written in collaboration with Jen from Go Family Adventure and Wyld Family Travel has inspired you to visit Chicago with teenagers. There are so many things to do in Chicago with teens that will have you entertained for your family stay in the Illinois capital.

Travel with teenagers and tweens and older kids has just as many issues as travelling with younger kids. Choosing the best teenage vacation destinations can be time-consuming. 

Use our travel with teenagers destination guides from all over the world for your next family vacation inspiration to make your family vacations with teens epic.

For more amazing ideas on where to holiday in the USA click through to our United States of America destination page for more brilliant family travel inspiration.

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