Things to do in Chicago with teenagers

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Sweet home Chicago, one of the great American cities is a major destination altogether, but it is also one of the best teenage vacation destinations for family travel. With all of the museums, sporting events, restaurants 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, you 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 activities in Chicago, we want to give you some simple tips for this specific family travel destination. Travelling to Chicago can be such an enriching experience for the whole family. There are so many things to do 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 to make it completely hassle-free.

Where to stay in Chicago with teens

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 I find it 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 I find particularly great for travel families with teenagers.

Luxury: The Peninsula- 5 star luxury with traditional Asian service centrally located on Michigan Avenue with bus stops near and just two blocks from the Red Line train-perfect for a trip to Wrigley Field. If you are celebrating with your teenagers in Chicago this is the ultimate Chicago hotel.  

Mid Range: The Hampton Inn, Chicago Downtown/Nloop/Michigan Avenue is well equipped in a great location to access all the best Chicago has to offer. Well-appointed rooms with wifi, tv and air conditioning for your stay in Chicago with family.

Budget: Featuring private rooms with ensuites the HI Chicago, The J.Ira & Nicki Harris Family Hostel is a great option for those travelling to Chicago on a budget. The hostel is located within walking distance of the Willis (Sears) Tower, Michigan Avenue/Magnificent Mile shopping. There are a shared kitchenette and lounge/seating areas.

Also, the Hotel Chicago Downtown Autograph Collection puts you very near the riverwalk and Michigan Avenue as well. The DoubleTree-Magnificent Mile gives great deals to families and has a fabulous pool. If you’re not keen on any of our picks or have specific needs, we recommend using Trip Advisor and Hotellook 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 you travel with teenagers then an apartment in Chicago is the best choice for you. There are so many options for singles, families and budget-friendly options as well.  Check out the map below to find the perfect Chicago apartment.

How to get to Chicago

  • There are two main airports available to fly into. 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 to 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 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

Chicago has an extensive public transportation system and many of your daily activities can be bundled to 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. Winning! Consider a CTA unlimited ride pass for 1,3, or 7 days (each person must have their own).

Get the Go Chicago Pass

Get digital delivery of the Go Chicago Pass to your device for easy use. The Go Chicago Pass offers the best choice for maximum savings and flexibility. Save on admission to 25+ top attractions and tours including Hop-on Hop-off Big Bus Tour and Sky Deck Chicago. Multi entry passes such as this are great for families visiting Chicago. There are 32 different passes to choose from. Buy your Go Chicago Pass today.

Using your phone in Chicago

Relying on Wi-fi when you are travelling and sightseeing in Chicago with family can be hard. Making calls and staying in contact when you travel with teenagers is a top priority. Plan your family trip to Chicago and order your sim before you leave home to stop any stress about travelling, data and calls on your family vacation in the USA.

The best things to do in Chicago with teenagers

There are so many activities in Chicago to choose from and this is by no means a comprehensive list. These are a few of the best things to do in Chicago with teenagers and build memories with your travelling teens.

Visit the animals at Lincoln Park Zoo

If you are looking for cheap things to do in Chicago, 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 people 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.

Millennium Park/Cloud Gate

The famous “bean” is a great place to get those creative Instagram photos your teens will undoubtedly love to post. Another great free activity in the city that keeps you outside for a while. Keep your eye on events and festivals that happen in and around this park during various parts of the year.

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 lakeshore! 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 one of the best places to go with teens in Chicago.

The ferris wheel at navi Park

Views from up above the city streets

If you want a bit of a thrill, head to the top of the Willis Tower or John Hancock buildings. Both of these skyscrapers offer their version of a top-level thrill. The Skydeck allows you to sit/stand/lean out in a glass window box overhang from the very top of the building. The 360/Tilt Experience at the top of the Hancock building for the teen thrill-seekers will be a memory forever!

>> Book your Chicago 360 experience tickets here

Head to the theatre in Chicago

Chicago 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. 

A night out at the theatre in Chicago

Museums in Chicago for families

I can’t choose just one museum as the best. There are several to choose from that may appeal to your travelling teens more than others. However, two that stand out are the Museum of Science & Industry and the Art Institute.

Both of these museums, although not totally unique, provide great entertainment and education that can be fun for teenagers in Chicago. Honourable mentions go to the Shedd Aquarium and the Field Museum where you can meet Sue, the famous resident TRex.

Segway tours in Chicago

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

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.

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 with teenagers in Chicago.

Riverwalk on the Chicago River

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

The riverside ion Chicago is a great place to walk

During the day, you can do a kayak tour along the river. 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!

6 flags Great America with teenagers

If your family is looking for thrills and excitement on your visit to Chicago, 6 flags is the right place. The park features nine themed areas over 45 rides and attractions, including high and 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

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. 

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 one of the fun things to do in Chicago with teenagers, both entertaining and educational.

See the Architecture

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 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 off the buildings and you finish the tour with the city lights sparkling.

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.

a man selling food at a sports event 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 is a must even if you can only do a tour in the offseason, but to catch a ballgame there is one great Chicago experience never to be forgotten.

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 night tour here!

The most instagramable spot 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.

The bean in Chicago at night

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 strategy to complete the objectives at hand. Escape rooms may consist of a large, single room, or span multiple rooms. 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 top things to do in Chicago with teenagers.

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 achieve 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 the 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 at.

Most bowling alleys these days are more an entertainment centre 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 lights 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 fog machine, dance music and black lights. Grab something to eat at Alley Dogs or play some pool in the billiard room.

Axe Throwing in Chicago

Axe Throwing is new phenomena that are 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 that does not mean you need to stop working out.

A teenager working out with weights at a gym in Chicago

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 at the Trainaway fit website

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, 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.

Best Restaurants in Chicago 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 pizza. Both have affordable prices and 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. 

Eating out in Chicago with teenagers

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 that 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 teenager 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.

Frequently asked questions about Chicago

How do I call the Police in Chicago?

Call 911 when in the USA

What type of power socket do they use in the USA?

For the USA there are two associated plug types, types A and B. Plug type A is the plug which has two flat parallel pins and plug type B is the plug which has two flat parallel pins and a grounding pin. The USA operates on a 120V supply voltage and 60Hz. Buy your A-Type adaptor today before you travel

Can you drink tap water in Chicago?

Yes, tap water is drinkable. If you are unsure we suggest you buy a drink bottle with a water filter on it for travelling. You can buy your water bottle here before you leave

Do I need to tip in Chicago?

A general rule for waiters is to tip 15 to 20 percent of the pre-tax bill

What currency is used in the USA?

You will need US Dollars for your family trip. We suggest you get a Transferwise Money card prior to leaving to save on withdrawal fees. You can transfer money from your home country into USD if you’re an international traveller.

Do I need travel insurance in the USA?
We always say if you can’t afford travel insurance you can’t afford to travel. Get your travel insurance now to protect your epic holiday in America from any small hiccup.
For Australian travellers, we recommend Fast Cover Travel Insurance
For worldwide travellers, we recommend AXA Travel Insurance

Where to stay in Chicago with teenagers

At the top of the article, we suggested 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 for you to find your perfect stay in Chicago on your family vacations with teens.

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. his makes Chicago a top spot for family vacations with teens.

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

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.

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

More travel inspiration for your trip to the USA

Having a beer in Pilsen Czech

Mark Wyld

Author Bio:

Father, husband, traveller and chief destination manager here at Wyld Family Travel. When Mark is not talking travel or planning travel you will find him working in disability support. Mark is a family travel advocate having travelled to over 45 countries with his kids from 10 months old, through to their teenage years. You will find his work here and on other popular websites.

Things to do in Chicago with teenagers

3 thoughts on “Things to do in Chicago with teenagers”

  1. Our son is a tween now, and what he wants to do on vacations is defintely changing. Chicago is a place we haven’t been to in the US, so will keep this guide in mind.

  2. This guide is PERFECT (and not just for teenagers…I totally want to do all the things on here, too)! I really wanted to do a segway tour when i was in Chicago, but the friends I was with voted for a river boat architecture tour (VERY cool, too…but I wanted to zip around the city!).


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