5 things to do with teens in Chicago

posted in: Blog, North America | 19

By Jess, aged 17:

Over summer, our family spent the most amazing week in Chicago. Though very full on, we all had a fantastic time, and there is not one activity which I didn’t enjoy. Chicago is a genuinely beautiful city; busy but not too loud or congested. There were things to do for all the family, and here are my highlights from the trip, which I think teenagers would particularly enjoy.


I had really wanted to go to a baseball match as I felt it was a typical American thing to do. Instead of watching the more famous Chicago Cubs, we opted for the White Sox, and I had a really fantastic time. Unlike football games in the UK, the atmosphere was much more relaxed, with people walking around the whole time. I definitely enjoyed this, as I can get very stressed when watching live sports!

White Sox Chicago
We really enjoyed watching the Chicago White Sox!

Despite never playing baseball before, the people sitting around us were more than willing to explain what was going on, and I found myself getting very engaged with the game. The experience felt very American, with an audience cam, lots of adverts for pizza, a fill in the song lyric game, and everyone standing up and singing “Take me out to the ball game” between the seventh and eight innings.

There were other activities in the stadium as well, such a speed pitching test and a free interactive centre for kids. Mum and I collected free badges and certificates to commemorate our first visit to the stadium, and the people sitting behind us were generous enough to give us White Sox temporary tattoos and t-shirts.

I would definitely recommend baseball games to people visiting the US – not only was the game exciting, but I loved getting a taste of what it’s like to be a real American. Mum says that it was expensive though – and we were all shocked by the cost of the food and drink inside the stadium (a bottle of Pepsi was over $6!)

Our tickets to the baseball cost around $50 (they were more expensive because we chose to be under cover – a good decision, as it was very hot!).

Second City

Second City is a famous sketch and improvisational comedy troupe, known for producing stars such as Tina Fey and Steve Carell. I am a huge fan of SNL, and it was especially exciting spotting lots of famous names in the programme we were given. Our family saw a production named “Grinning from Fear to Fear”, which included two sets of sketches and an improvisational section.

I thought the production was hilarious, and unlike anything I’d seen before. Ranging from meeting your girlfriend’s parents to sleepless late night anxieties, the production was very well done, and I laughed more times than I can count. They also used a lot of suggestions from the audience and even brought people up onto stage.

This was definitely one of the highlights of my holiday.

Second City is not for younger children – the show we went to started at 8pm and didn’t finish until nearly 11 and there was quite a lot of swearing in it. Tickets cost $52 each.

Cycling food tour

Cycling isn’t something we do very often, so I was somewhat terrified at the prospect of cycling around busy Chicago streets. However, I shouldn’t have worried: our Bikes, Bites and Brews tour with Bobby’s Bike Hike was great. Our guide Ro was extremely friendly and enthusiastic, and she toured us for 13 miles across Chicago.

Bobby's Bike Hike Chicago
We loved all the food on our cycling tour with Bobby’s Bike Hike, and the views were great too!

We sampled pizza, cupcakes, hot dogs, and drinks from all across Chicago, learning a lot about the city in the process. A particular highlight was eating delicious deep dish pizza from Lou Malnati’s, and spending half an hour cycling down a cycle path right next to Lake Michigan. The views were brilliant, and it was very relaxing. The tour was both interesting and exciting, and we definitely wouldn’t have had the confidence to ride around Chicago without a guide. The city was easy to ride around and the views were gorgeous.

I would definitely recommend cycling around Chicago, and there are lots of places to rent bikes from. Though we wouldn’t have been able to navigate the streets by ourselves, the cycle path by the lake boasted brilliant views and was easy to make our way around.

This Bobby’s Bikes, Bites and Brews cycling tour costs $66.75 for adults and $61.75 for students (Mondays to Thursdays) and lasts four hours. 

Disclosure: We were gifted the opportunity of taking part in Bobby’s Bike Hire, the Bikes, Bites and Brews tour, in order to write about it. However, the company had no input whatsoever into this blog post.

Escape room

Our whole family loved going to an escape room at The Escape Game Chicago. Though only an hour long, our experience probably provided us with the most fun of anything we did over the holiday. Our challenge was called “The Heist”, and our challenge was to retrieve a painting from the office of a man accused of stealing it.

The Escape Game Chicago
We were pleased to find the painting with only two minutes to go!

I’ve been to three other escape rooms before, but this one was definitely the best. It was so well maintained, and some of the parts were genius. It was very difficult, but definitely not unmanageable or frustrating, and we were pleased to escape with two minutes remaining!

Escape rooms can be found all over the world and there are a copious amount in the UK alone, but I would recommend doing this one if you’re in Chicago. We all had a fantastic time.

Read Rob’s post on the Escape Game (he really loved it too!)
The Heist at the Escape Game costs $35.99 per person.


Chicago is particularly special as it is on Lake Michigan, so there are a copious number of beaches to relax on. We were all struck by the sheer size of the water – it seemed unfathomable that it was only a lake and not the sea! We went to the North Avenue beach, which was great as it was quiet, and there was a lot of space to sit down and unwind.

North Avenue Beach, Chicago
Looking out to Lake Michigan on North Avenue Beach

The water was ridiculously cold, but we appreciated that it wasn’t salty like the sea. It also didn’t get deep quickly, providing ample space for wading in the water and swimming. Chicago’s beaches are especially notable as its gorgeous skyline is behind the lake, leading to gorgeous views wherever you look.

Overall, Chicago is a perfect place for teenagers, and I honestly enjoyed every aspect of the trip. Aside from these five highlights, there were so many other fantastic attractions, making the city perfect for all the family. I enjoyed incredible views of the city at the top of the Sears Tower, saw chicks being born at the Museum of Science and Industry, and looked at the largest T-Rex ever found at the Field Museum. Even activities which sounded boring, such as an architecture boat tour, were fascinating!

It may not a common holiday destination for those of us in the UK, but our trip to Chicago was great – both for the adults and the teens.

Read Rob’s post on his two favourite activities: 

We also found useful information on the Choose Chicago website and the Enjoy Illinois website.


19 Responses

  1. Nayna Kanabar

    Chicago sounds like a super place to visit and I am so glad that there is so much to see and do. We are planning a trip there next year so will keep this post in mind.

  2. Jennifer

    I am actually going to Chicago in January, I’m super excited an am definitely interested in doing a cycling food tour now!

  3. Margie

    By the time we end up in Chicago our kids will be teens, this is quite useful. Looks like a lot of fun activities for the whole family.

  4. Ali Rost

    My husband grew up on Chicago and tells the funniest stories of playing hooky from school to go to baseball games. He’d take the train downtown, eat a million hot dogs, and get sunburned every time. Those were the days. xx

  5. Andrea

    We love Chicago but we’ve never been with the kids. Great read and thanks for the ideas for when we do bring them.

  6. Rhian Westbury

    Some lovely things to do, and I’m so glad you enjoyed baseball. When I went to see a baseball game it didn’t interest me which was a shame, but I’m glad I’ve been x

  7. Jenny

    I would love to go to Chicago. Whilst not a typical tourist destination I’ve always thought it sounded a fun place to visit.

  8. Indri ani

    5 things to do with teens in Chicago that you discuss and share are very interesting and useful for me and my family. Thank you for sharing your experiences and knowledge about holidays.

  9. Kirsten

    Looks like you had a great time in the Windy City! Definitely a smart idea to see the White Sox instead of the Cubs because it can be quite difficult to get tickets. Fun to read this from a non-American POV. I love the comment about whether or not it is safe. We lived there for 14 years and loved every minute. Are there bad areas of town, sure, but you just don’t go there. It’s like every major city.

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