8 Things To Do In Chicago
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8 Things To Do In Chicago

A list of things to do in Chicago that are a bit different than the usual touristy spots.

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8 Things To Do In Chicago
Lizzie Lipscomb

The Magnificent Mile, the Willis Tower, Millennium Park, the museums – all of these things make Chicago the popular tourist destination it is. Along with these places, though, Chicago natives can make an even longer list of what little places and things make their city so great. If you’re ever in Chicago and want to escape the traditional touristy sports, these are a few places that, in my mind, are super fun to look into.

1. Surrey Bikes

This is an experience to remember. Yeah, you look kind of funny to the pedestrians you’ll be riding past. Yes, they’ll probably stare. But honestly, it’s worth every second glance. First, be sure to go with at least one person who has the leg strength to pedal. For me, being my height, I couldn’t even reach the pedals without having to practically stand up. Needless to say, it was a lot of work. But in a four-person bike, when you have the chance to be a passenger in the back is very relaxing because the view was absolutely beautiful. Riding along Lake Shore Drive and by the lake itself gives sightseeing in a totally different view.

2. Lucky Strike

If you like bowling, good food, and/or pool, this is the place to go. The very retro, yet modern environment gives off so much energy that it’s hard not to have a great time. You can get it all as you bowl in a super trendy area, lounge around on couches while you’re waiting your turn, and then get served some delicious food right where your lane is. Some tasty apps that I would recommend are mac and cheese bites, burger sliders, guac and chips, and spinach and artichoke flatbread.

3. Second City Improv Show

Improv at its finest. I don’t think there was a moment that I was not laughing. Located in Old Town, the area itself gives off such a vibrant, positive vibe that mixes perfectly with this sketch show spot. Sit back and laugh at edgy and unrestricted improv, with a crowd engaging show that you will not forget.

4. Riverwalk


This absolutely beautiful path along the Chicago River provides a perfect stroll on a nice day. It spans from Lake Shore Drive to Franklin Street and provides a variety of activities from kayaking to eating or just sitting on the side of the river.

5. Thrifting in Belmont/Wicker Park

A close stop right off the red or blue line train, Belmont and Wicker Park are perfect destinations with a mixture of cute boutiques, cafes, but most importantly, thrifty shops. The lively communities provide such a positive vibe to all their visitors. To get away from the commotion of shopping on Michigan Avenue, these two neighborhoods offer shops that are hipster and trendy, at a low cost as well. Some of my favorites are Buffalo Exchange, Belmont Army, and Ragstock.

6. Stan's Donuts

Delicious. That’s all there is to it. Located in now 6 different areas of Chicago, including Wicker Park and the Magnificent Mile, you will be sure to find one close to you. From donuts, to cakes, to specialties, it’s a hit no matter what you get.

7. Bottle and Bottega

You don’t have to be 21 to go here. Yes, it’s in the name, bring your own wine, paint with your glass. However, when I went, I just had a glass of water and it was a great time. You can book online and pick whatever painting you would like to paint, and don’t worry, there is step by step instructions for every little piece of the painting. No artistic skills needed – keep that in mind too.

8. Segway Tours

Whether you’re already a pro or just a beginner, these can be a great alternative to exploring the city. Tours are provided that show you the beautiful Chicago skyline and highlight some of the best parts of Chicago. Be careful not to fall, that’s pretty much the only advice to offer.

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This article has not been reviewed by Odyssey HQ and solely reflects the ideas and opinions of the creator.
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