13 Fun Things to Do in Chicago

Chicago is definitely one of my favorite cities on Earth. It has so much to offer, from cool out-of-the-way joints to world-class amenities. I’ve been here several times, and I find it exciting each and every time. Just to walk the streets is invigorating (just not in Winter!).

While this midwestern metropolis of over 2.7 million has been in the news lately for negative reasons, it’s perfectly safe to walk around. Fortunately for tourists but not for many Chicagoans, the most dangerous areas are clustered on the South Side and West Side, away from the biggest attractions.

I’ve compiled some of the highlights below

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1. Lake Michigan

Chicago, to be honest, does not offer much in terms of topography nor natural beauty. It’s really a place you go to for the urban appeal. Having said that, having Lake Michigan right there is incredible.

The lakefront affords excellent opportunities for walking, running, or biking. Just to find a bench and chill is a nice experience, watching the waves and the lights of the city, as well as people-watching.

Didn’t bring a bike? Rent one from Divvy, Chicago’s bikeshare program.

2. Architectural River Tours

Put on by the Chicago Architecture Center, a river tour is the defining experience to have in the heart of The Windy City. Lasting about an hour and a half and costing between $45 and $55, it’s worth every penny.

3. Comedysportz

A hilarious improv comedy troupe, Comedysportz has branches all across the country. Chicago is known as a comedy capital of the world, with such high-profile institutions as Second City. Comedysportz is a lot more informal, but every bit as funny. I’ve gone to their shows in Chicago and in Milwaukee and laughed my @$$ off both times.

4. Take the L

The “L”, Chicago’s (mostly) elevated public transportation system, is not just extremely convenient, but also fun in its own right. It is these elevated tracks circling the urban core of Chicago that give the downtown Loop its name. Between the L, buses, and Divvy, you’d have to go out of your way to need a car during your trip here.

Go on your own little architectural tour by taking either the Red Line or Blue Line through the heart of the Loop. Just be aware that the Red Line does run into the South Side and the Blue Line does extend out to the West Side, so depending on your comfort level, you may not want to go to the end of those lines at night.

For some of the best views of the skyline, take the Orange Line towards Midway Airport.

5. Millennium Park

Like Chicago’s backyard. Play a game of ultimate with your friends or catch a show at the pavilion.

Millennium Park on a rare quiet day

6. Field Museum

The Field Museum of Natural History is among the largest and most visited natural history museums in the world. Founded in 1893 (a pivotal year for Chicago), it is named after local department store magnate Marshall Field, its first patron.

Entering the main hall puts you face-to-face with “Sue,” one of the most complete T-Rex skeletons in the world. The skeleton, 90% intact, was discovered in 1990 by explorer Sue Hendrickson on the Cheyenne River Indian Reservation in South Dakota.


7. Museum of Science and Industry

Now this one is my personal favorite! One of the only surviving buildings from the 1893 World’s Fair, MSI is simply huge. So huge, there is an entire World War II German U-Boat housed within…and that’s just one section. One of the few places that I will honestly and confidently say is as much fun for kids as it is for adults. It’s seriously awesome and definitely worth the trip down south.

8. Shedd Aquarium

An architecturally pleasing aquarium with tanks showcasing sealife and riverlife from all over the world.

9. Adler Planetarium

For those interested in the cosmos, you can’t miss this one.

10. Lincoln Park Zoo

One of the premier zoos in the US, found in the North Side’s upscale Lincoln Park neighborhood, which is itself worth a stroll.

Photo courtesy of Expedia.com

11. Skydeck Chicago

The observation deck of the Sears Tower (Willis Tower). While it’s no longer the tallest building in the country, it’s still among the most impressive at 1,454 feet.

Skydeck allows you to see over 50 miles on a clear day. Wanna freak yourself out? Step out onto The Ledge, the glass box jutting out from the building, 1,353 feet above the ground. Don’t worry, it’s extremely strong material and attached very securely.

Photo courtesy of Afar.com

Having said that, the quintessential Chicago skyline photo includes the Sears Tower itself. To get that, head over to the Hancock Tower and go up to their own observation deck, 360 Chicago!

12. Giordano’s

One of the many, many places where you can get Chicago-style deep dish pizza. While the battle may rage on between New York-style pizza (also known as, you know, pizza) and Chicago-style pizza (also known as lasagna), there’s no denying that you have to grab a slice when you’re in The City of Big Shoulders.

13. Wow Bao

Not gonna lie, this one is probably out of place on this list. But if you get a chance, stop in to one of their locations and grab some baos, which are large dumplings. They have dinner baos filled with meat, and then desert baos filled with chocolate and bavarian cream. If nothing else, get yourself a desert bao. Super tasty.

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