11 of the Best Things to Do in Chicago!

Are you looking for things to do in Chicago? I’ll help you plan your ultimate trip (even if it’s the middle of winter!)!

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There are so many things to do in Chicago no matter what time of year it is!

I find a lot of people stray away from Chicago in the winter months because of how cold it is, but it can be so gorgeous to visit in December, January, or February, as long as you know some great things to do and keep warm!

I’ve gone several times all at different times of the year, so I will do my best to give you a well-rounded list of things to do in Chicago no matter what time works best for your schedule to plan your vacation!

As far as having good weather – April, May, September, and October are probably the best months. The winter can get pretty cold and the summer can get pretty hot – these months typically have a nice in-between fall or spring weather.

With Christmas coming up I just want to make a special mention of the holidays in Chicago! Yes – it gets cold – but yes it is so beautiful to celebrate Christmas in Chicago!

This post is all about things to do in Chicago!

Best Things to do in Chicago!

1.) Catch a show!

Chattanooga has a ton of amazing shows! I am a big fan of Broadway musicals and Chicago has some of the absolute best talent if you want to grab tickets! I got to see Hamilton one time while I was visiting, and it definitely did not disappoint!

If you want a great photo opportunity stroll by the iconic Chicago Theatre! They have tons of great shows to choose from as well!

It’s such a great place to snap a pic. I took this one in the middle of a beautiful little snowstorm in January last year.

2.) Architecture River Cruise

Chicago really has some of the most beautiful architecture you will see in the States! You will see tons of skyscrapers that are incredibly diverse in their styles.

In my opinion, the absolute best way to learn about Chicago architecture is to go on an Architecture River Cruise aboard Chicago’s “First Lady.” It’s #1 on TripAdvisor and it’s even partnered with the Chicago Architecture Center. Not only will you have the best view cruising around the Chicago River, but you will also have amazing commentary to teach you about so many of the incredible skyscrapers you pass, all while sipping signature cocktails and enjoying snacks along the way!

I’m a sucker for any kind of boat tour because I love the views of the city you typically get – and this one is perfect to learn in such a relaxing setting!

Check their website to find the latest updates on what time of year and what time of the day they are available!

3.) Check out the Magnificent Mile

The magnificent mile can be found on Michigan Avenue. It is known for amazing restaurants, shops, hotels, and many other more “upscale” attractions. The “Mag Mile” as many call it, is a great area to spend some time just walking around.

Check their website because they have tons of cool festivals that may be worth checking out when you visit!

*Lots of other things I’ll be covering in this list can be found along the Magnificent Mile!

4.) “Skydeck” Located in the Willis Tower

Located at the top of The Willis Tower, one of the tallest buildings in the world, is what is called “Skydeck” – one the best possible views of Chicago you can find.

At Skydeck (103 stories in the air) you will find a 30,000-square-foot museum that will teach you so much about the history, the neighborhoods, and the sights you may find throughout Chicago. The immersive museum is absolutely incredible and just by itself is enough to travel to the top of the tower.

But the reason most venture up is more to do with the incredible views and “the ledge.” From the top of the tower, you will be able to spot 4 other states. If you’re feeling brave venture out on “the ledge” – balconies with glass floors! It’s a great experience and makes for some incredible photos.

5.) Shedd Aquarium

Aquariums are always fun to check out when traveling to another city. The great thing about them is you can really do them in any kind of weather – so if it’s too cold, too hot, too rainy, or whatever it may be – you still have something to do in your spare time other than stay cooped up at the hotel wasting a day of your vacation.

There are tons of exhibits to check out! Also, make sure you catch a 4-D experience show or a Beluga encounter!

Want to have more fun with just the adults? Sometimes they have after-hours parties that are 21+ with DJs!

6.) Walk Around Millennium Park

There are TONS of areas to explore in Millennium Park. The park is open from 6 am to 11 pm and there is always something going on.

It’s a beautiful place to just walk around – but also check to see if there are any great events going on while you’re there! There are tons of art displays, festivals, and shows that all take place throughout the year in Millennium Park. And of course, while you’re there you have to get a picture of or with the stereotypical Chicago photo op – The Bean!

7.) Chicago Riverwalk

If you want to take a little stroll, the Chicago Riverwalk is just a little over a mile of a walkway that runs right by the river. There are a couple of little places to stop along the Riverwalk if you’d like – City Winery, Island Party Hut Tiki Bar and Grill, Sweet Home Gelato, Taco Rio, and so much more!

Definitely take a little walk if you want some pretty views and you need a snack or drink!

8.) Try a Rooftop Bar

Chicago is FILLED with rooftop bars, which is great because it means there are TONS of places where you can see the breathtaking views of Chicago.

My favorite one I’ve been to, and quite a popular one, is Cindy’s. Cindy’s is located on the 13th floor under a glass atrium. You CAN try to just walk in but I highly recommend you make a reservation if you really want to be able to sit and eat.

All dining is inside the atrium, but if you want to grab a drink from the bar and still enjoy the views there is some area outside to do so.

The views, the food, and the decor are all incredible!

9.) Navy Pier

Navy Pier has something for everyone! There are plenty of shops, restaurants, and even rides to keep you occupied throughout the day! One of the main attractions is the Centennial Wheel, essentially a big Ferris wheel that overlooks the Lake Michigan and the Chicago skyline. There are tons of other games and carnival-style rides to choose from as well!

If you’re up for shopping or food take a stroll up and down the pier to see what suits you! There are so many places – so see what draws your attention or maybe choose a couple of different places to snack at or stop in to!

Before you go make sure you check out the events schedule because sometimes they have fun festivals or other types of events you may want to stop by for!

10. ) Wrigley Field

If you’re a baseball fan, check and see if the Cubs are playing while you are in Chicago looking for things to do!

You can also do a tour of the stadium if you want! Certain areas will not be accessible during game days, but if you check their website you can get tickets and get to see more of the stadium than you would be able to just by sitting in your seats on a game day!

11.) Deep Dish Pizza

Okay look – Chicago has wayyyy more to offer on the food scene than pizza let’s be honest. I will try to do a deep dive blog post on their food scene before too long because they really have some amazing restaurants and amazing chefs – but I do always love to try some of the staple item signature meals from a city when I visit (just the first time lol) so I’d like to just give it a mention.

Ask around and you’ll hear tons of different answers on where has the best deep-dish pizza. Some are more touristy than others of course. The two names I hear SEVERAL people mention were Giordano’s and Lou Malnati’s and both were great!