I’ve been lucky to visit Chicago several times over the course of my lifetime. Of course, it helps that I’ve lived within a three hour drive of Chicago for most of my life. As long as I followed south right along Lake Michigan, I’d eventually hit Chicago, IL. Over numerous visits, I’ve done almost all of the tourist-y things, although there’s still plenty more that I haven’t done yet.
So, for people who are planning their first visit to Chicago, here’s a list of what I think are the best things to do in the city. This is not an exhaustive list of everything to do in Chicago, but rather is a list that can serve as a starting point for your trip planning.
The Best Things to Do in Chicago
See Chicago from the River
I’ve seen many city skylines, but Chicago is one of my favorites. The buildings are unique and they all work together to form a beautiful city skyline. Because of this, I’m adding Chicago’s skyline and architecture as number one on this list.
There are several ways to experience Chicago’s architecture. The easiest (and cheapest) is to do a self guided walking tour. Look up! But I think it’s a good idea to take one step further. The Chicago River runs right through the heart of downtown, emptying out into Lake Michigan. What better way to really see the Chicago skyline than from the river?
Again, you could take in the views as you walk Chicago’s Riverwalk, but I think there’s a better way. The Architecture Boat Tour takes tourists down the river, all the way out to Lake Michigan and back down the river to your starting point. Not only do you get some incredible city views, but you’ll also learn some of the fascinating history of this city.
For a more pricier, but more luxurious option, rent a boat (and optional boat captain) to take you on a private cruise down the river.
Chicago History Museum
Chicago has so many good museums, and we’ll cover several in this post, but I’m starting with the Chicago History Museum. It’s one of my favorites in Chicago.
As you may have guessed, this museum tells the story of Chicago. You’ll learn about the foundations of the city, the devastating fire that destroyed it in 1871, and how the city was rebuilt in time for the 1933 World’s Fair. Plus, you’ll go into more modern history as you learn about sports and the city as a transportation hub.
The museum is so well put together and was just endlessly fascinating. It’s one of my favorite museums in Chicago and is definitely worth a visit.
The Art Institute of Chicago
One more museum and then I’ll take a break and talk about some of the other great things Chicago has to offer. I’ve talked about museums for science enthusiasts, history buffs, animal lovers, but now it’s time for art aficionados. For those wishing to explore an amazing collection of art, you need to add the Art Institute of Chicago to your list.
This museum features iconic works by Georges Seurat, Vincent Van Gogh, Pablo Picasso, and so many more. Beyond the paintings, you’ll find 12th century Buddhas, a stunning window made by Tiffany Studios, and a collection of field armor. Besides its permanent collection, you’ll find a series of ever changing exhibitions featuring paintings, sculptures, and other art from around the world.
Museum of Science and Industry
I’ve been lucky enough to visit this museum on three separate occasions and every single visit was great. My first visit was on a sixth grade end of the year field trip, but I’ve since been back as an adult. Whether you’re traveling with kids or your an adult with a love of science, make sure to add this museum to your list.
You’ll find displays on all kinds of different sciences. Learn about mechanics, weather, math, and so much more. Plus there’s some other featured exhibits you should check out too. Did you know that the Museum of Science and Industry has U-505 German Submarine that you can tour?
If you have any interest in science, this museum needs to go on your list.
Chicago Deep Dish Pizza
I’m not usually one to put food items on my list of things to do, but it’s here that I’ll make an exception. Chicago Deep Dish pizza is a must try when you are here. But this is not a typical pizza. Admittedly, a Chicago Deep Dish pizza is more like a casserole than an pizza.
While you’ll find loads of options for Chicago pizza, the three most popular are Lou Malnati’s, Giordano’s, and Pequod’s. All are good, but I admit that I like Giordano’s the best. Lou Malnati’s sauce is better, but Giordano’s has a much better cheese-to-pizza ratio (is that a thing?).
Shedd Aquarium
Another popular option in Chicago is the Shedd Aquarium. For animal lovers, a visit here is a must. You’ll find fish, sharks, turtles, and more.
Now, I’ve been to the Shedd Aquarium, but I have to admit that it’s awhile. My first, and only, visit was back on that same 6th grade field trip I mentioned earlier—nearly twenty years ago. While I don’t remember a lot (it’s been 20 years!), I remember that I enjoyed my visit. And since the Shedd Aquarium is still one of Chicago’s most popular attractions, I have to include it on this list.
Wrigley Field
Baseball is America’s past time, so why not catch a game. In Chicago you have two options. If the Cubs are playing, hit up a game at Wrigley Field. Plus when you’re there, have a wander around Wrigleyville – the neighborhood surrounding the stadium.
Not a Cubs fan? You can watch the White Sox at Guaranteed Rate Field (formerly known as Cominskey Park).
Field Museum
There’s so many good museums in Chicago, that I have to keep going. The Field Museum is another top sight in Chicago and features an impressive collection of natural history. From dinosaur bones to precious gems, and everything in between, this museum has a little bit of everything.
Admittedly I have not been to the Field Museum (yet!). However, one of my best friends spent a summer interning at the Field Museum and highly recommends it.
Navy Pier
Despite my numerous trips to Chicago, one area I haven’t done much of is Navy Pier. Why? Because I typically visit in December. Navy Pier sits right on Lake Michigan and while I can handle the cold (I’m from Wisconsin), I’ve typically found warmer alternatives.
If you visit in summer (or are just braver than me), Navy Pier is home to numerous restaurants, some stores, and a handful of carnival rides, including the famous Centennial Wheel.
The Bean
This is just a quick photo stop, but it almost feels like you have to see the sculpture Cloudgate (referred to as The Bean by locals). As cheesy as it is, my friend was horrified a few years ago when I mentioned that I’d never seen it (despite my prior trips to Chicago). She dragged me over and now I can officially say that I’ve been to The Bean. It’s become an iconic sculpture in this city, so take the time to make a quick stop.
Adler Planetarium
I’m going to jump back to museums for one more entry on this list. The Adler Planetarium is one of the best in the country. Visit the planetarium to learn about space and astronomy, but don’t forget to experience one of the spectacular sky shows.
Lincoln Park Zoo
For one of the most famous zoos in the country, look no further than Lincoln Park Zoo. This zoo is home to nearly 200 different animal species, so you’ll be sure to see a lot on your visit. Plus, not only are you visiting a great zoo, but you’ll also be in Lincoln Park, which is a great place to take a break from the heart of downtown Chicago.
Are zoos not your thing? If you’re here in December, consider a visit to this area anyway. Lincoln Park puts on a great Christmas Light show.
How Long Do You Need in Chicago
I’ve spent numerous weekends down in Chicago and I still haven’t done it all. Heck, I’m still working my way through some of Chicago’s top sights. But, you can definitely travel more efficiently than I do. Chicago is the one place where I tend to slow down and travel slower (just because its so easy for me to visit again).
Two days will allow you a chance to see most of the top sights. It will be a busy two days, but you’ll be able to experience some of Chicago’s top museums, eat some great food, and take in its incredible architecture.
Three days will allow you to go at a more relaxed pace and to visit some extra museums.
Getting Around Chicago
Chicago is a city where you really do not need a car. In fact, when my friend and I travel down to Chicago every year, we never take a car. We take Amtrak to Union Station and just use public transportation for the rest of the visit. Chicago has very affordable public transportation in the form of city busses and the city’s elevated train subway (known as the L). And when I say affordable, I mean it.
It’s $5 for a 24 hour public transit card.
When to Visit Chicago
Chicago is a city that can be experienced all year round. In summer, there are plenty of events that can add a unique twist to your visit. Winter is low season, but it’s generally cheaper than going in summer (hence why I always visit in winter). Spring and fall can offer a good balance of decent weather and reasonable prices.
Final Thoughts
As a Wisconsinite, it pains me to say that I love this city. But I really do enjoy my visits to Chicago. I try to visit every year and I have yet to run out of things to do.
Continue Your Adventure
More in Chicago: Make sure to explore the Chicago River, whether that be through a tour or a private rental.
Indiana: Just a short drive away from Chicago is Indiana Dunes National Park, which sits on the shores of Lake Michigan.
Missouri: If you drive southwest across Illinois, you’ll hit the city of St. Louis with its famous Gateway Arch.
Nebraska: Just barely making it in the Midwest, is Nebraska with the city of Omaha.