The 10 Best Things to Do in Chicago

Visitors admiring the Chicago Bean

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Did Season 2 of Love is Blind give you major Chicago wanderlust? Or maybe, like us, you’re intrigued because the Windy City has more major railroads leading to it than any other city in the U.S.?

Whatever your reasons for visiting, you’ve made the right choice. Chicago has been a unique, bustling, gritty-in-a-good-way hub of food, beer, business, culture, and history for centuries — and that’s even more true today. 

Over two million people live in Chicago, and it’s okay to be jealous. Their days can consist of commuting via “El” trains to work in some of the oldest, tallest buildings in the country, then relaxing along Lake Michigan or the Chicago River and having world-class dinners afterward (which, yes, sometimes center around deep-dish pizza). 

We at Wanderu are your one-stop-shop for cheap bus and train tickets, but we love destinations just as much as we love journeys!  When you’re ready to join Chicagoans in enjoying this fantastic city, we’ve got all the best ideas to make the most of your trip. 

Whether you’re looking for cheap things to do in Chicago or you’re ready to drop some serious dough on having a great time, we’ve rounded up 10 of the best Chicago activities. But beware: if you haven’t already planned a trip to Chicago, reading this article will make it hard to resist!

1. Gangsters and Ghosts 2-Hour Walking Tour

Image of the Chicago Theatre at night

Clubs and bars offer plenty of things to do in Chicago at night, but skip the booze in favor of some “boo”s for an evening. 👻 Join your fellow ghostbusters in learning about Al Capone and the fascinating organized crime syndicate that once had a chokehold on the city.  Follow historians around Chicago’s Loop District on foot, making stops at the Chicago Theater, Palmer House, Cloud Gate, the Art Institute of Chicago — all one-time crime scenes —and a mystery “famous gangster hangout.” 

This Chicago walking tour offers free cancellation and you can take advantage of “reserve now, pay later” when you book today!

2. Chicago Underground Donut Tour

Glazed, powdered, or cream-filled, you’ll get ‘em however you want ‘em on the Chicago Underground Donut Tour. Hit four famous donut shops while a passionate donut expert (how do we get that job?!) sprinkles in some history and fun facts about Chicago’s top donut joints. 

This tour is great for parties and groups of all kinds and sizes, especially families visiting Chicago with kids. You have the choice of either staying in the heart of Chicago with the Classic Downtown Tour or taking the Wicker Park & Bucktown version. Reserve your spot today and enjoy free cancellation up to 24 hours in advance. Discover Chicago’s best donuts by clicking below!

3. Fireworks Buffet Dinner Cruise

Fireworks over the Chicago skyline at night

We’ll say it: dinner and a show aboard a riverboat is one of the best things to do in Chicago for couples. The expansive menu onboard caters to nearly every palate and dietary need, with options including fresh salads, meat and seafood courses, raw and cooked vegetables, pasta, and dessert. 

After you finish your meal, hit the dance floor and show off your best moves to the sounds of Chicago’s best DJs. Wrap up the 3-hour cruise under a fireworks display illuminating the stunning Chicago skyline. If your plans change, you can cancel this trip all the way up to 24 hours before departure for a full refund. Book your romantic cruise at the link below!

4. Willis Tower Skydeck and The Ledge Ticket

View of Chicago from the Willis Tower Skydeck at dusk

Formerly known as the Sears Tower, the Willis Tower is an iconic element of Chicago’s skyline. It’s also home to some of the best thrills in the Windy City. Ride the elevator up and stand over 100 stories above the city in one of the tallest buildings in North America! 

If the Skydeck isn’t quite exhilarating enough, check out The Ledge, which offers an even more stunning view of the city — and on clear days, four states! Best of all, because this activity is indoors, it’s one of the best things to do in Chicago in winter. Frozen lake views for days! Book skip-the-line tickets below, with the option to cancel up to 24 hours in advance, if necessary.

5. Chicago River: 1.5-Hour Guided Architecture Cruise

Tour boat on the Chicago River

All aboard, architecture enthusiasts! Wind through all three branches of the river on this cruise, taking in some of the most famous Chicago landmarks, including the Wrigley Building, Merchandise Mart, NBC Tower, and Aqua at Lakeshore East. 

The open-air deck and climate-controlled interior seating means this cruise sets sail year-round, whether you’re visiting Chicago in the heat of summer or depth of winter. The full-service cash bar serves up delicious Chicago eats, along with plenty of beer and spirits. Click below to get skip-the-line-tickets and book your spot today, with no money down!

6. Art Institute of Chicago Skip-the-Line Ticket

Visitors viewing art at the Art Institute of Chicago

Phil Roeder/ Flickr

Chicago is home to numerous renowned cultural destinations, including the Art Institute of Chicago, the second-largest art museum in North America. With skip-the-line tickets, you can get in faster to admire the over 300,000 pieces on exhibit. 

Downloadable audio guides enhance the experience and let you explore at your own pace. The in-depth narration highlights works by Pierre-Auguste Renior, Georges Seurat, Pablo Picasso, and others. Not included: a photographer to help you recreate the legendary Ferris Bueller & friends pose in front of the art. 📸

Enjoy free Wi-Fi and fast passes to permanent collections and special exhibits. Experience some of the greatest art in the world by clicking below!

7. Family Fun Urban Adventure River and Lake Cruise

Tour boat going under bridge on the Chicago River

For groups who might fall asleep if they hear the words “postmodern,” “gothic revival,” or “art deco,” try a different style of city cruise. The Family Fun Urban Adventure River and Lake Cruise glides past places like the Willis Tower, Marina City, Chicago Tribune Building, and others while a guide gives you the inside scoop on all things Chicago. The low-key yet fun environment makes it one of the best things to do in Chicago with kids. 

Start your vacation on the Chicago River to learn about the city’s iconic landmarks and get the lay of the land. As a bonus to nautical or engineering fans, the ship goes through the Chicago Harbor Lock (where water rises and lowers to let ships through to the harbor) en route to Lake Michigan. Set sail on this fun family cruise at the link below!

8. Downtown Family Food Tour by Bike with Sightseeing

Ride and dine your way through the Windy City with Bobby’s Bike Hike. Weave between some of the most famous Chicago landmarks, including Millennium Park (home of The Bean), Navy Pier, and Museum Campus, making snack stops along the way. Hop off at designated eateries to enjoy deep-dish pizza, hot dogs, Italian beef, and Italian desserts — all Chicago staples! 

This bike tour is excellent for casual riders of all ages and experience levels, and the timed stops allow plenty of breaks. If you’re looking for an even fuller experience (literally and figuratively), check out the VIP Craft Beer tour version of this activity. Book below and explore Chicago on two wheels!

9. 45-Minute Private Helicopter for 1-3 People

Aerial view of Chicago at dusk from the cockpit of a helicopter

A private helicopter ride over the city is one of the most exciting and romantic things to do in Chicago for couples. See Chicago’s skyscrapers from the sky, and pull out your phone for the panoramic views of picturesque Lake Michigan. 

Narrated by a local professional pilot, you can also opt to take a doors-off helicopter ride, provided the weather allows. Click the link below to take off today!

10. Navy Pier Centennial Wheel Regular & Express Ticket

Calling all thrillseekers! Ride the Centennial Wheel in Navy Pier, rising 200 hundred feet in the air to take in the breathtaking panoramic views of downtown Chicago and Lake Michigan. The gondolas are even heated, making this one of the best things to do in Chicago in winter!

The regular ticket allows you to skip the ticket line so you can board the Centennial Wheel faster. With the Fastpass Express, you can skip both the ticket and boarding line to walk right onto the ride in no time! With either ticket, you can schedule your visit within seven days. Get “high” in Chicago when you book your tickets today!

When to Visit Chicago

Both winter and summer in the Midwest, especially on the Great Lakes, are no joke, so the best time to visit Chicago is during the spring or fall. From double-decker bus rides to sightseeing cruises along the waterfront and walking food tours, the warm months offer plenty of things to do in Chicago. 

That’s not to say you can’t enjoy a lovely winter or summer in Chicago. Just pack accordingly, and don’t complain to any locals about the cold or heat!

How to Get to Chicago

Wanderu offers a variety of ways to help you get to Chicago faster and cheaper, from just about anywhere.

Fly to Chicago

Chicago has two airports: O’Hare International, the city’s largest, and Midway. O’Hare is 30-60 minutes north of downtown and offers far more flight options, while Midway is about 25 minutes south of downtown and offers fewer options but easier, quicker access. 

Take the Train to Chicago

Union Station is Chicago’s main train station, and dozens of trains to Chicago arrive daily from all over the country. It’s also worth noting that once in Chicago, the city has an excellent public train transit system for getting around.

Take the Bus to Chicago

There are a total of six bus stations in Chicago, but most buses arrive at Union Station. Several Amtrak lines, as well as Greyhound, Indian Trails, and Jefferson Lines, ensure that there’s nearly always a convenient bus to Chicago within a short timeframe. 

Drive to Chicago

It’s easy to rent a car to drive to Chicago from most major cities, and Wanderu offers the best rental car rates from all major rental companies. 

Chicago is calling and luckily, you’ve got plenty of ways to answer. Whether you hop on a plane, board a train, or drive yourself, Wanderu is here to help you get to the Windy City. And now you have a long list of experiences to seek out when you’re there!

Exploring beyond just Chicago? We rounded up the best destinations in Illinois so you can see even more of the Prairie State. Or head across the lake and check out the best destinations in Michigan!

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About the author
Taryn Shorr

Taryn Shorr

A classic Type A personality, Taryn's favorite aspects of travel are the planning and meeting new people. She's most drawn to the mountains and has a knack for quickly finding the best happy hour in new destinations. When she isn't writing for Wanderu or traveling, Taryn runs her own blog, Chasing Trail.