20 Best And Unusual Things To Do In Chicago , Illinois (USA)

Best and Fun Things To Do in Chicago

Chicago has all the offerings you'd expect from a major city: world-class museums, vibrant shopping districts and ample nightlife venues, just to name a few. If you're here to learn, plan to spend a fair amount of time in Grant Park: This area is home to such notable institutions as the Art Institute of Chicago and The Field Museum. For a more Windy City-centric education, start your vacation with an architecture river cruise – which can provide background on Chicago's famous skyscrapers like the Willis Tower and Tribune Tower – before exploring the city's innovative roots at the Museum of Science and Industry. Just save time for some of the city's quintessential experiences like catching a game at Wrigley Field and window-shopping along The Magnificent Mile.

Nestled inland in the MidWest, the Windy City is throwing its hat in the ring for the title of the premier American tourist destination. Chicago welcomes some 57.6 million tourists per year, and with such a diverse range of attractions, there’s an itinerary perfect for each and every one of them.

Art lovers, rejoice; foodies, celebrate; and history geeks, get excited – because there truly is something for everyone in this sprawling Illinois metropolis — you’ll be spoiled for choice when it comes to fun things to do in Chicago.

1 – Spend an afternoon at Navy Pier

Chicago’s iconic lakefront destination, Navy Pier plays host to renowned restaurants, shopping opportunities, boat tours, and so much more.

The waterfront space was conceived as merely a freight dock, however, its slowly evolved over the last century; today, the must-see destination features exhibits, rides, parks, and unbeatable views of the glistening Lake Michigan.

Countless walking tours pass through the area, which also serves as the main cruise departure point. The Explorer Pass gives you access to the attractions at Navy Pier, plus other 25 attractions and activities in Chicago.

2 – See it all from the 360 Chicago Observation Deck

Located on the 94th floor of the John Hancock Center, the 360 Chicago Observation Deck offers spectacular views of the city’s crowded skyline (including the Willis Tower) and the shimmering lake Michigan below.

From the soaring 1,030-feet-high viewing platform, all four of the nearby states are visible (Illinois, Wisconsin, Indians, and Michigan).

Step outside onto the thrilling tilting platform (TILT), then unwind at the bar and soak in the sunset.

3 – Catch a show at the Chicago Theatre

Besides sitting down for a show at the world-famous Chicago Theatre, visitors are blessed with the opportunity to go behind the scenes and explore the grand history and intricate architecture of this iconic entertainment venue.

Step on stage, visit the rehearsal space, admire the ceilings, and more, all with an expert guide leading the way.

The theatre is centrally located to countless bars and restaurants, which makes planning the evening outing a breeze.

4 – Explore the Lakefront on a segway tour

As the third-largest city by population across the entire country, Chicago is unquestionably massive. That means seeing everything on foot is next to impossible. Why not speed things up and tick off a few more attractions by joining a Segway tour?

Glide through downtown, the riverfront, or a number of other routes on offer, all while learning about the city from a seasoned local. These smooth-moving machines are fun for the whole family.

5 – Race against the clock at an escape room

Race against the clock and put your teamwork and puzzle-solving skills to the test with an epic escape room challenge.

Visit The Escape Game and choose from gold hunting, prison breaks, heist mysteries, even rocketing to Mars, all within 60 minutes of non-stop excitement.

6 – Learn the true stories behind the city’s mob past

Immerse yourself in Chicago’s criminal pastimes by embarking on a dedicated gangster tour through the city’s scorned streets.

Walk in the footsteps of infamous criminals, stand in historic crime scenes, and discover what made gangsters like Al Capone and John Dillinger tick.

Send some extra shivers down your spine by combining it with a ghost tour!

7 – See the real Chicago on a street art tour

Illinois’ largest city is teeming with urban art; get off the beaten track with a unique tour that steps away from the crowded sites and explores the underground and the backstreets instead.

Guides not only take you to some of the city’s premier murals but also explain their meanings and histories.

If the idea of all that walking makes you a little thirsty, choose one of the options which stop into a craft brewery or allow you to BYOB.

Instagrammers, this should be a priority when it comes to choosing between all the things to do in Chicago!

8 – Feed a giraffe at Brookfield Zoo

Catch the kangaroos at Australia House, feed the giraffes at Habitat Africa, admire the alligators at The Swamp, and wander through plenty more exhibits at the renowned Brookfield Zoo.

With so many cute animal ambassadors ready for a meet-and-greet, Brookfield Zoo promises to be a great day out for the whole family.

Take the experience to the next level by competing in a zoo-wide scavenger hunt!

9 – Take an architecture cruise on the Chicago River

The architecture in the Windy City is unique, historic, and complex, and there’s no better vantage point to admire it all than the waters of the Chicago River.

As you cruise under the city’s skyscrapers, you’ll pass the East Bank Club, the old Post Office Building, the Willis Tower, and plenty more.

Tours typically last an hour and a half, and the guides are notably informative and entertaining.

10 – Soak in the skyline from a Lake Michigan sightseeing boat tour

Get off your feet for a while; sit back and relax on a boat as the captain takes you down the Chicago River, pointing out the iconic landmarks and delving into the city’s rich history along the way.

If you’re fed up with the crowds, take the experience to the next level by booking a private, luxury tour on your very own sailboat, or grab a two-person pontoon.

11 – Satisfy your palate on a food tour

Chicago might be renowned for its deep-dish pizza, but the Windy City actually boasts a number of local delicacies.

Try them all as you loop around the city on foot, devouring Chicago-style hot dogs, dipped Italian beef sandwiches, a classic deep-dish slice, and treats of your choice for tea merchants, confectioners, and bakeries.

These locally-led tours take you off the beaten track and away from the tourist traps and chain restaurants; you’ll be guided exclusively through the doors of beloved and authentic local eateries.

Chicago Pizza Tours - Original Chicago Pizza Tour

Chicago Pizza Tours are a fun and informative way to explore the city's most famous culinary export. The tours adapted in 2020 to include a bit of a luxury upgrade. The Quarantine Pizza Tour features everything you love and expect from a food-focused adventure—with the addition of a limousine escort from where you're staying and YouTube videos guiding you along the way as the pizzerias deliver the pies to your door. They can fit groups as small as nine and large as 22.

Garfield Park Conservatory

Step into the humid, glass-enclosed domes of Garfield Park where the air is clean thanks to thousands of jewel-toned plant specimens filtering toxins throughout. The space is fashionably untamed across its verdant showcase of flora from wet and dry environments, and those between. Spread across twelve acres, there's abundance year-round, from the colorful spring flower show to permanent indoor exhibits and holiday displays. Plant and garden enthusiasts should make the conservatory—easily accessed by Green Line—one of their stops.

Museum of Contemporary Art, Chicago

The MCA is one of the city’s museums that’s in a near constant state of transition. With its relatively small permanent collection, it relies on special shows—from large scale installations to video, fashion, music, photography, and more—that showcase just as many rising local talents and underground, avant-garde renegades as recognizable names. Past exhibits include David Bowie Is, Takashi Murakami: The Octopus Eats Its Own Leg, and Virgil Abloh: Figures of Speech. The museum is also known for its hosted talks between writers and artists, and various performance series. It also has one of the best gift shops...ever.

Bloomingdale Trail (The 606)

Chicago's answer to New York's High Line, the Bloomingdale Trail—a.k.a. The 606—is a nearly three-mile, elevated greenway running west and east on the city’s North Side. Unlike its NYC counterpart, the trails are wide enough to accommodate active patrons running, walking and cycling without running off more casual strollers, the formerly abandoned rail line is also lined with public art installations and gardens. During fairer weather, the trail also hosts various free events for families with young children.

Art Institute of Chicago

If you're coming to Chicago for culture, you're hitting the Art Institute first. It is the city's grandest museum, a Beaux Arts gem flanked by two bronze lions that are as much a symbol of the city as the Willis Tower and it has as fine an impressionist collection as you'll find anywhere. While you're there, plan to take a stroll through Millennium Park next door.

Lincoln Park Zoo

Located in the heart of Chicago's Lincoln Park, this zoo offers free, family-friendly entertainment year-round including the festive Zoolights around the holidays (reservations are required for all visits though). The sprawling grounds are seamlessly woven into the park’s landscape, balancing open, natural spaces and numerous animal exhibits. If you skip the pricey concessions (but maybe spring for a paddle boat ride), Lincoln Park Zoo is a great option to keep all ages occupied while staying on a budget.

Chicago Lakefront Trail

The 18-mile long trail hugs the coast of Lake Michigan, offering almost all manner of activity along the shore. From sandy beaches and sprawling parks, to some of the best views of the Chicago skyline, the Lakefront Path is one of the city's great public treasures, enjoyed by visitors and locals alike. Runners and cyclists love the width and ease of use of the trail, while intramural type teams make use of the many open spaces found up and down the path. If you don't want to run around, there’s plenty of room to just sit and people watch, as well as check out a number of art installations that pop up throughout the year.

American Writers Museum

In the heart of tourist traffic on Michigan Avenue, the intimate American Writers Museum celebrates the power of the written word and the many voices that shape it. Interactive experiences, regular (and highly recommended) visits from writers, and exhibits like Tools of the Trade, featuring more than a dozen typewriters used by iconic writers such as Orson Welles, Hugh Hefner, Gwendolyn Brooks, Ernest Hemingway, Mae West, and Truman Capote keep things feeling fresh. The layout is easy to navigate, almost relaxing, and the number of attractions within the space are manageable, meaning you’ll be able to see everything in under two hours. So don’t rush. You may remember just how much fun reading is. Temporarily closed for the pandemic, it's reopening in May, 2021.

Humboldt Park

One of Chicago's prettiest parks, this 207-acre green space is located within the larger neighborhood of Humboldt Park (both are named for German naturalist Alexander von Humboldt). It's home to several statues—including one of its namesake, and two bison that were placed there during the 1893 World's Fair—as well as the National Museum of Puerto Rican Arts & Culture, located in the park's former stables. It's easy to drop in if you're headed down the 606 trail, but the park is big enough that it could take more than half a day to do all of it, so it's best if you're not in a rush.