Three Days in Chicago: The Best Things to do in Chicago

– This post was written by Callum Tyler –

If you’ve only got three days in Chicago, you’ll want to spend it wisely! Chicago is a pop-culture icon – home of the Blues Brothers, Christian Bale’s Gotham, and even a track by Sufjan Stevens – but what can you do in the USA’s Second City besides freeze during winter and reminisce about the glory The Bulls rained down on the city? Here’s the best things to do in Chicago, from free attractions to top museums.  

Best things to do in Chicago

Chicago broke its records for tourism in 2018 when some 58 million tourists visited, couple that with being the US’ third-most populous city, with a unique feel and culture you won’t find in New York or LA, and you’re guaranteed an interesting time. 

So what exactly makes Chicago so great? Well, it fostered some of the most influential talents to come out of America in the last half-century: Kanye West, Amy Poehler, Tina Fey, Steve Carrell, and renowned Space Jam actor – Michael Jordan. It’s also got a list of museums that rival anything you’ll find in New York, plus free public spaces that will leave you enchanted.

Making a shortlist of the best things to do in Chicago is no easy feat, but let’s start with the obvious so your three days in Chicago don’t go to waste.

Museums and Galleries to visit during your three days in Chicago

You could fill three days in Chicago with nothing but museums and not get bored. The city boasts some of the most impressive institutions in the country, so read on and find out what hidden artistic treasures reside in Chicago.  

Art Institute of Chicago

In all likelihood you aren’t skipping school, but you can make like Ferris Bueller and pay a visit to the Art Institute of Chicago.  A Sunday on La Grande Jatte is still in the museum’s possession, along with two American icons, Edward Hopper’s Nighthawks and Grant Wood’s American Gothic.

It’s arguably one of the best modern art museums in the world with the largest collection of Impressionist and post-Impressionist works outside of Paris’ Musée d’Orsay. You can expect to see Monet’s Water Lilies and Haystacks. Picasso’s The Old Guitarist, Warhol’s Pop art portraits, and Jackson Pollock’s drip canvasses. 

Museum Campus

This corner of Chicago has three attractions you won’t want to miss during your three days in Chicago: The Field Museum, the Adler Planetarium, and Shedd Aquarium. 

The Field Museum

A T-rex skeleton that’s 90% complete, a 120 foot long titanosaur, and more than 50 mummies inside a replica of an ancient burial tomb – it’s all waiting for you at The Field Museum. If you’re with kids, or simply inquisitive at heart, this museum offers unique sights. 

If you live in Chicago and want to get involved with the Field Museum, then adults can help scientists in community science projects, and kids can enjoy family-friendly activities.

The US is filled with incredible natural history museums, you can read about the best natural history museums in the world here. 

Adler Planetarium

Some like art, some like science. If you fall into the latter camp, then look no further than the Adler Planetarium, then look way further as you turn your eye to the sky and the far-flung reaches of outer space. 

If you want an out-of-this-world experience during your three days in Chicago, then stop in and see exhibits that showcase America’s exploration of the final frontier. Keep an eye out for the Gemini 12 space capsule, which was used by Buzz Aldrin in the last Gemini mission, and experience the real beauty of the universe with a show at the Grainger Sky Theater and its 69-foot wide dome.

Museum of Science and Industry

Located in the former Palace of Fine Arts from the World’s Columbian Exposition in 1893, the Museum of Science and Industry has some incredible sights on offer, including: a U-505 German submarine captured in World War II, a full-size replica coal mine, a 330 square-meter model railroad, the command module of Apollo 8, and a diesel-powered stainless-steel train from the 1930s that will make you wish design had stayed rooted in the past. Oh, and there’s a foucault pendulum to keep you fascinated as it proves the earth’s rotation.

Aquariums and Zoos to visit during your three days in Chicago

Shedd Aquarium

The final part of the Museum Campus trifecta. There’s more to see than just pretty fish with tickets for Shedd Aquarium, although you’ll meet plenty of those in a recreated reef that mimics sea life in the Philippines. 

During your three days in Chicago, don’t miss the chance to get up close with beluga whales, dolphins and penguins. If that isn’t enough, there’s a rainforest environment inside that will let you see a 14-foot anaconda, tarantulas, and even monkeys. There’s an amazing nine exhibits and some 32,000 animals inside, so if you love marine life, this is one you won’t want to miss. 

If you can’t get enough of aquariums, then check out our blog on the best aquariums in the world.

Lincoln Park Zoo

North America’s fourth oldest zoo has free admission! There’s around 200 species and more than 1,000 animals inside, so if you’re visiting for kids (or you just love mother nature) then it’s a great way to spend a few hours in the city. 

The zoo focuses on wildlife conservation and is home to everything from aardvarks to zebras, along with a wide-array of exotic birds, rhinos, monkeys, chimps, bears, and reptiles.

Parks and public spaces to visit during your three days in Chicago

Shopping on the Magnificent Mile

While it’s good to get cultured in one of the world’s finest art galleries and see colossal T-Rex skeletons, one of the joys of spending time in a new city is indulging in some retail therapy. It’s even better when that city is a metropolis of shopping. 

Chicago’s Magnificent Mile is the city’s answer to Rodeo Drive. If you’re looking for designer labels and boutique stores that are so fancy that by the time you’ve finished walking by them all you’ll have a turned up nose that will only want the finest of things. To name a few, you have the US’ flagship Burberry store, Tiffany & Co. Tom Ford, Chanel, and Gucci. If that’s not to your taste, there’s also Garrett Popcorn Shops – who needs a silver spoon in their mouth when there’s caramel crisp popcorn.

Millennium Park

Green utopia in summer, winter wonderland by December. What’s now iconic is, in fact, somewhat new to the city, having only opened in 2004. Surrounded by the city’s skyscrapers, this urban Eden offers an escape from the city streets. 

And, get this, you can watch movies for free in the Jay Pritzker Pavilion during summer! 

The Cloud Gate sculpture

Technically it’s part of Millennium Park, but this world-famous sculpture deserves its own segment. It would be remiss to miss The Bean during any visit to Millennium Park.

Navy Pier

It’s been a dock, a jail, an army training center, and a place of study for the University of Chicago, but now the Navy Pier is home to restaurants, rides, shopping and art exhibitions. 

Jumping on the Centennial Wheel is wheel worth your time, 200 feet above Chicago you’ll get stunning views of the Chicago coast line. 

The Buckingham Fountain

There’s something appealing about a grand fountain at the center of a park, and Chicagoans know how to do it right. Well, they know how to imitate right, it’s based on the Latona Fountain in the Palace of Versailles.

Wrigley Field

Build it, they will come. Wait, wrong field…get out of here, Kevin Costner! Yankees caps are an oversaturated market. Walk out of this stadium with a Cubs cap, a foam finger, and if you’re lucky a home run ball. You can catch tickets from as low as $26.

Views you won’t want to miss during your three days in Chicago

See the skyline from Lake Michigan

The Windy City boasts a skyline to rival NYC’s. After the Great Chicago Fire, the city rebuilt big and they haven’t looked back. A cruise of Chicago River and Lake Michigan is the best way to see the city’s architecture and to catch a snapshot of your trip.

Stare over the city from the Willis Tower

Skydeck Chicago at The Willis Tower has the best panoramas of Chicago on offer. Despite its 1,450 feet height – technically it’s higher than NYC’s tallest building in terms of where man can stand – it takes less than 40 seconds to reach the observation deck. The One World Observatory’s elevator still wins out, though, with it’s multimedia display taking you through the history of New York as you climb up. 

360 Chicago

A contender for the best view of the city – 360 CHICAGO Observation Deck offers up panoramic views of city blocks, skyscrapers, Lake Michigan, and even four states (Wisconsin, Michigan, Indiana, and Illinois). Journey up to the 94th floor in one of the US’ fastest elevators and learn more about the landmarks from interactive panoramic touchscreens. If you choose the Sun and Stars option you can come back for a second visit within 48 hours.

Chicago Riverwalk

Here’s a freebie, all it’s going to cost is a few extra calories. Walk beside the Chicago River and pass through colossal skyscrapers, discover great places to eat, and wind down beside one of the city’s biggest public projects. 

Can’t make it to the US just yet? Here’s how to live an American lifestyle from wherever you are in the world.