[ Things to Do in Chicago ]

Things to Do

Planning a vacation? If so, you’ll find plenty of things to do in Chicago making it an excellent place to visit for those of all ages. One-of-a-kind sights? Entertaining attractions? Delicious food? Check, check and check! Chicago truly has it all. Want to learn more about ways to play in Chicago? Read on.

Getting a picture in front of The Bean is a classic thing to do in Chicago.

Attractions & Tours

From top-of-the-world observatories like the SkyDeck Chicago to the underwater exploration of Shedd Aquarium and endless things to do at Navy Pier, there’s always something to keep you entertained in Chicago! The fun continues at Millenium Park, home to the “The Cloud Gate Sculpture” otherwise known as The Bean, as well as places like Lincoln Park Zoo and Wrigley Field. As a result of the combination of attractions and tours in Chicago, it’s the top destination in the Midwest.

If you’re a first-timer in Chicago, take a tour to get an introduction to the Windy City. Helpful guides can give you an insider’s look into the one-of-a-kind food, architecture, history, and so much more of this city.

The Chicago River is dyed green for St. Patrick’s Day.


Adding to the things to do in Chicago are their world-class events. Chicago takes celebrations seriously, with everything from fine art to film, craft beers, music and heritage being at the forefront of festivals.  Check out the some of the featured events that keep Chicago busy all season long:

January: Chicago Sketch Comedy Festival

February: Chicago Auto Show

March: St. Patrick’s Day Downtown Parade & River Dyeing

April: Chicago Cubs Opening Day

May: Mayfest

June: Chicago Blues Festival

July: Taste of Chicago

August: Lollapalooza

September: World Music Festival Chicago

October: Chicago International Film Festival

November: Christkindlmarket Chicago

December: Winter WonderFest at Navy Pier

Chicago Style Deep Dish Cheese Pizza with Tomato Sauce
Chicago-style deep dish pizza is so good, you’ll go back for seconds!


When you visit Chicago, one thing is for sure: you better be hungry! The city is famous for its deep dish pizza (which is to die for!), but the culinary scene doesn’t end there. In fact, the city is home to some of the top 100 places to eat in the country as well as Michelin award-winning restaurants and James Beard award-winning chefs. The cuisine available spans the globe, too, with a wide range of ethnicities and cultures represented throughout the city.

The Chicago Theatre, a symbol of State Street, hosts performances throughout the year.

Chicago Arts & Culture

In Chicago, there is a robust arts and culture scene that is the beating heart of the city. Everything from culture to history, science and art are on display at museums and galleries, of which there are over 60 to explore. Carve out a segment of time during your Chicago vacation to experience these cultural offerings.

Adler Planetarium: America’s first planetarium, the Adler Planetarium focuses on the study of astronomy and astrophysics.

Art Institute of Chicago: Houses a permanent collection of over 300,000 works, including Georges Seurat’s A Sunday on La Grande Jatte — 1884, Pablo Picasso’s The Old Guitarist, and Grant Wood’s American Gothic.

Field Museum: One of the largest natural history museums in the world.

The arts scene doesn’t stop there, though. The theater scene is also thriving, with Broadway-style shows to concerts celebrated on stage. Of course, Chicago is the birthplace of improv comedy so a stop at a comedy club should be on any Chicago itinerary.

You can catch a live music show in Chicago any night of the week.


Once the sun goes down, the nightlife scene in Chicago really heats up. And let’s be honest—this town knows how to party! In fact, Chicago was voted the “Greatest Drinking City in America by GQ Magazine in 2014. So, the city’s reputation is legit.

There are numerous bars in Chicago, with an atmosphere to fit every mood and budget. Whether you’re a trendy cocktail type, love a good craft beer, or want to taste locally-made spirits, Chicago has you covered. If you need a nudge in the right direction, browse the list below:

Breweries & Bars: Goose Island and Piece and Revolution Brewing have downtown breweries focused on award-winning domestic brews. However, if you’re an international beer fan bars like The Map Room and Local option are good choices.

Spirits: If you want to sample locally-made spirits, CH Distillery features vodka while whiskey connoisseurs can tour KOVAL Distillery.

Concert Halls & Music Clubs: The Chicago Theatre and Aragon Ballroom are prime picks for major concerts, while the Metro and Empty Bottle are ideal spots to find up-and-coming artists.

Comedy Clubs: The comedy scene in Chicago is the real deal, launching the careers of comic standouts like John Belushi to Tina Fey. Get your fill of laughs at clubs like The Second City, Zanies and ComedySportz.

Wicker Park, Andrew Jameson / Wikimedia


Leave some room in your luggage when you visit Chicago. The Windy City has some of the best shopping in the Midwest. As a result, whether you’re a serious shopper or just someone looking for a kitschy souvenir you’re sure to leave with at least a few things. To give you a head start on shopping in Chicago, I’ve compiled a list of the go-to places for both tourists and shop-’til-you-drop pros.

The Magnificent Mile: The ultimate in Chicago shopping, the Magnificent Mile boasts more than 450 retailers ranging from trendy brands to lux labels.

Oak Street: Right off the Magnificent Mile is Oak Street, where shoppers will find designer boutiques.

Chicago’s Loop: Anchored by State Street, Chicago’s Loop is a historic shopping paradise catering to all tastes and budgets.

Lakeview: There is a diverse mix of retro-wear, music shops and recognizable brands lining the streets of Lakeview, compromised of

Wicker Park/Bucktown: Eclectic shopping is the signature of Wicker Park/Bucktown. Everything from local labels to famous designers are showcased in posh boutiques throughout this neighborhood.

Discover More

As you can see there is an endless array of things to do in Chicago. No matter if it’s your first time visiting or you’re an old friend of the city, you can always find a way to discover more.

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