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23 Ultimate Things to Do in Chicago

Discover the best things to do in Chicago.

Chicago is truly a world-class city. Full of beauty, great food, and historic landmarks, there’s no shortage of places to visit and attractions to experience. Famous for its deep-dish pizza, Mag Mile shopping, and gorgeous riverwalk, there’s an activity for everyone to enjoy. So whether you want to enjoy the view from atop of the Willis Tower, visit the Bean at Millennium Park, or dine at a Michelin-starred restaurant, you are sure to have a one-of-a-kind experience.

The CTA and Metra trains are convenient, making almost every neighborhood easily accessible and just a short ride away. Getting out of downtown and into the areas that make Chicago a beautiful melting pot of culture is highly recommended. Have tacos in Pilsen, discover Black History in Bronzeville, or check out President Obama’s old stomping grounds in Hyde Park. Here is your ultimate guide to some of the best things to see and do in Chicago.

WHEN IS THE BEST TIME TO VISIT CHICAGO?Chicago’s winters are no-joke cold, but off-season can be a great time to see the world-class museums. Spring and fall offer mild weather for sightseeing, and while summers can be hot and humid, the city is alive with festivals, outdoor dining, and waterfront fun.

 

Please note that the COVID pandemic is ongoing and restrictions may be in place in Chicago. Visit the official website of the City of Chicago to get the latest advice and information.

RELATED: Don’t List to People Who Tell You Not to Go to Chicago’s South Side

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Enjoy the Many Attractions at Millennium Park

Millennium Park is worthy of a visit year-round, whether it’s for free weekly concerts and films every summer at the Frank Gehry-designed Pritzker Pavilion or ice skating in the winter. Snap an obligatory selfie in front of Anish Kapoor’s “Cloud Gate” stainless steel mirrored art sculpture ( nicknamed “the Bean”) before wandering through the blooms in Lurie Garden. This is an excellent spot for a picnic. Kids will love splashing around in Crown Fountain, a reflecting pool bookended by two interactive video sculptures showcasing the faces of real Chicagoans.

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Check out a White Sox Game

Spring is the perfect time to head to the South Side and check out a White Sox game. The season opener kicks off in April. So head to Guaranteed Rate Field, grab a hot dog and a beer and cheer on the 2005 World Series champs. Take the CTA red line train to the 35th street stop, and you’re right where you need to be. The park is wheelchair accessible, children ages 3 under don’t need a ticket to enter, and the Xfinity Kids Zone provides activities for youth ages 13 and under like Wiffle ball, pitching cages, and swing boxes–so feel free to bring the whole family. You’ll also get to take advantage of giveaways and watch the fireworks during home games.

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Savor Michelin-Rated Cuisine

Chicago is undoubtedly one of the best culinary destinations in the country and one of just a handful of cities in the United States with a dedicated Michelin guide that honors the best fine dining the city has to offer. The 2021 Michelin guide awarded 24 diverse restaurants with stars, including North Pond, and Spiaggia. New entries this year include Moody Tongue, where a 12-course menu is paired with creative culinary beers, as well as a seafood-centric Porto, which celebrates the culinary heritage of coastal Portugal and Spain. New Bib Gourmand entries highlight affordable and equally delicious dining options and include Kasama for Filipino cuisine in Bucktown, Tzuco for contemporary French-Mexican fare in River North, and Vajra for Nepalese food in West Town.

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Expand Your Mind on Museum Campus

A trio of Chicago’s most notable natural science museums sit side by side on this 57-acre park on Lake Michigan. At the Field Museum, the bones of Sue (the gigantic T. Rex) and Máximo (the largest dinosaur that ever lived) are the main attractions, but there are also rich collections of artifacts from Ancient Egypt and China. The Shedd Aquarium’s fantastically colored fish, dolphins, and whales are fun to visit year-round. Spring is the nest-building and breeding season for one of the Shedd Aquariums’ most popular aquatic species: penguins! Finally, there’s the Adler Planetarium that takes you beyond planet earth on a journey through the stars with high-tech exhibits and immersive theater experiences.

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Feel Like You're on Top of the World at the Willis Tower Skydeck

Zoom up to the 103rd floor of the Willis Tower (locals still call it the Sears Tower) for panoramic city views at Skydeck Chicago. On a clear day, you can see as far as Michigan, Wisconsin, and Indiana. If you aren’t scared of heights, step out onto The Ledge, a small glass-bottomed box extending from the Skydeck, and look straight down to the city 1,353 feet below. Before checking out The Ledge, make sure to stop by the brand new lower-level museum, delivering an interactive experience that celebrates the unique personality, history, neighborhoods, and sites of Chicago.

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Enjoy the Suite Life at One of Chicago's Top Hotels

Four Seasons Chicago brings a fresh new look after a multi-million dollar, year-long renovation that includes a sleek new lobby, newly designed specialty suites, and a swanky new restaurant by James Beard Award-winning Chef Jonathon Sawyer. The Langham Chicago is located in a Mies van der Rohe building, and it’s worth splurging on a club-level room here. The stunning 12th-floor club lounge offers sweeping views across the Chicago River and Lake Michigan and delectable food presentations morning, noon, and night. Plus, the Langham’s Chuan Spa is the best hotel spa in the city, with an authentic array of Traditional Chinese Medicine treatments in addition to massages and facials. If you’re looking for something more boutique, Publishing House B&B is a hidden gem in the West Loop, within walking distance from many of the city’s top restaurants. There are only 11 one-of-a-kind rooms, each inspired by authors who wrote books set in Chicago, from Upton Sinclair’s The Jungle to Audrey Niffenegger’s The Time Traveler’s Wife.

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Cruise the Chicago River on a Historic Fireboat

Cruise the Chicago River and lakefront in a retired historic fireboat that served the Chicago Fire Department until 1981 with Chicago Fireboat Tours. When it was built in 1936, the Fred A. Busse was the largest diesel-powered fireboat globally. Now the passenger vessel includes a miniature museum with artifacts and firefighting paraphernalia. The Chicago Architecture Center’s popular river cruises are always entertaining and informative, thanks to the knowledgeable volunteer docents that will give you the inside scoop on new buildings like Jeannie Gang’s St. Regis Chicago and the Sable Hotel on Navy Pier.

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See a Comedy Show at Second City

Chicago’s beloved comedy club, where Tina Fey, Amy Poehler, and Dan Aykroyd got their start, has been an institution for live comedy since 1959. Second City holds a variety of cool shows like their improv Sunday brunch paired with food and mimosas or the weekly Together at Last performance, which pokes fun at the trying times of the pandemic. All theater patrons are required to show proof of vaccination. After the show, enjoy beer, bites, and bar games upstairs at Utopian Tailgate, a playful rooftop party-scape with super-sized Jenga, Plinko, and PutterBall.

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Support Minority-Owned Businesses at Navy Pier

Take a ride on Navy Pier’s iconic Centennial Wheel or check out the thrilling new Drop Tower ride. Grab a drink and take in extraordinary views from the hip and swanky Offshore Rooftop and Bar, North America’s largest rooftop venue. For a taste of Chicago’s famous cuisine, sweet treats, and craft cocktails, visit the more than 70 local businesses on the Pier and support some of the city’s most beloved minority and women-owned establishments, like Brown Sugar Bakery and Tiny Tavern. For unique clothing and accessories inspired by Chicago’s diverse communities, browse through the Pier’s small, local retailers like Fashion Bazaar and Nakamol Chicago. Free summer programming includes outdoor fitness classes, live music, outdoor movie series, and summer fireworks every Wednesday and Saturday night through Labor Day weekend.

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Don’t Leave Without Trying Chicago’s Deep Dish Pizza

You can’t visit Chicago without trying the pizza. Chicago is famous for its deep-dish pie layered with meat, cheese, sauce, and other yummy ingredients, and Giordano’s, Pequods, and Lou Malnati’s are top contenders in this arena. But for those who enjoy a more traditional slice, there are a lot of other options. Aurelio’s, which got its start in Homewood, IL, has been serving up thin-crust in the Chicagoland area for more than 60 years. Italian Fiesta is a popular South Side staple that is so good, President Obama served slices at his 2009 inauguration. And for a fancier thin slice, head to Humboldt Park for Testaccio’s “Nduja Sausage” pizza with truffle honey, whipped ricotta, and wild greens.

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Stroll the Historic Streets of Hyde Park

Chicago’s Hyde Park neighborhood is home to the beautiful University of Chicago campus, the Frederick C. Robie House, Hyde Park Art Center, and its sprawling 57th Street Beach, which welcomes visitors near and far every summer. Hyde Park Summer Fest, Silver Room Block Party, and the 57th Street Art Fair are neighborhood events that kick off what the locals like to call “Summertime Chi.” Check out the famed Valois restaurant for a quick breakfast with no frills, or stop by Virtue Restaurant, where award-winning Chef Erick Williams serves up gizzards and gravy, BBQ pork steak, blackened catfish, and the most buttery grits.

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Play a One-Of-A-Kind Game at WhirlyBall

A multi-level entertainment mecca in the heart of Chicago’s Bucktown, WhirlyBall is a must-try for sports enthusiasts and game lovers. WhirlyBall combines lacrosse, basketball, and bumper cars into a lively and raucous extravaganza. They also have bowling and laser tag paired with classic American fare and a rotating craft beer selection or refreshing cocktails. In between gaming, guests can take in a scenic view of the city skyline beside the fire pits on WhirlyBall’s rooftop terrace.

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Find Inner Peace at the Baha'i Temple

Chicago is known for its incredible architecture, but one of the most majestic masterpieces lies just north of the city. The Baháʼí House of Worship in Wilmette was completed in 1953, the oldest and largest surviving Baháʼí House of Worship and one of just 10 Baháʼí temples in the world, serving all of North America. Elements of neoclassical, Islamic, Gothic, and Romanesque architecture are interwoven in this impressive concrete and quartz haven, welcoming people of all religions and spiritual beliefs. Anyone can step inside to learn more about the tolerant Baháʼí faith and visit the beautiful surrounding gardens.

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Sip Experimental Beers at Pilot Project Brewing

Chicago is known for its strong craft beer scene, with more than 150 breweries big and small throughout the metropolitan area. Try a few of the city’s most interesting and newest brews at Pilot Project Brewing in Logan Square, a brewery incubator and tasting room with an ever-rotating selection of limited edition beers on tap to sample. Founder Dan Abel aims to lower the barrier to entry for commercial brewing, creating a collaborative space for craft brewers like Azadi Brewing and Rovm Hard Kombucha to thrive.

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Explore Pilsen, Chicago’s Hispanic Neighborhood

Pilsen is known for its colorful street art, and this dynamic neighborhood is worth touring whether you do it independently or with the assistance of the Chicago Greeter program. Check out Pilsen Yards, a bar-centric and music-driven hangout in the heart of the neighborhood. Executive chef Juan Gutierrez’s affordable menu of inspired Latin street food— from tacos to ceviches, hummus to carne asada—is accompanied by a great selection of mezcal, tequila, and whiskey. If you’re looking to support a small, woman-owned business and you love Puerto Rican food, check out the Jibarito Stop. This casual storefront serves up delicious plantain sandwiches with both meat and veggie options as well as a host of other dishes native to the Caribbean island.

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Pay Homage to Chicago’s “Black Metropolis” in Bronzeville

Once home to Pulitzer Prize-winner Gwendolyn Brooks, civil rights activist Ida B. Wells, and legendary musician Louis Armstrong—today the neighborhood of Bronzeville is embracing its legacy as a mecca for civil rights, jazz, blues, and gospel music. Pay tribute to these luminaries at the Bronzeville Walk of Fame and dine on old-school Southern soul food at Peach’s Restaurant and Pearl’s Place. Discover emerging multicultural artists at Gallery Guichard, located at the Bronzeville Artist Lofts.

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Immerse Yourself in the Museum of Illusions

For fans of immersive art, Chicago’s WNDR Museum features new one-of-a-kind installations from artists and collectives, reopening with brand-new touchless experiences. The Museum of Illusions Chicago also invites visitors to engage with over 80 mind-bending exhibits of absurd and clever optical illusion, explaining the math, psychology, and science behind how the human brain works to play tricks on us. Mirror infinity rooms, scale-distorting rooms, holograms, a vortex tunnel, and an anti-gravity room are just a few highlights. If you missed Immersive Van Gogh, then the Immersive Frida Kahlo exhibit is a must-see. This 360-degree experience inside of the renovated landmark Germania Club Building provides 600,000 cubic feet of flawless projections that transport viewers through the world of this iconic Mexican-born artist with landscapes, scenes, and paintings created by Kahlo herself.

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Tour Chinatown

Begin at the entrance of Chinatown Square, where the guardian lions stand sentry, then browse the independent boutiques and cafes at the outdoor Chinatown Square Mall. Find your Chinese Zodiac sign among the statues located in the middle of the mall. The Chicago Chinese Cultural Institute and Chinese American Museum of Chicago are great places to learn more about Chicago’s Chinese American community. Finally, feast on dim sum at MingHin or Triple Crown, or opt for Cantonese and spicy Sichuan fare at MCCB Chicago.

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Ponder the Past at Pullman

The neighborhood we know today as Pullman was the first industrial planned community in the U.S., built specifically in the 1880s for employees of the Pullman Palace Car Company. In 2015, the Pullman National Monument was designated by President Barack Obama, making it the first National Park Service unit in Chicago. Pullman is home to a vibrant community rich with history and renowned for its architecture, especially the stunning row houses and restored company buildings. Also nearby is The National A. Philip Randolph Pullman Porter Museum, which details the work of the highly trained, mostly African American porters who worked for Pullman and their contributions to the Civil Rights Movement. If you are feeling hungry, head to One Eleven Food Hall to choose from several local vendors, including Majani, AndySunflower Café, and Lexington Betty Smokehouse.

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Salute Chicago's Sports Heroes

The interactive Chicago Sports Museum, nestled right on the Magnificent Mile, celebrates Chicago sporting legends while giving you a chance to play, too, with simulated experiences like shooting hoops with Scottie Pippen. Baseball fans can book a variety of Wrigley Field tours and basketball aficionados can attend a Bulls game at the United Center and snap a selfie with the bronze Michael Jordan sculpture inside. There are many more professional sports teams you can book tickets to watch, including the Chicago White Sox and Chicago Fire in spring and summer, or watch the Chicago Bears, Chicago Sky, and Chicago Blackhawks in the fall and winter.

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Decide Which of These Iconic Chicken Joints Serves the Best Wings

Harold’s Chicken Shack and Uncle Remus have had a friendly competition that continues to this day. With both restaurants opening on different sides of the city—Harold’s in 1950 on the Southside and Uncle Remus in 1969 on the West—the argument over who serves the best bird depends on who you ask. Either way, it’s all in the sauce! Harold’s is famous for having a tangier mild sauce that is drizzled over piping hot chicken and served with fries and slaw. Uncle Remus’ sauce is much sweeter, and served the same. But you can’t visit Chicago without judging both iconic restaurants for yourself. Harold’s has become so popular over the years that they’ve expanded to Vegas, Atlanta, California, Indiana and Arizona. And Uncle Remus has several locations in both the city and suburbs.

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Treat Yourself to Garrett’s Popcorn

From buttery and salty to sweet and savory, Garrett’s Popcorn has been serving up its delicious family recipe for over 70 years. It all began in 1949 by a female entrepreneur who developed the CarmelCrisp, CheeseCorn, Buttery and Plain and sold it for 5 cents a bag. Since then, their one-of-a-kind flavors made fresh every morning have wowed customers and Garrett’s now has multiple shops in nine countries. The most famous and highly recommended is the “Garrett Mix,” which includes both cheese and caramel.

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Don’t Skip on Chicago’s Summer Festivals

Summer in Chicago is the best time of year to visit because there is a festival for every walk of life. From food and art to music and culture, it’s a surefire way to create memories. This year, Lollapalooza kicks off at the end of July with world-class music across the spectrum. Or you can get funky at Chicago Blues Fest. The Taste of Chicago gives visitors a sample of some of the best restaurants in the city and Northalsted Market Days is one of the country’s most inclusive LGBTQIA+ gatherings with an explosion of color and fun. On the Southside of town, check out the annual Chosen Few Picnic, which is an ode to house music and draws 40,000 fans each year.

1 Comments
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jacketwatch April 12, 2022

So fine to see a White sox game but to omit Wrigley field is a huge error. Wrigley is historic in that its the 2nd oldest ballpark in the US. Fenway in Boston is the oldest and Wrigley has a charm and character that Sox park does not have with its ivy covered walls and its locale in a cozy neighborhood. You can also tour Wrigley Field when the Cubs are on the road.  You just have to schedule it ahead of time for a moderate fee.