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Chicago Travel Guide

20 Ultimate Things to Do in Chicago

Discover the best the Windy City has to offer.

Welcome to the Windy City, famous for its deep-dish pizza, ballparks, beer, comedy clubs, world-class museums, and blues. Most visitors stay in River North or the Gold Coast, the city’s tourism center where restaurants and shopping options abound. However, to fully experience the city’s culinary and cultural riches, you’ll have to step away from the big brands on Michigan Avenue.

Chicago is arranged on a grid plan centered around Madison and State in the Loop. Most neighborhoods are easily accessible via the CTA ‘L’ trains and the city is pretty compact, so neighborhoods like Hyde Park, Pilsen, and Bronzeville are just a short ride away.

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1 OF 20

Meander Through 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 a great spot for a picnic, and kids will love splashing around in Crown Fountain, a reflecting pool bookended by two interactive video sculptures. Two new public art structures have debuted that will be on display until April 2022.

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PHOTO: I-Ta Tsai[CC BY-NC-SA 2.0]/Flickr
2 OF 20

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, honoring the best fine dining the city has to offer. The 2021 Michelin guide awarded 24 diverse restaurants with stars including Yūgen, Parachute, 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 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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3 OF 20

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, 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. This autumn, the Biomechanics traveling exhibition returns, showing how the bodies of animals work like machines. The Shedd Aquarium’s fantastically colored fish, dolphins, and whales are fun to visit year-round. Spring is nest-building and breeding season for one of Shedd’s most popular aquatic species–penguins! Finally, there’s the Adler Planetarium (still temporarily closed) that takes you beyond planet earth on a journey through the stars with high-tech exhibits and immersive theater experiences.

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4 OF 20

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

Zoom up to the 103rd floor of the Willis Tower (née 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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PHOTO: Courtesy of The Langham, Chicago
5 OF 20

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

Four Seasons Chicago just reopened after a multi-million dollar, yearlong renovation with 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 along with 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 of 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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6 OF 20

Shop 'Til You Drop Along the Magnificent Mile

Just north of the Chicago River, a mile-long stretch of Michigan Avenue boasts some of the best shopping in Chicago, mostly international brands who can afford the pricey real estate. The further north you go, the more exclusive the shops get, with Patek Philippe, Harry Winston, and Loro Piana lining Oak Street. Before you get started, admire fragments from some of the world’s greatest landmarks embedded into Tribune Tower, from St. Peter’s Basilica to the Taj Mahal, smuggled back by reporters stationed worldwide. Stop for lunch at NoMI Kitchen on the seventh floor of the Park Hyatt for the best views of the Historic Water Tower, one of the few structures that survived the Great Chicago Fire in 1871.

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7 OF 20

Cruise the Chicago River

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 in the world and 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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8 OF 20

Laugh Your Pants Off at Second City

Chicago’s beloved comedy club–where Tina Fey, Amy Poehler, and Dan Aykroyd got their starts–has been an institution for live comedy since 1959. After being closed due to the pandemic, Second City is reopening with two new improv shows: The Second City: Happy to Be Here and Safer, Shorter, and Still So Funny. The shows will be 60 minutes, with no intermission, and masks are required. 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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9 OF 20

Visit the Newly Reopened Navy Pier

Navy Pier, Chicago’s treasured non-profit and lakefront destination, has officially reopened for guests to experience world-class attractions like the iconic Centennial Wheel and the thrilling new Drop Tower ride. Grab a drink and take in extraordinary views from 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 nearly 70 local businesses on the Pier and support some of the city’s most beloved minority and women-owned establishments, such as 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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10 OF 20

Try All of Chicago's Pizza

Chicago-style deep dish pizza is thick and cheesy, with so many layers of sauce and cheese that it’s more like lasagna than traditional pizza. Pequod’s and Pizano’s nail deep dish, with a hearty caramelized cornmeal crust, but there’s a lot more great pizza throughout the city, and here’s a secret: Most real Chicagoans don’t like or eat that much deep dish. We prefer the Quad-Cities-style pizza at Roots Handmade Pizza, Neapolitan-style thin crust at Spacca Napoli, and Roman-style pizza at Bonci Pizzeria.

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11 OF 20

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 St Beach, which welcomes visitors near and far every summer. The Midwest’s oldest juried Art Fair, the 57th St. Art Fair, takes place the first weekend in June. Stop for Southern American fare at Virtue Restaurant, where Chef Erick Williams serves up gizzards and gravy, BBQ pork steak, blackened catfish, and the most buttery grits.

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PHOTO: TheeErin [CC BY-SA 2.0]/Flickr
12 OF 20

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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13 OF 20

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.

14 OF 20

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 Odious Cellars to thrive.

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15 OF 20

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 Pilsen. Executive chef Armando Gonzalez’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. For a family-operated and locally-owned restaurant in Pilsen, visit El Berrinches. Their New Mexican cuisine and drinks are inspired by Mexico City and Puebla’s gastronomy, with extensive vegan and vegetarian options.

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16 OF 20

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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PHOTO: Pavel Trebukov [CC BY-NC-SA 2.0]/Flickr
17 OF 20

Immerse Yourself in a Museum

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.

Blockbuster art experience Immersive Van Gogh made its U.S. premiere at Lighthouse ArtSpace Chicago, a new venue within Chicago’s recently renovated landmark Germania Club Building. The 600,000 cubic feet of flawless projections transports viewers through Vincent van Gogh’s oeuvre–from sunny landscapes and night scenes to portraits and still life paintings. There are even CorePower Yoga classes being offered Wednesday, Saturday, and Sunday mornings. The exhibit will run through November 28, 2021.

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18 OF 20

Tour Chinatown

Begin at the entrance of Chinatown Square where the guardian lions stand sentry, then browse the independent boutiques and cafes at 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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19 OF 20

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. If you are feeling hungry, grab a snack at The Pullman Cafe or head to One Eleven Food Hall to choose from several local vendors including Majani, AndySunflower Café, and Lexington Betty Smokehouse.

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PHOTO: Eric Allix Rogers [CC BY-NC-ND 2.0]/Flickr
20 OF 20

Salute Chicago's Sports Heroes

The interactive Chicago Sports Museum, nestled right on the Mag 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. And there are many more professional sports teams – you can catch the Chicago White Sox and Chicago Fire in spring and summer, or watch the Chicago Bears, Chicago Sky, and Chicago Blackhawks in fall and winter.

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jacketwatch May 12, 2021

The Wrigley tours are fun. Its a nominal fee and of course have to be done when the Cubs are on the road.