Welcome to Chicago, the Windy City! Chicago is a vibrant metropolis known for its rich history, stunning architecture, diverse culture, and mouth-watering cuisine. Whether you’re here for a weekend or an extended stay, this guide will help you navigate the best things to do in Chicago, divided into sections based on landmarks, culture, food, entertainment, shopping, outdoor activities, sports, and nightlife.
Landmarks
1. Willis Tower (formerly Sears Tower)
A trip to Chicago isn’t complete without visiting Willis Tower. Standing at 1,450 feet, it’s one of the tallest buildings in the Western Hemisphere. Head to the Skydeck on the 103rd floor for breathtaking views of the city. For the daring, step onto “The Ledge,” a glass balcony extending four feet outside the building.
The Skydeck offers more than just stunning views; it’s an interactive experience where you can learn about the history of Chicago and its architecture. For the best experience, visit during sunset to see the city transform from day to night.
2. Navy Pier
Navy Pier is a must-see landmark offering 50 acres of attractions, including rides, restaurants, shops, gardens, and parks. The Centennial Wheel, a 200-foot-tall Ferris wheel, provides stunning views of Lake Michigan and the Chicago skyline.
Navy Pier is also home to the Chicago Children’s Museum, the Chicago Shakespeare Theater, and the IMAX Theater. Seasonal events such as summer fireworks, winter ice skating, and various festivals make Navy Pier a year-round destination.
3. Millennium Park
Famous for its public art installations, Millennium Park is home to the iconic Cloud Gate sculpture, affectionately known as “The Bean.” The park also features the Crown Fountain, a reflecting pool with digital displays, and the Jay Pritzker Pavilion, a state-of-the-art outdoor concert venue.
Millennium Park is a cultural hub where you can attend free concerts, film screenings, and fitness classes. Don’t miss Lurie Garden, a beautiful oasis within the park, perfect for a relaxing stroll or a quiet moment in nature.
4. The Art Institute of Chicago
One of the oldest and largest art museums in the United States, the Art Institute of Chicago houses an extensive collection of art from around the world. Highlights include works by Monet, Van Gogh, and Seurat, as well as modern and contemporary art exhibits.
The museum also features the Thorne Miniature Rooms, which showcase meticulously crafted miniatures of European and American interiors. With rotating exhibitions and special events, there’s always something new to discover at the Art Institute.
5. Chicago Riverwalk
The Chicago Riverwalk is a pedestrian path along the south bank of the Chicago River. It offers beautiful views of the city’s architecture, boat tours, dining options, and public art installations. It’s a great place for a leisurely stroll or a guided architectural tour.
Enjoy a drink at one of the many riverfront bars, take a water taxi, or rent a kayak for a unique perspective of the city. The Riverwalk is a vibrant and lively area, perfect for both relaxation and exploration.
Culture
1. The Field Museum
Dive into natural history at The Field Museum, home to Sue, the largest and most complete T. rex skeleton ever discovered. The museum’s vast exhibits include ancient Egyptian artifacts, gemstones, and interactive science displays.
The Field Museum’s extensive collection also features exhibits on cultures from around the world, including Native American, African, and Pacific Islander artifacts. Interactive displays and hands-on activities make it an engaging experience for all ages.
2. Shedd Aquarium
Located on the Museum Campus, Shedd Aquarium is one of the largest indoor aquariums in the world. It features over 32,000 aquatic animals, including dolphins, belugas, sharks, and penguins. Don’t miss the aquatic shows and interactive exhibits.
Shedd Aquarium offers unique experiences such as animal encounters and behind-the-scenes tours. The Wild Reef exhibit, featuring a recreation of a Philippine coral reef, is a highlight that shouldn’t be missed.
3. Museum of Science and Industry
The Museum of Science and Industry is one of the largest science museums in the world. Highlights include a full-size replica of a coal mine, a German U-505 submarine, and the Apollo 8 spacecraft. The hands-on exhibits make it a great destination for families.
The museum’s interactive exhibits cover a wide range of topics, from genetics and biotechnology to transportation and energy. The annual Christmas Around the World exhibit showcases holiday traditions from various cultures.
4. Adler Planetarium
Also located on the Museum Campus, Adler Planetarium offers an immersive journey through space. Enjoy interactive exhibits, star shows in the Grainger Sky Theater, and stunning views of the city skyline from the planetarium’s terrace.
The planetarium’s exhibits include the historic Atwood Sphere, which provides a glimpse of the night sky as it appeared in 1913. Special events such as stargazing parties and lectures make Adler a fascinating destination for space enthusiasts.
5. Chicago Cultural Center
The Chicago Cultural Center, located downtown, hosts free art exhibits, performances, and cultural events. Its stunning architecture features the world’s largest Tiffany stained-glass dome, making it a visual treat as well as a cultural hub.
The Cultural Center offers a diverse range of programming, including concerts, dance performances, and film screenings. It’s a great place to experience Chicago’s vibrant arts scene and discover new artists and performers.
Food
1. Deep-Dish Pizza
No visit to Chicago is complete without trying its famous deep-dish pizza. Head to Lou Malnati’s, Giordano’s, or Pequod’s for a slice of this cheesy, saucy delight. The thick crust and generous toppings make it a must-try.
Deep-dish pizza is a hearty meal that’s perfect for sharing. Be prepared to wait, as the pizza takes about 45 minutes to cook, but it’s well worth it for the delicious, gooey goodness.
2. Chicago-Style Hot Dog
A Chicago-style hot dog is an all-beef frankfurter on a poppy seed bun, topped with yellow mustard, chopped onions, neon green relish, a pickle spear, tomato slices, sport peppers, and a dash of celery salt. For the authentic experience, visit Portillo’s or Superdawg.
The Chicago-style hot dog is a symphony of flavors and textures, with each ingredient adding its own unique twist. Remember, no ketchup allowed!
3. Italian Beef Sandwich
The Italian beef sandwich is a Chicago classic. Thinly sliced roast beef, simmered in a seasoned broth, is piled onto a long Italian roll and often topped with giardiniera (spicy pickled vegetables) or sweet peppers. Al’s Beef and Mr. Beef are iconic spots to try this hearty sandwich.
For an authentic experience, order your sandwich “dipped” in the beef juices for extra flavor. The combination of tender beef, crunchy peppers, and soft bread makes it a satisfying meal.
4. Fine Dining
Chicago boasts a vibrant fine dining scene with numerous Michelin-starred restaurants. Alinea, run by chef Grant Achatz, offers an avant-garde dining experience, while Girl & the Goat, led by chef Stephanie Izard, is known for its innovative, globally inspired dishes.
Other notable fine dining establishments include Smyth, with its farm-to-table approach, and Oriole, offering a multi-course tasting menu. Reservations are recommended, as these popular spots often book up quickly.
5. Ethnic Cuisine
Chicago’s diverse neighborhoods offer a taste of global cuisine. Visit Chinatown for authentic dim sum, Pilsen for Mexican fare, or Devon Avenue for Indian and Pakistani delicacies. Greektown and Little Italy are also great areas to explore for ethnic eats.
From Korean BBQ to Ethiopian injera, Chicago’s food scene is a melting pot of flavors. Take a culinary tour to sample the best of the city’s ethnic cuisine and discover new favorites.
Entertainment
1. Theater District
Chicago’s Theater District is bustling with world-class performances. Catch a Broadway show at the historic CIBC Theatre or the Cadillac Palace Theatre. The Chicago Theatre, with its iconic marquee, hosts a variety of concerts, comedy shows, and special events.
The Theater District is also home to smaller, avant-garde venues like Steppenwolf Theatre and the Goodman Theatre, which showcase innovative productions and emerging talent.
2. Live Music
Chicago is a city with a rich musical heritage. Visit the legendary blues club Buddy Guy’s Legends or the Green Mill Cocktail Lounge, a famous jazz club once frequented by Al Capone. For a modern twist, check out the indie scene at venues like The Metro or Lincoln Hall.
Chicago’s music scene is diverse, with genres ranging from classical and opera to hip-hop and electronic dance music. There’s always a concert or music festival happening, so check out the local listings for the latest events.
3. Comedy Clubs
Chicago is the birthplace of improv comedy. The Second City, where many famous comedians got their start, offers hilarious improv and sketch comedy shows. iO Theater is another top spot for improv, featuring performances from both emerging and established comedians.
The Annoyance Theatre and Comedy Bar also offer a variety of comedic performances, from stand-up to improv. Comedy lovers will find plenty of laughs in Chicago’s vibrant comedy scene.
4. Sports
Chicago is a sports-lover’s paradise. Catch a Cubs game at the historic Wrigley Field or see the White Sox at Guaranteed Rate Field. The United Center is home to the Chicago Bulls (NBA) and the Chicago Blackhawks (NHL). For soccer fans, the Chicago Fire plays at Soldier Field.
Chicago’s sports culture is passionate and energetic. Even if you’re not a die-hard fan, attending a game is a fun and exciting way to experience the city’s spirit and camaraderie.
5. Festivals
Chicago hosts numerous festivals throughout the year. The Taste of Chicago is a food festival showcasing the city’s diverse culinary scene. Lollapalooza, held in Grant Park, is a major music festival featuring top artists from around the world. The Chicago Air and Water Show, held on the lakefront, is a thrilling event with aerial acrobatics and water stunts.
Other notable festivals include the Chicago Blues Festival, the Chicago Jazz Festival, and the Chicago International Film Festival. There’s always something happening in Chicago, so check the event calendar for upcoming festivals and events.
Shopping
1. The Magnificent Mile
The Magnificent Mile is Chicago’s premier shopping destination, stretching along Michigan Avenue. This bustling thoroughfare is home to high-end retailers, department stores, and luxury boutiques. Flagship stores like Nike, Apple, and Burberry make it a shopper’s paradise.
The Magnificent Mile also features historic landmarks such as the Wrigley Building and the Tribune Tower. Take a break from shopping to explore these architectural gems and enjoy the vibrant street atmosphere.
2. State Street
State Street is another iconic shopping destination, known for its historic department stores. Macy’s on State Street (formerly Marshall Field’s) is a must-visit, with its stunning Tiffany ceiling and extensive shopping options.
State Street also offers a mix of retail stores, restaurants, and entertainment venues. The Chicago Theatre and the Goodman Theatre are nearby, making it a great area to explore both shopping and cultural attractions.
3. Fulton Market District
The Fulton Market District is a trendy area known for its boutique shops, art galleries, and stylish restaurants. Once an industrial area, it has transformed into a vibrant neighborhood with a unique blend of old and new.
Explore the local shops for one-of-a-kind fashion, home goods, and art pieces. The district’s lively atmosphere and creative vibe make it a great place for an afternoon of shopping and dining.
4. Lincoln Park and Lakeview
These charming neighborhoods offer a mix of local boutiques, vintage shops, and specialty stores. Armitage Avenue in Lincoln Park is lined with unique shops, while Belmont Avenue in Lakeview is known for its vintage clothing stores and record shops.
These areas are perfect for a leisurely shopping trip, where you can find everything from handmade jewelry to rare vinyl records. The neighborhood’s tree-lined streets and historic architecture add to the shopping experience.
5. Southport Corridor
Southport Corridor is a lively shopping district in the Lakeview neighborhood. It features a mix of national retailers, local boutiques, and trendy restaurants. The area’s relaxed vibe and family-friendly atmosphere make it a popular destination for locals and visitors alike.
Stroll down Southport Avenue to discover unique shops, cozy cafes, and lively bars. It’s a great place to spend a sunny afternoon exploring and shopping.
Outdoor Activities
1. Lakefront Trail
The Lakefront Trail is an 18-mile path along the shores of Lake Michigan, offering stunning views of the city skyline and the lake. It’s perfect for walking, running, biking, and rollerblading. The trail connects several beaches, parks, and cultural attractions, making it a scenic route for outdoor enthusiasts.
Rent a bike and explore the trail at your own pace, stopping at popular spots like North Avenue Beach and Oak Street Beach. The trail is a great way to enjoy Chicago’s natural beauty and stay active.
2. Lincoln Park
Lincoln Park is Chicago’s largest park, spanning over 1,200 acres. It offers a variety of outdoor activities, including the Lincoln Park Zoo, the Peggy Notebaert Nature Museum, and the Alfred Caldwell Lily Pool. The park also features numerous sports fields, playgrounds, and picnic areas.
Take a leisurely walk through the park’s gardens, visit the free-admission zoo, or rent a paddleboat at the South Lagoon. Lincoln Park is a green oasis in the city, perfect for a day of outdoor fun.
3. Grant Park
Known as “Chicago’s front yard,” Grant Park is a large urban park located in the heart of downtown. It’s home to several major attractions, including Buckingham Fountain, the Art Institute of Chicago, and the Museum Campus. The park hosts numerous festivals and events throughout the year, making it a lively and dynamic space.
Enjoy a picnic by the fountain, attend a summer concert at the Jay Pritzker Pavilion, or explore the park’s gardens and sculptures. Grant Park offers a mix of natural beauty and cultural experiences.
4. Chicago Botanic Garden
Located just outside the city in Glencoe, the Chicago Botanic Garden is a beautiful and tranquil escape. The 385-acre garden features 27 display gardens, including a Japanese Garden, an English Walled Garden, and a Rose Garden.
Stroll through the gardens, take a boat tour of the lakes, or participate in a gardening workshop. The Botanic Garden is a peaceful retreat that offers a diverse array of plant collections and scenic landscapes.
5. Kayaking on the Chicago River
For a unique outdoor adventure, rent a kayak and paddle along the Chicago River. Several companies offer guided tours and rentals, allowing you to explore the city’s architecture from the water. It’s a fun and active way to see the city from a different perspective.
Kayaking tours often include historical and architectural commentary, providing insights into the city’s landmarks and history. It’s an exciting way to combine outdoor activity with sightseeing.
Sports
1. Wrigley Field
Wrigley Field, home of the Chicago Cubs, is one of the oldest and most iconic baseball stadiums in the United States. Catching a game here is a quintessential Chicago experience. The stadium’s ivy-covered outfield walls and historic charm make it a beloved destination for baseball fans.
Before the game, explore Wrigleyville, the lively neighborhood surrounding the stadium. Enjoy a pre-game meal at one of the local bars or restaurants, and soak in the festive atmosphere.
2. United Center
The United Center is the home of the Chicago Bulls (NBA) and the Chicago Blackhawks (NHL). It’s a state-of-the-art arena that hosts thrilling basketball and hockey games, as well as concerts and other events.
Attending a game at the United Center is an exhilarating experience, with passionate fans and high-energy performances. Check the schedule for upcoming games and events, and be sure to arrive early to explore the arena’s attractions and dining options.
3. Soldier Field
Soldier Field is home to the Chicago Bears (NFL) and the Chicago Fire (MLS). The stadium’s lakefront location and historic architecture make it a striking venue for sports events.
Tailgating is a popular pre-game activity, with fans gathering to enjoy food and drinks before the game. Inside the stadium, the atmosphere is electric, with cheering fans and thrilling plays.
4. Guaranteed Rate Field
Guaranteed Rate Field is home to the Chicago White Sox (MLB). Located on the South Side, the stadium offers a more modern and spacious experience compared to Wrigley Field.
The stadium features a wide range of food options, from classic ballpark fare to local specialties. Check out the Goose Island Craft Kave for a selection of craft beers, and enjoy the post-game fireworks on select nights.
5. Chicago Marathon
The Chicago Marathon is one of the six World Marathon Majors and attracts runners from around the globe. Held annually in October, the race takes participants through a scenic route that showcases the city’s diverse neighborhoods and landmarks.
Whether you’re a participant or a spectator, the marathon is a major event in Chicago’s sports calendar. The enthusiastic crowds and festive atmosphere make it a memorable experience for everyone involved.
Nightlife
1. River North
River North is one of Chicago’s most vibrant nightlife districts, known for its upscale bars, nightclubs, and lounges. Popular spots include Three Dots and a Dash, a tiki bar with creative cocktails, and TAO Chicago, a stylish nightclub with Asian-inspired decor.
River North’s nightlife scene offers a mix of high-energy dance clubs and sophisticated cocktail bars, making it a great destination for a night out on the town.
2. Wicker Park and Bucktown
These trendy neighborhoods are known for their eclectic bars, live music venues, and artsy vibe. The Violet Hour, a speakeasy-style bar, offers expertly crafted cocktails in a chic setting, while The Empty Bottle is a popular spot for live music and indie bands.
Wicker Park and Bucktown’s nightlife scene is diverse, with options ranging from dive bars to trendy lounges. It’s a great area to explore for a laid-back and artsy night out.
3. Lincoln Park
Lincoln Park offers a mix of casual pubs, sports bars, and lively nightclubs. Kingston Mines, one of Chicago’s oldest blues clubs, features live music every night of the week. For a more relaxed evening, visit Delilah’s, a cozy whiskey bar with an extensive selection.
Lincoln Park’s nightlife is friendly and welcoming, with options to suit all tastes. Whether you’re looking for live music, craft cocktails, or a fun dance floor, you’ll find it here.
4. Logan Square
Logan Square is known for its hipster vibe and unique nightlife spots. The Whistler, a combination bar and live music venue, offers inventive cocktails and nightly entertainment. Logan Arcade, a barcade, features classic arcade games and pinball machines.
Logan Square’s nightlife scene is quirky and creative, with a focus on craft cocktails and unique experiences. It’s a great area to explore for something a little different.
5. Downtown Rooftop Bars
For stunning views of the city skyline, visit one of Chicago’s many rooftop bars. Cindy’s Rooftop, located on top of the Chicago Athletic Association Hotel, offers panoramic views of Millennium Park and Lake Michigan. LondonHouse Rooftop, perched atop the LondonHouse Chicago hotel, provides breathtaking views of the Chicago River and the surrounding skyscrapers.
Rooftop bars are perfect for a sophisticated night out, with expertly crafted cocktails, delicious small plates, and stunning views. They’re a great way to experience Chicago’s skyline and nightlife in style.
Conclusion
Chicago is a city that truly has something for everyone. Whether you’re exploring its iconic landmarks, immersing yourself in its rich cultural offerings, savoring its diverse cuisine, enjoying its vibrant entertainment scene, indulging in retail therapy, engaging in outdoor activities, cheering on your favorite sports teams, or experiencing its dynamic nightlife, you’re sure to have an unforgettable experience. So pack your bags, grab your camera, and get ready to explore all that the Windy City has to offer!