Discover the vibrant city of Chicago and its captivating attractions. We’re a local’s guide, here to show you 15 unforgettable experiences. These will make your visit to the Windy City truly memorable. Whether it’s your first time or you’re a Chicagoan, this guide will show you the city’s diverse offerings.
Get ready to explore the best of Chicago’s 77 neighborhoods. Each one has its own charm and personality. Let’s start this journey through the city’s hidden gems.
Key Takeaways
- Discover Chicago’s iconic landmarks, such as the Willis Tower, Cloud Gate (The Bean), and Navy Pier1
- Explore Instagrammable places like Buckingham Fountain, the Chicago Pedway, and Promontory Point1
- Dive into the city’s vibrant neighborhoods and uncover hidden gems, from the Lurie Garden to the Secret ‘Bat Cave’1
- Immerse yourself in the city’s world-class museums and art galleries, including the Art Institute of Chicago1
- Experience the best of Chicago’s outdoor spaces, from the Bloomingdale Trail to the Morton Arboretum2
Eat and Drink the Best of Chicago
Chicago is a food lover’s dream, offering a wide range of delicious foods and drinks. You can enjoy everything from deep-dish pizzas and hot dogs to Michelin-star restaurants. It’s a city that delights any food enthusiast.
Visit Chinatown for amazing dumplings, then head to Garrett Popcorn Shop for their famous caramel-and-cheese mix. Try the jibarito, a unique sandwich with crispy plantains and tasty fillings4.
Classic Chicago Eats
Make sure to try the Italian beef sandwiches, known for their tender meat on a crusty roll. The caramel-and-cheese mix from Garrett Popcorn is a must-try, blending sweet and savory flavors. Don’t miss out on the global flavors in areas like Chinatown and Little Village for dim sum and tacos4.
| Iconic Chicago Dish | Best Spot to Try It |
|---|---|
| Deep-Dish Pizza | Lou Malnati’s4 |
| Italian Beef Sandwich | Al’s Italian Beef4 |
| Chicago-Style Hot Dog | Portillo’s4 |
| Jibarito Sandwich | Papa’s Cache Sabroso4 |
| Buttermilk Old-Fashioned Doughnut | Do-Rite Donuts4 |
Explore the city’s foodie neighborhoods for a taste of global flavors. From dim sum in Chinatown to amazing tacos in Little Village4.
Chicago boasts over 8,000 restaurants, showing its rich food culture. The city is home to hundreds of Chicago food festivals each year. These festivals highlight the role of food in the community.
“Chicago is a food lover’s paradise, with iconic dishes that have become synonymous with the city’s culture and identity.”
Explore Chicago’s Vibrant Neighborhoods
Chicago is more than just famous landmarks. It’s full of diverse neighborhoods with their own cultures and foods. You can dive into the unique sights, sounds, and tastes of each area. From trendy spots like Wicker Park and West Loop to historic areas like the Loop, and multicultural spots like Chinatown and Little Village5.
Foodie Havens
Chicago’s food scene is amazing, and you can find it in its neighborhoods. In Chinatown, try real Chinese food and see the Chinese Lunar New Year Parade6. Little Village is great for Mexican food, with delicious tacos and tamales5. For something new, check out the Fulton Market District, known for its creative dining spots6.
West Rogers Park is a place where you can feel the culture of Chicago’s Jewish community and new immigrants. Devon Avenue in Little India is a sensory delight, full of Indian flavors and traditions6. Logan Square is trendy, with cool food spots, craft cocktail bars, and indie coffee shops7.
| Neighborhood | Highlights |
|---|---|
| Chinatown | Authentic Chinese cuisine, vibrant cultural displays, Chinese Lunar New Year Parade |
| Little Village | One of the largest Mexican American communities in the country, mouthwatering tacos and tamales |
| Fulton Market District | Chicago’s “restaurant row,” diverse array of upscale and experimental dining options |
| West Rogers Park | Vibrant hub for Chicago’s Jewish community and recent immigrants, Little India on Devon Avenue |
| Logan Square | Thriving food and drink scene, farm-to-table eateries, innovative craft cocktail bars, indie coffee shops |
From the fancy Gold Coast to the cool Wicker Park, Chicago’s areas are full of culture and food6. Whether you want real global food or the newest food trends, Chicago’s neighborhoods will amaze and inspire you7.
“Chicago’s neighborhoods are a mosaic of cultures, each with its own distinct character and culinary offerings. Exploring these pockets of the city is the ultimate way to immerse yourself in the true essence of Chicago.”
Discover Chicago’s Music and Nightlife Scene
Feel the buzz of Chicago’s famous music and nightlife. Dive into the deep roots of blues, jazz, and house music at places like Buddy Guy’s Legends, the Green Mill Jazz Club, and the Aragon Ballroom8. See up-and-coming comedians at The Second City, a top improv club9. Explore the lively music spots, from cozy clubs to big theaters.
Experience a mix of music styles across the city. The World Famous Gospel Brunch at the House of Blues in River North happens every Sunday, celebrating gospel music8. The Winter’s Jazz Club plays various jazz styles, like gypsy jazz and swing8. For those who love outdoor music, the Gospel Music Festival and Chicago Blues Festival in Millennium Park offer free shows8.
- The Grant Park Music Festival at Millennium Park has free classical music from June to September.
- The Chicago Jazz Festival in August and the World Music Festival in September are big music events in Chicago8.
- Pitchfork in July showcases alternative and indie bands8.
- The Windy City Smokeout event features country music, barbecue, and craft beer8.
- Lollapalooza in August offers four days of big shows from top artists in Grant Park8.
Chicago’s nightlife has a wide range of music venues for every taste. Metro is known for its lineup of artists and intimate indie, alternative, and rock shows in a 100-year-old building10. House of Blues hosts rock and blues but also welcomes artists from pop, rap, and electronica10. The city’s venues, from Thalia Hall to Chicago Theatre, cater to many musical tastes.
Looking for live music, comedy, or Chicago’s nightlife? The city’s entertainment scene has endless options for memorable times9.
Marvel at Chicago’s Architectural Wonders
Chicago is famous for its amazing architecture. You’ll see Chicago skyscrapers that reach high up and Chicago landmarks that tell stories of the past. Don’t miss the Robie House, a UNESCO site by Frank Lloyd Wright. Also, check out the Tribune Tower and Marina City, key buildings in the skyscraper history11.
Go up the Willis Tower’s Skydeck or 360 CHICAGO for views of the city. Visit the Chicago Cultural Center with its huge Tiffany glass dome. And, take a trip to the Pullman National Monument to step back in time11.
Must-See Landmarks
Chicago’s architecture is a mix of old and new. See the famous12 Tribune Tower, Wrigley Building, and Millennium Park. These places show off the city’s beauty. Also, check out the Art Institute of Chicago and Astor Street in the Gold Coast12.
Don’t miss the Open House Chicago festival in October. It lets you see private places usually closed to the public12.
Chicago’s architecture shows the city’s strength, creativity, and beauty. It draws in people who love architecture and admire the city’s looks12.
| Landmark | Year Built | Architectural Style |
|---|---|---|
| The Chicago Theatre | 1921 | Rapp and Rapp |
| The Rookery Building | 1888 (redesigned 1905-1907) | Frank Lloyd Wright |
| Willis Tower (formerly Sears Tower) | 1974 | Skyscraper |
| 875 N. Michigan Ave. (formerly John Hancock Center) | N/A | Observation deck |
| Chicago Water Tower and Pumping Station | N/A | Survived the 1871 Chicago Fire |
| The Monadnock Building | 1893 | Transitional architecture |
Chicago’s historic sites and buildings take you on an exciting journey. From tall skyscrapers to historic spots, they show the city’s creativity and strength1112.
Experience Chicago’s World-Class Museums
Chicago is a city full of cultural wonders, with museums that are famous worldwide. You can see the biggest Titanosaur at the Field Museum13. Or check out the Art Institute of Chicago for its Impressionist art collection13.
At the Field Museum, meet SUE, the biggest and most complete T. rex13. It has over 24 million items in its collection13. The Museum of Science and Industry has over 2,000 exhibits13. You can even stand inside a tornado or a U-boat.
The Art Institute of Chicago is perfect for art lovers, with works by Andy Warhol and others13. The DuSable Museum of African American History has over 13,000 objects13. It shows the history and culture of African Americans.
There are also interactive exhibits at the Adler Planetarium and the Chicago History Museum14. The Peggy Notebaert Nature Museum has a live butterfly house13. It’s a place to learn and help protect butterflies.
Chicago’s museums have something for everyone, from science to art to history. With over 67 museums13, there’s a lot to explore.
| Museum | Highlights | Annual Visitors |
|---|---|---|
| The Art Institute of Chicago | Vast collection of Impressionist art | 1.5 million13 |
| Field Museum | Home to the largest Titanosaur and SUE the T. rex | 2 million13 |
| Museum of Science and Industry | Over 2,000 interactive exhibits, including a tornado simulator | 1.5 million13 |
| DuSable Museum of African American History | Showcases over 13,000 objects related to African American history and culture | N/A |
| Chicago Children’s Museum | Serves over 650,000 community members annually | 650,000+13 |
“Chicago’s museums offer a remarkable journey through art, history, and science, captivating visitors from around the world.”
Embrace the Great Outdoors in Chicago
Escape the city and dive into Chicago’s parks, beaches, and outdoor spots. The city is full of activities that let you connect with nature. From exciting adventures to peaceful spots, there’s something for everyone.
Urban Escapes
Walk the 18-mile Lakefront Trail to see sandy Chicago beaches, green spaces, and the city skyline15. Visit the calm Lurie Gardens in Millennium Park. Don’t miss the hidden Alfred Caldwell Lily Pool in Lincoln Park and the big Garfield Park Conservatory16.
For fun, try ice skating at Maggie Daley Park or climb the outdoor wall15. Find hidden spots in Chicago parks, like the Skate Park in Grant Park and the Chicago River activities16.
Enjoy Chicago nature with various outdoor activities. Try golfing, archery, stand-up paddleboarding, and bird watching16. With CityPASS, save up to 48% on attractions like the Shedd Aquarium, Field Museum, and Skydeck Chicago15.
Chicago’s great outdoors has thrilling and peaceful spots to explore. Dive into nature and make memories to last a lifetime151617.
Chicago’s Must-See Attractions and Unique Experiences
Experience the iconic sights and activities that make Chicago a top destination. Take a selfie with the famous Cloud Gate, also known as “The Bean,” in Millennium Park. Enjoy breathtaking views from the Skydeck at Willis Tower or 360 CHICAGO observation deck.
Walk along the lively Chicago Riverwalk, where you’ll find outdoor dining and bars. Discover the city’s architecture on a boat or kayak tour. Don’t miss the thrill of a Ferris wheel ride and summer fireworks at Navy Pier. Visit the Buckingham Fountain and the Chicago Cultural Center to see what makes the city special.
Explore with CityPASS
For a budget-friendly way to see Chicago’s best spots, get a CityPASS. This ticket lets you visit several attractions at a lower cost. You have 9 consecutive days to use it, starting from when you first visit. You can visit attractions in any order you like18.
You can see as many attractions as you want in one day18. Each attraction can be visited once with your CityPASS unless noted otherwise18. Some attractions might need reservations in advance18. CityPASS doesn’t cover parking18, but some attractions offer discounts with it18.
Outdoor Oasis: Embrace the Green Spaces
Chicago has 28 miles of freshwater coastline with public beaches19. The city offers 50 free public swimming pools through the Chicago Park District19. With over 600 public green spaces, finding a spot for a picnic is easy19.
Navy Pier has fireworks shows twice a week from May to September, lighting up the sky19. The updated Chicago Riverwalk has restaurants, bars, and scenic spots to enjoy the river views19. The 606, a former railway track, now connects several neighborhoods with a 2.7-mile path19.
For a taste of local food and culture, check out Time Out Market Chicago. It has 18 kitchens, three bars, and a rooftop terrace over three floors1918.
Attend Unforgettable Events and Festivals
Dive into the vibrant world of Chicago’s world-class events and festivals. Celebrate the Lunar New Year with traditional shows, colorful parades, and tasty foods20. Don’t miss the St. Patrick’s Day fun, including the famous Chicago River dyeing. Check out the Chicago Auto Show, the biggest car show in North America, or the C2E2: Chicago Comic and Entertainment Expo for pop culture fans. Cheer on runners at the Chicago Marathon and join the joy of the Chicago Pride Parade.
Enjoy music festivals like Lollapalooza and the Chicago Blues Festival, or the magical Christkindlmarket holiday market. The Glenwood Avenue Arts Fest is back for its 23rd year, featuring over 100 artists20. The Sangria Festival Chicago lets you sip on red wine and enjoy live music20.
FAN EXPO Chicago will feature stars like Mark Hamill and Marisa Tomei20. The Oak Park Micro Brew Review offers over 200 beers and supports a green cause20. The Evanston Art & Big Fork Festival will showcase art by over 150 artists20. The International Gem & Jewelry Show in Schaumburg features nearly 80 vendors with great deals20.
Chicago’s events range from the lively KOCO Fest to the unique Dim Sum & Drag event20. Music fans will love the Final Fantasy VII Rebirth Orchestra World Tour, with over 100 musicians20. For thrill-seekers, the Xtreme Xperience at Autobahn Country Club lets you drive exotic cars on a track20.
Chicago has events for everyone, from theater and dance to car lovers. Dive into the city’s culture and make memories at these top events and festivals20.
| Event | Description |
|---|---|
| “Back to the Future: The Musical” | Brings the sci-fi classic to the stage with music by Emmy and Grammy Award-winning artists20. |
| Chicago SummerDance | Offers multidisciplinary dance lessons at parks throughout the city, suitable for all ages and skill levels21. |
| Millennium Park Summer Workouts | Provide free cardio kickboxing, yoga, pilates, and Zumba classes every Saturday from May through August21. |
“Chicago’s event calendar is a testament to the city’s vibrant culture and diverse offerings. From music and art to food and sports, there is always something exciting happening in this dynamic metropolis.” – Chicago Local
Root for Chicago’s Beloved Sports Teams
Chicago is a city that loves sports. It has iconic places like Wrigley Field and the United Center. These spots are full of passion and pride for fans22. Whether you’re a big fan or visiting for the first time, experiencing Chicago’s sports culture is unforgettable.
Iconic Venues
See a Cubs game at Wrigley Field, the second-oldest ballpark in the U.S23. Cheer for the Cubs as they aim for another World Series win. Then, head to Guaranteed Rate Field for a White Sox game and enjoy the fireworks after23. Don’t miss a Bears game at Soldier Field and join in singing “Bear Down, Chicago Bears”23.
If you like hockey, watch the Blackhawks at the United Center23. For basketball fans, catch a Bulls game in the same arena. These games are a must for anyone visiting Chicago.
Chicago isn’t just about the big leagues. It’s also home to the WNBA’s Chicago Sky and the Chicago Red Stars, who often make the playoffs24. The city supports college sports too, with fans cheering for the DePaul University Blue Demons and Loyola University Chicago Ramblers23.
Whether you’re a fan of the Cubs, Bears, Blackhawks, or other teams, Chicago’s sports passion is unmatched22. With historic venues and winning teams, Chicago’s sports scene will impress every visitor24.
Explore Chicago’s Hidden Gems
Chicago is more than just famous landmarks. It has many hidden treasures waiting for you. Step off the main path to find Chicago’s hidden gems, secret spots, and unique attractions. These spots make the city truly special25.
Begin at the Bahai House of Worship, a beautiful building 45 minutes from downtown. It’s a place of peace and beauty for this unique faith25. Then, visit the Garfield Park Conservatory, one of the biggest in the country. Don’t miss the calm of Lurie Gardens in Millennium Park25.
Walk through the quiet Alfred Caldwell Lily Pool in Lincoln Park. It’s a hidden spot full of native plants and animals. For a taste of Japan, check out the Japanese Garden in Jackson Park25.
Check out the Wabash Arts Corridor for amazing Graffiti Murals. These show off the city’s street art scene. From these off-the-beaten-path spots to hidden places in different areas, Chicago has lots to offer25.
“Chicago’s hidden gems offer a deeper, more authentic glimpse into the city’s cultural tapestry, inviting visitors to explore beyond the well-trodden path.”
| Hidden Gem | Highlights |
|---|---|
| Bahai House of Worship | A stunning piece of architecture located just 45 minutes from downtown Chicago25 |
| Garfield Park Conservatory | One of the largest conservatories in the country, offering a tranquil oasis25 |
| Lurie Gardens | A zen-like haven in the heart of Millennium Park25 |
| Alfred Caldwell Lily Pool | A secluded oasis in Lincoln Park, teeming with native flora and fauna25 |
| Japanese Garden | An authentic Japanese garden nestled away in Jackson Park25 |
| Wabash Arts Corridor | A vibrant showcase of the city’s thriving street art scene25 |
Indulge in Sweet Treats and Unique Eats
Give in to your sweet cravings and explore Chicago’s best treats. Try a rich, cakey Chicago donut from Stan’s Donuts. Or, enjoy the delightful pastries and macarons at Alliance Bakery26.
For a special treat, visit The Chocolate Shoppe. There, you can enjoy a handcrafted scoop of Chicago ice cream. They offer vegan options and Wisconsin-made flavors26. Don’t forget to try their lavish hot chocolate with house-made marshmallows.
Local Favorites
Check out the Original Rainbow Cone, a beloved spot in Chicago. They serve colorful, layered scoops of their signature Chicago desserts26. You can also try the classic Chicago-style jibarito or the famous deep-dish pizza.
| Iconic Chicago Treats | Description |
|---|---|
| Stan’s Donuts | Renowned for their rich, cakey Chicago donuts26 |
| Alliance Bakery | Exquisite pastries and macarons in a charming setting26 |
| The Chocolate Shoppe | Handcrafted Chicago ice cream with vegan options26 |
| Original Rainbow Cone | Iconic Chicago institution serving up colorful, layered Chicago desserts26 |
Looking for a decadent donut, creamy ice cream, or a slice of deep-dish pizza? Chicago’s bakeries have you covered. Dive into the city’s sweet and unique eats for a memorable food adventure26.
Sip Craft Cocktails and Locally Brewed Beers
Chicago is famous for its lively bar and brewery scene. It’s a top spot for craft cocktails and local beers27. Places like Three Dots and a Dash offer a unique vibe, while Celeste bar has themed floors and rooftop views28. Three Dots and a Dash even made it to The World’s 50 Best Bars list28.
Explore Chicago’s craft beer scene at The Map Room and Navigator Taproom. Here, you can pour your own beer and enjoy snacks27. Check out ERIS Brewery & Cider House for their hard ciders or Crushed by Giants Brewing Company for a variety of beers27. For something different, try the Up Room in Wicker Park for amazing views or dance at the Legendary Hangge-Uppe29.
Enjoy Negroni slushies at Parson’s Chicken & Fish or the tamale guy in Logan Square bars. Chicago’s bars cater to all tastes, from cozy spots to big, lively places29.
Chicago’s craft cocktail and beer scene is always changing. New bars and unique drinks keep popping up29. Try botanical beers at Forbidden Root or barrel-aged brews at Moody Tongue Brewing Company. The city celebrates new tastes and local flavors27.
Whether you’re an expert or just starting out, Chicago’s Chicago bars, nightlife, breweries, and Chicago craft cocktails offer an amazing experience. You’ll want to come back for more272928.
Conclusion
Chicago is a vibrant city, offering something for everyone who loves travel, culture, and exploration. From iconic landmarks like the Art Institute of Chicago and Millennium Park’s Cloud Gate to hidden gems in diverse neighborhoods, the city is rich in history and culture. Whether you’re visiting Intuit: The Center for Intuitive and Outsider Art, discovering the Couch Tomb in Lincoln Park, or enjoying the Berghoff, Chicago continuously reveals new experiences.
Prepare to explore a city that captivates and leaves a lasting impression. Whether you’re a first-time visitor or a longtime resident, Chicago’s unique charm and endless attractions promise an unforgettable experience.
