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Things to do in Chicago

• Chicago's Skyline from the River: Architecture Cruise

  
  

  Get ready to see Chicago's famous skyline from a whole new angle on this 90-minute boat tour along the Chicago River. As you cruise past towering skyscrapers and iconic landmarks, you'll learn all about the city's fascinating architectural history from knowledgeable guides who really know their stuff.

  The tour covers all three branches of the river, giving you a comprehensive look at Chicago's most impressive buildings old and new. You'll see everything from historic early skyscrapers like the Wrigley Building to sleek modern marvels like the glassy Trump Tower. The guides point out interesting details and share stories about the buildings and architects that have shaped the city over the decades.

  Whether you grab a seat on the open-air top deck or stay cozy inside, you'll have great views the whole way. There's a full bar on board if you want to sip a local beer or cocktail while you take in the sights. By the end, you'll have a new appreciation for Chicago's world-famous architecture and skyline. It's a fun, relaxing way to see the city from a unique vantage point on the water.

  
  
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• Enjoy the View from 360 CHICAGO

  
  

  For breathtaking views of Chicago and Lake Michigan, head up to 360 CHICAGO in the John Hancock Center. This observation deck offers a 360-degree panorama of the city from 1,000 feet up. On a clear day, you can see for miles, and the views are especially stunning at sunset.

  If you're feeling brave, try TILT - an enclosed moving platform that tilts you out over Michigan Avenue. It's not for the faint of heart, but it's an unforgettable experience. After taking in the views, relax with a drink at the bar. It's a great way to appreciate Chicago's impressive skyline and get your bearings in the city.

  
  

• Chicago's Dark Side: Gangsters and Ghosts Tour

  
  

  Experience a glimpse of Chicago’s turbulent past on this guided walking tour through the city’s South Loop. The journey explores the darker chapters of the 1920s, taking you to locations once frequented by notorious figures such as Al Capone. Former speakeasies and historic streets set the stage for stories of organized crime and Prohibition-era exploits.

  As the tour winds along the Chicago Riverwalk and through landmark neighborhoods, the guide shares eerie ghost stories and urban legends. Notable stops include the Palmer House and the Chicago Theatre, where tales of hauntings and mysterious events have lingered for decades. The route also leads to the Congress Hotel, often regarded as one of Illinois’ most haunted buildings.

  This two-hour experience offers a unique way to explore a lesser-known side of Chicago. With its mix of unsettling history, true crime accounts, and local folklore, the tour is both informative and engaging. Walking through places like Death Alley adds an extra sense of atmosphere, making it a memorable addition to any visit.

  
  
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• Art Institute of Chicago: Skip-the-Line Access

  
  

  The Art Institute of Chicago is an essential stop for anyone interested in art while visiting the city. A Fast-Pass ticket allows visitors to skip the usual lines and head directly into one of the most renowned art museums in the world. Its collection includes iconic American works such as "American Gothic," alongside European masterpieces by Monet, Van Gogh, and Picasso, offering a wide range of pieces for different interests.

  The museum spans 5,000 years of artistic expression, with galleries dedicated to everything from ancient Egyptian artifacts to modern and contemporary art. Many visitors spend considerable time in the Impressionist wing, where Seurat’s "A Sunday Afternoon on La Grande Jatte" and Monet’s water lily series are displayed. Beyond the major exhibits, the museum features other standout collections, including medieval armor, Asian art, and the detailed Thorne Miniature Rooms.

  For those looking to explore further, the museum’s free mobile app offers helpful self-guided tours, while the daily guided tours provide expert perspectives on various exhibits. Comfortable footwear is recommended due to the museum's size and the amount of walking involved. Visitors can take a break at the on-site café before continuing their visit, and the gift shop offers a variety of art-inspired souvenirs worth browsing before leaving.

  
  
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• Cruising Chicago's Lakefront Neighborhoods by Bike

  
  

  Experience Chicago’s scenic lakefront neighborhoods on a relaxed bike tour that highlights areas often missed by typical visitors. The route takes you past the stately mansions of the Gold Coast, offering a glimpse into the lives of the city’s most affluent residents. As you continue through Old Town, the historic architecture and charming streets give a sense of Chicago’s rich past.

  Riding along the shores of Lake Michigan provides impressive views of the skyline and beaches. The route includes stops near Lincoln Park Zoo and a look at the original Playboy Mansion. Throughout the ride, the guide shares interesting stories and insights into Chicago’s history and culture, offering a different perspective from the usual downtown attractions.

  This leisurely three-hour tour is suitable for all skill levels, with most of the ride taking place on designated bike paths. The guide ensures a safe and enjoyable experience for everyone in the group. Bringing a camera is recommended, as the tour includes plenty of opportunities to capture memorable sights along the way.

  
  
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• Chicago's Barrel Bus Brewery Adventure

  
  

  Climb aboard a distinctive barrel-shaped bus and explore Chicago’s thriving craft beer scene on this four-hour guided tour. The experience includes visits to three popular breweries, where guests can sample between 45 and 55 ounces of locally crafted beers. One of the highlights is a VIP, behind-the-scenes tour at one of the city’s renowned nano-breweries, offering an inside look at the brewing process and the chance to discover unique flavors.

  This tour is more than just beer tasting; it is an engaging and interactive experience. The guide shares insightful facts about the breweries and the city’s beer culture while keeping the atmosphere lively with games and fun commentary. Traveling through Chicago in a one-of-a-kind vehicle adds an extra layer of excitement, making it a memorable alternative to traditional pub crawls.

  Designed for both seasoned beer enthusiasts and newcomers, the tour showcases a variety of breweries, from well-established names to emerging spots. Participants can expect a broad sampling of Chicago’s diverse brewing styles. Comfortable footwear is recommended, and it may be a good idea to eat lightly beforehand to fully enjoy the generous tastings offered throughout the experience.

  
  
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• Chicago Skyscraper Experience: Willis Tower Skydeck

  
  

  For a panoramic view of Chicago, the Willis Tower Skydeck offers an impressive vantage point. Visitors ascend 103 floors in a high-speed elevator, learning about the city’s architectural history along the way. From the top, the views stretch for miles in every direction, and on clear days, it is possible to see as far as four different states.

  One of the most memorable experiences at the Skydeck is stepping onto The Ledge, a glass box extending from the building’s side. Standing 1,353 feet above the ground, visitors can look straight down through the transparent floor to the city below. The experience is brief, with only about a minute on The Ledge, but the perspective is both thrilling and unique.

  After taking in the views, there are exhibits on the lower floors that explore Chicago’s history and its well-known buildings. A free mobile app is also available to help identify landmarks visible from the observation deck. Whether you are a resident or a visitor, seeing the city from this height offers a new appreciation of its scale and beauty. Visitors should plan for potential wait times, particularly during busy travel seasons.

  
  
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• Picnic in Grant Park

  
  

  Grant Park is often called Chicago's 'front yard', and it's easy to see why. This massive green space in the heart of the city is perfect for a leisurely afternoon. Pack a picnic and find a spot on the lawn to relax and people-watch.

  The park is home to several attractions, including Buckingham Fountain, a beautiful Beaux Arts-style fountain that puts on impressive water shows. You can also check out the gardens, walk along the lakefront, or join in a game of softball or frisbee. If you're visiting in summer, you might catch one of the many festivals or concerts held in the park. It's a great way to enjoy some downtime in the middle of the bustling city.

  
  

• Explore Millennium Park

  
  

  Millennium Park is a must-visit spot in Chicago. It's a huge urban park right in the heart of downtown, and it's packed with cool stuff to see and do. The big showstopper is the Cloud Gate sculpture, which everyone calls 'The Bean'. It's this massive, shiny, bean-shaped thing that reflects the city skyline in a really trippy way. It's basically impossible to resist taking a selfie with it.

  But there's more to the park than just The Bean. In summer, you can catch free concerts at the Jay Pritzker Pavilion, which looks like a giant silver flower made of metal. The Crown Fountain is another highlight - it's two big glass block towers with faces projected on them that spit water. Kids love playing in the shallow reflecting pool between them. There's also a beautiful garden called the Lurie Garden that's great for a peaceful stroll.

  
  

• Stroll through Lincoln Park Zoo

  
  

  Lincoln Park Zoo is a fantastic place to spend a few hours, especially if you're traveling with kids or just love animals. What's really cool about this zoo is that it's completely free to visit. It's one of the oldest zoos in North America, but it's kept up with the times with modern, animal-friendly habitats.

  You can see all sorts of animals here, from lions and tigers to penguins and polar bears. The gorilla exhibit is particularly impressive - you can get really close to these amazing primates. There's also a beautiful butterfly haven where you can walk among hundreds of fluttering butterflies. The zoo is set in Lincoln Park, which is a huge green space that's perfect for a picnic or a walk after you've finished with the animals. In the summer, they often have events like outdoor movie screenings and concerts, so it's worth checking their calendar.

  
  

• Explore Chinatown

  
  

  Chicago's Chinatown is a lively and culturally rich neighborhood that offers a unique perspective on the city. Centered around Cermak and Wentworth Avenues, the area is filled with authentic Chinese restaurants, specialty shops, and notable cultural landmarks. Visitors are greeted by a prominent red gate marking the entrance, which serves as a popular photo opportunity and symbol of the community’s heritage.

  The neighborhood is known for its diverse dining options, ranging from dim sum and hot pot to bubble tea and traditional Chinese pastries. In addition to its culinary appeal, Chinatown features several attractions, such as the Pui Tak Center, an impressive example of Chinese architectural design, and Chinatown Square, a two-level outdoor mall with numerous stores and a zodiac-themed sculpture garden. Tea enthusiasts can explore local tea shops that offer tastings of various blends. For those interested in history and culture, the Chicago Chinese Cultural Institute occasionally organizes walking tours that provide deeper insights into the area’s background and traditions.

  
  

• Visit the Field Museum

  
  

  The Field Museum is one of those places where you can easily spend a whole day and still not see everything. It's huge, and it's packed with fascinating exhibits about natural history, ancient cultures, and science. The star of the show is Sue, the largest and most complete T. rex skeleton ever found. It's pretty mind-blowing to stand next to this massive prehistoric predator and imagine it roaming the earth millions of years ago.

  Beyond Sue, there are halls filled with ancient Egyptian artifacts, including real mummies. You can explore recreations of different ecosystems from around the world, from the savannas of Africa to the rainforests of South America. There's also a cool underground adventure exhibit where you can see what life is like for insects and other tiny creatures living in the soil. The museum does a great job of making everything interactive and engaging, so it's fun for both kids and adults.

  
  

• Visit the Museum of Science and Industry

  
  

  The Museum of Science and Industry in Chicago is one of the largest science museums in the Western Hemisphere, offering a wide range of interactive exhibits that make science and technology engaging for visitors of all ages. One of its most notable features is the U-505 submarine, an authentic German vessel from World War II that guests can explore inside. Other highlights include an expansive model railroad that traces the route from Chicago to Seattle, a mirror maze designed to demonstrate mathematical concepts, and a walk-through giant heart. The Science Storms exhibit allows visitors to experiment with natural forces by creating tornadoes and triggering avalanches.

  In addition to the hands-on exhibits, the museum houses an IMAX theater that presents science and nature documentaries on an impressive large-format screen. With such a variety of displays and activities, the Museum of Science and Industry offers an experience that can easily fill an entire day. Visitors are encouraged to set aside at least half a day to explore the exhibits in depth and make the most of the museum's many attractions.

  
  

• Visit the Chicago Cultural Center

  
  

  The Chicago Cultural Center is often overlooked by visitors, yet it offers an experience well worth the time. Admission is free, and the building itself is a remarkable example of architectural beauty. Once serving as the city’s first public library, it features exquisite Tiffany glass domes, including the largest Tiffany dome in the world. The craftsmanship and design make it a standout destination for those interested in historic architecture.

  In addition to its striking interior, the Cultural Center hosts a variety of free events and exhibitions throughout the year. These include art displays, musical performances, lectures, and film screenings, with programming that changes regularly. Even on quieter days without major events, it remains an excellent place to explore. Free guided tours of the building are available, offering more insight into its history and design. Located directly across from Millennium Park, it is conveniently placed for those planning to explore downtown Chicago.

  
  

• Explore Wicker Park

  
  

  Wicker Park is the place to go if you want to experience Chicago's hipster side. This neighborhood is packed with cool indie shops, vintage stores, coffee shops, and restaurants. It's the kind of place where you can spend hours just wandering around, popping into interesting stores and cafes.

  One of the main draws is the amazing food scene. You can find everything from gourmet donuts to high-end farm-to-table restaurants. There are also tons of great bars and music venues if you want to experience Chicago's nightlife. During the day, check out places like Myopic Books, a massive used bookstore that's a book lover's paradise. The 606, an elevated park built on an old railway line, is great for a walk or bike ride. Wicker Park has a really creative, artsy vibe that makes it feel totally different from downtown Chicago.

  
  

• Catch a Game at Wrigley Field

  
  

  Attending a game at Wrigley Field offers a classic Chicago experience, whether or not you are a dedicated baseball fan. Opened in 1914, this historic ballpark retains a unique charm that modern stadiums often lack. The ivy-covered outfield walls and hand-operated scoreboard create an atmosphere that feels rooted in baseball’s earlier days. The setting makes it easy to appreciate the tradition and history tied to this iconic venue.

  The energy during a Cubs game is lively, with dedicated fans creating a strong sense of community throughout the stadium. Even those unfamiliar with the sport can enjoy the experience, from sampling Chicago-style hot dogs to joining the crowd in singing "Take Me Out to the Ball Game" during the seventh-inning stretch. For those who are not able to attend a game, guided tours are available, offering insight into Wrigley Field’s history and exclusive access to areas not open to the general public. The surrounding Wrigleyville neighborhood adds to the visit with its selection of sports bars and Cubs-themed shops.

  
  

• Experience Navy Pier

  
  

  Navy Pier offers a vibrant, carnival-like atmosphere along the edge of Lake Michigan. Stretching out over the water, the pier is filled with restaurants, shops, and popular attractions. Its most recognizable feature is the large Ferris wheel, which provides sweeping views of both the lake and the Chicago skyline. The experience is particularly striking at night when the city lights reflect off the water.

  In addition to the Ferris wheel, there are plenty of other activities to enjoy. Visitors can watch a performance at the Chicago Shakespeare Theater, explore the stained glass museum, or simply stroll the pier and take in the lively surroundings. During the summer months, free fireworks displays are often held over the lake. While it tends to be crowded on weekends and warm evenings, the energy of the place makes it an engaging spot to experience the dynamic spirit of Chicago.

  
  

• Explore the Magnificent Mile

  
  

  The Magnificent Mile is Chicago's most famous commercial area, running along Michigan Avenue. Known for its wide selection of shops, it offers everything from luxury designer boutiques to well-known retail chains. Beyond shopping, the district provides a range of attractions and activities that appeal to visitors with different interests.

  The area is also recognized for its notable architecture, featuring landmarks such as the Wrigley Building and Tribune Tower, alongside sleek modern skyscrapers. Visitors can relax at one of the many cafes or restaurants in the area or visit the Museum of Contemporary Art for a cultural experience. As evening approaches, the avenue is illuminated with lights, creating a pleasant atmosphere for an evening walk.

  
  

Where to stay in Chicago

Best hotels in Chicago:

• Kimpton Gray Hotel (luxury hotel)

  
  
  
  
  
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  The Kimpton Gray Hotel is a stylish spot right in the heart of Chicago's Loop. A historic building but has a totally modern vibe inside. The rooms are spacious and well-designed, with cool details like marble bathrooms and library-inspired decor.

  One of the best things about the Gray is its location - you're just steps from Michigan Avenue shopping, Grant Park, and tons of restaurants and theaters. After a day of exploring the city, head up to the rooftop bar Boleo for amazing views and Latin-inspired cocktails. Or grab a drink at the lobby bar Vol. 39, which has a cozy library feel.

  The staff here are super friendly and go out of their way to make your stay great. Little perks like the free evening wine hour add a nice touch. While it's not the cheapest option in Chicago, the Gray offers a luxe experience in a prime spot for those wanting to be in the middle of the action.

  
  

• Club Quarters Hotel Wacker (medium range hotel)

  
  
  
  
  
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  Club Quarters Hotel Wacker, the location can't be beat - you're steps away from Michigan Avenue shopping, Millennium Park, and all the action of downtown Chicago. The rooms are simple but comfortable, with nice touches like free WiFi and coffee makers. Some even have kitchenettes if you want to save money on meals out.

  The hotel has a cool historic vibe, being housed in the 1928 Mather Tower. But don't worry, the amenities are modern. There's a fitness center if you want to work out, and a club room to hang out in with free coffee and snacks. The staff is friendly and helpful with recommendations.

  Overall, it's a solid mid-range option if you want to be right in the heart of the city without breaking the bank. The rooms may not be huge, but you probably won't spend much time in them anyway with so much to see and do right outside the door. It's perfect for a weekend getaway or business trip to the Windy City.