Top Chicago Tours, Sightseeing & Cruises

Soak up the views of Lake Michigan and the Chicago skyline with a 2-hour sailing tour. This private charter is completely customizable, giving you the chance to choose your music, route, and up to 5 additional guests. Sail into the sunset with your own drinks and snacks (refrigerator and ice on board) and your family or friends by your side.

If you’ve ever dreamed of sailing away on your own private sailboat, this is the perfect excursion for you. You and up to five other invited guests will have the exclusive use of a sailboat, complete with captain and crew for the duration of your tour. Sail on Lake Michigan and enjoy the sights of Chicago’s striking skyline. If you want, you could even take a turn at the helm.

Chicago dogs, deep-dish pizza, cupcakes and craft beer are all sampled on this half-day bike tour through the Windy City. Cover about 13 miles (21 km), following an informative guide at a moderate pace through the Chicago neighborhoods of Wrigleyville, the Gold Coast, Old Town, Lakeview and Lincoln Park. Stop along the way at a popular downtown bakery, pizza shop, hot dog stand and two breweries for a taste of local flavors.

Take in sweeping views of Chicago from the air during a scenic helicopter flight that offers a premier experience of the Windy City. This private 45-minute flight provides an aerial look at landmarks such as Millennium Park, Navy Park, and Wrigley Field. Ideal for a special occasion, this helicopter tour accommodates up to three people and includes the use of noise-cancelling headsets to hear the pilot clearly.

Take a gourmet dinner cruise on a high-end luxury yacht with the stunning skyline of Chicago serving as your backdrop. Climb aboard your recently renovated vessel, featuring a sumptuously-appointed rooftop lounge and stylish interior design, for your cruise along Lake Michigan. Then sit down for a 3-course dinner, informed by some of the world’s top celebrity chefs and composed of fresh ingredients cooked right on-board. After dinner, enjoy coffee and tea, captivating views of Chicago landmarks like the Willis (formerly Sears) Tower and Navy Pier, plus musical entertainment provided by the onboard DJ.

An excellent choice for first-time visitors, this tour provides a comprehensive overview of the city and hits on both classic attractions and little-known sites. Beginning at the Chicago Theatre, work your way to the Chicago Pedway, an elaborate network of underground tunnels used by locals and commuters. Stroll the Chicago Riverwalk and the Magnificent Mile, then embark on a food tour to taste some of the city’s famous foods.

Perfect for families, groups, and corporate outings, the Spirit of Chicago lunch cruise lets you kick back and enjoy a great meal while taking in the sights of Chicago's most famed landmarks. See and photograph the dramatic city skyline, Navy Pier, Soldier Field, and Shedd Aquarium. The cruise includes a delicious buffet lunch with salads, entrees, desserts, and unlimited nonalcoholic beverages. There's also a DJ, games, and a dance floor to keep your group entertained.

Pedal past the lakefront neighborhoods of Chicago's North Side on this bike tour of the Windy City. Follow a local guide along quiet streets, city parks and scenic beaches, starting at Lake Shore Drive and continuing along Rush Street and the Magnificent Mile. Catch a glimpse of the Playboy Mansion, Oprah’s penthouse and the Victorian houses of Old Town. Select from several departure times in the morning or afternoon.

Learn about Chicago’s brewpub scene and taste different types of craft beer on this guided brewery tour. Visit unique breweries for craft beer samples plus an additional brewing production facility for an in-depth tour. Discover the science behind the brewing process, complete with step-by-step procedures, and enjoy plenty of beer samples throughout the tour. Round-trip transportation in a Prohibition-era-styled barrel bus is included.

Make your evening in Chicago one to remember with this luxury sunset cruise featuring dinner, sightseeing and dancing along the shores of Lake Michigan. Feast your eyes on incredible views of iconic Windy City sights like Navy Pier, the Willis (Sears) Tower, Buckingham Fountain and Soldier Field, then fill your belly with a bountiful all-you-can-eat buffet. Continue the celebration with a live DJ who will mix up a selection of dance favorites.

See the overlooked highlights of Chicago’s Loop district with a 2-hour walking tour that takes in the best of the bustling, vibrant neighborhood’s inside spaces. Get behind the façades to explore stunningly designed interiors as you follow a specially-designed route with an experienced guide. Learn about the city’s architecture, art and history while visitng a side of Chicago that’s beyond the tourist trail, and experience the Windy City with a local perspective.

Board a luxurious yacht at Navy Pier for a 2-hour lunch cruise along Chicago’s scenic shoreline. Enjoy a three-course gourmet meal as you take in views of the Windy City from a climate-controlled observation deck, then sip coffee or tea while the yacht’s onboard DJ spins a leisurely afternoon playlist.

Tour the historic Chicago Theater, a must-see city landmark, with a guide providing in-depth commentary. You'll get the most out of your visit by traveling with a guide and get access to some areas of the theater that the public never sees. Learn about its architecture, history, and famous performers throughout the years.

Get off the beaten path to experience some of Chicago's best street art on this immersive tour. With a guide in the lead, you can leave the navigation to them and simply take in the scenery. Listen to in-depth commentary focused on the street-art community, the artists, and the history and meaning behind the art.

Experience Lake Michigan from a perspective rare to visitors and locals alike on a pirate–themed sailboat tour. Your guides tell true but little–known stories about pirates, battles, and treasure hunts as you cruise past sweeping views of the Chicago skyline. Relax on deck while or join your guides for an interactive experience—the flexibility of the tour makes this a popular choice for families with children.

Experience a colorful side of Chicago history with this Gangsters and Ghosts Tour. With a historian as your guide, you’ll step back to the roaring 20’s, when the Chicago Loop was a hub for bootleggers, speakeasies, and gangsters like the infamous Al Capone. Visit onetime gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley.

Explore Chicago's buzzing food scene with a small group on this small group walking tour. Stroll around the 'Loop', stopping at hidden gems and hearing tales of the city from your guide. Taste classic Chicago foods, from deep-dish pizza to dipped Italian beef sandwiches.

Get a taste of the deliciousness that finds a home in the Loop of Chicago. Lots of creative eateries ply their wares in the West Loop, and this guided tour helps you find some of the best. You will sample dishes at each stop with a bit of walking through the bustling neighborhood between each.

Taste food from around the world on this half-day cycling and tasting tour of Chicago. Follow your biking guide through the Chicago streets, stopping for views of Chicago’s famous architecture as well as bites like Polish pierogis, locally made chocolates, and Mexican tacos.

Chicago is full of unique and delicious food, but you don’t need to waste time chasing down each dish individually throughout the city. This food tour of Navy Pier will conveniently introduce you to some of the most authentic Chicago cuisine, all in one handy location. Get insider tips from your ‘food ambassador’ tour guide, who will make sure you end the tour full of delicious food and new knowledge.

Cruise down the Chicago River to see the city's famous architecture on this boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including more than 40 notable buildings like Navy Pier, the Wrigley Building, and the John Hancock Building. Cover all three branches of the Chicago River, passing the East Bank Club, the old Post Office Building and the Willis Tower (formerly known as the Sears Tower).

Enjoy waterfront views of downtown Chicago on a 2-hour brunch cruise through the heart of the city. Board a luxurious yacht at Navy Pier then relax on deck with a complementary mimosa. Find a comfortable spot on the three climate-controlled observation decks, and enjoy a sumptuous buffet while the onboard DJ spins a leisurely afternoon playlist. Capture unforgettable images of downtown skyscrapers and architectural landmarks as you navigate along the historic shoreline, then loop back and finish your outing at the bustling Navy Pier.

Aviation fanatics can take to the skies and try flying an actual helicopter with this Schaumburg flight experience that's perfect for first-timers. You enjoy helpful advice from your instructor before taking the controls on a flight that whisks you past Sears Centre Arena, Woodfield Mall, and Boomers Stadium. With free parking, noise-canceling headphones, and one-on-one attention from the pilot, this beginner-friendly experience is a near-perfect way to try flying for yourself.

Explore Chicago’s most iconic sites on a bike tour that explores Museum Campus, parks, and monuments. Follow your guide along the waterfront as you soak up the city skyline and enjoy the breeze along the easy-going route. Circle the Buckingham Fountain while you learn the history of the city’s public art, parks and museums, and capture unforgettable images of the Windy City.