Tours & Sightseeing in Chicago

Discover the 'dark side' of the Windy City thanks to this 2.5-hour, bus-based, nighttime crime history tour of Chicago. Explore the lives of notorious mobsters like Al Capone, Frank Nitti, Bugs Moran, and more as you explore infamous crime scenes like the St. Valentine's Day Massacre, learn about 'The Enforcer's Safe,' and stop by local watering holes.

Get an overview of Chicago's famous architectural history on this 3.5-hour bus tour. Learn about the city's history through your guide's history, from its founding to the present. Stops include the Loop, Mies van der Rohe's IIT campus, Frank Lloyd Wright's Robie House, and the Museum Campus.

Glide through the city of Chicago by moonlight on this haunted Segway tour. Follow your costumed local guide for 2 hours as they show you the sites of some of the most gruesome murders and disasters in Chicago's colorful history. See Chicago's iconic landmarks lit up during the spookiest time of year and hear about the mysterious, haunted history of this storied city.

Explore the affluent North Shore of Chicago on this guided, half-day sightseeing tour. Enjoy a scenic ride along Lake Michigan, passing by four cities, plus majestic mansions and historic American homes. Stop in downtown Evanston, with a visit to the Shakespeare Garden and the campus of Northwestern University. See other popular locations like Rogers Park, Loyola University, the Bahai House of Worship, the Chicago Botanic Garden and much more. All entrance fees plus a Chicago hotel pickup and drop-off are included.

You may never have thought of the back alleys of Chicago's North Loop as particularly photogenic. This small group tour will change your perceptions by helping you find the overlooked interesting shots and scenes that make for unforgettable photographs. You don't have to have a fancy camera to participate, just a mind that's open to the art in unexpected places.

See more of the Windy City with this money-saving, 2.5-hour, hop-on, hop-off sightseeing bus ticket. Enjoy informative on-board narration as you cruise by 13 Chicago landmarks including the Art Institute, Field Museum, John Hancock Building, and much more. A range of ticket validation periods, ranging from 24 to 72 hours, also help ensure maximum flexibility.

Don't spend time figuring out what to see in Chicago and how to get there - this hop-on hop-off tour provides a mapped-out itinerary of the city's top sights. With 14 strategically located stops, the tour allows you to explore the Windy City at your own pace. See the world-class Art Institute and landmark skyscrapers, while live commentary on board gives you insight into the city's colorful history. Don't forget to snap a selfie in front of the shiny steel bean in Millennium Park!

Experience Chicago like never before on this guided, 2-hour, small-group Segway tour. Visit popular Grant Park and see famous Buckingham Fountain's breathtaking, evening light show, with an illuminated Windy City skyline as the perfect backdrop. Glide along the lakefront, taking in views of the Field Museum of Natural History, Shedd Aquarium, Soldier Field and Michigan Avenue. Guided Segway training plus the use of a helmet are included. Dress in weather-appropriate clothes with flat, closed-toed shoes.

Cruise through Chicago on this 2-hour Segway Tour. First-time visitors will see major attractions and get a great overview of the city. Those familiar with Chicago will deepen their knowledge with little-known facts and anecdotes. This tour includes tickets to the Skydeck at Willis Tower for incredible views of the lake and skyline. 

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 iconic landmarks on this 2-hour sightseeing tour led by an expert guide. Board a comfortable, large-windowed minibus with a small group of twelve people or less. This ensures an intimate touring experience as you enjoy downtown and some North side neighborhoods. You will have a chance to get out and visit several locations such as the 1888 skyscraper called The Rookery, with its Frank Lloyd Wright designed lobby and the unparalleled skyline views from Museum Campus. Listen as your guide talks about the historical and cultural factors that make Chicago unique. The city tour ends at Millennium Park, home of the famous Cloud Gate sculpture, commonly referred to as "the bean." Opt to upgrade your tour with a popular 75-minute open-top boat tour on the Chicago River that focuses on the city's renowned architecture. Pick-ups from most downtown Chicago hotels are included.

Experience Chicago like never before on this guided, 2.5-hour, small-group Segway tour. Visit popular Grant Park and see famous Buckingham Fountain, with the Windy City skyline as the backdrop. Glide along the lakefront, taking in views of the Field Museum of Natural History, Shedd Aquarium, Soldier Field, Adler Planetarium and Michigan Avenue. Guided Segway training plus the use of a helmet are included. Dress in weather-appropriate clothes with flat, closed-toe shoes.

Spend an evening in Chicago on a Segway tour along the lakefront and through the city's popular parks. You'll enjoy views of the Chicago skyline as you glide from Millennium Park past landmarks such as Shedd Aquarium, the Buckingham Fountain, and Museum Campus.

Experience Chicago like never before on this guided, 2-hour, small-group Segway tour. Visit popular Grant Park and see Buckingham Fountain's breathtaking, evening light show, with an illuminated Windy City skyline as the perfect backdrop. Glide along the lakefront, then witness Chicago's weekly summer fireworks display at Navy Pier from a secret location. Guided Segway training plus the use of a helmet are included. Dress in weather-appropriate clothes with flat, closed-toed shoes.

Soak up the Windy City's festive holiday feel and explore local landmarks with ease on this 2-hour Segway tour in Chicago. Hop onto your Segway and spin through Chicago's Millennium Park to the Loop. With your guide, you'll watch skaters enjoying the ice rink, explore Michigan Avenue and admire festive displays at Macy's department store. See the German Christmas market stalls at Daley Plaza, where locals sip hot chocolate and munch 'bratwurst,' and enjoy the atmosphere beneath the city's Christmas tree. Numbers are limited to eight for a small-group experience.

On a Chicago hop-on hop-off tour, you can enjoy easy transportation around the city to see the sights that interest you most at your own pace. Select the pass you want when booking, and create your own itinerary in Chicago to check out attractions such as the Michigan Avenue, Navy Pier and Millennium Park. Hop off and on the double-decker bus whenever you wish, and listen to narration about the city on board.

Explore the art and architectural highlights of Chicago on a Segway during this 2-hour guided tour. This family-friendly tour takes visitors by the outdoor sculptures, landmark buildings and iconic skyline of the city. Accompanied by educational and informative commentary, this city tour saves you from hours of walking and lets you see all of Chicago's top art and architectural attractions in one tour.

See the landmarks of Chicago's South Side on a 2-hour coach tour through this historic, diverse and culturally-rich neighborhood. Take in views of Jackson Park and the University of Chicago, pause at the foot of the stunning Lake Point Towers then watch the bustling crowd at Navy Pier. Get a glimpse of American history as you explore President Obama's former neighborhood and see the President and First Lady's home; with an optional upgrade, you can finish your trip with a scenic cruise along the Chicago River.

This Chicago grand tour covers four hours of sightseeing with admission to 360 Chicago (John Hancock Observatory). Get oriented to the Windy City on a coach tour that takes you along a scenic route on Lake Shore Drive, and past North Side and South Side highlights including Museum Campus, Lincoln Park, Washington Park, Grant Park and Wrigley Field. Finish on the 94th floor of the Hancock Center, one of Chicago's tallest landmarks, for panoramic views of the Magnificent Mile from the open-air observation deck.

Experience Chicago like never before on this guided, 2-hour, small-group Segway tour. Visit Chicago's 'front yard,' the beautiful lakefront and 57-acre Museum Campus. Glide along the fragrant floral paths and rose gardens of Grant Park to famous Buckingham Fountain. Then travel along the banks of Lake Michigan, past Monroe Harbor to the Museum Campus for a breathtaking view of the city's iconic skyline. Guided Segway training plus the use of a helmet are included. Dress in weather-appropriate clothes with flat, closed-toed shoes.