Top Chicago Tours by Duration - page 2

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.

Have only a short stay planned in the Windy City? See the best of Chicago in just half a day on this small-group tour. Following hotel pickup, travel in an air-conditioned vehicle to Skydeck Chicago at the Willis Tower for spectacular city panoramas. Next, head to Millennium Park, go on an architecture river cruise, discover Buckingham Fountain, and more.

Have only a short stay planned in Chicago? Make the most of your time in the Windy City, and see more of the city in less time, when you book a private driving tour of Chicago. Pick between several convenient tour times, and meet your guide and driver directly at your hotel. Over the course of your excursion, you’ll make stops at highlight attractions like the Lincoln Park Conservatory, Millennium Park, and Museum Campus. You’ll also learn about Chicago’s history and can spy other remarkable sights as you go.

Immerse yourself in Chicago’s rich and dynamic African American heritage during this half-day tour. Highlights include interior visit to an African American museum, a stop at the birthplace of gospel music in Bronzeville, and a look at the Obama home in Hyde Park and Jennifer Hudson's childhood home.

Enjoy a memorable, one-of-a-kind night out on Lake Michigan aboard this combination dinner, dancing, and sightseeing cruise. Make your own way to Navy Pier, and set off as the evening begins. You can admire views of Chicago’s picture-perfect skyline as the sun starts to set. While on board, take advantage of the all-you-can-eat buffet dinner, drinks to purchase, a DJ-helmed soundtrack, and even a fireworks display (weather permitting).

Enjoy Chicago’s fireworks in 3D during a 2-hour boat cruise on the Chicago River or Lake Michigan. Capture stunning photos of Chicago’s skyline from the Lake on Saturdays or from the mouth of the river on Wednesdays. Before the fireworks begin, learn about the history of The Windy City as your boat cruises along the waterfront, passing sights including Buckingham Fountain, Museum Campus and the John Hancock Building. Hear informative commentary from your onboard guide about the landmarks, the locks system and more, then sit back with the best seats in the city for the spectacular fireworks show.

Learn about the history and legends surrounding the 1893 Chicago World's Fair and notorious criminal H.H.Holmes on a half-day tour inspired by the popular book ‘The Devil in the White City.’ Explore important locations such as the Prairie Avenue Historic District, Jackson Park, Midway Plaisance Park, and the ‘Murder Castle’ of H.H. Holmes as you learn more about the World's Columbian Exposition and Victorian Chicago.

See the best of the Windy City, all in just half a day—and learn the stories behind its best-known sights—on this private tour. In the morning, meet your driver at your Downtown hotel, hop aboard your private vehicle, and set off with a tour guide in tow. You can look forward to seeing sights like Grant Park, Navy Pier, and Buckingham Fountain—and stopping for photo opportunities along the way.

See Chicago light up with a 4-hour bicycle tour of the Windy City’s most iconic sights and neighborhoods. Follow your guide along a leisurely route, watch the Buckingham Fountain light show and take in daytime or evening views of Millennium Park and the Museum Campus. Sample culinary classics of Chicago, like deep-dish pizza, a true Chicago hot dog, and a tasty dessert for good measure. As you pedal through downtown streets, capture unforgettable images of Chicago’s magnificent skyline then finish your tour in the heart of the city.

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.

Immerse yourself along the Chicago River and admire the astonishing architecture and landmarks that have shaped the Windy City and beyond. Our expert guides will show you Chicago through a new lens and explore this city’s history, architecture, and legacy with you.

Step off the typical tourist trail, and discover one of Chicago’s oldest and most scenic neighborhoods, on this walking tour of the Prairie District. Meet your guide in the morning at the Chicago Athletic Association, and set off with just a small group for company. The Prairie District is just a short L ride away; you can look forward to seeing the Second Presbyterian Church, Glessner House, Motor Row, and otherwise discovering how Chicagoans lived at the turn of the 20th century.

Get an insider’s look at the Windy City’s most iconic monuments during this 3-hour private tour. Travel through Chicago aboard a private vehicle as you discover some of the city’s top neighborhoods, including the Loop, River North, the Magnificent Mile (along Michigan Avenue), Streeterville, the Gold Coast and much more. Your private driver-guide and vehicle, bottled water and round-trip hotel transport are all included.

Foodies will enjoy this tour of Chicago that focuses on one of the city’s most popular dishes: pizza. Although your guide can’t tell you once and for all whether Chicago or New York has the best pizza in the USA, they will teach you about Chicago’s ten different types of pizza, let you sample four, and give you exclusive access to pizza kitchens. A fun tour for all pizza lovers.

Most people have to decide between a boozy Sunday and a river cruise. During this special boat ride in Chicago, you get the best of both worlds. Enjoy a range of mimosas and other brunch drinks for purchase as you cruise down the Chicago River. Enjoy front-row seats as you pass by iconic skyscrapers and other downtown landmarks, with staff available to answer your questions.

Explore Chicago like a local—and visit the city’s distinctive, characterful neighborhoods, in addition to its major landmarks—on this Half-day tour. Set off from downtown with just a small group for company, and leave the driving to your guide—you’ll explore dozens of Windy City neighborhoods, from Hyde Park and Bronze Ville to Lincoln Park and the Gold Coast. Learn all about Chicago culture and history as you go.

One of Chicago’s earliest and most vibrant areas, this cultural melting pot is made up of multiple historic neighborhoods and bustling avenues. Immerse yourself in the sights and sounds of its tree-lined streets filled with galleries, local shops, award-winning restaurants, and stunning architecture all unique to this enclave of the city. Featured on the tour is the longest continually operating settlement house in the country, local art, shops, and a walk through a historic mansion-filled neighborhood.

Discover the architectural splendor of downtown Chicago—and learn all about the city’s early skyscrapers, urban planning, and modern history—on this small-group tour. Meet your guide in the morning on Michigan Avenue and set off by foot and by L train. You’ll see world-renowned landmarks like the Rookery Building, will visit the Chicago Cultural Center to admire the world’s largest Tiffany dome, will explore the Fine Arts Building, and much more.

Pedal through Chicago’s scary heritage with a 3-hour Halloween bike tour that includes hauntings, tragedies and overflowing cemeteries. Experience the creepiest parts of the city as you follow your professional actor guides through the Halloween streets, and watch them bring Chicago’s ghosts to life. Learn about the infamous ‘Resurrection Mary,’ figure out why the Levee District is so famously haunted, and hear the story of H.H. Holmes, Chicago’s most notorious serial killer.

Stroll through Chicago's winter streets, lit up for the holidays, on this gourmet walking tour. Learn about Chicago's celebrated holiday traditions like the European-inspired Christkindlmarket, the beautiful decor and windows on State Street, and ice skating at Millennium Park. Sample generous tastes of classic Chicago foods and holiday treats as you walk. Seasonal craft beer tastings help you stay warm and toasty; please note this tour operates in all weather conditions, so dress appropriately.

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.

Set sail on Lake Michigan aboard a luxury yacht for a gourmet dinner cruise with views of the Chicago fireworks display. During the 3-hour cruise, the crew serves a 3-course plated meal with dishes prepared by your onboard chef. You can enjoy the stylish interior of the rooftop lounge, dance to DJ entertainment, or relax and soak in the views of the Chicago skyline.

It isn’t a trip to Chicago without tasting deep-dish pizza—and this private tour for food lovers will introduce you to true Chicago-style pizza, plus other Windy City specialties. Meet your guide downtown, and be sure to come hungry: You’ll eat hot dogs, Italian beef sandwiches, pizza, donuts, and more. Along the way, see highlights like the Wrigley Building and Magnificent Mile, and learn more about the city’s history and culture.