ShowingFilter 1-20 of 20 listings.
Chicago Segway Art and Architectural Tour
$ 70
2 Hours Segway Tours
Free Cancellation
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.
View Tour
2.5-Hour Cupcake Tour Of Chicago
$ 25
2 Hours 30 Minutes Food Tours
Free Cancellation
Visit the best dessert boutiques along the Magnificent Mile in Chicago on a 2.5-hour cupcake tour led by a guide. Skip-the-line access and all cupcakes are included as you visit up to five bakeries. You'll also see landmarks like the Wrigley Building, Water Tower Place, John Hancock Center, and the Chicago River, and hear commentary about Chicago from your guide.
View Tour
Private Chicago Architecture Tour
$ 660
3 Hours Private Sightseeing Tours
Hotel Pickup Offered Free Cancellation
Ever since Chicago became the birthplace of the modern skyscraper, the city has been renowned for its architectural creativity and ingenuity. Led by an expert guide, explore some of the city's most iconic buildings such as Sears Tower, The John Hancock Building, historic brownstones, and the homes of Oak Park designed by beloved architect Frank Lloyd Wright. You will be able to explore the insides of some locations on this completely customizable tour.
View Tour
Historic Chicago Walking Bar Tour
$ 38
2 Hours 30 Minutes Walking Tours
Explore downtown Chicago on a pub crawl with an educational twist! Your expert guide shares entertaining facts about the history of jazz, theater, social clubs, and the Prohibition era in the Windy City as you take in historic buildings and architecture. Use iPads to view historic photos and videos that accompany your guide's stories as you stop in both famous and hidden bars for drinks and appetizers. A short walk allows plenty of time to see Chicago's famous architecture and pubs on this tour "“ great for visitors and locals alike!
View Tour
Chicago Lakefront Neighborhoods Bicycle Tour
$ 46
3 Hours Bike & Mountain Bike Tours
Free Cancellation
Pedal past the lakefront neighborhoods of Chicago's North Side on this 3-hour 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.
View Tour
Cultural Mile Walking Tour of Chicago
$ 30
2 Hours Walking Tours
Free Cancellation
Discover the sights and sounds of Chicago's various cultural scenes on a 2-hour walking tour. The 1.5-mile route covers music, literature, art, and architecture within the Windy City. Hear insider stories about Chicago's cultural movements and visit little-known locations linked to iconic artists. Be sure to have your camera ready for the pièce de r esistance, the Tiffany stained glass dome at the Chicago Cultural Center.
View Tour
Best in Chow: Chicago River North Food Tour
$ 57
2.30 to 3 Hours Food Tours
Free Cancellation
Go beyond deep-dish on this 3-hour culinary walking tour of Chicago, which includes five tastings of classic Windy City cuisine. Navigate the endless options of downtown dining with a guide who can provide insight into the best food Chicago has to offer, and skip the lines and the wait with VIP access to popular restaurants.
View Tour
Chicago Crime and Mob Tour
$ 40
1 Hour 30 Minutes Historical & Heritage Tours
Free Cancellation
Explore Chicago's gangster past on this 1.5-hour mafia tour in a coach vehicle. Drive around the Windy City to see where Al Capone, The Untouchables, Hymie Weiss, and John Dillinger, among other thugs hung out. A history-savvy guide introduces you to some of the most storied locations of Chicago's criminal past, including Holy Name Cathedral, Biography Theatre, and the site of the bloody St. Valentine's Day Massacre. You'll be able to get out and pose for pictures in front of a historic courthouse, among other infamous sites.
View Tour
Private Chicago Highlights Driving Tour
$ 99
3 Hours Private Sightseeing Tours
Hotel Pickup Offered
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.
View Tour
City Sightseeing Chicago Hop On Hop Off Tour
$ 37
1 to 3 Days Hop-on Hop-off Tours
Free Cancellation
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.
View Tour
Chicago City Minibus Tour with Optional Architecture River Cruise
$ 37
2 Hours Half-day Tours
Hotel Pickup Offered Free Cancellation
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.
View Tour
Chicago Grand Tour and Admission to 360 Chicago (formerly John Hancock Observatory)
$ 65
4 Hours Bus & Minivan Tours
Free Cancellation
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.
View Tour
Chicago Grand Half-Day Tour
$ 50
4 Hours Bus & Minivan Tours
Free Cancellation
Get the perfect introduction to the wealth of sights in the Windy City during this 4-hour Chicago day tour. Discover the many landmarks spanning both the city's North Side and South Side, enjoying a scenic ride along Lake Michigan on Chicago's Outer Drive along the way. You'll also have the chance to admire the city's Washington and Grant Parks, explore inside the Lincoln Park Conservatory, see Adler Planetarium and visit the iconic Wrigley Building. This Chicago in a half day tour also includes transport between all sites and tour narration.
View Tour
Chicago Holiday Lights Tour by Segway
$ 70
2 to 2.15 Hours Segway Tours
Free Cancellation
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.
View Tour
Chicago North Side Tour
$ 32
2 Hours Bus & Minivan Tours
Free Cancellation
Explore the North Side of Chicago on this guided sightseeing tour by coach. During this 2-hour tour, experience the bustle of the Loop, the central business district and one of the financial centers of the country. Visit State Street, an important thoroughfare in Chicago's history and the Magnificent Mile along Michigan Avenue. Learn about the history and culture of the city from your local guide; upgrade your tour to include a Chicago River cruise.
View Tour
Viator VIP: Willis Tower Skydeck Early Access, Trolley City Tour and Chicago River Cruise
$ 124
6 Hours Free Cancellation
See Chicago from several angles, including the 103rd floor of Willis (Sears) Tower, where you have early access to the Skydeck. This Viator VIP package "” available nowhere else "” provides a crowd-free morning overlooking city landmarks from glass-enclosed balconies. Follow up your vista with a 2-hour narrated trolley tour past Grant Park, the John Hancock Center, the Wrigley Building and more. Finish with an afternoon cruise on the Chicago River and enjoy a complimentary drink as you discover the city's distinctive skyscrapers from an architecture-savvy guide.
View Tour
Chicago City Lights Segway Tour
$ 65
2 Hours Segway Tours
Free Cancellation
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.
View Tour
Chicago City Hop-on Hop-off Tour
$ 31
3 Days Hop-on Hop-off Tours
Free Cancellation
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.
View Tour
Underground Donut Tour - Chicago's First Donut Tour
$ 30
2 Hours Walking Tours
Free Cancellation
Sample some of the Windy City's tastiest donuts on this 2-hour Underground Donut Tour, celebrating the magic of Chicago's tastiest sugar-filled concoctions. Donut-lovers are sure to enjoy this visit four of Chicago's tastiest donut purveyors, offering a chance to savor all of your favorite varieties, on the city's only donut-themed excursion. All tastings are included, and gluten- and nut-free options are also available.
View Tour
Chicago Holiday Lights Trolley and Christmas Market Tour
$ 28
1 Hour 30 Minutes Christmas
Free Cancellation
Celebrate the holidays in style during this 90-minute excursion, featuring a trolley tour of Christmas lights at some of Chicago's most famous sights, followed by a shopping trip to the German-themed Christkindlmarket. See Lincoln Park, Daley Plaza and Michigan Avenue adorned with lights for the holiday season. Then find something for the important people on your list at the Christkindlmarket, a German-tinged Christmas offering unique gifts and fun-filled activities for the whole family.
View Tour