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Chicago Small-Group City Tour with Optional Architecture River Cruise

Overview
Enjoy Chicago’s famous sights and fabulous views on this award-winning small-group sightseeing tour of the city.
On this tour, you will travel through Chicago with an expert guide in a comfortable minibus, enjoy world renowned architecture including the world's first skyscrapers, Museum Campus (for the BEST skyline view in town), Millennium Park (Home of "The Bean"), Buckingham Fountain, The Magnificent Mile, Lincoln Park, Chicago River, The Gold Coast, Lake Shore Drive and more!
Along the way, your guide will provide historical, informational and at times humorous commentary about the area.
Four photo stops are a part of each tour. The small-group atmosphere with a maximum of 10 people ensures a more personal experience. 

You also have the option to upgrade to include THE most popular Architecture River Cruise in Chicago! For good reason, our partner Shoreline Sightseeing, has been the most booked tour on TripAdvisor for the last 5 years! And yes, there is a bar on the boat.

City: Chicago
Tue 10 Jun
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You can choose the date already on the booking website
Starting at $48.95
Tue 10 Jun
Starting at $48.95
Make a reservation
What's Included
Local guide
Transport by 12-passenger, air-conditioned minibus
Complimentary pickup at most DOWNTOWN CHICAGO hotels. Combination bus and boat tour ends at the boat
Four photo stops
Chicago River Architecture Boat Tour (if option selected)
Additional Info
  • Infants and small children can ride in a pram or stroller
  • Service animals allowed
  • Public transportation options are available nearby
  • Infants are required to sit on an adult’s lap
  • Suitable for all physical fitness levels
  • Operates in all weather conditions, please dress appropriately
  • You MUST contact the local supplier to reconfirm your reservation
What To Expect
1
The Magnificent Mile
Chicago's main shopping street
2
Navy Pier
Popular tourist attraction
3
Millennium Park
The extremely popular home of The Bean, Pritzker Pavillion, Crown Fountain and more. We slowly pass by it on the tour and can drop you off there at the end if you wish.
4
Chicago River
See the Wrigley Building, Tribune Tower, Marina City, the Chicago River and much more at this stop!
5
Clarence F. Buckingham Fountain
One of the most beautiful fountains in the world. It's the fountain seen in the opening credits of Married W/Children!! We stop here when it is on, which is between May and October.
6
Museum Campus
The VERY BEST skyline view and really popular stop!
7
Lincoln Park
1,600 acre park. Home of the Lincoln Park Zoo, beautiful gardens, fountains, sculptures and much more.
8
Gold Coast
Popular nightlife district and upscale residential area. Cool restaurants, The Original Playboy Mansion, brownstones and more!
9
The Rookery Building
One of the world's very first skyscrapers. Frank Lloyd Wright designed the beautiful lobby. It was also used as Elliott Ness' office in the movie The Untouchables and was Duncan's Toy Chest in Home Alone 2 !
10
Chicago Skyline
One of the most beautiful skylines in the world, from the BEST perspective in the city.
11
The Art Institute of Chicago
Home of the second most French impressionist paintings in the world. Also American Gothic, The Picture of Dorian Gray, Nighthawks, and much much more!
12
Shoreline Sightseeing
The most popular tour in the USA, according to Tripadvisor. If this option is selected, you'll enjoy a 75-minute cruise on the stunning Chicago River. Tours can be taken back to back or not. It's your choice.
Show 9 more stops
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Traveler Photos
Reviews (635)
Tony_T
Feb 2025
It wasn’t a very informative tour and we were finished very early - interesting in places but didn’t feel we got a comprehensive tour of the city
Beth_W
Feb 2025
Stay at a hotel that had a pick up stop. It is so convenient. The driver was friendly and very knowledgeable, the photo ops were excellent,
Response from Host
Feb 2025
Thanks for the great review!
Gloria_S
Jan 2025
This is one of the best tours we have been on! It was freezing outside and the mini tour bus was warm and comfortable! Our tour guide, Rick,was great- he knew Chicago very well and he added just the right amount of humor to keep us laughing! We had wonderful opportunities to get out and take in the view, and take pictures. Our driver drove smoothly thru Chicago traffic while telling us everything we wanted to know, and answered all questions we might have. I would absolutely recommend this tour- don't hesitate- just do it!

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