Insider's Guide to Chicago

Major attractions, tips and our top things to see and do.

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Tour code: 5538MINI
Explore Chicago's iconic landmarks on this 2-hour sightseeing tour led by an expert guide. Board a comfortable minibus with a small group of twelve people or less, ensuring an intimate experience, and ride through the city stopping at locations like the Loop and the Willis Tower (formerly the Sears Tower). Listen as your guide talks about the historical and cultural factors that make Chicago unique. Opt to upgrade your tour with a 1-hour open-top boat tour on the Chicago River that focuses on the city's renowned architecture. Round-trip transportation from select Chicago hotels is included.


  • Chicago sightseeing tour by luxury mini-coach
  • Stop for three picturesque photo opportunities and travel through 'the Loop,' Chicago's downtown area
  • See the Willis Tower (formerly known as the Sears Tower) and Millennium Park
  • Get historical insight about Chicago from your guide!
  • Tour handouts available in Spanish, French and Italian
  • Upgrade to include a boat tour on the Chicago River!
  • Small-group tour limited to 12 passengers ensures a more personalized experience

Recent Photos of This Tour

What You Can Expect

Chicago City Tour with Optional River Cruise

Birds eye Chicago

After pickup from your Chicago hotel, board your climate-controlled minibus with a small group of twelve people or less. Embark on a sightseeing tour which has won Chicago's Concierge Preferred award several years running. French-, Spanish- and Italian-language handouts will be provided upon request.

Listen to historical and informational commentary from your guide as you admire the world's first skyscrapers in downtown Chicago, known as ‘the Loop’. Take in panoramic views of Lake Michigan and other sights through the oversized windows on the minibus.

Drive through several Chicago neighborhoods like Gold Coast and Lincoln Park to get a feel for daily life in the city. Make photo stops at Museum Campus, which boasts the best view of the Chicago skyline, and other locations like the Willis Tower and Millennium Park. Please see the Itinerary section for a full list of attractions visited.

Optional Upgrade:
For more sightseeing by water upgrade your tour to include a boat ride down the Chicago River. This 60-minute open-top boat tour provides an in-depth look at the architecture of Chicago. Additionally, learn about the role the river has played in the city’s history.

After your tour, enjoy drop-off at selected Chicago hotels.


Chicago sights visited include:
  • Lincoln Park
  • Chicago River
  • Zoo gardens
  • Museum Campus
  • The Willis (Sears) Tower
  • Millennium Park
  • The Magnificent Mile
  • Hugh Hefner's Original Playboy Mansion
  • The Water Tower
  • Navy Pier

Customer Reviews

Kenneth P

5 star rating: Highly Recommended June 2016

Both the bus and fiver tour exceeded our expectations. Very informative with an interesting presentation. Victor was especially good on the architectural Boat Tour. His passion for architecture enhanced the tour

Teresa M T

5 star rating: Highly Recommended June 2016

Awesome! This two hour tour was a very nice informative tour without a big crowd. For anyone traveling who wants a smaller more intimate tour, this is the tour. This was our second day in Chicago so this tour was the kick off to our week long vacation. The sky line pictures we took were awesome, museums, monuments, stores and the restaurants.

What we loved the best about this tour was a smaller crowd so we were able to hear the tour guide with no interruptions. The door-to-door service was also a plus. I truly enjoyed booking through Viator.

I would also like to note that the customer service at Viator is the best. I had the pleasure of speaking to Deborah on 5/18/16 and she was so helpful with correcting my dates and noting I was traveling with my disabled mother, she called to confirm the times of pick-up and drop off, which was so thoughtful. She went above and beyond to help us and I truly appreciated her kindness. Viator will definitely be our tour of choice when we return to Chicago again.

Teresa T.

sheila m

5 star rating: Highly Recommended June 2016

We took your tour the first day of our visit and used the introduction all week long. Our driver was very knowledgeable and full of good humor. The stops were good photo ops and refreshing. I highly recommend the tour as a great overview.

Erika B

5 star rating: Highly Recommended June 2016

Amazing tour, knowledgeable tour guide, and what a beautiful city!

Joy W

5 star rating: Highly Recommended June 2016

Very informative. Paul was an excellent guide!

Mary Ellen P

5 star rating: Highly Recommended April 2016

The tour was excellent. Ray was our tour guide and did an awesome job. He kept us laughing with his jokes and was very informative. Only wish was that we could have stopped for photos at the bean. Would highly recommend this tour!


5 star rating: Highly Recommended April 2016

Just the right length. Our amusing guide made the time fly!

Jennifer V

5 star rating: Highly Recommended February 2016

If your not familiar with the city and how to get around to see the amazing architecture then this is the way to go.. our driver was very nice and informative about the city and its history

Barbara P

5 star rating: Highly Recommended November 2015

Fabulous driver, Great narration, on time pick-up, and special consideration for my 94 year old mother on the tour--What more could I ask for!

Stuart J

5 star rating: Highly Recommended October 2015

Brilliant. Very entertaining guides on both the bus and the river cruise. We chose to do the optional river cruise as well and it was fantastic. Both tours are well worth the money

From USD $ 36.99

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