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

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

Arelis R

5 star rating: Highly Recommended September 2015

We were delayed in our arrival to Chicago and could not make it as scheduled. I called the contact number and met with no problem in changing the tour for the next day. Our guide Bill was very knowledgable, and fun. His tour bus was comfortable and clean. We toured the entire city and he gave us a good orientation as to where everything was with important history references. He dropped us by the river terminal where we took our architectural cruise. Our guide was so passionate about all the buildings' history, and how they came to be that it was impossible not to enjoy everything he had to say. It was a great tour and we highly recommend it!

Kim S

5 star rating: Highly Recommended August 2015

Great tour guide. Very knowledgeable. Friendly.

Mary H

5 star rating: Highly Recommended August 2015

As first time visitors to Chicago, my husband and i really enjoyed and appreciated the bus tour and the river cruise. We were only in town for three days one of which was to be spent at Wrigley Field!, so this gave us to see a lot in a short period of time. The river architectural cruise was absolutely fantastic!

doris w

5 star rating: Highly Recommended July 2015

great tour

Patricia E

5 star rating: Highly Recommended June 2015

Informative, entertaining and thoroughly enjoyed by all four of us!

From USD $ 36.99

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