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Inside Chicago Walking Tours

Closed Now: 10:00 am - 6:00 pm
Open today: 10:00 am - 6:00 pm
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  • Excellent95%
  • Very good3%
  • Average0%
  • Poor1%
  • Terrible1%
Travellers talk about
“the loop”(144 reviews)
“open your eyes”(46 reviews)
“great tour”(76 reviews)
Walking tours that delight visitors with the "second side of the Second City," with gorgeous, fascinating, and often hidden details behind many doors. Get to know Chicago through its real-life stories: the explorers, settlers, architects, business...more
Closed Now
Hours Today: 10:00 am - 6:00 pm
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109 S Michigan Ave, Chicago, IL 60603-6110
Downtown / The Loop
+1 312-799-0164
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Reviews (1,034)
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All reviews the loop open your eyes great tour inside buildings small group highly recommend this tour architectural details two hours river north booked this tour wealth of knowledge interesting facts architecture tour great city hillary dazzling gems
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1 - 10 of 1,020 reviews
Reviewed 1 week ago

Tour guide, Hillary, toured us through 5 historic downtown high rises, each with a dazzling interior. Hillary had connections in some of the buildings for extra-special viewing opportunities. Her engaging personality made historical facts fun and she had a wealth of knowledge and trivia to...More

Date of experience: February 2019
Thank KimKn4
Reviewed 2 weeks ago via mobile

If you enjoy architecture, this is the tour for you! Hillary is very knowledgeable, very enthusiastic and very friendly. Lots of hidden gems on this tour that you may have a hard time finding by yourself. Highly recommended!

Date of experience: February 2019
Thank ivom472
Reviewed 12 January 2019 via mobile

We really enjoyed our tour with Hillary. She is friendly and her enthusiasm for the history and architecture of Chicago is infectious. It was great to see the lobbies and interiors of some of the earliest skyscrapers, we never would have known where to look...More

Date of experience: November 2018
Thank Jac B
Reviewed 11 January 2019

A really interesting way to explore the city. Well paced, guide "Adam" was entertaining, full of fantastic facts, highly recommended!! We only wished we could have done them all!!

Date of experience: September 2018
Thank Trekkerz23
Reviewed 3 January 2019

It was wonderful getting to be a part of this tour. We were enlightened with the details of the buildings and their architecture in the Loop. This experience left us in awe of the history and details that went into the construction and inspiration behind...More

Date of experience: November 2018
Thank Sonia Q
Reviewed 1 January 2019 via mobile

We often participate in walking tours. You should put this on your list of things to do when you visit Chicago. Hilary is a great guide. The tour is informative and insightful. A most enjoyable 2 hours discovering the jewels and vaults of the city....More

Date of experience: December 2018
Thank BarkerSJ
Reviewed 30 December 2018 via mobile

Today we participated in a small walking tour of Chicago and saw a side of the city we never expected to see. Our guide Hilary was both enthusiastic and well informed opening a door to the jewels of the city and indeed the vaults. We...More

Date of experience: December 2018
Thank stephenbW5580KE
Reviewed 26 December 2018

Hillary took us through interiors of several lobbies that we would never have seen or known about. She is a delightful guide that, as far as I can tell, knows everything there is to know about these buildings. My favorite was the Board of Trade...More

Date of experience: October 2018
Thank Brooks G
Reviewed 22 December 2018

Very nice walking tour, interesting spots you otherwise would not have found. Very nice guide. Small diverse groups make it personal. An architectural tour is a must for Chicago. Easy and fast online booking.

Date of experience: September 2018
Thank Pfendt
Reviewed 21 December 2018

Hillary is a great tour guide and this is an excellent tour. She is engaging, knowledgeable, and made the tour interesting and fun. It's definitely different from the usual tours. We saw several "secret" things and hidden treasures that I never knew existed, despite them...More

Date of experience: December 2018
Thank Michelle M
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Questions & Answers
Ask a question
24 June 2018|
AnswerShow all 2 answers
Response from Hillary M | Property representative |
Hello! I actually just had a woman on my tour yesterday who had a baby strapped to her back the whole time, and it was not a problem. Every once in a while I'll get a guest using a stroller, which is not a problem (though... More
24 June 2018|
AnswerShow all 3 answers
Response from jbutlerriskmanag2018 | Reviewed this property |
If it will fit in with her/his eating schedule and you have her/him in a carrier. I don’t think you’d enjoy pushing a stroller around on this. There are some stairs involved.
14 March 2018|
AnswerShow all 2 answers
Response from Donna W | Reviewed this property |
I found the tour on Groupon. There is a fee, $20.00 for seniors. Check out their website at insidechicagowalkingtours