Eat, drink and learn about Chicago's entertainment history with appetizers, beer or wine, and beautiful historic architecture.
Join us for a historic Chicago pub crawl with an educational twist! You’ll explore Chicago’s entertainment history and learn about prohibition, jazz, theater, vices, and social clubs. In addition to the tour guide’s stories, guests interact with historic photos and videos on shared iPads to connect with Chicago’s party past.
Our evening walking tour stays mostly indoors, making it great for any kind of weather. We’ll enjoy our appetizers and choice of wine or beer at three drink stops and explore history and architecture in between. In addition to bar stops, our groups see magnificent lobbies, Gilded Age mansions, and Chicago’s multiple underground layers.
Who comes on a historic pub crawl tour of Chicago? Many tour guests enjoy the tour’s fun and social dynamic. Solo travelers often join us. As a great Chicago date idea, it can be a fun thing to do in Chicago with your boyfriend or girlfriend. Groups of friends make the tour into a cool weekend event, too. Family groups love it!
This tour more than a historic Chicago pub crawl – you’ll eat, drink, and learn about architecture, Prohibition-era history, and party culture.
We’d like to say it’s a Speakeasy Tour or a Chicago Prohibition Tour, but truthfully very few bars in Chicago remaining today were ever speakeasies. We did find one stop on our tour that was a true speakeasy though, and an early Chicago jazz club to boot!
Who wants to listen to a volunteer tour docent rambling dates and names? Don’t fret with us – our tour guides are highly trained, smart and fun! We are proud to be a top-rated Chicago tour company, with five-star ratings on Yelp and TripAdvisor.
The Historic Chicago Bar Walking Tour is like a mix of a food tour, an architecture walking tour, and a mobile documentary film. Book your tour early as the historic Chicago pub crawl often sells out. It’s a unique Chicago thing to do this summer!
Reservations are $34 per person. Guests bring cash for beverages. Total cost is $37-54 per tour guest inclusive of tour, food, beer, wine, gratuities, taxes.
Drinks and server gratuities. All guests must choose a beverage for the walking tour and bring cash to cover 2.5 servings of beer ($23), wine ($29), soda ($8) or water ($3).
Walking distance: 1.2 miles
Link to the meeting point map:
https://www.google.com.my/maps/place/Fannie+May/@41.8880344,-87.626475,17z/data=!4m5!3m4!1s0x880e2caedb378317:0x27ecb374ec7d52e8!8m2!3d41.8880344!4d-87.6242863?hl=en
Tour starts at Fannie May Candies, 343 N. Michigan Ave.
Tour ends at the Intercontinental Hotel, 505 N. Michigan Ave.
Map above is necessary to locate tour meeting point.
We hope you can join us!
You will get
100% refund if cancel 7 days before tour starts.
80% refund if cancel within 6 days before tour starts.
50% refund if cancel within 5 days before tour starts.
NO refund if cancel within 3 days before tour starts.
You will be refunded for all costs EXCEPT Processing Fees.
Guests can get full refunds at any time of cancellation prior to the actual date of the tour if that cancellation is due to a Force Major reason. Force Major reasons include but are not limited to war, civil insurrection, strikes, volcanoes, extreme weather, earthquake, and natural disasters.
Eat, drink and learn about Chicago's entertainment history with appetizers, beer or wine, and beautiful historic architecture.
Join us for a historic Chicago pub crawl with an educational twist! You’ll explore Chicago’s entertainment history and learn about prohibition, jazz, theater, vices, and social clubs. In addition to the tour guide’s stories, guests interact with historic photos and videos on shared iPads to connect with Chicago’s party past.
Our evening walking tour stays mostly indoors, making it great for any kind of weather. We’ll enjoy our appetizers and choice of wine or beer at three drink stops and explore history and architecture in between. In addition to bar stops, our groups see magnificent lobbies, Gilded Age mansions, and Chicago’s multiple underground layers.
Who comes on a historic pub crawl tour of Chicago? Many tour guests enjoy the tour’s fun and social dynamic. Solo travelers often join us. As a great Chicago date idea, it can be a fun thing to do in Chicago with your boyfriend or girlfriend. Groups of friends make the tour into a cool weekend event, too. Family groups love it!
This tour more than a historic Chicago pub crawl – you’ll eat, drink, and learn about architecture, Prohibition-era history, and party culture.
We’d like to say it’s a Speakeasy Tour or a Chicago Prohibition Tour, but truthfully very few bars in Chicago remaining today were ever speakeasies. We did find one stop on our tour that was a true speakeasy though, and an early Chicago jazz club to boot!
Who wants to listen to a volunteer tour docent rambling dates and names? Don’t fret with us – our tour guides are highly trained, smart and fun! We are proud to be a top-rated Chicago tour company, with five-star ratings on Yelp and TripAdvisor.
The Historic Chicago Bar Walking Tour is like a mix of a food tour, an architecture walking tour, and a mobile documentary film. Book your tour early as the historic Chicago pub crawl often sells out. It’s a unique Chicago thing to do this summer!
Reservations are $34 per person. Guests bring cash for beverages. Total cost is $37-54 per tour guest inclusive of tour, food, beer, wine, gratuities, taxes.
Drinks and server gratuities. All guests must choose a beverage for the walking tour and bring cash to cover 2.5 servings of beer ($23), wine ($29), soda ($8) or water ($3).
Walking distance: 1.2 miles
Link to the meeting point map:
https://www.google.com.my/maps/place/Fannie+May/@41.8880344,-87.626475,17z/data=!4m5!3m4!1s0x880e2caedb378317:0x27ecb374ec7d52e8!8m2!3d41.8880344!4d-87.6242863?hl=en
Tour starts at Fannie May Candies, 343 N. Michigan Ave.
Tour ends at the Intercontinental Hotel, 505 N. Michigan Ave.
Map above is necessary to locate tour meeting point.
We hope you can join us!
100% refund if cancel 7 days before tour starts.
80% refund if cancel within 6 days before tour starts.
50% refund if cancel within 5 days before tour starts.
NO refund if cancel within 3 days before tour starts.
You will be refunded for all costs EXCEPT Processing Fees.
Guests can get full refunds at any time of cancellation prior to the actual date of the tour if that cancellation is due to a Force Major reason. Force Major reasons include but are not limited to war, civil insurrection, strikes, volcanoes, extreme weather, earthquake, and natural disasters.
Ash T
2019-08-31 11:54:08
"Fun, interactive and super educational tour!" My husband and I live in Chicago but like to go on tours occasionally to learn fun new facts about our city. We ended up going on the 1893 World's Fair tour, with Elizabeth as our tour guide, and had...
Valerie M
2019-06-04 14:43:42
"These people really know what they are doing" This was a fun, interactive, and interesting way to check out the Fulton Market neighborhood in Chicago. I had actually lived in this area for about a decade, and was impressed by how much they had...
Leslie W
2019-05-06 10:36:40
"Monadnack Building Plus" We took a short walking tour of the historic preservation of the Monadnock Building with a most knowledgeable guide. We learned the difference between renovation and restoration, the fascinating...
Ann W
2019-04-24 11:08:45
"Super Tour" Had a super tour with Alex. He provided a great amount of information. Learned some interesting facts about the sights and history of the buildings we toured or passed by. Alex used a couple of quiz...
Karen M
2019-02-03 07:14:49
"Interior Loop Tour" An excellent tour led by a very knowledgeable guide, Marie. What made this tour different from other tours I’ve been on was the interactive nature of the tour. While seeing sights I know well I not...
Relax40106931211
2019-01-30 04:17:25
"Worth it even in the winter" Our tour guide had just enough energy to keep you engaged. I learned a lot and got to see some sites I’d never seen or noticed.
MarshallL114
2019-01-29 04:33:50
"Excellent tour!" Mostly indoor tour in January in Chicago! Perfect! Our tour guide, Elizabeth, was both knowledgeable and very enthusiastic! Highly recommended!
Roving08894519782
2019-01-24 13:45:28
"Pedway Tour" I thought this tour was going to show more of the Pedway system than it did, and I didn't realize we would be walking outside at all, but I enjoyed it. I've been on a few other Chicago architecture...
HKIdaho1
2019-01-09 06:39:03
"Fun Detour" We had a great time seeing some hidden gems of the city. This tour did not talk about H. H. Holmes, but did go into the history of the 1893 World’s Fair quite a bit. I did like the games. Quite...
Curious08836092098
2019-01-09 05:45:35
"Insightful and Engaging Tour" Our tour guide was wonderful and she was so insightful. I have lived in Chicago most of life and somewhat knowledgeable about the history of my city. Not after this tour, I learned so many cool...
Ken S
2019-01-09 05:11:51
"Great Tour" Everyone is our group was really delighted with the interior loop architecture tour we attended last weekend. The guide was knowledgeable and the content fascinating.
Coastal11092
2018-12-25 17:16:55
"Great experience!" Alex was a great guide and a wealth of knowledge. I live in Chicago and was blown away by how much I learned. I also took family from out of town and they thoroughly enjoyed it too!
Explore67841206936
2018-12-25 06:59:37
"Great tour for a first timer." This was the first walking tour my wife and I had ever gone on. We've been to Chicago many times but have never taken the time to do something like this. I can definitely say we'll be back for more...
jean4666
2018-12-24 08:45:29
"Enjoyed this tour of downtown Chicago with our family" We took this architectural- pedway tour of the loop area with our family. We enjoyed all the tips and information which our tour guide, Elizabeth shared and our teenage and young adult sons enjoyed...
Krista R
2018-12-14 11:40:51
"Highly recommend Chicago Detours!" We at the Institute of Design do a custom neighborhood tour annually with Chicago Detours as a recruitment tour for prospective graduate students. Amanda has designed several custom tours to appeal...
Venture475039
2018-12-12 02:26:50
"Great date night’" Such a nice tour! Learned so much about the places we walk by everyday! Thank Marie for making Chicago even more awesome!
Sightseer42020148729
2018-12-11 05:33:10
"Chicago Detours was great!" Our very friendly and knowledgable tour guide gave us a great insight into many details of Chicago architecture during this delightful two-hour walking tour. Highly recommended for anyone that wants...
Philip M
2018-11-12 11:21:48
"Great team building activities" My office has done a few tours with Chicago Detours as a private group outing and had a great time with them. Besides the culture and history aspects, we also love the scavenger hunt that got built...
DayTrip68314491284
2018-11-10 09:28:09
"Walking tour" The guide spend time showing videos, and we visit too few buildings. Otherwise she was competent and explained clearly .
Nomad113927
2018-11-09 05:38:42
"Best way to see the city!" I've been on a couple of team-building tours with Amanda at this point, and loved every minute. A great way to get our team out of the office and bonding over some drinks and fun facts. We saw some...
Terra M
2018-11-06 05:22:09
"architectural tour" This tour was excellent, My guests were from Baltimore and thought the tour was very well done and the guide was well informed. He answered all our questions. I would highly recommend this company...
Lydia W
2018-11-01 06:03:21
"Not your average!" We took the Historic Chicago walking bar tour. It was ideal for our family, including older members who don’t fancy too much walking or need a regular break. The bars visited were varying and...
sedelman2018
2018-10-22 02:00:48
"Great tour!" Very enjoyable, knowledgeable guide and reasonably priced. Tour covered several classic buildings and also several pieces of outdoor art. Stories were so interesting, I thought I knew a lot about...
joeleaht
2018-10-20 07:40:46
"Nice tour for the subjects covered" My wife and I recently took Chicago Detour’s Loop Interior Architecture Walking Tour with Pedway. We enjoyed that it was partially indoors so that we were out of the cold and wind. Our tour guide had...
ThatGuy1004
2018-10-17 07:54:11
"Best Tour we had while in Chicago" Best Tour we had while in Chicago. Our tour guide new quite a bit of information and the games did help keep us engaged. I only wished we had a bit more time for the games. We had to rush through...
IdahoGlt
2018-10-15 15:59:12
"Best tour we did in Chicago" This was an awesome, fun, interactive tour that I loved. It was very well done and our tour guide was so informative about the topics. We did the 1893 World's Fair Tour and it was great!
lisaaa2016
2018-10-10 05:25:21
"Not worth the time and money" While the tour guide was very nice and a good speaker, the tour itself is lacking. Part of the tour was outside construction, but we were supposed to imagine what it used to be (?) and we spent time...
jmiller114
2018-10-09 07:32:48
"History and Beer! Perfect!" Very informative yet fun. History for some can be a bit boring but not this way. Great guide-Megan, who was knowledgeable yet light hearted. Highly recommend!
dholkest
2018-10-08 18:20:32
"Great tour with lots to discover and learn about" We had a great time and really enjoyed our tour guide. The tour was informative and fun, and we learned a lot about some of the buildings history and got a great taste of the Pedway.
mcarnaghan
2018-09-29 05:50:12
"Great walking tour with food" Thoroughly enjoyed walking tour of Old Polonia and Wicker Park. Covered charges throughout last century to the areas, and great food.our guide fun and knowledgeable. I loved hearing and seeing about...
Micharmour
2018-09-25 12:25:39
"Architectural walking tour" Marie was awesome!!!. Knowledgable, kind, funny, and helpful ! Had fun, learned a lot. Saw some real highlights. Can’t wait to come back to Chicago for a extended amount of time. Highly recommend...
Rachel S
2018-09-22 09:44:08
"Loop interior architecture tour " Marie was fantastic!! Loved this tour. Educational and fun at the same time. Got to see many hidden gems.
Plou727
2018-09-06 18:31:30
"Eyes Opened on the South Side" My family arranged a private tour for my 65th birthday: A mix of Bronzeville, Back of the Yards, Bridgeport, and Hyde Park (2 bars and food included). Amanda opened our eyes to neighborhoods we...
jcarterw00d
2018-08-19 17:46:41
"Informative and entertaining" We had only a few days in Chicago and wanted to learn a bit more about the local architecture, so we took the "Best Architecture Tour for Design Lovers" offered by Chicago Detours, and we really...
Deanna C
2018-08-04 18:13:20
"Custom Tour of Marina City" We had oringally inquired with Chicago Detours (Amanda) regarding a tour of Marina City only a week or two before a business trip to Chicago. Even though this particular landmark wasn’t offered in...
suzannebrady
2018-08-03 15:25:43
"Brilliant " We did the pedway and loop architecture tour with Marie and it was superb. Marie was very engaging and incredibly enthusiastic which all made this walking tour a real treat. It was interactive with...
HJGB502
2018-07-20 15:15:42
"Wonderful learning experience!" Alex led us on the Best Architecture Walking Tour for Design Lovers. We learned so much and had great fun with his back and forth participative style. He related each building to its place in history...
TeamSmith7
2018-07-19 10:48:02
"Terrific architecture tour" Loved the deep-dive approach. Marie was so knowledgeable and really made the experience for us. We learned so much history about the city. Seeing the blend of form and function, old and new...
Ann Marie d
2018-07-03 04:36:43
"So much fun!" Excellent way to see Chicago and have fun doing so! The tour was great and I didn’t want it to end! They made it easy to learn how to ride and be safe.
Mona C
2018-06-22 14:05:53
"Best Architecture Walking Tour for Design Lovers" I have now taken two walking tours with Chicago Detours, and both were superb! Alex was an energetic, knowledgeable, very likable tour guide. The presentation of information was clear and...
Sebastian I
2018-06-18 14:45:09
"Loop Architecture With Pedway" Morgan was our guide, she was excellent! Very well informed, she had answers to all questions and gave us extras along the way. There were eight of us total. We stayed mostly inside, used iPads that...
Tobi-Velicia J
2018-06-17 10:04:48
"Fun Tour!" My son and I really enjoyed this tour. Although we are frequently in and about the Wicker Park neighborhood, we learned interesting facts that we didn’t know. Amanda was a very friendly and...
Tavinator
2018-06-17 08:18:53
"Delightful Walking Tour" Tour guide Morgan did a wonderful job introducing me to the wonders of Noble Square and Wicker Park. Learned a great deal about the history of these dynamic communities and enjoyed great Polish and...
robcalice
2018-06-03 10:37:29
"Worlds Fair Walking Tour" Can’t say enough about this tour - an absolute blast. We enjoyed the tour as a group of friends celebrating a birthday (Chicago locals and out-of-towners alike). It was a highlight of the weekend and...
Lynn R
2018-05-14 18:39:24
"Bridgeport tour is the best!" The Bridgeport tour was absolutely the best tour we have ever been on! Amanda explained the rich history and culture exactly! My mother in law and father in law had experiences in all the places she...
David L
2018-05-13 09:40:21
"Private Party - Stellar Event" Hired Chicago Detours for my birthday party to give a 'stationary tour' of the view from the event space in my South Loop apartment. Amanda gave a great presentation (informative and fun) and handled...
Ticketless55
2018-05-08 14:37:53
"Big Shoulders Tour" We did this tour as a post wedding event for the many out of staters we had. Everyone is still talking about it. Great tour, so much yummy food and a grand way to spend time with friends from start...
cycleguy390
2018-04-20 16:01:54
"Great tour guide, bad tour design" The imagery for the tour says you’ll see a lot of hidden gems and Tiffany ceilings, but the actual experience was quite a bit different. We spent a lot of time in and walking through retail spaces...
Debb35
2018-04-17 13:58:07
"Fun and informative tour. " Guide was very knowledgeable. We learned a lot of Chicago trivia and explored a bit of the mysterious pedway system.
Luke A
2018-03-03 16:59:41
"Great tour" What can I say thank you Amanda for an insightful and well presented tour. We did 2 private tours back to back with a lunch break in between I can’t recommend detours enough!
Steven L
2018-02-21 06:29:48
"New Student, New Visitors" I took the occasion of my son's visit to Chicago colleges to learn about the city, and found Chicago Detours a great way to do this. We wanted to get to know the city as a resident might, so went on...
Sean W
2018-02-18 06:08:41
"Fascinating, funny, and functional" Fascinating, funny, and functional would be how I would describe our first (of many to come) trips with Chicago Detours. We did the Architectual/ Pedway tour. It was amazing how many spots I have...
Mark G
2018-02-13 09:42:49
"5th year in a row! This year's Holiday Tour of Drinks, Daleys and Dead Guys" Our family gathers for the holidays and taking a tour with Chicago Detours is always a highlight of our family time together. This year our tour-guide was Elizabeth, and it was our first time with...
DrummersMom19
2018-01-04 10:51:21
"Private Chicago Blues Tour" We took an interesting 2 hour private driving tour, although we were able to hop out and explore some interesting locations in the frigid Chicago air of New Year's Eve afternoon, and learned about...
Joan and Larry D
2017-12-16 14:34:22
"Cold day but we stayed warm popping in and out of the Pedway" Six of us took the train into the city and felt our chicago Detours Interior Architecture Walking Tour was worth every penny. We learned lots, gained some insights about Chicago and its fascinating...
Anonymous
2017-12-12 13:42:10
"Fun & Engaging!" I would highly recommend adding a tour from Chicago Detours to your next visit to the Windy City. The creative and interactive approach did a great job at helping to break down the barriers that you...
my1stmac
2017-12-03 08:44:05
"Well worth the investments " Recommended by my hotel during a conference, and as a new visitor to Chicago and the US.... These guys are well worth the investment. Energetic, Enthusiastic and well delivered. I would use their...
David L
2017-11-22 04:36:10
"Chicago Bar Tour" Wonderful Tour Entertaining Educational Tour Guide Was Superb I will definitely recommend to anyone visiting The Windy City
Elaine L
2017-11-20 16:25:16
"Historic Bar Tour" The historic bar tour was entertaining and informative. Our tour guide was knowledgeable and entertaining. I can not wait to go on another tour when I visit Chicago. The Holiday tour sounds great.
TBassingDavis
2017-11-20 10:10:39
"Tesla drive tours" We decided last minute to see what tours of Chicago were available and got a tour right away. We were driven around in a new Tesla and hit many well known spots in Chicago. We got out a couple of...
lizzylou21864
2017-11-05 07:01:34
"Fantastic!!!" Amanda did a great job combining architecture...history...and fun!!!!! The drinks/food was fun....and buildings were amazing!!
Chase W
2017-10-15 19:57:56
"Wicker park tour" I took the Wicker Park walking tour. Our guide, Elizabeth, was very knowledgable and entertaining. She took us to great spots and told us everything about the history of the neighborhood. The food...
MargotU761
2017-10-15 13:37:58
"Fantastic walking tour" I really loved the Interior Architecture Walking Tour. We went to places I would not have seen without the tour. Amanda was wonderful and had really done her research. She kept everything...
JanMaino
2017-10-02 17:34:18
"1893 World’s Fair and Bar tour" So much fun! Our guide Elizabeth was knowledgeable and entertaining. This tour was a mix of Chicago history, silly games, drinks, and architectural history. I highly recommend you spend 3 hours on...
ConnieMartz
2017-09-18 21:11:46
"Amazing!!! " We took the interior architecture walking tour with Amanda, who had the most interesting facts about places in Chicago that you wouldn't imagine. It is outstanding the amount of precious details the...
plum176
2017-09-18 12:07:26
"Interior and Pedway Loop Tour" Sonny took us on the tour a week ago..the group was small and the tour was interactive amongst the group which was so different - rather than just being lectured too. She took us to some amazing...
Joseph C
2017-09-18 12:02:47
"Architecture and the Loop" This was a walking tour, but that's loosely used. The tour itself went in and around the downtown "Loop" of Chicago and stopped at interesting and historically relevant places. We were really into...
crunch6
2017-09-11 08:00:07
"We loved the Prohibition Pub Crawl!" Elizabeth was a great guide as she showed us so many things in our city that we had no idea were there....and I've lived in the Chicago area for 55 years! The interior of the Intercontinental was a...
Peter R
2017-09-08 17:39:23
"Great tour. See the unseen." Great tour. Out guide Elizabeth was super. Using iPad tablets for historic photos and maps and short videos is inspired way the expand tour experience while keeping it up close and personal. Chicago...
Angela F
2017-08-31 04:52:42
"Amazing way to learn about the city!" I've lived in Chicago for 13 years, but had a friend visiting and decided to do the tour with them, and glad I did. This tour was a trifecta, I got to see the city, learn things about the...
cschneider6660
2017-07-17 05:35:02
"Good even for a native" The Historical Chicago walking bar tour was fun. Elizabeth didn't stop talking the entire time with history and tid-bits of info. Not sure how she can memorize all that! But eat before you go...
Delawnda A
2017-07-15 06:55:14
"Fascinating historical look at Chicago" Sonny was our guide and she was fantastic. She was very friendly and knowledgeable. The tour showed us very interesting sites in downtown Chicago including the Pedway (wow!) and Chicago Temple. Also...
VLFrank
2017-07-10 07:20:17
"Fun & engaging tour" We very much enjoyed the indoor architecture tour. Our good-natured guide, Eric, took us to some interesting spots (like a church in a high rise building) that we never would have found otherwise. He...