Chicago Gangsters and Ghosts Tours

Loved this tour! Matthew was an amazing and fun tour guide who was super well-versed with great stories. It was fun learning about Al Capone but also getting a sprinkling of spookier stories as well. I’m a fan of spooky, my husband is a fan of gangsters. It was truly a great tour for the pair of us. I’d recommend this tour for anyone who wants a little true crime pizazz to their Chicago trip!

Really fun time exploring Chicago and hearing it's history. Our guide Taka was fascistic and our whole group had a wonderful time. It was also a beautiful day for a walk. I'm pretty sure our guide made that happen 😁. Highly recommend you check them out if you're looking for some fun exploration in Chicago.

For any city I visit, I always do a ghost tour, and the Chicago Gangsters and Ghosts Tour was one of the top rated in Chicago. I appreciate the fact that it was a walking tour, since I feel it is more immersive than those that operate by bus or trolley. Our guide, Alan, was very funny, knowledgeable, and engaging. I was able to see parts of the city that I would not have experienced if I didn’t do the tour. I appreciated the history that was shared through each of the locations visited. My only complaint is that it was more history based than paranormal. Nonetheless, I’d recommend it to anyone who enjoys these kinds of tours.

We’re visiting from Toronto and I’m so happy that Avery was our tour guide. He knew a lot about the history of Chicago and was also willing to answer any questions we had. His humor was on point and appealed to all ages. It was a joy listening to him tell the history of this wonderful city, even though some of the stories were sad, he showed empathy. Thank you Avery for a wonderful experience!

Such an amazing and informative tour! Our tour guide Matthew was absolutely wonderful! So knowledgeable, personable, friendly, and does a great job capturing not only the history of the Chicago mob scene but also a bunch of other interesting facts about Chicago as well! You can truly tell he’s passionate about what he does. I would 100% recommend this tour and Matthew.

We are visiting Illinois for a week and had to check out Chicago. We booked the tour just to get to see some of the City. Avery did an amazing job. His humor and knowledge made the tour so enjoyable. He had knowledge to share beyond just what the tour coveted. If you are in Chicago I would highly recommend this your and ask for Avery if you can!

We did the 8pm tour with Avery and it was awesome! The night time atmosphere made it really cool, and the stories and entertainment provided by Avery was awesome. Highly recommend this tour to anyone in Chicago who wants a fun and interesting way to see the city!

An extremely enjoyable tour!!! Not only did I learn all about the "folk lore" of the city, but also about real historical events, stories, trivia facts, architectural facts, and so much more!! Learning about the gangsters was also super fun!!! Very fascinating and lots of facts. Being able to walk around the main parts of the city was a blast and I would do it again any day. BUT!!! Hands down the best part of this whole tour was my incredible, eccentric, charismatic tour guide, Karena!! (Kareena? Karina? She knows) She was a lovely person with a real passion for her work and a love for her city and it's history, she made an already fun tour over the top enjoyable!! Not only with her fun facts and fun personality, but also with her conversation!! Keeping the walls between stops full of life and laughs!! She kept up the vibes!! I highly recommend this tour, and I can see myself showing up again to show more friends and family!!!

Tour was fun and informational! Shout out to our tour guide Matthew for being so knowledgeable! Would have liked a smaller group though because it was hard to hear with all the people and excitement in downtown Chicago!

Taka did an outstanding job leading our group. You could tell she really understood what she was talking about, but equally as important, she was just good at giving tours. Her voice carried well even on the busy streets, and she always seemed to make sure our group felt safe and comfortable navigating our route. Very enjoyable tour!

We had a great time this morning on the walking tour. George was our guide. He was fun, friendly, easy to understand, and could raise his voice above the street noise. Totally recommend this. It's about an hour and a half about 2 mi so not super strenuous. Beautiful weather this week too.

We had a nice time with Taka our tour guide on this tour. We saw a lot of really neat things by foot (I don't want to ruin the tour for the person reading this). She had an in depth knowledge and really added a great flair to each story. I would definitely recommend her and this tour for anyone looking to know more of Chicago.

Mathew was amazing tour guide. Great story telling. Enjoyed learning about interesting historical events. The walk pace and flow was nice and easy. Highly recommend to locals or tourists. Thank you.

Great tour! Taka was extremely knowledgeable and her voice carried well despite the noisy surroundings. Definitely enjoyed the tour and highly recommend it!

Did this tour this past Halloween weekend. Ty was our tour guide and he was great! Very knowledgeable and also cracking jokes along the way. This tour is mainly heavily focused on gangsters, especially Al Capone. They do mention some ghost stories but not as much as I would hope. Maybe Chicago isn't as haunted as I thought it was! They did mention The Devil in the White City which was great (as it is one of my favorite books!) It is a walking tour and it is a very doable walk for everyone. They can modify the tour is exclude stairs in someone in the group cannot walk up stairs, which is very accommodating. Overall, I would recommend this tour to anyone visiting Chicago and wanting to learn for about our gangster history!

Took the Gangsters & Food tour with Ty & would highly recommend - he was informative & funny - we ate steak, deep dish pizza & Chicago hot dawg.

Fun tour, a bit long and a ton of walking (hence walking tour) but we had a nice break in the middle. Ty our tour guide was excellent

It was a great introduction to the city. The tour guide was super knowledgeable and funny.

Willis was an amazing tour guide. He was funny, enthusiastic, and knowledgable. The stops were laid out nicely and the overall speed of the trip was just right.

Our tour guide, Sarah was absolutely amazing. She really knew her stuff. She is well read on the topic, and extremely knowledgeable. What really shined about Sarah was her personality and sense of humor. She was awesome!

DO NOT GIVE YOUR MONEY. Pretty sure it's a scam. They took our money and then there was no one to meet up at the start location. Tried to call to make sure we were in the right spot and the number didn't work. Now I'm out $80

I really enjoyed our night tour with Grant. We walked around Chicago and heard some really neat stories about ghosts and gangsters. We stopped at the Palmer Hotel for a bit and it was really nice. I would recommend this tour to anyone visiting the city!

At first we had a hard time finding the ghost and gangster tour meetup point because we thought that it was inside the hotel but it was actually next to the hotel and outside. Our tour guide for the ghost and gangsters tour was Allan, and he did a fantastic job. It was about an hour and 40 minutes of walking around pointing out historically significantly buildings that had some association with either ghosts or gangsters with one break at the Palmer hotel. One of the coolest things we learned was that al capones ghost is somewhere lingering around the bar at the congress hotel. A couple of the saddest things we learned Included a fire where hundreds of people had to jump off the 4th floor to their deaths, as well as a meat plant tbst used to just dump their left over meat organs and fat into the river only to eventually cause a grease fire that killed everyone that was on the lake one day. The tour was educational, fun and funny too, and the tour guide had a great personality for the job. A+

Both entertaining and informative. Sophia was a fantastic guide with plenty of energy. We learned a lot and left with smiles on our faces.

We did the luxury mini-bus version instead of the walking by the same company. The whole tour was awesome. Ty was a great guide, funny and informative. The bus was very nice. If you're tired of all the walking the bus tour is great.

We really enjoyed this tour! It was interesting hearing about some of Chicago's darker history and the life of Al Capone and his crew. Matthew was a great storyteller and fantastic tour guide!

This is a fantastic walking tour. It's a great tour through downtown Chicago's history of gangster activity and major tragedies. Our tour guide was Brandon and he was purposefully loud and clear. He brought great energy to the narration of historical facts. This tour is not a loop. You will not end the tour where you started so plan appropriately. My husband and I were also surprised at how long this tour felt on our feet despite only being "1.5 miles" over a 2 hr period. We did walk to dinner first and then to this tour so we had some extra steps beforehand but be prepared for it to feel a little more than 1.5 miles. It is also helpful to bring a bottle of water. Midwest summers are hot and humid. This tour is a unique way to explore Chicago and worth the ticket! Photos: gangster activity at the Chicago Theater and tragedy at Death Alley/Nederlander.

Our tour was so fun! Gary was an amazing guide and he shared great ghost and gangster stories! He also did a great job and keeping our pretty big group together. Highly recommend!

Friendly tour guide and knowledgable. However, the tour itself was too long, could have been done under 1 hour. Palmer house was a sight to see but the rest, alley and cultural center was not worth the hype.

A Deaf friend and I wanted to go on this tour. They not only refused to provide an ASL interpreter, but I found a friend to interpret for us-they just had to comp her ticket, and they also refused that. ***NOT ACCESSIBLE*** and NOT willing to BE accessible.

Max was an informative, entertaining and friendly guide on this interesting and fun historic tour.

Avery was so energetic and made the tour so fun! His knowledge and the way the information flowed was by far superior than what I expected! Highly recommend

Our guide Joseph was great! He showed a lot of enthusiasm and knowledge about the city! A few tips: Make sure to dress appropriately for the weather and wear your best walking shoes, because you'll be walking a lot...and briskly. And while doing the tour, don't be shy. Ask your guide any questions you might have regarding the historical subjects and topics they are sharing. That's what they're there for. And most importantly, enjoy the tour!

ty was a great guide! loved learning the history of chicago. throughout the tour ty shared jokes and stayed energetic the whole two hours. he was also very informative when asked about chicago in general for out of town tourists needing recommendations of food and stores. thank you ty for a great time.

It was a good walking tour. Give you a little bit of history about the gangs and some of the tragedies of the city.

My friend and I had the pleasure of having Stefan as a tour guide. He was extremely knowledgeable and provided fun facts about Chicago's history. Highly recommend!

Was ignored and taken advantage of. Being from out of town we had small hiccups arriving on time due to our uber. This tour place was greedy and unwilling to help or provide customer service. I've worked in customer service for 12 years and I have never once simply ignored customers to avoid a refund or even an explanation. I hope anyone who books with these people don't run into any unforeseen issues or hiccups as they will take your money, ignore you, and then still have the audacity to send a review request. I highly DO NOT recommend. You're better off trying another touring company. Big mistake trying to give these people a chance.

Taka was a great tour guide. Tour was awesome! I highly recommend doing this if you are in the area.

Just finished my tour with Baylor, she was fantastic and knowledgeable about the city and its history. It was a fun tour with a lot of information about all of Chicago's sordid history. Gangsters, ghosts, disasters, architecture, and serial killers. I would highly recommend this tour with Baylor and her wonderful outgoing personality.

Avery was great! Highly recommend this tour and guide. He was enthusiastic and provided an interesting (albeit fantastically morbid) history of the area and inhabitants.

We took this tour last weekend. Sophie from Louisiana was our tour guide and she was darling.! She was very knowledgeable of the city, and very personable and easy to talk to.! I highly recommend this tour for anybody who has never been to Chicago as well of those who have made multiple trips. Just make sure you wear your walking shoes.

Best two hours spent in Chicago. Connor was the best tour guide. Packed a ton in a comfortable 2 hour walk with lots of stops. Highly recommend taking the tour after dark because it adds so much more to the experience. Learned a ton and had a blast doing so bc he's such a natural storyteller. Love that he's an actual historian and could answer lots of questions. Will never see Chicago the same way again. This is not an either or your. I've taken both the architectural boat tour and this walking gangster and ghost tour and it's worth doing both bc they cover very different topics and one is a sitting experience and one is a walking get your exercise in a fun way experience.

The night I intended to do this tour, it was POURING rain. There's two "gangster" tours in Chicago, and I thought I was booking the one on the bus. I accidentally booked this one, which is a walking tour. As soon as I booked it, I realized my mistake and reached out to them telling them I wouldn't be coming and asking for a refund. They did not reserve a spot for me and my guests because they knew immediately I wouldn't be coming. I told them that I am a disabled veteran and could not walk the 2+ miles they expected, and to ask that on a night that was pouring rain was a bit silly. They pretty much told me I was SOL and that i could just come a different night. I expressed that I couldn't, I'm a disabled veteran with zero ability to walk like that and that I was just visiting Chicago for the weekend anyway. They expect me to make friends in Chicago and sell them this privilege of walking around in the pouring rain for 4 hours. Absolutely bonkers. No respect for the disabled, no respect for veterans, and I would NEVER direct somebody - even a stranger - to partake in a business like that. They've spent the last 2 months fighting with my bank to get the charge to go through, so I figured since they're so hard up for the cash I'd just let it go through. They clearly needed the 2 spots that they knew would never be filled in order to survive, but I wanted to warn everyone else to BE CAREFUL WHEN BOOKING. On a lighter note, the bus tour that I actually went on was awesome, if you're looking for something fun to do definitely check out that instead! I attached a copy of the email which took place at around 630 when the tour stepped off at 8. They had no expectation of me or my party being there, knew I was disabled and couldn't partake and that I became disabled in the military, and still spent months fighting with my bank. Do you really want to allow a company like that access to debit YOUR bank account?

We went on the tour Saturday evening, April 20th. The tour was fantastic and Takka (sp?) was even more fantastic. She was engaging and informative. It was definitely a highlight to our Chicago weekend and one we will always remember!

We did this tour last night. It was just about everything we were looking for in the tour. Learned a lot about Al Capone and the Chicago gangs of old. We also learned some history of the Chicago fire and other tragedies of Chicago's history. Our tour guide, Ty, was very well-informed and a great story-teller. Between stops he gave us great advice on other places to see and places to eat in Chicago. The tour is pretty well split between ghost themes and gangster themes so if you're looking for more of one over the other, just ask Ty during the walk for some follow-on details and he'll have plenty to share. This is also a great excuse to get out and explore the city. We've lived here for a few months and haven't gotten out. This tour takes you all around Chicago's Loop area and into some great historical spots.

This is such a great way to see Chicago! Brandon was our guide, and showed us a lot of the top sites of the city, but with lots of interesting (and wild and weird!) stories. The tour starts near the river walk and ends kind of by the Buckingham Fountain. I recommend going to see the fountain after the tour and then taking a pedicab ride. He was great about making sure that everyone on the tour could see and hear, and was a brilliant storyteller. Definitely worth the price! I did the 8 pm tour in late August, which was totally perfect for the vibe of the tour.

I can't believe it has taken me this long to write a review for such a wonderful experience. This tour was one of the highlights from my trip to Chicago in October. Our tour guide, Kai, was wonderful. I loved how she spoke loudly enough for everyone to hear and that she was a good storyteller as well. I also like that she has a graduate degree in history. This makes her more than qualified to be a good tour guide. I learned a lot about Chicago and different things that happened there over the course of time. I definitely gained a new perspective at the conclusion of the tour. One of the things I learned on this tour that was never taught in any history book growing up was the Eastland tragedy in 1917. I also didn't know that the company who hosted the party would go on to become a very big name corporation in America. It was also great to have an intermission at a historic hotel and purchase their delicious brownies. The intermission or break gave ample opportunity to get a refreshment, purchase a brownie, explore part of the hotel or to use the restroom before resuming the tour. Kai also made sure that everyone was accounted for before resuming the tour. I was impressed by this. Not the, too bad we're leaving although everyone isn't back at the designated time. You get plenty of steps in while walking around various parts of the downtown area. I enjoyed learning more things about Al Capone as well and how he got to Chicago. I definitely knew that he was born in NY and migrated to Chicago via organized crime. The tour does end with a tragic story that I wasn't aware of prior to attending this. Find out what it was by attending yourself. History is filled with tragedy and Chicago is no exception. It's part of the human story. If you're on the fence or want to know about the "shadow" side of Chicago, I highly recommend this tour! I loved the stickers that were offered at the conclusion. I would actually consider signing up for this again, the next time in Chicago. You will definitely walk away educated from this! Again, kudos to Kai! She was great!

Drove around for 45 minutes never found a place to park lost out 75 dollars will never go to Chicago to do any thing again

This was pretty interesting, not much walking. Compared to a similar tour I did in Boston; there wasn't as much to learn but it wasn't a waste of time. If you can only do one your I would recommend the CAC River architecture tour. That was a major standout surprise during my visit here. The tour guide was a great story teller though!

Max was our tour guide and he was FANTASTIC - knowledgeable, friendly, funny, good pace, kept our group together, unfazed by a little rain delay and then finished on time. This was such a fun evening. HIGHLY recommend!

Fun and informative tour- extra spooky at night! Our tour guide, Brandon, was very nice and personable. Would definitely recommend if you're at all interested in the ghosts/gangsters aspect of Chicago's history.

We had a really nice time on the Gangsters & Ghosts walking tour. Our guide, Declan, was funny, friendly, knowledgeable, and gave a great tour. It was fun to hear some of the history of Chicago - both good and tragic - and learn a bit more about a city we visit often. The walking pace was great and we learned a lot. A word of caution for those with mobility challenges - we did take stairs a few times, and I did not see a work-around for a ramp option. Otherwise, a great experience.

We really enjoyed this tour! Connor, our guide, was knowledgeable and personable, and he did a great job projecting his voice to the group over the cacophony of downtown noises. I know some chicago history but most of the stories Connor told, I had never heard before. I always love walking around in the Loop anyway because the architecture is amazing, and then knowing the stories behind some of the buildings makes it so much better. The tour lasts about 1 1/2 hours and you get a little break in the middle at the Palmer House if you need to warm up, get a snack or use the bathroom - or just go in and marvel at the beauty of the place! I recommend this tour!

Willis was amazing! He remembered all the little details and incorporated his humor and charm. Made the tour very informative and entertaining. So thankful for his personable nature and his expertise. Awesome tour!

We had Kris as our tour guide! He was amazing and insightful. We learned a lot and had so much fun. I would definitely recommend this tour. :)

Did the Gangsters food tour. It was fun. Taka, our guide, was an excellent communicator and a good story teller. Had a good steak sample, a good piece of deep dish pizza and a good hot dog. The two hours was a nice pace. Learned some very interesting history!

Sara is an EXCELLENT guide and super knowledgable of Chicagos most interesting history! She was a pleasure to follow around for the afternoon. So many great stories that I had no idea about!! Highly recommend booking this tour for a little extra fun on your trip.