![Get Your Guide logo](data:image/svg+xml,%3Csvg fill="none" xmlns="http://www.w3.org/2000/svg" viewBox="0 0 382 302" width="56" height="64"%3E%3Cpath d="M98.273 125.538c-5.904 0-10.574 4.553-10.574 10.574s4.67 10.574 10.574 10.574 10.574-4.553 10.574-10.574-4.67-10.574-10.574-10.574zm60.37-51.987h-37.392V55.594h33.329V37.637h-33.329V19.925h36.775V1.84h-56.944v89.795h57.561V73.551zm-41.668 54.2c5.904 0 10.574-4.553 10.574-10.574s-4.67-10.574-10.574-10.574-10.575 4.553-10.575 10.574 4.671 10.574 10.575 10.574zM38.498 93.475c13.042 0 24.478-6.638 31.243-16.85v15.01h17.713V41.701H39.977v17.222h19.925c-1.84 9.223-9.968 16.362-19.808 16.362-10.947 0-19.808-8.862-19.808-21.776V40.222c0-12.67 9.468-22.02 22.754-22.02 10.33 0 19.553 5.659 22.627 13.903l18.702-6.52C79.199 9.84 62.476 0 43.168 0 18.818 0 .606 16.361.606 40.222v13.287c.01 22.988 16.978 39.966 37.892 39.966zm172.909-66.401h-19.903v28.69h19.903v-28.69zM235.396 1.84h-68.147v18.085h68.147V1.84zM33.829 195.887h20.17v-34.063l33.817-55.721H65.061l-21.275 36.775-21.032-36.775H0l33.829 55.966v33.818zM211.407 62.923h-19.903v28.68h19.903v-28.68zM364.87 195.887l-24.478-34.318c11.936-3.692 20.297-14.149 20.297-26.935 0-16.234-13.403-28.542-30.382-28.542h-11.808v18.201h11.074c5.904 0 10.457 4.671 10.457 10.819 0 6.149-4.553 10.83-10.457 10.83h-11.074v17.222l21.893 32.723h24.478zm-99.964 14.35h-29.648v89.912h29.648c27.796 0 47.477-19.063 47.477-44.892 0-25.829-19.681-45.02-47.477-45.02zm1.595 71.827h-11.074v-53.753h11.074c15.01 0 25.212 11.563 25.212 26.935 0 15.372-10.202 26.818-25.212 26.818zm78.104-17.956h33.328v-17.957h-33.328v-17.712h36.775v-18.074h-56.945v89.784h57.562v-18.085h-37.392v-17.956zm-32.137-98.582-10.426-14.776 10.287-14.946-10.425-14.766 10.298-14.935-20.797.01-10.298 15.095 10.436 14.777-10.298 14.946 10.436 14.765-10.297 14.957 11.074 15.372h21.02l-11.308-15.542 10.298-14.957zm-45.924-4.564v-54.859h-20.053v55.232c0 10.329-7.383 17.957-17.467 17.957-10.085 0-17.468-7.628-17.468-17.957v-55.232h-20.052v54.859c0 21.159 15.872 36.776 37.52 36.776 21.648 0 37.52-15.627 37.52-36.776zM156.452 265.586c0 10.33-7.383 17.957-17.468 17.957-10.084 0-17.467-7.627-17.467-17.957v-55.232h-20.053v54.86c0 21.159 15.872 36.775 37.52 36.775 21.649 0 37.52-15.616 37.52-36.775v-54.86h-20.052v55.232zm-116.475 1.851h19.925c-1.84 9.223-9.968 16.361-19.808 16.361-10.946 0-19.807-8.861-19.807-21.775v-13.287c0-12.67 9.467-22.021 22.754-22.021 10.33 0 19.553 5.66 22.627 13.904l18.701-6.521c-5.17-15.744-21.892-25.584-41.2-25.584-24.35 0-42.563 16.361-42.563 40.222v13.287C.606 285.022 17.584 302 38.488 302c13.042 0 24.478-6.638 31.244-16.85v15.01h17.712v-49.935H39.977v17.212z" fill="%23F53"/%3E%3Cpath d="M132.102 104.252v18.946c14.765 0 26.446 12.053 26.446 27.797s-11.681 27.797-26.446 27.797c-14.755 0-26.446-12.053-26.446-27.797h-20.67c0 26.201 20.915 46.743 47.105 46.743 26.201 0 47.105-20.542 47.105-46.743 0-26.202-20.893-46.743-47.094-46.743zm82.497 148.377c2.978-2.691 7.968-7.191 7.968-15.435 0-8.245-4.99-12.744-7.968-15.436a9.787 9.787 0 0 0-.373-.33c-1.489-1.563-1.744-3.808-1.776-4.872v-6.319h-20.201v8.404h.01c0 .107-.01.202-.01.309 0 8.244 4.989 12.744 7.967 15.435 2.139 1.936 2.139 2.032 2.139 2.809 0 .776 0 .872-2.139 2.808-2.861 2.585-7.574 6.862-7.925 14.532h-.021c0 .148-.021.287-.021.425 0 .085.01.16.01.234 0 .085-.01.16-.01.234 0 .149.01.287.021.426h.021c.351 7.67 5.064 11.946 7.925 14.531 2.139 1.936 2.139 2.032 2.139 2.808 0 .777 0 .873-2.139 2.809-2.978 2.691-7.967 7.191-7.967 15.435 0 .107 0 .213.01.309h-.01v8.404h20.201v-6.319c.032-1.053.287-3.308 1.776-4.872.117-.107.234-.213.373-.33 2.978-2.691 7.968-7.191 7.968-15.436 0-8.244-4.99-12.744-7.968-15.435-1.904-1.713-2.117-1.989-2.138-2.564.021-.574.234-.851 2.138-2.564z" fill="%23F53"/%3E%3C/svg%3E)
Embark on a history-based guided walking tour and discover the stories of Chicago’s gangsters and ghosts. Learn about the city’s darker side and creepy past as you explore the Chicago Loop district.
About this tour
- Free cancellation
- Cancel up to 24 hours in advance for a full refund
- Reserve now & pay later
- Keep your travel plans flexible — book your spot and pay nothing today.
- Duration 2 hours
- Check availability to see starting times
- Live tour guide
- English
- Wheelchair accessible
Highlighted reviews from other travelers
Allain was amazing . Very informative and funny. The tour wouldn’t have been the same without him :)
Great fun tour from an entertaining guide, Adam gave us some interesting background on the city mixed with tales of its darker side.
Select participants and date
Itinerary
Starting location:
Chicago Gangsters and Ghosts Tours
Chicago Riverwalk
The Chicago Theatre
Palmer House A Hilton
Cloud Gate
Art Institute of Chicago
The Congress Plaza Hotel & Convention Center
Finish at:
The Congress Plaza Hotel & Convention Center
Main stop
For reference only. Itineraries are subject to change.
Highlights
- Learn about the dark history of Chicago's South Loop from a historian guide
- Hear true tales of Chicago's gangster past and learn how Al Capone ran his empire
- Listen to eerie tales of ghosts that are said to lurk around historic landmarks
- Explore Death Alley, Chicago Riverwalk, the Palmer House and the Chicago Theatre
- Visit the Congress Hotel and learn about the creepy incidents on the 12th floor
Full description
Discover a different side of Chicago on a family-friendly guided tour, either on foot or by bus. Hear the tales of the ghosts, and gangsters, that haunt the city. Explore the Chicago South Loop district with your historian guide, uncovering the many mysteries hidden behind every turn.
Meet your guide and kick off your guided walk through Chicago's notorious South Loop, known as a vice district during the 1920s and 30s. Stroll through his now upmarket area of the city which was once home to underground speakeasies, secret tunnels, and bootleggers.
Hear the true stories of Chicago's bloody past and the gangsters who caused havoc in the city. See the places notorious figures such as Al Capone used to party, make deals, and carry out "business". You will also enjoy a short rest stop at a famous former gangster hangout.
Discover the legends of the ghosts that are said to lure along the Chicago Riverwalk and the aptly named Death Alley. Stop at haunted locations including Palmer House, and the Chicago Theatre, before finishing with a visit to the Congress Hotel, one of the most haunted places in Illinois.
Meet your guide and kick off your guided walk through Chicago's notorious South Loop, known as a vice district during the 1920s and 30s. Stroll through his now upmarket area of the city which was once home to underground speakeasies, secret tunnels, and bootleggers.
Hear the true stories of Chicago's bloody past and the gangsters who caused havoc in the city. See the places notorious figures such as Al Capone used to party, make deals, and carry out "business". You will also enjoy a short rest stop at a famous former gangster hangout.
Discover the legends of the ghosts that are said to lure along the Chicago Riverwalk and the aptly named Death Alley. Stop at haunted locations including Palmer House, and the Chicago Theatre, before finishing with a visit to the Congress Hotel, one of the most haunted places in Illinois.
Includes
- Guided walking tour
- Historian guide
- Visits inside the Congress Hotel and the Palmer House
- Tips (optional)
Not suitable for
- People with mobility impairments
Meeting point
Please meet your guide outside "Hoyt's Tavern", which is adjacent to the Royal Sonesta hotel.
Open in Google MapsImportant information
What to bring
- Comfortable shoes
- Water
- Comfortable clothes
Not allowed
- Luggage or large bags
Know before you go
- This tour is not recommended for people with infants
- The tour is 1.5 miles total walking, with a 20-minute break at a famous gangster hangout
- Children aged 6 and under can join this tour for free
