About This Tour
Nightly Spirits’ Haunts and Hooligans Tour will illustrate Chicago’s haunted history of secret parlors, underground tunnels, murderous movie theaters and supernatural speakeasies. Whether you’re a recent transplant to Chicago or have lived among the Windy City’s ‘others’ for years, you’re about to get a haunted history that may leave you with more memories than you dare to retain. Tours begin at the haunted Harry Caray’s Italian Steakhouse in downtown Chicago. A costumed guide will lead tour goers on a walking journey exploring the creepy past of one of Chicago’s most famous bootleggers, offering glimpses into the past and revealing the stories of long-dead phantoms and specters who still call Chicago home.
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Chicago Haunts and Hooligans Tour
This 1.5-hour walking tour with Nightly Spirits explores Chicago's darker history, focusing on notorious criminals and chilling tales. It's ideal for those interested in true crime and local lore who prefer a historical narrative over sensationalism.
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What's Included
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Additional Information
Meeting Point
Harry Caray’s Italian Steakhouse Meet the guide inside Harry Caray’s Italian Steakhouse. They will be wearing a Roaring 20s costume and standing near the front.
Special Instructions
Your tour begins at Harry Caray's Italian Steakhouse, 33 West Kinzie Street. Your guide will meet you INSIDE. Just look for the flapper or gangster near the famous bust of Harry Caray. Please try to arrive 10-15 minutes prior to your reservation time, in order to allow time for check-in. How do we get there?? Parking in this area is extremely limited so we strongly recommend using ride-share or public transportation. Click this link for a list of transportation recommendations. Running Late for the tour?? We will wait 5 minutes for everyone, then the group will be at the starting location for approximately 15-20 minutes. If you are later than that, please reach out to us by phone, 844-678-8687, and we will do our best to catch you up to the group. Tours beginning at 7:30pm or later are for guests 18+ only!!
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
✓ Free cancellation due to bad weather
Tour Operator
Nightly Spirits
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Trusted local operator
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Frequently Asked Questions
Common questions about Chicago Haunts and Hooligans Tour
Who operates this experience?
This experience is operated by Nightly Spirits, a local food & drink provider.
What's included?
This tour includes Local guide and Tour escort/host. All inclusions are provided by the tour operator.
How long is this tour?
The experience lasts approximately 1.5 hours, giving you time to fully enjoy your chosen activity.
Can I cancel this tour?
Yes, you can cancel up to 24 hours before the scheduled departure time for a full refund. If weather conditions are unsafe, the tour may be canceled by the operator. In such cases, you'll be offered a refund or reschedule.
What should I bring?
Come with an appetite and comfortable walking shoes. All food and beverages are included.
Will I receive instant confirmation?
Yes, you'll receive instant confirmation when you book.
What to expect on this tour?
This food & drink experience lasts approximately 1.5 hours and includes all necessary equipment and guidance. You'll have access to Local guide and more.
What's the best time to do this tour?
This culinary experience is typically best enjoyed during meal times, allowing you to fully appreciate the local food culture.
Are dietary restrictions accommodated?
Dietary restrictions may be accommodated depending on the tour. Please inform the operator of any dietary requirements when booking so they can make appropriate arrangements.
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