Chicago ยท Private & Group Tours
Chicago Private Nightmares and Nightcaps Tour
A nightcap at a haunted Lincoln Park bar, then ninety minutes of the North Side's darkest stories with nobody but your own group listening. The Private Nightmares and Nightcaps Tour is our shorter, grimmer Chicago walk.
๐ Departs from: Glascotts, 2158 N Halstead. INSIDE - ask bouncer where our table is โ please arrive about 15 minutes early to check in with your guide.
Your group meets its costumed guide at a haunted Lincoln Park bar and orders an optional nightcap while the guide explains who else is drinking there, and for how many decades. Then you head out for about a mile of walking through historic North Chicago, past brownstones, alleys and the edges of a park that was once the city cemetery and never entirely stopped being one. The stories are the ones we save for adults: unmarked graves, violent ends and residents who refused to be evicted by anything as minor as death.
This is the right call for a friends' night out, a bachelorette crew that wants chills with its cocktails, a date night with a pulse or a work team that prefers one good drink and a lot of good stories to a long bar crawl. Private tours run every day with start times from 1 pm to 8:30 pm, and the duration, meeting location and drink stop can be adjusted to your group. If your hotel is close to the route, the guide may be able to meet you there.
Pricing starts at $325 for up to 10 guests, with additional tickets from $25, and rises to $375 from mid-September through mid-November. One guide takes 18 to 22 guests depending on the date; groups of 16 or more book by email and larger groups add a guide. This Chicago version is 21 and over with valid ID. Parking is tight, so ride-share or the train to Fullerton Station is the easy way in.
What's included
- 90-minute private ghost walk for ages 21+
- Opening stop at a haunted Lincoln Park bar with optional nightcap
- Costumed guide and storyteller for your group only
- About one mile of walking through historic North Chicago
- Flexible start time, 1 pm to 8:30 pm, any day
- Not included: drinks, food, taxes, fees and gratuity
On the tour in Chicago






Chicago Private Nightmares and Nightcaps Tour FAQs
What is the age requirement?
This Chicago tour is 21 and over with valid ID. The nightcap itself is optional.
How does this differ from the Booze and Boos?
Shorter and darker. One bar stop instead of three or four, ninety minutes instead of two and a half hours, and stories told without the family filter.
How do we book a group of 16 or more?
Email us so we can arrange a second guide. Groups up to 15 can reserve online. Base pricing covers 10 guests with per-person tickets after that.
Does it run in winter?
Yes, year-round, rain, snow or shine. The first stop is indoors and the walk is about a mile. Bundle up.
More ways to meet Chicago's spirits
Plan your group's night
Pick your date and group size, see your price, and hold it with a card โ nothing is charged until we confirm your guide, no later than open of business the next day.
Reserve this tour