Chicago: Haunted Pub Crawl & Ghost Stories Walking Tour

Summary

Chicago’s haunted bars, ghost tales and secret speakeasy doors

You’ll follow a costumed local through Chicago’s most storied bars on this haunted pub crawl & ghost tour. Sip drinks where gangsters once hid out, walk past shadowy alleys near Biograph Theater, hear chilling tales in Lincoln Park, and end up swapping laughs (and maybe shivers) with fellow travelers under city lights.

What’s the experience like?

“You ever feel watched in an old bar?” That’s what our guide, Sam, asked as we squeezed into Glascott’s — the kind of place where the wood feels sticky and the air smells like old whiskey and something sweet I couldn’t place. Sam was dressed like a 1920s barkeep, suspenders and all. He told us about the building’s past as a Prohibition speakeasy (I tried to picture it full of flappers and whispered passwords), and honestly, I half-expected a ghost to slide up next to me at the bar. First drink down, nerves settled — or maybe just fuzzier.

We wandered out into Lincoln Park after that, shoes scuffing on cracked sidewalks. It was colder than I thought it’d be for September — that sharp Chicago wind finds every gap in your jacket. Sam pointed out spots where people swear they’ve seen shadows darting after midnight. Someone in our group swore she felt a chill on her neck (I didn’t, but who knows). The main keyword here is haunted pub crawl Chicago, but really it felt more like wandering through layers of city memory with a bunch of strangers who were quickly becoming friends.

The alley by Biograph Theater is where it got weirdly quiet. Sam dropped his voice to talk about John Dillinger — shot right there in 1934 — and for a second nobody said anything. Just distant traffic and someone’s laugh echoing from the next block over. We ducked into another bar after that (the one with firefighter helmets everywhere), and I tried saying “cheers” in my worst Chicago accent. The owner grinned but didn’t correct me; he just slid us menus and let Sam tell us about their supposed ghostly regulars. I’m not sure if I believe any of it, but when you’re holding a cold glass in a hundred-year-old building listening to ghost stories… well, you want to.

We passed Oz Park too — statues peeking out of shadowy corners — and ended outside the Red Lion Pub with its creaky floorboards and stories about spirits who never left. My feet hurt by then but I kind of didn’t want it to end; there’s something about wandering Chicago at night with new friends and old ghosts that sticks with you longer than you expect.

Step-by-step itinerary

Day 1 — Haunted Chicago pub and ghost tour

• Meet group at Glascott's bar
• Hear Glascott's speakeasy history
• Explore Lincoln Park's spooky history
• Learn about John Dillinger's ghost
• Stop for a drink and ghost stories
• Visit Hook and Ladder bar
• Hear about bar's ghostly owner
• Pass by Oz Park and learn about L. Frank Baum
• Pass Chicago’s Spirit Lounge, King of Cups
• Stop outside the Red Lion pub
• Hear Red Lion's haunted stories

Top questions

Is alcohol included on the Haunted Pub Crawl & Ghost Stories Walking Tour?

No, drinks are not included; you purchase your own at each stop.

How long does this Chicago haunted pub tour last?

The walking tour lasts approximately 2.5 hours.

Do I need to bring ID for this tour?

Yes, all guests must be 21 or older with valid ID.

What bars do we visit on this haunted pub crawl?

You’ll visit several historic bars including Glascott’s Saloon, Hook & Ladder/Halligan Bar, King of Cups, plus stops outside Red Lion Pub and others along the route.

Does the tour run if it rains or gets cold?

Yes, the tour operates in all weather conditions—dress appropriately for Chicago weather.

Is there much walking involved?

You should have at least moderate fitness; expect to walk between bars around Lincoln Park area.

Are costumes required for guests?

No costumes required for guests; only your guide will be costumed.

What’s included

Your evening includes a 2.5-hour guided walking tour led by a costumed local expert through Chicago’s most storied bars and neighborhoods—drinks are at your own expense but plenty of history (and shivers) are provided along the way before you wander home under city lights.