Haunted Hotels in Chicago: The Real Stories Behind the Ghost Tours

A ghost tour guide told my group outside the Congress Plaza that Room 441 has been “the” haunted room since the hotel opened in 1893. I’d just spent an afternoon reading old newspaper archives and talking to staff who’d worked there for over a decade. Neither source backed that up. What they backed up was something funnier: for years, guides apparently just picked a room number on the spot, and 441 stuck only after enough articles repeated it. That’s not a ghost story. That’s a game of telephone with a hotel invoice at the end of it.

My hot take after doing this properly across three of Chicago’s most name-checked haunted hotels: the city’s real history — a decade-long labor strike, a specific and much smaller Al Capone footnote, a hotel rebuilt twice on the same ground since 1871 — is more interesting than the ghost stories layered on top of it. I stayed at all three and tried to figure out where the documented history stops and the sidewalk theater starts.

If you’re building out a bigger haunted-hotel trip rather than just a Chicago weekend, it’s worth reading our wider roundup of the most haunted hotels in America first — Chicago’s Congress Plaza gets a mention there too, and it’s useful context for how this city’s stories stack up against Savannah’s documented bones or the Stanley’s tuberculosis history.

The Hotels — Real Talk on Each One

1. Congress Plaza Hotel — 520 South Michigan Avenue (built 1893)

The Congress Plaza is Chicago’s self-declared most haunted hotel, and it leans into that branding harder than anything else on this list — there’s a haunted-room package, and two separate groups in the lobby the day I checked in were comparing Room 441 notes without actually staying in it. The building opened in 1893 as overflow housing for the World’s Columbian Exposition, and it’s genuinely worth knowing on its own merits: it sat through a nearly ten-year hotel workers’ strike (2003–2013), one of the longest in U.S. labor history, and Al Capone reportedly played cards there Friday nights overlooking Grant Park — he didn’t stay under an alias as the myth goes, but his associate Jake “Greasy Thumb” Guzik really did once phone him in Florida from a phone inside the building.

The ghost story is where I had to slow down. Room 441 as “the” haunted room is a newer addition than the marketing implies — tour guides reportedly used to just assign a random room number for years before that specific number got repeated in enough articles to become the standard answer. The older “one sealed haunted room” legend turns out to be two different rooms merged in the retelling: Room 666, now a storage closet, and Room 209, pulled from inventory separately. Two unrelated closed rooms became one dramatic sealed room somewhere between tour guides. None of that makes the hotel less worth visiting — the Grant Park address and price are genuinely good — it just means the ghost story is the least reliable part of an otherwise real history. Full version, including the labor strike, in our standalone Congress Plaza review.

Rooms: ~$95–165/€87–151/£75–130 per night, depending on renovation status — this building is unevenly updated floor to floor, so check recent photos before booking the cheapest room.

Check availability at the Congress Plaza Hotel →

2. The Drake Hotel — 140 East Walton Place (built 1920)

The Drake doesn’t market itself as haunted, which is exactly why its one piece of ghost-adjacent lore interests me more than most hotels’ official legends. It opened New Year’s Eve 1920 at the top of the Magnificent Mile, facing Lake Michigan, and hosted Queen Elizabeth II, Amelia Earhart, and Sinatra without ever needing a ghost tour to stay relevant. The story that circulates locally involves something stranger than a ghost: Secret Service agents reportedly found old hidden passageways in the building during visits by Chicago-native President Obama.

I want to be straightforward about where that story sits — it’s local legend, told to me by more than one Chicagoan who swears they heard it from someone on security detail. The hotel itself doesn’t confirm specifics publicly, and I couldn’t independently verify it beyond that circulating version. A century-old luxury hotel having forgotten service corridors or staff passages that read as “hidden” to a modern security sweep is architecturally plausible — old hotels are full of them — but “plausible” and “confirmed” are different categories. Treat it as good Chicago lore. The lobby, the Palm Court, and the Cape Cod Room’s 1933 lobster bisque are the parts of this hotel I’d vouch for without a caveat. Full history in our standalone Drake review.

Rooms: ~$320/€295/£255 per night — this is the priciest of the three, and it’s priced for lake views and Magnificent Mile positioning, not for ghost-tour traffic.

Check availability at The Drake →

3. Palmer House Hilton — 17 East Monroe Street (current building 1927)

The Palmer House is technically the third hotel on this exact site since 1871 — the first burned down in the Great Chicago Fire just 13 days after it opened, which is either terrible luck or the most Chicago origin story a hotel can have. The current 1927 building has the Versailles-style lobby ceiling that stops guests mid-stride, and it’s the one carrying the ghost-tour lore now: local legend centers on reports of an apparition on the eighth floor, sometimes connected in guide scripts to a woman tied to the hotel’s early 20th-century history.

I’ll be honest about the sourcing here because it’s thinner than the Congress Plaza’s, not thicker: I couldn’t find verified specifics behind the eighth-floor story — no coroner’s record, no confirmed identity, nothing beyond what gets repeated on the ghost-tour circuit. That doesn’t mean nobody’s had an unsettling experience there; hotel staff I spoke with were noncommittal in a way that read more like “we don’t discuss it” than “here’s what happened.” Hear this one as circulating local ghost-tour lore, not as something with paperwork behind it. I’d actually recommend booking the Palmer House for the birthplace-of-the-brownie history and that lobby ceiling, both real. Full details in our standalone Palmer House review, and if you haven’t settled on a neighborhood yet, our Chicago city guide is a decent starting point.

Rooms: ~$220/€202/£173 per night.

Check availability at Palmer House Hilton →

Things Ghost Tours Never Tell You

• The most “official” haunted room is often the newest part of the story. Room 441 wasn’t always the room — it became the room after enough repetition made it stick. If a guide gives you a suspiciously specific room number with total confidence, ask how long that number has been part of the story.

• Two vague legends often get merged into one dramatic one. The Congress Plaza’s “sealed haunted room” is really two separate closed rooms — 666 and 209 — collapsed into a single legend somewhere in the retelling.

• The hotels that don’t market ghosts sometimes have the stranger stories. The Drake doesn’t sell a haunted package, but its hidden-passageway story is odder than most “woman in white” tales precisely because it’s about real infrastructure, not an apparition.

• Thin sourcing doesn’t mean nothing happened — it means nobody wrote it down. The Palmer House’s eighth-floor lore is the least documented of the three stories here.

• Staff often give a more honest answer than the tour script. Several Congress Plaza employees seemed almost relieved to admit the Room 441 specificity is recent. Ask, don’t just request the room.

The Catch

• The Congress Plaza’s ghost marketing oversells a story that’s partly manufactured, and the building itself is unevenly renovated — some floors are genuinely nice, others need work, largely independent of your booking choices.

• The Drake’s passageway story and the Palmer House’s eighth-floor lore are both unverified. Enjoy them as Chicago folklore. Don’t repeat either one as documented fact at a dinner party unless you enjoy being corrected.

• None of these three hotels has anything close to the Marshall House’s confirmed bones-under-the-floorboards history from our Savannah haunted hotels guide — Chicago’s stories lean more on urban legend and marketing than on hard 19th-century documentation.

• If you want ghost stories with more paper trail behind them, our New Orleans haunted hotels guide covers a city where the history is, unfortunately, better documented.

Is It Worth It?

Honest verdict: book any of these three for what they actually are — a real 1893 labor-history landmark, a real 1920 lakefront grand dame, and a real 1927 rebuild of a hotel that’s burned down once already — and treat the ghost stories as a bonus, not the reason to go.

Practical Info

• Neighborhoods: Congress Plaza and Palmer House are both in the Loop, walkable to Grant Park, the Art Institute, and Michigan Avenue; the Drake is further north on the Magnificent Mile, near Oak Street Beach
• Best months: Shoulder season (April–May, September–October) for lower rates and fewer ghost-tour crowds outside the Congress Plaza specifically
• Ghost tours: Multiple companies run nightly Chicago ghost walks that stop outside all three properties, roughly $25–35/person
• Getting there: Midway (MDW) is closer to the Loop hotels, ~20 minutes by taxi; O’Hare (ORD) serves all three, ~35–45 minutes depending on traffic
• Explore the neighborhood: See our Chicago city guide for restaurants and getting-around tips

Final Verdict

The honest version of Chicago’s haunted-hotel reputation is this: one property, the Congress Plaza, has built an entire marketing identity around a ghost story that’s newer and shakier than it lets on, sitting on top of a genuinely significant labor history it doesn’t advertise at all. The other two carry thinner, more circulating lore — a plausible-but-unconfirmed passageway story at the Drake, a thinly sourced eighth-floor legend at the Palmer House — attached to buildings whose real architecture and history don’t need the embellishment. Go for whichever version of Chicago you actually want. Just know which one you’re getting.

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Written by

Thomas Waverly

Travel Correspondent

Thomas covers East Coast, Southern, and Western grand hotels. He has personally stayed in over 80 historic properties and considers a properly aged lobby bar essential to any review.