The Drake Hotel

I checked in on a Tuesday afternoon in January, which means I got the view for free — Lake Michigan doing its flat, gray, endless thing outside the window of a room on a high floor, no summer haze, no boats, just water to the horizon. The woman at the front desk mentioned, without being asked, that the hotel opened on New Year’s Eve in 1920. I did the math while she was still talking. This building has been standing at the top of Michigan Avenue for longer than commercial aviation has existed.

The Drake doesn’t feel like a hotel that’s trying to prove anything anymore. It proved it a century ago. What it feels like now is a very good, slightly formal, occasionally creaky grand dame that still knows exactly where she is — which is precisely where Michigan Avenue stops being a shopping street and becomes a view of Lake Michigan and Oak Street Beach. That positioning was not an accident. It was the entire plan.

I’ve stayed in a lot of hotels that lean on a founding date like it’s the only argument they have. The Drake is not one of those. Yes, it opened in 1920. But it’s also just a genuinely well-run large hotel — the elevators work, the front desk is fast, the housekeeping is sharp — wrapped around a building that happens to be older than sliced bread. That combination is rarer than you’d think.

Plenty of “historic” hotels trade on a plaque out front and not much else once you get past the lobby. The Drake keeps the history visible in the places that matter — the lobby ceiling, the Palm Court fountain, the Coq d’Or’s Prohibition-era bones — while quietly running a modern, professional operation everywhere the average guest actually interacts with it.

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📍 Location	140 East Walton Place, Near North Side, Chicago, Illinois
💰 Price range	~$320/€295/£255 per night
⭐ Best for	Lake views, classic Chicago, couples, afternoon tea, business travelers
⏱️ Sweet spot	Late spring through fall for the lake views; December for the lobby at Christmas
🚫 Skip if	You want a modern boutique feel or a rooftop pool scene
📖 Book	The Drake Hotel on Booking.com

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The History Nobody Tells You

The Drake opened on December 31, 1920 — New Year’s Eve, on purpose, because brothers John B. Drake and Tracy C. Drake wanted their new hotel’s first night to be a party the whole city talked about. They built it at the northern tip of Michigan Avenue, at the exact point where the street stops being lined with shops and starts facing Lake Michigan and Oak Street Beach. That’s not a coincidence of geography. It’s the entire architectural argument of the building: this is where the Magnificent Mile ends and the lake begins, so put the anchor here.

Italian Renaissance Revival was the style, which in practice means limestone, symmetry, and a lobby that wants you to lower your voice a little when you walk in. It worked. Over more than a hundred years, the guest list has included Queen Elizabeth II, Princess Diana, Amelia Earhart, Walt Disney, Rudolph Valentino, and Frank Sinatra — a spread of royalty, aviation, animation, and Rat Pack that tells you the Drake has never been a niche hotel. It was, and mostly still is, the place you stay in Chicago when you want everyone to know you stayed somewhere serious.

Think about what else was happening on Michigan Avenue in 1920. Most of the Magnificent Mile as shoppers know it today didn’t exist yet — the Wrigley Building was brand new, the Michigan Avenue Bridge had only just opened a couple of years earlier, and the whole northward expansion of downtown Chicago was still being decided in real time. The Drake brothers weren’t just building a hotel. They were betting on which direction the city would grow, and they bet on the lake. They won.

The best-kept piece of hotel lore, and I mean this in the local-legend sense rather than the verified-history sense, involves Secret Service agents allegedly finding old hidden passageways somewhere in the building during visits by Chicago’s own President Obama. Nobody at the front desk will confirm details, and I wouldn’t stake anything on it, but every longtime Chicagoan I mentioned it to nodded like it was common knowledge. Old hotels accumulate stories the way they accumulate coats of paint.

The hotel has changed ownership groups more than once across a century — that’s normal for a building this age — but each transition seems to have landed on the same conclusion: don’t touch the bones. The lobby’s proportions, the Walton Place entrance, the general sense that you’ve walked into 1920 with better plumbing, have all survived multiple decades of hotel-industry fashion swings that killed off plenty of the Drake’s contemporaries.

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The Rooms — Real Talk

The rooms have been renovated more than once across a century, and it shows in a good way — you get modern beds and updated bathrooms without losing the crown moldings and the sense of scale that a 1920 building was built with. Ceilings are taller than what you’ll find in most new-build Chicago hotels. Windows are real windows, not the sealed-glass slivers newer towers get away with.

Room Type	Price/night	Best for
Classic Room, city view	~$280/€258/£223	Budget-conscious travelers who still want the address
Deluxe Room, lake view	~$360/€332/£287	The actual reason to book this hotel
Drake Suite	~$650/€600/£518	Special occasions, longer stays, showing off

The honest note: not every room has the view. The Drake is a big, deep building, and a meaningful number of rooms face the interior courtyard or the avenue rather than the water. If the lake view matters to you — and it should, it’s the whole point — confirm it at booking rather than trusting the room name. “Deluxe” alone doesn’t guarantee it.

One more thing nobody warns you about: the hallways are long and the layout is old-hotel logic, not modern-hotel logic. It takes a night or two to stop getting turned around near the elevators.

Bathrooms vary more than you’d expect for a hotel this consistent elsewhere. Some have been fully modernized with walk-in showers and heated floors; others retain a more classic, slightly smaller footprint. If a big soaking tub or a rainfall shower is non-negotiable for you, mention it when you book rather than assuming every room got the same renovation budget.

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Food & Drink

The Cape Cod Room is the reason people who’ve never stayed here still know the Drake’s name. It’s been open in the hotel’s lower level since 1933 — red-checked tablecloths, dark wood paneling, the kind of seafood restaurant that predates the word “seafood restaurant” being a marketing category. The lobster bisque is the signature dish, and the story that gets repeated (accurately or not, but repeated constantly) is that Frank Sinatra liked it enough to have it flown out to him in Las Vegas. Whether that happened exactly as told, I can’t verify. That it’s still on the menu, unchanged, ninety-plus years later, I can.

• Breakfast: the Palm Court, quieter in the morning before the tea crowd arrives, ~$28/€26/£22 for a full plate
• Lunch: Cape Cod Room, chowder and a sandwich rather than the full dinner production, ~$32/€30/£26
• Signature experience: Afternoon tea in the Palm Court, served daily under the fountain and the palms — ~$65/€60/£52 per person, book ahead on weekends
• Dinner: Cape Cod Room for the lobster bisque, full stop
• Skip: room service breakfast — it’s fine, but the Palm Court is one floor away and much better

For drinks, the Coq d’Or bar just off the lobby has been pouring since Prohibition ended and looks it, in the best way — dark wood, a piano some nights, and bartenders who’ve clearly been asked “is this where Sinatra sat” more times than they can count.

If you’re only doing one meal here and you’re not staying the night, make it tea. It’s the most distinctly Drake experience on the menu, more so than the bisque, because you can’t easily replicate a daily formal tea service anywhere else on the Mile.

Reservations for the Cape Cod Room and for tea both go through the same front-of-house system, and both fill up around holidays and major conventions in town — Chicago hosts a lot of conventions. If your dates overlap with anything large downtown, book food before you book the flight.

Things I Noticed That Most Reviews Miss

The lake-facing rooms get genuinely dramatic weather. Chicago storms roll in off the water and you can watch them arrive from a window seat with a much better view than the weather app gives you. Ask for a high floor if this appeals to you.

Afternoon tea is a real daily institution, not a special-occasion add-on. Most hotels that offer tea do it a few days a week or seasonally. The Drake runs it every day in the Palm Court, and it’s a genuine local tradition — plenty of Chicagoans who’ve never spent a night in the hotel come just for tea.

The lobby is a functioning shortcut, not just a photo op. Because of where the hotel sits, locals cut through the lobby to get between Michigan Avenue and the lakefront path. You’ll see people in gym clothes walking briskly through a room that looks like it belongs in a period drama. It’s a nice reminder that this is a working part of the city, not a museum.

Oak Street Beach is a two-minute walk. In summer, this matters more than most Drake reviews mention. You can go from marble lobby to sand in less time than it takes to order a coffee.

The elevators are original in feel if not in mechanics. Small cabs, brass details, a slower ride than a modern high-rise. It’s charming until you’re in a hurry with luggage during a busy checkout window. Build in a few extra minutes.

The building is deeper and quieter than you’d expect from the exterior. Rooms on the courtyard side lose the view but gain real quiet, which is worth considering if you’re a light sleeper on a high floor above a busy avenue.

The staff have clearly fielded the Obama-era passageway question before. Ask about it and you’ll get a knowing smile rather than a denial. Nobody confirms it, nobody laughs it off entirely either.

Christmas is a whole separate reason to book. The lobby gets a large tree and seasonal decor that leans into the building’s age rather than fighting it — it reads as elegant rather than mall-adjacent. If you can time a visit for December, do it.

The doormen remember returning guests. More than one person I talked to in the lobby mentioned being greeted by name on a return visit, sometimes years apart. That’s either an excellent internal system or genuinely long staff tenure. Possibly both.

The Catch

You’re paying for address and history, not for the newest bathroom fixtures. If you want a hotel that feels like it opened in 2023, this isn’t it. The Drake feels like 1920 wearing a well-maintained 2020s renovation.

Not every room has the lake view that makes the hotel famous. Interior and avenue-facing rooms exist at the same general price bracket as some lower lake-view rooms. Read the room description carefully or call ahead.

Parking is expensive and it’s downtown Chicago, so that’s not really the Drake’s fault — but budget for valet, because street parking near Michigan and Walton is close to nonexistent.

Winter wind off the lake is not a joke. The same location that makes the lake views spectacular also means the corner outside the hotel catches wind straight off the water in January and February. Dress for it, or you’ll regret the two-block walk to the beach you were excited about ten minutes earlier.

Afternoon tea and the Cape Cod Room both book up on weekends. If either is the reason you’re staying here, reserve them when you book the room, not when you arrive.

The building’s age means occasional quirks. A slightly uneven floor in a hallway, a door that needs a firmer push than you’d expect, a bathroom layout that’s efficient rather than spacious in some of the older room configurations. None of it is a maintenance problem. It’s just what a 1920 building feels like next to a 2020 one.

The catches here are mostly the ordinary tradeoffs of staying somewhere old and famous in an expensive part of an expensive city. None of them are reasons to skip it.

Is It Worth It?

	Worth it?
First-time Chicago visitors	✅ Iconic address, hard to beat the location
Couples wanting a classic experience	✅ Afternoon tea, the Coq d’Or, the lake
Business travelers on the Mile	✅ Central, dignified, good meeting spaces
Budget travelers	⚠️ You’re paying for history and address
Anyone wanting a modern boutique vibe	❌ Wrong hotel entirely
Solo travelers who want anonymity	⚠️ It’s grand, but the staff will remember your name

Honest verdict: yes, if you know what you’re booking. The Drake isn’t the flashiest hotel in Chicago and it isn’t trying to be. It’s the one that’s been standing at the top of the Magnificent Mile since a New Year’s Eve in 1920, and it still delivers the thing it was built to deliver — a serious address, a lake view, and a bowl of lobster bisque that hasn’t needed to change in ninety years.

If what you actually want is the cheapest bed on the Mile, keep looking. If what you want is to understand why Chicago’s old-money residents still default to this hotel for anniversaries, out-of-town parents, and the occasional royal visit, book the lake view and stop overthinking it.

Practical Info

• Address: 140 East Walton Place, Near North Side, Chicago, IL 60611
• Check-in/out: 3pm / 12pm
• Parking: Valet only, ~$75/€69/£60 per night
• WiFi: Included, reliable
• Nearest airport: O’Hare International (ORD), ~35-45 min by car depending on traffic; Midway (MDW), ~30 min
• Getting there: Taxi, rideshare, or the Blue Line plus a short walk from downtown
• Getting around once you’re there: Everything on the Magnificent Mile is walkable from the hotel; the Red Line and multiple bus routes are a few minutes away for anything further south or west
• Languages spoken: English, with multilingual staff available
• Pet friendly: Check directly with the hotel for current policy
• Nearby: Oak Street Beach (2 min walk), the Magnificent Mile shopping (steps away), John Hancock Center observation deck (5 min walk)

Final Verdict

The Drake has been the anchor at the top of Michigan Avenue since 1920, and everyone from Queen Elizabeth II to Amelia Earhart to Frank Sinatra has walked through that lobby at some point. The Cape Cod Room has served the same lobster bisque since 1933. Afternoon tea happens every single day in the Palm Court, whether or not anyone famous is in town.

It’s not the cheapest room on the Mile and it’s not the newest. It is, still, the most Chicago answer to “where should I stay.” A century after the Drake brothers bet on the lake side of Michigan Avenue, the bet still pays off every time a guest opens the curtains for the first time.

For more on how it compares to the city’s other grand dames, see our Chicago hotels guide — this review finally gives the Drake the standalone treatment our historic Chicago hotels roundup only had room to summarize. If you want to compare it against another Chicago institution, the Palmer House Hilton is the other Chicago historic hotel worth cross-shopping before you book.

📖 Check availability at The Drake Hotel on Booking.com

Prices start at ~$280/€258/£223 per night and climb fast for lake-view rooms and suites. Book lake-view rooms and the Cape Cod Room in advance, especially on weekends. This post contains affiliate links — if you book through them, this site earns a small commission at no extra cost to you.