If you walked down East Chestnut Street ten years ago, the Tremont Hotel Magnificent Mile Chicago felt like the soul of the neighborhood. It was that rare breed of boutique hotel—stately, slightly old-school, and home to a legendary steakhouse where you might actually spot Mike Ditka himself.
But things have changed. A lot.
Honestly, if you're looking to book a room there today, you might be confused. The brass plaques are different. The vibe has shifted from "European boutique" to something much more modern and, frankly, divisive. Here is the real story of what happened to the Tremont, what it’s like right now, and whether it’s still worth your money.
The Rebranding: From Tremont to Selina
For decades, the Tremont Chicago Hotel at Magnificent Mile was the go-to for travelers who wanted to be near the luxury of Michigan Avenue without the cold, corporate feel of a massive high-rise. It had those heavy fabrics, dark woods, and the kind of "hush" you only find in buildings from the 1920s.
Then, the world of hospitality shifted.
In the late 2010s, the property went through a series of ownership changes. Marriott sold it off, and eventually, the lifestyle brand Selina took over. They didn't just change the name on the door; they changed the entire DNA of the place.
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Today, it is officially Selina Chicago.
You've got to understand the Selina model to know what you’re walking into. They target "digital nomads." This means the lobby that once felt like a quiet library is now a coworking space. The traditional hotel rooms have been supplemented with "community rooms"—basically upscale dorms with bunk beds. It’s a bold move for a building with this much history, and to be blunt, the transition hasn't been perfectly smooth.
The Mike Ditka Factor
You can’t talk about the Tremont Hotel Magnificent Mile Chicago without talking about Mike Ditka's Restaurant. For a long time, the two were inseparable. It was a Chicago institution. You’d go there for a massive steak, a cigar in the upstairs lounge, and the hope of seeing "Da Coach" in the corner booth.
When the hotel transitioned, the restaurant also saw major changes. While the spirit of Ditka’s lingered for a while, the classic, white-tablecloth steakhouse era has largely faded from this specific location. For many locals, this was the end of an era. The current dining scene at the hotel is more focused on quick bites and coffee for people working on their laptops.
It’s efficient, sure. But it’s not the same.
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Location: The One Thing That Never Changes
Whatever you think about the rebranding, you cannot beat where this building sits. 100 East Chestnut Street is a prime piece of real estate.
- The John Hancock Center (875 North Michigan) is essentially your neighbor.
- Water Tower Place is a three-minute walk.
- Oak Street Beach is close enough that you can smell the lake on a breezy day.
You are tucked just a half-block off the main drag. This is the "Gold Coast" side of the Magnificent Mile, which feels a bit more residential and polished than the tourist-heavy areas further south toward the river. You can duck out of the hotel, grab a coffee at the Starbucks across the street, and be at the Gucci or Prada storefronts before your espresso is cold.
The "Old Building" Reality Check
Living in a 1920s building—which was originally the Mozart Apartment Hotel—comes with a lot of character. It also comes with 1920s problems.
The elevators can be slow. The hallways are sometimes narrow. While the new owners have done renovations, you're still dealing with a century-old skeleton. Some guests rave about the "personality" of the rooms, while others find the lack of central climate control in certain units a dealbreaker during a humid Chicago July.
Kinda like a classic car. It looks great, but you might have to jiggle the key.
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Is it Still a "Luxury" Stay?
This is where things get tricky. If your definition of luxury is a 24-hour marble-clad spa and a personal butler, the current state of the Tremont Hotel Magnificent Mile Chicago (as Selina) will disappoint you.
It has moved into the "lifestyle" category. It’s for the traveler who wants a high-speed Wi-Fi connection, a cool bar, and a place to meet people from other countries. It’s less about being pampered and more about being "connected."
The Pros:
- Price Point: It is often significantly cheaper than its neighbors like the Peninsula or the Four Seasons.
- Vibe: If you're under 40 or a solo traveler, the social atmosphere is actually pretty great.
- Accessibility: You are in the heart of the city for a fraction of the cost of "Old Guard" luxury hotels.
The Cons:
- Noise: Thinner walls and the social lobby can make it louder than a traditional hotel.
- Amenities: You might find yourself missing things like in-room TVs (some rooms don't have them) or standard hotel breakfasts.
- Maintenance: As an older building under a new, rapid-growth brand, some guests have noted that the "polish" isn't always consistent.
Actionable Advice for Your Visit
If you're planning to stay here, don't just book the first room you see on a travel site.
- Check the Room Type: Selina lists everything from "Suites" to "Bunk Bed in a 6-Bed Community Room." If you want the old Tremont experience, you must book a Private Room or Suite. Don't accidentally book a hostel bed because the price looked too good to be true.
- Ask About the AC: If you're visiting in the summer, call the front desk and confirm your specific room has a dedicated cooling unit. It’s an old building; airflow varies.
- Use the Workspace: If you're a remote worker, don't pay for a separate coworking pass. The lobby is designed for this, and it’s one of the best "free" perks of staying here.
- Explore the Backstreets: Instead of just walking to Michigan Avenue, walk West. You’ll hit Rush Street and the heart of the Gold Coast's local dining scene, which is much more interesting than the chain restaurants on the Mile.
The Tremont Hotel Magnificent Mile Chicago isn't the place it was in 1995. It's younger, leaner, and a bit more chaotic. But for the right traveler—one who values location and social energy over velvet curtains and hushed hallways—it remains one of the most interesting pivots in the Chicago hotel market.
Before you book, decide what you actually need. If it’s a quiet, traditional anniversary getaway, look at the Drake. But if you want to be in the middle of everything, meet a few interesting strangers, and save enough money to actually afford a shopping spree on the Mile, this weird, historic hybrid might be exactly what you need.
Next Steps:
- Confirm the Name: Ensure you are searching for "Selina Chicago" on booking platforms to see current rates and availability, as the Tremont name is being phased out of digital search.
- Check Recent Reviews: Specifically look for reviews from the last 90 days. Management and maintenance standards in high-turnover boutique hotels can change quickly.
- Validate the Restaurant Status: If your heart is set on a specific dining experience at 100 E Chestnut, check their current house restaurant's menu, as the kitchen concepts have been revolving lately.