A modern bridge with a reflection in the water, surrounded by historic buildings and tall skyscrapers.

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Check availability on Great Lakes Luxury Hotels

Tonight
22 Sept - 23 Sept
Tomorrow
23 Sept - 24 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 Oct

Our top choices for Great Lakes luxury hotels

A rooftop lounge with outdoor seating and a city skyline view.
The exterior of the Carbide and Carbon Building with large windows and a balcony area.
An indoor cafe with tables and chairs, large windows, and a view of the cityscape.
A spacious living area with a green sofa, a coffee table, and a bookshelf filled with plants and decorative items.

1. Pendry Chicago

Pendry Chicago
Downtown Chicago
  • Indulge in architectural splendour and upscale amenities at this Art Deco Chicago hotel, where luxury meets city centre convenience.
S$849
includes taxes & fees
25 Sept - 26 Sept
Pendry Chicago
A modern dining area with round tables and chairs, large windows, and a view of a cityscape.
A hotel room with a large bed, a chair, a window with a city view, and a bathroom area with a toilet and a sink.
A modern high-rise building with a curved glass facade, surrounded by other tall buildings.
A person in a white robe sitting by a window with a view of modern high-rise buildings.

2. Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile
Downtown Chicago
  • Art deco elegance and city views blend at this city centre Chicago hotel near Michigan Avenue.
S$582
includes taxes & fees
4 Oct - 5 Oct
Sofitel Chicago Magnificent Mile
A hotel entrance with a marquee sign, a glass awning, and a blue carpet leading to the door.
A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.
A modern bathroom with a dual sink vanity, a large mirror, and a toilet.

3. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
Downtown Chicago
S$567
includes taxes & fees
7 Oct - 8 Oct
Hilton Vacation Club Hotel Blake Chicago
A rooftop terrace with outdoor seating, a view of the city skyline, and a river.
A modern hotel room with a large bed, a desk, a sofa, and a view of the city.
A modern living room with a sofa, coffee table, and ottoman, a fireplace, and a large window with a city view.
A modern room with a view of a river and high-rise buildings.

4. LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
  • Unwind in city centre Chicago's LondonHouse with rejuvenating spa treatments and riverfront luxury.
S$572
includes taxes & fees
2 Oct - 3 Oct
LondonHouse Chicago, Curio Collection by Hilton
An outdoor seating area with a fire pit, wooden benches, and tables, surrounded by large windows and string lights.
A modern lobby with a sofa, coffee table, and potted plants.
A window with a view of a cityscape, a wooden desk with a radio, and a small window ledge.
A modern lounge area with a sofa, chairs, and a large potted plant.

5. The Emily Hotel

The Emily Hotel
Downtown Chicago
S$402
includes taxes & fees
4 Oct - 5 Oct
The Emily Hotel
A modern lounge with a curved glass wall offering a city view, plush seating, and ambient lighting.
A modern interior with wooden shelves, a fireplace, and a round mirror.
A spacious indoor area with a high ceiling, a dining area with tables and chairs, and a seating area with sofas and armchairs.
A modern lobby with a large mirror, bookshelves, seating areas, and a reception desk.

6. Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt
Downtown Chicago
  • Lavish city centre retreat offers pillowtop beds, rainfall showers, and two stylish bars in Chicago's heart.
S$567
includes taxes & fees
27 Sept - 28 Sept
Thompson Chicago, by Hyatt
A spacious bar area with high ceilings and large windows, offering views of a cityscape.
A hotel room with a bed, a sofa with cushions, a large window with a view of a cityscape and water.
A bar with a circular liquor display, seating with stools, and a city view through large windows.
A cityscape with modern high-rise buildings, a river, and a boat.

7. Hyatt Regency Chicago

Hyatt Regency Chicago
Downtown Chicago
S$537
includes taxes & fees
27 Sept - 28 Sept
Hyatt Regency Chicago
A modern living room with a grey sofa, a round coffee table with a plant, and a TV mounted on the wall.
A modern conference room with a long table, blue chairs, and a unique ceiling light fixture.
A modern high-rise building with multiple balconies, large windows, and a city skyline in the background.
A modern kitchen with a gas stove, white cabinets, and a view of the city through large windows.

8. Level Chicago Fulton Market

Level Chicago Fulton Market
Downtown Chicago
S$511
includes taxes & fees
27 Sept - 28 Sept
Level Chicago Fulton Market
An outdoor seating area with a glass table, orange cushions, and potted plants.
A modern building with a large glass facade and a river in front.
A modern living room with a fireplace, large windows, and a flat-screen TV mounted on the wall.
A modern hotel lobby with a bar area, seating arrangements, and decorative lighting.

9. Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
Downtown Chicago
S$544
includes taxes & fees
24 Oct - 25 Oct
Sheraton Grand Chicago Riverwalk
A modern restaurant with high ceilings, exposed beams, and large windows. Tables are set with blue napkins and pink glassware.
A bar with multiple shelves of bottles, a long counter, and several stools.
A rooftop pool area with lounge chairs and a view of the city skyline.
A cozy reading area with a dark blue sofa, multiple bookshelves, and a small table with a drink and a glass.

10. The Hoxton, Chicago

The Hoxton, Chicago
Downtown Chicago
S$537
includes taxes & fees
27 Sept - 28 Sept
The Hoxton, Chicago
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Top Great Lakes Hotel Reviews

Oakes Hotel Overlooking the Falls

Oakes Hotel Overlooking the Falls

10/10 Excellent
"When booking this property we booked the court yard view, which pictures are not provof this part of the hotel, it looks like a run down motel on the outside. We were offered to upgrade for a small fee and happily agreed lesson learned when booking properties"
Patti 1-night trip
Posted less than an hour ago
Oakes Hotel Overlooking the Falls
Toronto Don Valley Hotel and Suites

Toronto Don Valley Hotel and Suites

8/10 Good
"The staff was helpful, but some housekeeping didn't seem to show they were interested in being helpful when questions were asked of them. The manager of the housekeeping staff on my floor was very helpful when we asked for help with our room's heating/air-conditioning unit. One of the desk clerks sent me in the wrong direction when I asked how to get to my car parked at the back of the hotel. (It was not in the basement.) Another one led me in the right direction and I found my car."
Agnes 2-night trip
Posted less than an hour ago
Toronto Don Valley Hotel and Suites
Wyndham Grand Fallsview Hotel

Wyndham Grand Fallsview Hotel

10/10 Excellent
"Great experience, amazing and attentive staff"
Candy 3-night trip
Posted less than an hour ago
Wyndham Grand Fallsview Hotel
Hilton Chicago

Hilton Chicago

10/10 Excellent
"Great location, easy access to everything Chicago"
Dane 5-night trip
Posted 1 hour ago
Hilton Chicago
Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"Iโ€™ve stayed here for years. Every riot"
James 4-night trip
Posted 2 hours ago
Congress Plaza Hotel
One King West Hotel & Residence

One King West Hotel & Residence

10/10 Excellent
"The One King Hotel and Residence was clean, the suite was excellent, the staff were helpful and friendly and the location was very convenient to all the venues."
Nancy 4-night trip
Posted 2 hours ago
One King West Hotel & Residence
River Hotel

River Hotel

10/10 Excellent
"I had a fantastic stay! The location was perfectโ€”right next to the Hello Kitty Cafรฉ and directly across from the Trump Hotel, which made for a beautiful view from my room. Everything was clean, comfortable, and overall a great experience. The only downside was that only one elevator was operating on the Club Level, which caused some delays during busier times. Aside from that, everything was wonderful, and I would definitely stay here again!"
Tia 2-night trip
Posted 3 hours ago
River Hotel
Cambridge Suites Toronto

Cambridge Suites Toronto

10/10 Excellent
"Excellent place and close to everything! Staff was great!"
Shannon 1-night trip
Posted 4 hours ago
Cambridge Suites Toronto