A river with a yellow boat, surrounded by tall buildings and a bridge.

Find Chicago Hotels with Shuttle Services from S$179

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Check availability on Chicago Hotels with shuttle

Tonight
3 Oct - 4 Oct
Tomorrow
4 Oct - 5 Oct
Next weekend
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct

Our top choices for Chicago hotels with transport

A modern kitchen with a marble island, fruit bowls, and a city view.
A modern bar area with a central bar, seating, and a distinctive ceiling design.
A modern lounge area with a central bar, seating arrangements, and a decorative chandelier.
A modern hotel room with a city view, a seating area with two sofas and a coffee table, and a dining area with a table and chairs.

1. Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
Downtown Chicago
United States
Ruby
S$303
includes taxes & fees
31 Oct - 1 Nov
Fairmont Chicago at Millennium Park
A long dining table with chairs, overhead lighting, and a marble wall with a decorative ceiling.
A modern building with large glass windows and a covered walkway.
A grand hall with a central aisle, ornate chandeliers, and rows of chairs.
A grand lobby with ornate ceiling artwork, chandeliers, and a prominent 'P' emblem.

2. Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
Downtown Chicago
United States
Gabriella
S$327
includes taxes & fees
31 Oct - 1 Nov
Palmer House a Hilton Hotel
A large, historic building with a central courtyard surrounded by trees.
A modern hotel lobby with a curved white sofa, two side tables with lamps, a black coffee table, and a large chandelier.
A marina with numerous boats docked, surrounded by a cityscape with high-rise buildings and a stadium.
A hotel room with two beds, a desk with a television, a chair, a desk lamp, and a painting on the wall.

3. Hilton Chicago

Hilton Chicago
Downtown Chicago
United States
Alan
S$289
includes taxes & fees
30 Oct - 31 Oct
Hilton Chicago
A dining table set for six with a cityscape view through large windows.
The exterior of the Swissotel building with its distinctive glass facade and the hotel's name displayed prominently.
A modern hotel room with a large window offering a cityscape view, a green sofa, two armchairs, and a coffee table with flowers.
A modern hotel room with a large bed, a desk, a chair, and a view of the cityscape through large windows.

4. Swissotel - Chicago

Swissotel - Chicago
Downtown Chicago
United States
Michael
S$336
includes taxes & fees
31 Oct - 1 Nov
Swissotel - Chicago
A modern dining area with round tables and white chairs, a kitchen area with a coffee machine, and a view of the outdoors through large windows.
A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.
A hotel room with two beds, a nightstand, a telephone, and a wall with printed text.
Front of property

5. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
Downtown Chicago
United States
John
S$261
includes taxes & fees
3 Nov - 4 Nov
Hilton Vacation Club Hotel Blake Chicago
The Intercontinental hotel facade with a large American flag and a floral display.
A person lying on a bed with a bottle of champagne, surrounded by food and a magazine.
A person sitting by a window with a cityscape view.
A swimming pool area with a glass-bottomed pool, a high ceiling with hanging lights, and a staircase with people sitting on it.

6. InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago
United States
Kenan
S$408
includes taxes & fees
1 Nov - 2 Nov
InterContinental Chicago Magnificent Mile by IHG
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 multi-level hotel lobby with a glass elevator, a seating area, and a dining space.

7. Hyatt Regency Chicago

Hyatt Regency Chicago
Downtown Chicago
United States
Mark
S$421
includes taxes & fees
31 Oct - 1 Nov
Hyatt Regency Chicago
A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.
A hotel reception area with a modern design, featuring a wooden panel wall and a marble reception desk.
Transparent igloo-like structures with seating inside, set on a wooden deck with snow on the ground, surrounded by tall buildings.
A modern lobby with a seating area, a bar, and a green wall.

8. DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
Downtown Chicago
United States
Poua
S$194
includes taxes & fees
1 Nov - 2 Nov
DoubleTree by Hilton Chicago - Magnificent Mile
A hotel room with a large window offering a city view, a bed, a desk, and a chair.
A coffee shop interior with a display case of pastries, a coffee machine, and a menu board.
A reception area with a modern design, featuring a large window, a reception desk, and artwork on the wall.
A Courtyard Marriott hotel with a glass facade, a self-park sign, and a Marriott logo.

9. Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile
Downtown Chicago
United States
Tim
S$201
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott Chicago Magnificent Mile
A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.
A grand ballroom with ornate ceiling decorations, multiple chandeliers, and a central table with a white tablecloth.
A cityscape with various buildings, including a prominent skyscraper and a classical building with arched windows.
Outdoor seating with yellow umbrellas labeled "Twisted Tea," wicker chairs, and tables.

10. Congress Plaza Hotel

Congress Plaza Hotel
Downtown Chicago
United States
Guadalupe
S$179
includes taxes & fees
1 Nov - 2 Nov
Congress Plaza Hotel
View all properties

Top Chicago Hotel Reviews

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

8/10 Good
"Close to the Loop, Union Station, and Millennium Park. Stylish bar in the lobby. Room was clean and the bed comfortable. Bathroom was on the small side"
Agnes 2-night trip
Posted less than an hour ago
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"I took a chance on this hotel and I am glad I did. It was right in the center of EVERYTHING! We rented a car, but never drove it because everything we wanted to see and do was within walking distance. I paid for the upgrade and was able to check in early, which was perfect considering my flight arrived at 7:55AM. We had free breakfast, two cocktails daily & 4 bottles of water per day, along with late check out. However, the only drawback was we had no hot water the entire 4 days I was there. They managed to fix it and we had one night of hot water, but every day after was luke warm. Overall it was a great stay, location and experience."
Kosha 3-night trip
Posted less than an hour ago
The Chicago Hotel Collection - Magnificent Mile
Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

10/10 Excellent
"Clean and quite."
Jacqueline 3-night trip
Posted less than an hour ago
Sports Illustrated Resorts Chicago
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent
"The hotel was a very convenient location from downtown and Lake Michigan. Definitely one of the better breakfasts I've had recently and the pricing sits just right for the amenities and convenience this hotel offers"
Sudeep 1-night trip
Posted 13 hours ago
The Chicago Hotel Collection Ambassador Gold Coast

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