Southwest Side Hotels from from S$88

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Our top choices for Southwest Side hotels

Rainbow Motel

Rainbow Motel
2.0 star property
Garfield Ridge
5.6 out of 10, (19 reviews)
"It was a good stay the rooms are small tho but if you are going to have fun and just have somewhere to sleep then it’s perfect for a couple people "
United States
Conner
The price is S$128
includes taxes & fees
20 Apr - 21 Apr
Rainbow Motel

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG
2.5 star property
West Lawn
8.2 out of 10, Very good, (998 reviews)
"Great staff , enjoyed our stay , very close to where we needed to be "
United States
Wafa
The price is S$184
includes taxes & fees
9 Apr - 10 Apr
Holiday Inn Chicago – Midway Airport S by IHG

Carlton Inn Midway

Carlton Inn Midway
2.0 star property
Archer Heights
6.2 out of 10, (1,001 reviews)
"It is a good place to stay."
United States
Paul Adrian
The price is S$152
includes taxes & fees
17 Apr - 18 Apr
Carlton Inn Midway

Skylark Motel

Skylark Motel
2.0 star property
Garfield Ridge
4.8 out of 10, (122 reviews)
"This place should shut down. It is the worst accommodation I have ever stayed at. "
United States
Roop
The price is S$118
includes taxes & fees
19 Apr - 20 Apr
Skylark Motel

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2,446 reviews)
"Just an amazing place to stay. The staff is lovely, the rooms are wonderful and the location is perfect for a day at the waterline. "
United States
Christopher
The price is S$350
includes taxes & fees
16 Apr - 17 Apr
Sable at Navy Pier Chicago, Curio Collection by Hilton

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
Downtown Chicago
8.0 out of 10, Very good, (10,062 reviews)
"The stay is well worth the affordable price."
United States
Thomas
The price is S$174
includes taxes & fees
26 Apr - 27 Apr
Congress Plaza Hotel

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,758 reviews)
"Great hotel "
United States
Marina
The price is S$230
includes taxes & fees
13 Apr - 14 Apr
Hotel Riu Plaza Chicago

Hilton Chicago

Hilton Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,716 reviews)
"We love staying here "
United States
Carrie
The price is S$336
includes taxes & fees
9 May - 10 May
Hilton Chicago

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,950 reviews)
"Hotel was really nice"
United States
LaCarr
The price is S$184
includes taxes & fees
28 Apr - 29 Apr
Hilton Garden Inn Chicago Downtown South Loop

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,171 reviews)
"Nice location and good hotel"
United States
Taneshia
The price is S$182
includes taxes & fees
12 Apr - 13 Apr
Aloft Chicago Mag Mile

River Hotel

River Hotel
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (5,059 reviews)
"very beautiful hotel and great location "
United States
Ciandra
The price is S$162
includes taxes & fees
27 Apr - 28 Apr
River Hotel

FOUND Hotel Chicago River North

FOUND Hotel Chicago River North
2.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (536 reviews)
"Love this place. Kind of like a college dorm with community kitchen. Will stay there again. "
United States
William
The price is S$115
includes taxes & fees
14 Apr - 15 Apr
FOUND Hotel Chicago River North

Central Loop Hotel

Central Loop Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,054 reviews)
"For the price, it was a very nice a room and location. "
United States
Anna
The price is S$140
includes taxes & fees
9 Apr - 10 Apr
Central Loop Hotel

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Downtown Chicago
8.2 out of 10, Very good, (1,358 reviews)
"Very beautiful place to stay"
United States
angie
The price is S$171
includes taxes & fees
22 Apr - 23 Apr
The Chicago Hotel Collection Ambassador Gold Coast

Best Western Grant Park Hotel

Best Western Grant Park Hotel
2.5 star property
Downtown Chicago
8.2 out of 10, Very good, (2,671 reviews)
"Nice, quiet place to stay at, close to a lot of places to eat and to adventure out to."
United States
Kristin
The price is S$169
includes taxes & fees
16 Apr - 17 Apr
Best Western Grant Park Hotel

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,403 reviews)
"Loved this hotel!"
United States
Ellen
The price is S$209
includes taxes & fees
12 Apr - 13 Apr
DoubleTree by Hilton Chicago - Magnificent Mile

The Hoxton Chicago

The Hoxton Chicago
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,007 reviews)
"Super cute hotel. Great bar and food "
United States
Patricia
The price is S$293
includes taxes & fees
12 Apr - 13 Apr
The Hoxton Chicago

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,367 reviews)
"Beautiful property, great resturant on site, an the pool and spa was amazing."
United States
Tim
The price is S$300
includes taxes & fees
9 May - 10 May
Palmer House a Hilton Hotel

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Downtown Chicago
8.2 out of 10, Very good, (2,813 reviews)
"Every thing was in walking distance and the hotel is beautiful I will definitely be back "
United States
Shannon
The price is S$247
includes taxes & fees
12 Apr - 13 Apr
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (3,875 reviews)
"Loved the stay here !"
United States
Alisha
The price is S$285
includes taxes & fees
12 Apr - 13 Apr
L7 Chicago by LOTTE
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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