Search Southwest Side Cottage Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months
No exact matches found, but these alternatives could be just right

Recommended hotels in Southwest Side

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, (1,003 reviews)
"Great stay!"
United States
Nancy
The price is S$215
includes taxes & fees
7 Jun - 8 Jun
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, (1,003 reviews)
"The staff were very kind and understanding but we had to get a refund due to bed bugs in the room."
United States
Malachi
The price is S$145
includes taxes & fees
25 May - 26 May
Carlton Inn Midway

Rainbow Motel

Rainbow Motel
2.0 star property
Garfield Ridge
5.4 out of 10, (21 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
25 May - 26 May
Rainbow Motel

Skylark Motel

Skylark Motel
2.0 star property
Garfield Ridge
4.6 out of 10, (124 reviews)
"This place should shut down. It is the worst accommodation I have ever stayed at. "
United States
Roop
The price is S$148
includes taxes & fees
25 May - 26 May
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, (2,505 reviews)
"I loved it here and will definitely stay again."
United States
Gina
The price is S$355
includes taxes & fees
26 May - 27 May
Sable at Navy Pier Chicago, Curio Collection by Hilton

Hilton Chicago

Hilton Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,808 reviews)
"Great staff and location. "
United States
Robert
The price is S$340
includes taxes & fees
27 May - 28 May
Hilton Chicago

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, (1,485 reviews)
"A nice stay and lovely location. "
United States
Robin
The price is S$234
includes taxes & fees
2 Jun - 3 Jun
The Chicago Hotel Collection Ambassador Gold Coast

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2,246 reviews)
"Close to many attractions and shopping and nice unique hotel"
United States
Brittany
The price is S$220
includes taxes & fees
25 May - 26 May
Silversmith Hotel Chicago Downtown

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
Downtown Chicago
8.0 out of 10, Very good, (10,130 reviews)
"Nice clean hotel downtown."
United States
Richard
The price is S$203
includes taxes & fees
25 May - 26 May
Congress Plaza Hotel

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, (2,004 reviews)
"Great location and clean room"
United States
Hyacinthe
The price is S$234
includes taxes & fees
27 May - 28 May
Hilton Garden Inn Chicago Downtown South Loop

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,336 reviews)
"Wonderful location right on the river. Fitness area wonderful, staff helpful. Would stay again!"
United States
Saleem
The price is S$299
includes taxes & fees
25 May - 26 May
Swissotel - Chicago

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very good, (1,836 reviews)
"Excellent location, clean modern rooms."
United States
Molly
The price is S$231
includes taxes & fees
25 May - 26 May
The Wade

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,164 reviews)
"Great place"
United States
JOSE
The price is S$300
includes taxes & fees
25 May - 26 May
Fairmont Chicago at Millennium Park

Aloft by Marriott Chicago Mag Mile

Aloft by Marriott Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,239 reviews)
"Nice place to stay"
United States
Jimmie
The price is S$195
includes taxes & fees
25 May - 26 May
Aloft by Marriott Chicago Mag Mile

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,721 reviews)
"Can't beat the location; it's next to Michigan Avenue and across from the Riverwalk; we'd stay there again."
United States
Matson
The price is S$379
includes taxes & fees
26 May - 27 May
LondonHouse Chicago, Curio Collection by Hilton

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,446 reviews)
"My favorite place to stay!"
United States
Teresa
The price is S$318
includes taxes & fees
25 May - 26 May
Palmer House a Hilton Hotel

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,626 reviews)
"It was very clean, beautiful place"
United States
Grisel
The price is S$409
includes taxes & fees
25 May - 26 May
Sheraton Grand Chicago Riverwalk
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Southwest Side Hotel Reviews

Find out more about Southwest Side

Southwest Side Cottages information

Number of reviews
38,376
Accommodation
1 Cottages
Lowest Price
S$128
Highest Price
S$409

Explore a world of travel with Expedia