Search Southwest Side Cottage Accommodations

  • 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
8.4 out of 10, Very good, (1,015 reviews)
"Staff very friendly "
United States
Kali
The price is AU$198
includes taxes & fees
5 Apr - 6 Apr
Holiday Inn Chicago – Midway Airport S by IHG

Carlton Inn Midway

Carlton Inn Midway
2.0 star property
Archer Heights
6.4 out of 10, (1,006 reviews)
"It is a good place to stay."
United States
Paul Adrian
The price is AU$147
includes taxes & fees
11 Mar - 12 Mar
Carlton Inn Midway

Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10

Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
Brighton Park
10.0 out of 10, Exceptional, (1 review)
"Family-friendly, quiet, perfect for a family or friends vacationing in Chicago. The apartment is very clean and the host was always available and responded quickly. The next time I come to Chicago, i will definitely stay at the apartment [if available]. "
United States
Fabian H.
The price is AU$393
includes taxes & fees
16 Mar - 17 Mar
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10

W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade

W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade
Brighton Park
9.4 out of 10, Exceptional, (9 reviews)
"Great location, spacious, and family friendly. Had cousins over and they had a blast playing the video games. "
United States
Jessica H.
The price is AU$402
includes taxes & fees
17 Mar - 18 Mar
W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade

Skylark Motel

Skylark Motel
2.0 star property
Garfield Ridge
4.6 out of 10, (120 reviews)
"Easily one of the worst places ever. Slightly better than spending the night in Chicago Midway terminal."
United States
Stephen
The price is AU$130
includes taxes & fees
24 Mar - 25 Mar
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, (2,404 reviews)
"Great stay"
United States
Blake
The price is AU$282
includes taxes & fees
24 Mar - 25 Mar
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, (2,675 reviews)
"Yes it was a great stay"
United States
Rita
The price is AU$258
includes taxes & fees
1 Apr - 2 Apr
Hilton Chicago

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,229 reviews)
"Place is always top notch..stay here anytime we stay in Chicago."
United States
Jon
The price is AU$253
includes taxes & fees
29 Mar - 30 Mar
Swissotel - Chicago

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
Downtown Chicago
8.0 out of 10, Very good, (9,938 reviews)
"Great location, beautiful historic hotel with clean, updated rooms. "
United States
Jennifer
The price is AU$276
includes taxes & fees
21 Mar - 22 Mar
Congress Plaza Hotel

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,485 reviews)
"Clean room, great staff, great location "
United States
Tiffany
The price is AU$304
includes taxes & fees
5 Apr - 6 Apr
Hyatt Regency 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, (1,894 reviews)
"Absolutely enjoyed my time here"
United States
Quayshaun
The price is AU$197
includes taxes & fees
5 Apr - 6 Apr
Hilton Garden Inn Chicago Downtown South Loop

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very good, (1,719 reviews)
"Thoroughly enjoyed my stay at The Wade"
United States
Danielle
The price is AU$181
includes taxes & fees
22 Mar - 23 Mar
The Wade

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,499 reviews)
"Amazing place, breakfast is great , location is great - honestly great hotel! "
United States
Brisa
The price is AU$268
includes taxes & fees
18 Mar - 19 Mar
Hotel Riu Plaza Chicago

Le Méridien Essex Chicago

Le Méridien Essex Chicago
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,012 reviews)
"Great place to stay..awesome staff!"
United States
Veronica
The price is AU$178
includes taxes & fees
1 Apr - 2 Apr
Le Méridien Essex Chicago

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,076 reviews)
"Great place "
United States
Kamilah
The price is AU$331
includes taxes & fees
24 Mar - 25 Mar
Fairmont Chicago at Millennium Park

Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (2,410 reviews)
"Super comfy beds, helpful staff, free coffee and snacks and an amazing location "
United States
Stephanie
The price is AU$233
includes taxes & fees
20 Mar - 21 Mar
Hyatt Centric The Loop Chicago

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,902 reviews)
"The staff and the cleanliness of the Hotel was amazing and the views where great!!"
United States
Oliver
The price is AU$172
includes taxes & fees
17 Mar - 18 Mar
Hilton Chicago/Magnificent Mile Suites

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,147 reviews)
"Great location and friendly staff. "
United States
Pablo
The price is AU$179
includes taxes & fees
22 Mar - 23 Mar
Aloft Chicago Mag Mile

Best Western Grant Park Hotel

Best Western Grant Park Hotel
2.5 star property
Downtown Chicago
8.2 out of 10, Very good, (2,697 reviews)
"Clean room and the staff are great. "
United States
Doug
The price is AU$166
includes taxes & fees
16 Mar - 17 Mar
Best Western Grant Park Hotel

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,646 reviews)
"Staff was friendly and loved the decor at this hotel…will definitely be staying again"
Canada
Osama
The price is AU$380
includes taxes & fees
21 Mar - 22 Mar
LondonHouse Chicago, Curio Collection by Hilton
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.

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
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
52,083
Accommodation
14 Cottages
Lowest Price
AU$130
Highest Price
AU$380

Explore a world of travel with Expedia