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Find Cheap Hotels in Southwest Side, IL

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Check availability on Southwest Side Cheap Hotels

Our top choices for Southwest Side cheap hotels

Skylark Motel

Skylark Motel
2.0 star property
Garfield Ridge
4.6 out of 10, (119)
"Easily one of the worst places ever. Slightly better than spending the night in Chicago Midway terminal."
United States
Stephen
The price is ¥13,590
¥15,953 total
includes taxes & fees
Dec 21 - Dec 22
Skylark Motel

Carlton Inn Midway

Carlton Inn Midway
2.0 star property
Archer Heights
6.4 out of 10, (1001)
"The room was clean and satisfied our needs. Was handy using their shuttle to Midway Airport."
United States
Charles
The price is ¥15,425
¥18,106 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Carlton Inn Midway

Rainbow Motel

Rainbow Motel
2.0 star property
Garfield Ridge
5.8 out of 10, (18)
"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 ¥15,114
¥19,302 total
includes taxes & fees
Dec 15 - Dec 16
Rainbow Motel

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG
2.5 star property
West Lawn
8.4 out of 10, Very Good, (1000)
"Great stay"
United States
Maria
The price is ¥16,516
¥20,946 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Holiday Inn Chicago – Midway Airport S by IHG

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2961)
"Great location and great staff!!"
United States
lynne
The price is ¥12,309
¥14,451 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Aloft Chicago Mag Mile

Freehand Chicago

Freehand Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very Good, (2643)
"The room was spotless and the staff where great!"
United States
Maria
The price is ¥9,115
¥13,443 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Freehand Chicago

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3485)
"Great place to stay "
United States
RaShawna
The price is ¥12,649
¥14,847 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Hilton Chicago/Magnificent Mile Suites

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, (2261)
"This place was amazing !"
United States
Jayla Danyell
The price is ¥14,437
¥22,253 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (2746)
"Clean room and friendly staff, overall good stay "
United States
eesaa saalik
The price is ¥12,091
¥18,767 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

River Hotel

River Hotel
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (4855)
"Great location, comfortable room, and nice staff."
United States
Claudia
The price is ¥12,957
¥15,211 total
includes taxes & fees
Dec 16 - Dec 17
River Hotel
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.

Top Southwest Side Hotel Reviews

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