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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 NT$2,776
NT$3,259 total
includes taxes & fees
Dec 15 - Dec 16
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 NT$3,088
NT$3,625 total
includes taxes & fees
Jan 1 - 2026/1/2
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 NT$3,026
NT$3,864 total
includes taxes & fees
Dec 16 - Dec 17
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 NT$3,307
NT$4,194 total
includes taxes & fees
Jan 4 - 2026/1/5
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 NT$2,464
NT$2,893 total
includes taxes & fees
Jan 14 - 2026/1/15
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 NT$1,825
NT$2,691 total
includes taxes & fees
Jan 4 - 2026/1/5
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 NT$2,532
NT$2,973 total
includes taxes & fees
Jan 5 - 2026/1/6
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 NT$2,865
NT$4,425 total
includes taxes & fees
Dec 23 - Dec 24
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 NT$2,471
NT$3,816 total
includes taxes & fees
Jan 11 - 2026/1/12
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 NT$2,594
NT$3,045 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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