Search Southwest Side hotels

Start date: Check-in selected.
To Date
End date: Check-out

    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

Filter by

Guest rating
Guest rating
Star rating

Top hotels and accommodation in Southwest Side

Carlton Inn Midway
2.0 star property
6.4 out of 10, (1009)
"Front Desk attention was great."
The price is AU$214
includes taxes & fees
31 Oct - 1 Nov
Carlton Inn Midway
Capital O Rainbow Motel Chicago
2.0 star property
5.8 out of 10, (12)
"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 "
Capital O Rainbow Motel Chicago
Skylark Motel
2.0 star property
4.6 out of 10, (118)
"Easily one of the worst places ever. Slightly better than spending the night in Chicago Midway terminal."
The price is AU$161
includes taxes & fees
16 Oct - 17 Oct
Skylark Motel
Eurostars Magnificent Mile
4.0 star property
8.8 out of 10, Excellent, (3082)
"Very nice location and everything was a 10/10"
The price is AU$216
includes taxes & fees
10 Nov - 11 Nov
Eurostars Magnificent Mile
River Hotel
4.0 star property
8.8 out of 10, Excellent, (4747)
"Staff friendly and helpful..and accommodations just right..great location! "
The price is AU$185
includes taxes & fees
11 Nov - 12 Nov
River Hotel
DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
8.8 out of 10, Excellent, (2093)
"Great hotel"
The price is AU$287
includes taxes & fees
3 Nov - 4 Nov
DoubleTree by Hilton Chicago - Magnificent Mile
Aloft Chicago Mag Mile
3.0 star property
8.6 out of 10, Excellent, (2867)
"Had a great stay!"
The price is AU$249
includes taxes & fees
10 Nov - 11 Nov
Aloft Chicago Mag Mile
citizenM Chicago Downtown
4.0 star property
9.2 out of 10, Wonderful, (3952)
"Great place to stay. "
The price is AU$237
includes taxes & fees
9 Nov - 10 Nov
citizenM Chicago Downtown
Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
9.4 out of 10, Exceptional, (2193)
"Great hotel "
The price is AU$340
includes taxes & fees
9 Nov - 10 Nov
Sable at Navy Pier Chicago, Curio Collection by Hilton
Congress Plaza Hotel
3.5 star property
8.0 out of 10, Very good, (9423)
"Beautiful hotel!"
The price is AU$231
includes taxes & fees
2 Nov - 3 Nov
Congress Plaza Hotel
Freehand Chicago
4.0 star property
8.0 out of 10, Very good, (2475)
"Great place"
The price is AU$149
includes taxes & fees
10 Nov - 11 Nov
Freehand Chicago
Hilton Chicago
4.0 star property
8.4 out of 10, Very good, (2261)
"We loved this hotel it was beautiful and convenient . "
The price is AU$376
includes taxes & fees
10 Nov - 11 Nov
Hilton Chicago
Hilton Garden Inn Chicago Downtown/Magnificent Mile
3.0 star property
8.4 out of 10, Very good, (4082)
"Clean room , staff were friendly, a lot of restaurants in the area."
The price is AU$255
includes taxes & fees
6 Nov - 7 Nov
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Hilton Chicago/Magnificent Mile Suites
3.5 star property
8.8 out of 10, Excellent, (3113)
"Our stay was great"
The price is AU$260
includes taxes & fees
9 Nov - 10 Nov
Hilton Chicago/Magnificent Mile Suites
FOUND Hotel Chicago River North
2.0 star property
8.2 out of 10, Very good, (275)
"Perfect location! Tons of restaurants and shopping nearby! "
The price is AU$145
includes taxes & fees
10 Nov - 11 Nov
FOUND Hotel Chicago River North
Best Western River North Hotel
2.5 star property
7.8 out of 10, Good, (1027)
"Great stay"
The price is AU$182
includes taxes & fees
10 Nov - 11 Nov
Best Western River North Hotel
Hotel Riu Plaza Chicago
4.0 star property
9.4 out of 10, Exceptional, (2604)
"Great place to stay "
The price is AU$299
includes taxes & fees
9 Nov - 10 Nov
Hotel Riu Plaza Chicago
Hyatt Centric The Loop Chicago
4.0 star property
9.0 out of 10, Wonderful, (2181)
"It was an amazing stay!"
The price is AU$329
includes taxes & fees
9 Nov - 10 Nov
Hyatt Centric The Loop Chicago
voco Chicago Downtown - Riverwalk by IHG
3.5 star property
8.8 out of 10, Excellent, (3213)
"Great stay "
The price is AU$288
includes taxes & fees
9 Nov - 10 Nov
voco Chicago Downtown - Riverwalk by IHG
La Quinta Inn & Suites by Wyndham Chicago Downtown
3.0 star property
8.6 out of 10, Excellent, (2585)
"Good place to stay"
The price is AU$279
includes taxes & fees
2 Nov - 3 Nov
La Quinta Inn & Suites by Wyndham Chicago Downtown
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

Stay near popular Great Lakes attractions

Learn more about Southwest Side

Explore attractions like Balzekas Museum of Lithuanian Culture and Union Stock Yard Gate as you discover things to see and do in Southwest Side.

Photo by by Midway Intl Airport
Open Photo by by Midway Intl Airport

Top Southwest Side Hotel Reviews

More cheap accommodation in Southwest Side

Explore a world of travel with Expedia