Photo by by Midway Intl Airport

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

Our top choices for Southwest Side hotels

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 AU$175
includes taxes & fees
1 Jan - 2 Jan 2026
Carlton Inn Midway

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 AU$202
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Chicago – Midway Airport S by IHG

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 AU$154
includes taxes & fees
15 Dec - 16 Dec
Skylark Motel

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 AU$186
includes taxes & fees
15 Dec - 16 Dec
Rainbow Motel

Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1482)
"I really liked this location - we will stay here again. "
United States
Lynnsey
The price is AU$166
includes taxes & fees
21 Dec - 22 Dec
Claridge House Chicago, Tapestry Collection by Hilton

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, (2260)
"This place was amazing !"
United States
Jayla Danyell
The price is AU$215
includes taxes & fees
13 Jan - 14 Jan 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1296)
"Great hotel!"
United States
Julie
The price is AU$283
includes taxes & fees
28 Dec - 29 Dec
Thompson Chicago, by Hyatt

Moxy Chicago Downtown

Moxy Chicago Downtown
3.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (853)
"Great place to stay"
United States
Mason
The price is AU$199
includes taxes & fees
21 Dec - 22 Dec
Moxy Chicago Downtown

Level Chicago Fulton Market

Level Chicago Fulton Market
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (357)
"Great hotel!"
United States
Giselle
The price is AU$337
includes taxes & fees
21 Dec - 22 Dec
Level Chicago Fulton Market

Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
3.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1003)
"Good place to stay in."
United States
Joan
The price is AU$224
includes taxes & fees
21 Dec - 22 Dec
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

citizenM Chicago Downtown

citizenM Chicago Downtown
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (4111)
"Great stay"
United States
Ericka
The price is AU$182
includes taxes & fees
21 Dec - 22 Dec
citizenM Chicago Downtown

The Hoxton Chicago

The Hoxton Chicago
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1005)
"Awesome hotel"
United States
Eligija
The price is AU$283
includes taxes & fees
26 Dec - 27 Dec
The Hoxton Chicago

Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2261)
"The staff, food, and service were great. "
United States
Randy
The price is AU$328
includes taxes & fees
17 Dec - 18 Dec
Sofitel Chicago Magnificent Mile

Springhill Suites by Marriott Chicago Downtown/ River North

Springhill Suites by Marriott Chicago Downtown/ River North
3.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1002)
"We enjoyed the staying for the location "
United States
CARLOS ALBERTO
The price is AU$212
includes taxes & fees
1 Jan - 2 Jan 2026
Springhill Suites by Marriott Chicago Downtown/ River North

Hampton Inn Chicago West Loop Fulton Market Area

Hampton Inn Chicago West Loop Fulton Market Area
2.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1002)
"Good service & nice clean rooms "
United States
Yessica
The price is AU$210
includes taxes & fees
21 Dec - 22 Dec
Hampton Inn Chicago West Loop Fulton Market Area

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3434)
"Great Hotel!"
United States
Siranush
The price is AU$230
includes taxes & fees
4 Jan - 5 Jan 2026
LondonHouse Chicago, Curio Collection by Hilton

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, (1255)
"Solid stay in a great part of town"
United States
Michael
The price is AU$236
includes taxes & fees
15 Dec - 16 Dec
The Chicago Hotel Collection Ambassador Gold Coast

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile
3.0 star property
Downtown Chicago
8.4 out of 10, Very good, (4242)
"Clean room, very friendly staff and great location "
United States
Marcia
The price is AU$147
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1783)
"Friendly staff and good location to all of the city"
United States
Mark
The price is AU$286
includes taxes & fees
28 Dec - 29 Dec
Radisson Blu Aqua Hotel Chicago

Hyatt House Chicago West Loop

Hyatt House Chicago West Loop
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (1129)
"I always come back to this Hotel everything is close the area is full of things to do really love staying here !!"
United States
Sandra
The price is AU$238
includes taxes & fees
21 Dec - 22 Dec
Hyatt House Chicago West Loop
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 Central United States 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.

Chicago, IL showing interior views, heritage elements and an airport
Photo by by Midway Intl Airport
Open Photo by by Midway Intl Airport

Top Southwest Side Hotel Reviews

Recent Reviews in Southwest Side

More cheap accommodation in Southwest Side

Explore a world of travel with Expedia