Photo by by Midway Intl Airport
Find hotels in Southwest Side, IL from CA $96
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Go beyond your typical stay in Southwest Side
Family friendly
Apart hotel
Check prices for these dates
Our top choices for Southwest Side hotels
Rainbow Motel
Rainbow MotelGarfield Ridge
5.2 out of 10, (22 reviews)
"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 "
Conner
The price is CA $118
CA $138 total
includes taxes & fees
Jun 2 - Jun 3
Skylark Motel
Skylark MotelGarfield Ridge
4.6 out of 10, (124 reviews)
"This place should shut down. It is the worst accommodation I have ever stayed at. "
Roop
The price is CA $127
CA $149 total
includes taxes & fees
Jun 2 - Jun 3
Carlton Inn Midway
Carlton Inn MidwayArcher Heights
6.2 out of 10, (1,002 reviews)
"The staff were very kind and understanding but we had to get a refund due to bed bugs in the room."
Malachi
The price is CA $128
CA $151 total
includes taxes & fees
Jun 21 - Jun 22
Holiday Inn Chicago – Midway Airport S by IHG
Holiday Inn Chicago – Midway Airport S by IHGWest Lawn
8.4 out of 10, Very good, (1,006 reviews)
"Great stay!"
Nancy
The price is CA $181
CA $226 total
includes taxes & fees
Jun 21 - Jun 22
Sable at Navy Pier Chicago, Curio Collection by Hilton
Sable at Navy Pier Chicago, Curio Collection by HiltonDowntown Chicago
9.4 out of 10, Exceptional, (2,512 reviews)
"Great views of the lake, staff very helpful the rooms were clean and comfortable. Would stay there again!"
Deborah
The price is CA $319
CA $427 total
includes taxes & fees
Jun 30 - Jul 1
The Chicago Hotel Collection Ambassador Gold Coast
The Chicago Hotel Collection Ambassador Gold CoastDowntown Chicago
8.2 out of 10, Very good, (1,520 reviews)
"A nice stay and lovely location. "
Robin
The price is CA $216
CA $256 total
includes taxes & fees
Jun 22 - Jun 23
Freehand Chicago
Freehand ChicagoDowntown Chicago
8.0 out of 10, Very good, (3,033 reviews)
"Great location nice room"
Nolan
The price is CA $201
CA $264 total
includes taxes & fees
Jun 29 - Jun 30
Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown ChicagoDowntown Chicago
7.4 out of 10, Good, (2,611 reviews)
"Staff was friendly and helpful.. location was great"
Amber
The price is CA $185
CA $220 total
includes taxes & fees
Jun 28 - Jun 29
The Chicago Hotel Collection - Magnificent Mile
The Chicago Hotel Collection - Magnificent MileDowntown Chicago
7.8 out of 10, Good, (1,488 reviews)
"Great stay"
Ontario
The price is CA $210
CA $249 total
includes taxes & fees
Jun 28 - Jun 29
Hilton Chicago
Hilton ChicagoDowntown Chicago
8.6 out of 10, Excellent, (2,836 reviews)
"great hotel and excellent to stay"
Ruben
The price is CA $330
CA $432 total
includes taxes & fees
Jun 30 - Jul 1
Silversmith Hotel Chicago Downtown
Silversmith Hotel Chicago DowntownDowntown Chicago
9.2 out of 10, Wonderful, (2,245 reviews)
"Close to many attractions and shopping and nice unique hotel"
Brittany
The price is CA $221
CA $304 total
includes taxes & fees
Jun 28 - Jun 29
Congress Plaza Hotel
Congress Plaza HotelDowntown Chicago
8.0 out of 10, Very good, (10,124 reviews)
"Excellent stay"
Jennifer
The price is CA $180
CA $213 total
includes taxes & fees
Jun 29 - Jun 30
Best Western Grant Park Hotel
Best Western Grant Park HotelDowntown Chicago
8.2 out of 10, Very good, (2,705 reviews)
"Fantastic AC, clean rooms, friendly staff and an excellent location to walk to a ton of things"
Derrick
The price is CA $259
CA $308 total
includes taxes & fees
Jun 3 - Jun 4
Warwick Allerton - Chicago
Warwick Allerton - ChicagoDowntown Chicago
8.6 out of 10, Excellent, (3,033 reviews)
"Clean room, friendly staff, nearby lots of stores and restaurants. "
Nadiah
The price is CA $207
CA $286 total
includes taxes & fees
Jun 28 - Jun 29
LondonHouse Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by HiltonDowntown Chicago
9.4 out of 10, Exceptional, (3,721 reviews)
"Can't beat the location; it's next to Michigan Avenue and across from the Riverwalk; we'd stay there again."
Matson
The price is CA $321
CA $422 total
includes taxes & fees
Jun 21 - Jun 22
Millennium Hotel Knickerbocker Chicago
Millennium Hotel Knickerbocker ChicagoDowntown Chicago
8.6 out of 10, Excellent, (1,971 reviews)
"Loved everything including location and food options. Great hotel. "
Eileen
The price is CA $188
CA $256 total
includes taxes & fees
Jun 28 - Jun 29
Hotel Chicago Downtown, Autograph Collection by Marriott
Hotel Chicago Downtown, Autograph Collection by MarriottDowntown Chicago
9.0 out of 10, Wonderful, (1,003 reviews)
"The staff and up keep of the maintenance of the hotel was spectacular"
Oziel Silva
The price is CA $219
CA $302 total
includes taxes & fees
Jun 28 - Jun 29
Staypineapple, An Iconic Hotel, The Loop
Staypineapple, An Iconic Hotel, The LoopDowntown Chicago
9.4 out of 10, Exceptional, (1,077 reviews)
"Such a lovely hotel with a beautiful, excellent staff, and lots of character!"
Debby
The price is CA $309
CA $408 total
includes taxes & fees
Jun 29 - Jun 30
Eurostars Magnificent Mile
Eurostars Magnificent MileDowntown Chicago
9.0 out of 10, Wonderful, (3,593 reviews)
"Great location, large rooms, we loved our stay and would definitely recommend "
Belinda
The price is CA $309
CA $367 total
includes taxes & fees
Jun 29 - Jun 30
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile SuitesDowntown Chicago
9.0 out of 10, Wonderful, (4,351 reviews)
"Great property, perfect area to walk around in, excellent cafe."
Kayla
The price is CA $240
CA $285 total
includes taxes & fees
Jun 28 - Jun 29
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 Southwest Side attractions
Learn more about Southwest Side
Explore attractions like Balzekas Museum of Lithuanian Culture and Ephraim Bajar Cultural Center as you discover things to see and do in Southwest Side.
Photo by by Midway Intl Airport
Open Photo by by Midway Intl Airport
More cheap stays in Southwest Side
Motel 6 Elk Grove Village, IL - O'Hare
2881 Touhy Ave Elk Grove Village IL
The price is CA $85 per night from Jun 24 to Jun 25
CA $85
CA $96 total
Jun 24 - Jun 25
includes taxes & fees
7.8/10 Good! (1,937 reviews)
Hotels in Southwest Side with star rating
5 Star Hotels
9 properties
Explore a world of travel with Expedia
- 1 Star Hotels in South Englewood
- Cheap Hotels in Archer Heights
- Hotels with Free Parking in Archer Heights
- Romantic Hotels in Archer Heights
- Archer Heights Hotels
- Armour Square Hotels
- Hotels near Ashland-63rd Station
- Hotels near Bridgeport Art Center
- Bridgeport Hotels
- Boutique Hotels in Brighton Park
- Cheap Hotels in Brighton Park
- Brighton Park Hotels
- Canaryville Hotels
- Chicago Hotels
- Beach Hotel Hotels in Chicago Lawn
- Boutique Hotels in Chicago Lawn
- Family Hotels in Chicago Lawn
- Hotels with a Pool in Chicago Lawn
- Hotels with Bar in Chicago Lawn
- Lgbt Friendly Hotels in Chicago Lawn
- Romantic Hotels in Chicago Lawn
- Spa Hotels in Chicago Lawn
- Chicago Lawn Hotels
- Downtown Chicago Hotels
- Cheap Hotels in Englewood
- Englewood Hotels
- All Inclusive Resorts and in Gage Park
- Business Hotels in Gage Park
- Cheap Hotels in Gage Park
- Luxury Hotels in Gage Park
- Gage Park Hotels
- Hotels near Garfield Station
- Inns in Garfield Station
- Motel 6 Hotels in Glendale
- Grand Boulevard Hotels
- B&B in Halsted Station
- Hotels near Halsted Station
- Heart of Chicago Hotels
- Little Village Hotels
- Hotels near Marquette Park
- Boutique Hotels in McKinley Park
- Four Seasons Hotels in McKinley Park
- Ski Hotels in McKinley Park
- Mckinley Park Hotels
- Hotels near Midway Intl.
- B&B in Midway Station
- Hotels near Midway Station
- Motels in Midway Station
- Beach Hotel Hotels in New City
- Boutique Hotels in New City
- Hotels with a Pool in New City
- Lgbt Friendly Hotels in New City
- Luxury Hotels in New City
- Pet-Friendly Hotels in New City
- New City Hotels
- Hotels near Pulaski Station
- Hotels near Rate Field
- Sleepy Hollow Hotels
- Washington Park Hotels
- Washington Park Court Hotels
- Cheap Hotels in West Englewood
- West Englewood Hotels
- Luxury Hotels in West Lawn
- Pet-Friendly Hotels in West Lawn
- West Lawn Hotels
- Hotels near Zhou B Art Center
- Flights to Chicago
- Flights from Midway Intl.
- Porter Airlines Toronto (YTZ) to Chicago (MDW) flights
- Porter Airlines Ottawa (YOW) to Chicago (MDW) flights
- Flights from Buffalo (BUF) to Chicago (MDW)
- Flights from Detroit (DTW) to Chicago (MDW)
- Flights from South Bend (SBN) to Chicago (MDW)
- Flights from Edmonton (YEG) to Chicago (MDW)
- Flights from Hamilton (YHM) to Chicago (MDW)
- Flights from Halifax (YHZ) to Chicago (MDW)
- Flights from Kelowna (YLW) to Chicago (MDW)
- Flights from Ottawa (YOW) to Chicago (MDW)
- Flights from Windsor (YQG) to Chicago (MDW)
- Flights from Thunder Bay (YQT) to Chicago (MDW)
- Flights from Sudbury (YSB) to Chicago (MDW)
- Flights from Timmins (YTS) to Chicago (MDW)
- Flights from Toronto (YTZ) to Chicago (MDW)
- Flights from Montreal (YUL) to Chicago (MDW)
- Flights from Vancouver (YVR) to Chicago (MDW)
- Flights from Winnipeg (YWG) to Chicago (MDW)
- Flights from Saskatoon (YXE) to Chicago (MDW)
- Flights from North Bay (YYB) to Chicago (MDW)
- Flights from Calgary (YYC) to Chicago (MDW)
- Flights from Toronto (YYZ) to Chicago (MDW)
- Flights from Toronto (YYZ) to Chicago (ORD)
