Photo by by Midway Intl Airport
Southwest Side Hotels
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Go beyond your typical stay in Southwest Side
Apart hotel
Check prices for these dates
Our top choices for Southwest Side hotels
Carlton Inn Midway
Carlton Inn MidwayArcher Heights
6.2 out of 10, (1,000 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 €97
includes taxes & fees
21 May - 22 May
Holiday Inn Chicago – Midway Airport S by IHG
Holiday Inn Chicago – Midway Airport S by IHGWest Lawn
8.2 out of 10, Very good, (1,000 reviews)
"Great stay!"
Nancy
The price is €150
includes taxes & fees
24 May - 25 May
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 €100
includes taxes & fees
21 May - 22 May
Rainbow Motel
Rainbow MotelGarfield Ridge
5.4 out of 10, (21 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 €86
includes taxes & fees
21 May - 22 May
Hyatt Place Chicago/O'Hare Airport
Hyatt Place Chicago/O'Hare AirportRosemont
8.4 out of 10, Very good, (3,377 reviews)
"Great place to stay"
abhishek
The price is €127
includes taxes & fees
25 May - 26 May
SureStay Plus Hotel by Best Western Chicago Lombard
SureStay Plus Hotel by Best Western Chicago LombardHighland Hills
9.0 out of 10, Wonderful, (2,741 reviews)
"Friendly staff and great breakfast!"
Dylan
The price is €88
includes taxes & fees
16 Jun - 17 Jun
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, (2,508 reviews)
"I loved it here and will definitely stay again."
Gina
The price is €227
includes taxes & fees
26 May - 27 May
Swissotel - Chicago
Swissotel - ChicagoDowntown Chicago
9.0 out of 10, Wonderful, (3,334 reviews)
"Wonderful location right on the river. Fitness area wonderful, staff helpful. Would stay again!"
Saleem
The price is €202
includes taxes & fees
25 May - 26 May
Aloft by Marriott Chicago Mag Mile
Aloft by Marriott Chicago Mag MileDowntown Chicago
8.6 out of 10, Excellent, (3,236 reviews)
"Nice place to stay"
Jimmie
The price is €163
includes taxes & fees
26 May - 27 May
L7 Chicago by LOTTE
L7 Chicago by LOTTEDowntown Chicago
9.6 out of 10, Exceptional, (4,059 reviews)
"Clean hotel great restaurant "
ELIZABETH
The price is €253
includes taxes & fees
24 May - 25 May
Hyatt Regency Chicago
Hyatt Regency ChicagoDowntown Chicago
9.4 out of 10, Exceptional, (3,527 reviews)
"Very good place to stay. I really liked the lobby — it’s very spacious. The lobby design is also very open and artistic."
Tong
The price is €255
includes taxes & fees
25 May - 26 May
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHGDowntown Chicago
9.2 out of 10, Wonderful, (3,069 reviews)
"Great location ,service and staff "
Tamar
The price is €247
includes taxes & fees
27 May - 28 May
Hotel Riu Plaza Chicago
Hotel Riu Plaza ChicagoDowntown Chicago
9.4 out of 10, Exceptional, (4,197 reviews)
"Great location & breakfast was amazing."
sierra
The price is €177
includes taxes & fees
25 May - 26 May
Congress Plaza Hotel
Congress Plaza HotelDowntown Chicago
8.0 out of 10, Very good, (10,171 reviews)
"The bar was very welcoming and the historic ambience and location was exceptional"
Patricia
The price is €137
includes taxes & fees
25 May - 26 May
Freehand Chicago
Freehand ChicagoDowntown Chicago
8.0 out of 10, Very good, (3,025 reviews)
"Great central location, lots to do nearby."
Michael
The price is €107
includes taxes & fees
25 May - 26 May
River Hotel
River HotelDowntown Chicago
8.8 out of 10, Excellent, (5,184 reviews)
"excellent stay"
Jaeyoung
The price is €130
includes taxes & fees
25 May - 26 May
LondonHouse Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by HiltonDowntown Chicago
9.4 out of 10, Exceptional, (3,714 reviews)
"I had a great stay and would book again."
Brandi
The price is €246
includes taxes & fees
25 May - 26 May
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Sonesta ES Suites Chicago Downtown Magnificent Mile - MedicalDowntown Chicago
8.6 out of 10, Excellent, (2,453 reviews)
"Perfect location, very comfortable rooms, friendly staff."
Annabelle
The price is €156
includes taxes & fees
25 May - 26 May
The Chicago Hotel Collection Ambassador Gold Coast
The Chicago Hotel Collection Ambassador Gold CoastDowntown Chicago
8.2 out of 10, Very good, (1,478 reviews)
"A nice stay and lovely location. "
Robin
The price is €151
includes taxes & fees
3 Jun - 4 Jun
The Whitehall Hotel, BW Premier Collection
The Whitehall Hotel, BW Premier CollectionDowntown Chicago
8.4 out of 10, Very good, (3,933 reviews)
"Nice location , good service, and tastier breakfast"
Rogelio
The price is €134
includes taxes & fees
26 May - 27 May
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 €58 per night from 25 May to 26 May
€58
25 May - 26 May
includes taxes & fees
7.8/10 Good! (1,924 reviews)
5 Star Hotels
9 properties
Explore a world of travel with Expedia
- 4 Star Hotels in Southwest Side
- 5 Star Hotels in Hyde Park
- 5 Star Hotels in The Loop
- Hotels near Anna and Frederick Douglass Park
- Archer Heights Hotels
- Beverly Hotels
- Bronzeville Hotels
- Burbank Hotels
- Guest Houses in Chicago
- Hostels in Chicago
- Adventure Sport Hotels in Chicago
- Casino Hotels in Chicago
- Hotels with Bar in Chicago
- La Quinta Inn & Suites Hotels in Chicago
- Romantic Hotels in Chicago
- Rosewood Hotels in Chicago
- Chicago Hotels
- Hotels with Pool in Chinatown
- Hotels near Credit Union 1 Arena
- Hotels near DePaul University-Loop Campus
- Englewood Hotels
- Evergreen Park Hotels
- Apartments in Far Southwest Side
- Oakwood Hotels in Garden Homes
- Oakwood Hotels in Grace Abbott Homes
- Hotels near Grant Park
- Hometown Hotels
- Hotels with Spa in Hyde Park
- Hyde Park Hotels
- Little Village Hotels
- Lower West Side Hotels
- Hotels near McCormick Place
- Hotels near Midway Intl.
- Hotels near Midway Station
- Near South Side Hotels
- North Lawndale Hotels
- Hotels near Ogilvie Transportation Center
- Hotels near Old St Patrick’s Church
- River North Hotels
- Lgbt-Friendly Hotels in South Loop
- South Loop Hotels
- B&B in South Side
- Beach Hotels in South Side
- Hyatt Hotels in South Side
- Marriott Hotels & Resorts in South Side
- Motel 6 Hotels in South Side
- Romantic Hotels in South Side
- Extended Stay America Hotels in Southwest Side
- Romantic Hotels in The Loop
- Tri-Taylor Hotels
- Hotels near University of Chicago
- West Englewood Hotels
- West Loop Hotels
- Hostels in West Side
- Hotels near Willis Tower
- Woodlawn Hotels
- Flights from Austin (AUS) to Chicago (MDW)
- Flights from Columbus (CMH) to Chicago (MDW)
- Flights from Grand Rapids (GRR) to Chicago (MDW)
- Flights from Jackson (JAN) to Chicago (MDW)
- Flights from New York (JFK) to Chicago (MDW)
- Flights from Kraków (KRK) to Chicago (MDW)
- Flights from Lexington (LEX) to Chicago (MDW)
- Flights from Lafayette (LFT) to Chicago (MDW)
- Flights from Makurdi (MDI) to Chicago (MDW)
- Flights from Macomb (MQB) to Chicago (MDW)
- Flights from Green River (RVR) to Chicago (MDW)
- Flights from Springfield (SGF) to Chicago (MDW)
- Flights from Salt Lake City (SLC) to Chicago (MDW)
- Canalport Riverwalk Park
- Chicago Board of Trade Building
- Visit Canaryville
- Visit Chinatown
- Visit Grand Boulevard
- Visit Lower West Side
- Visit Near West Side
- Visit North Lawndale
- Visit Printers Row
- Visit South Commons
- Visit South Loop
- Visit Washington Park
- Chicago Holidays
- Credit Union 1 Arena
- Garfield Park Conservatory
- Grant Park
- Hometown Holidays
- Hyde Park Hair Salon
- Hyde Park Holidays
- Robie House
- Car hire near Chicago
- Car hire near Essex
- Car hire near Hyde Park
- Enterprise Rental Cars in Midway Intl.
- Europcar Rental Cars in Hyde Park
- Maggiore Rental Cars in Printers Row
- Pickup Car Hire in Chicago
- Rent A Wreck Rental Cars in Chicago
- Sixt Rental Cars in Central Chicago
- Sixt Rental Cars in South Loop
- Thrifty Car Rental Rental Cars in South Loop
