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
Pet friendly
Apartment
Apart hotel
Condo
Family friendly
Waterpark
Check prices for these dates
Tonight
19 Aug - 20 AugTomorrow
20 Aug - 21 AugThis weekend
21 Aug - 23 AugNext weekend
28 Aug - 30 AugOur top choices for Southwest Side hotels
1. Holiday Inn Chicago – Midway Airport S by IHG
Holiday Inn Chicago – Midway Airport S by IHGWest Lawn
Diane
€124
includes taxes & fees
8 Sept - 9 Sept
2. Rainbow Motel
Rainbow MotelGarfield Ridge
Noel
€78
includes taxes & fees
25 Aug - 26 Aug
3. Carlton Inn Midway
Carlton Inn MidwayArcher Heights
Kevin
€106
includes taxes & fees
20 Aug - 21 Aug
4. Sable at Navy Pier Chicago, Curio Collection by Hilton
Sable at Navy Pier Chicago, Curio Collection by HiltonDowntown Chicago
Dawn
€203
includes taxes & fees
7 Sept - 8 Sept
5. Congress Plaza Hotel
Congress Plaza HotelDowntown Chicago
Christina
€118
includes taxes & fees
8 Sept - 9 Sept
6. Hilton Chicago
Hilton ChicagoDowntown Chicago
Konner
€199
includes taxes & fees
7 Sept - 8 Sept
7. Staypineapple, An Iconic Hotel, The Loop
Staypineapple, An Iconic Hotel, The LoopDowntown Chicago
Beth
€172
includes taxes & fees
7 Sept - 8 Sept
8. The Chicago Hotel Collection Ambassador Gold Coast
The Chicago Hotel Collection Ambassador Gold CoastDowntown Chicago
Kristen
€147
includes taxes & fees
30 Aug - 31 Aug
9. Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown ChicagoDowntown Chicago
Lorena
€116
includes taxes & fees
31 Aug - 1 Sept
10. Arlo Chicago
Arlo ChicagoDowntown Chicago
Robert
€187
includes taxes & fees
8 Sept - 9 Sept
11. Homewood Suites by Hilton Chicago Downtown South Loop
Homewood Suites by Hilton Chicago Downtown South LoopDowntown Chicago
AMBER
€161
includes taxes & fees
7 Sept - 8 Sept
12. Claridge House Chicago, Tapestry Collection by Hilton
Claridge House Chicago, Tapestry Collection by HiltonDowntown Chicago
Christie
€142
includes taxes & fees
7 Sept - 8 Sept
13. citizenM Chicago Downtown
citizenM Chicago DowntownDowntown Chicago
lakadria
€175
includes taxes & fees
8 Sept - 9 Sept
14. Hilton Garden Inn Chicago Central Loop
Hilton Garden Inn Chicago Central LoopDowntown Chicago
Dawn
€173
includes taxes & fees
7 Sept - 8 Sept
15. Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Embassy Suites by Hilton Chicago Downtown Magnificent MileDowntown Chicago
JENNIFER
€189
includes taxes & fees
1 Sept - 2 Sept
16. Palmer House a Hilton Hotel
Palmer House a Hilton HotelDowntown Chicago
G.
€204
includes taxes & fees
8 Sept - 9 Sept
17. Hampton Inn Majestic Chicago Theatre District
Hampton Inn Majestic Chicago Theatre DistrictDowntown Chicago
Richard
€176
includes taxes & fees
30 Aug - 31 Aug
18. River Hotel
River HotelDowntown Chicago
Sarah
€134
includes taxes & fees
23 Aug - 24 Aug
19. Thompson Chicago, by Hyatt
Thompson Chicago, by HyattDowntown Chicago
Steve
€209
includes taxes & fees
7 Sept - 8 Sept
20. Hotel Riu Plaza Chicago
Hotel Riu Plaza ChicagoDowntown Chicago
Peter
€216
includes taxes & fees
1 Sept - 2 Sept
Stay near popular Southwest Side attractions
Marquette Park
9.4/10 (3 reviews)
After visiting Marquette Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.
Balzekas Museum of Lithuanian Culture
10.0/10 (1 review)
You can spend time studying the exhibits at Balzekas Museum of Lithuanian Culture in Chicago. Stroll along the lakeside in this vibrant area or visit its top-notch restaurants.
S.S. Peter and Paul Church
After visiting S.S. Peter and Paul Church, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.
Union Stock Yard Gate
You can find out about the history of Chicago with a trip to Union Stock Yard Gate.
Ephraim Bajar Cultural Center
Enjoy an outing to Ephraim Bajar Cultural Center during your stay in Chicago. Amble around the area's parks or visit its churches.
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.
See all hotels in Southwest Side
Photo by by Midway Intl Airport
Top Southwest Side Hotel Reviews
Hyatt Regency O'Hare Chicago
10/10 Excellent
"This hotel is absolutely beautiful! And just across the street from the convention center! Our room was spotless, so clean and tidy. The restaurant serves an amazing breakfast buffet for under $30 per person.... well worth it for the variety and quality of the food. My only contention is that you have to pay for parking ($45 per night) which I've never ever heard of in the 50 years of my life. Apparently, most hotels in Chicago don't own their parking lots. They are owned by a separate company who collects their fees thru the hotel. For that reason alone I'm not sure i ever want to stay in Chicago again. I can find a million other places to visit that don't charge extra to park at the hotel. Otherwise, this hotel is very nice and clean and in an excellent location."
Congress Plaza Hotel
10/10 Excellent
"The valets were very helpful in procuring my sister and I with taxis, Uber and Lyft services during our stay. All staff interactions were supremely pleasant. Our room was spotless."
Eurostars Magnificent Mile
8/10 Good
"Fantastic location. Staff was friendly, efficient & helpful. Nice room. Hotel is near lots of restaurants & shops. Really enjoyed our stay."
Crowne Plaza Chicago West Loop by IHG
10/10 Excellent
"Free coffee Free printing Early check in fee available"
L7 Chicago by LOTTE
10/10 Excellent
"Great hotel, great location, great staff. Very convenient for a first time in Chicago. Would definitely stay here again."
InterContinental Chicago Magnificent Mile by IHG
10/10 Excellent
"We loved it! Absolutely amazing location and hotel"
The Chicago Hotel Collection - Magnificent Mile
10/10 Excellent
"Good location very clean"
Kasa Magnificent Mile Chicago
8/10 Good
"Loved the check-in and check-out process. Very easy and excellent communication through texts, emails and the Kasa desk in the lobby. The security via the fobs and designated elevators was excellent. The water pressure was good in the shower, and the towels were fluffy. The view in this corner unit is phenomenal, and that was the clear highlight of the rental, along with the location as long as you don’t mind the street noise. The rental unit was adequate for our needs, but we expected more modern furnishings and a usable fold-out couch. The coils are coming through the mattress. We realize it’s been a hot summer, but the couch smelled of stale perspiration. Not fresh at all. Same with the refrigerator. Ice cube trays for the freezer would be helpful. We had to run to the store for ice. The bathroom is sad. It needs an update badly. There was a big chunk of the tub chipped off of the floor of the bathtub. The toliet was very slow in flushing."
More cheap stays in Southwest Side
Motel 6 Naperville, IL
1585 Naperville Wheaton Road Naperville IL
€55
8 Sept - 9 Sept
includes taxes & fees
Red Roof Inn PLUS+ Chicago - Willowbrook
7535 Kingery Highway Willowbrook IL
€61
27 Aug - 28 Aug
includes taxes & fees
6.4/10 (1,253 reviews)
Quality Inn & Suites Orland Park - Chicago
8800 W 159th St Orland Park IL
€84
9 Sept - 10 Sept
includes taxes & fees
Travelodge by Wyndham Downtown Chicago
65 E Harrison St Chicago IL
€116
31 Aug - 1 Sept
includes taxes & fees
7.6/10 Good! (2,781 reviews)
Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
€124
8 Sept - 9 Sept
includes taxes & fees
Hampton Inn Chicago Downtown/Magnificent Mile
160 E Huron Street Chicago IL
€156
7 Sept - 8 Sept
includes taxes & fees
5 Star Hotels
9 properties
4 Star Hotels
147 properties
3 Star Hotels
229 properties
2 Star Hotels
222 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
