5 Star Hotels in Southwest Side, Chicago
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check availability on Southwest Side 5 Star Hotels
Tonight
19 Aug - 20 AugTomorrow
20 Aug - 21 AugThis weekend
21 Aug - 23 AugNext weekend
28 Aug - 30 AugOur top choices for Southwest Side 5-star hotels
€550
includes taxes & fees
30 Aug - 31 Aug
2. Trump International Hotel & Tower Chicago
Trump International Hotel & Tower ChicagoDowntown Chicago
Jorge
€481
includes taxes & fees
30 Aug - 31 Aug
€573
includes taxes & fees
7 Sept - 8 Sept
€637
includes taxes & fees
30 Aug - 31 Aug
€546
includes taxes & fees
30 Aug - 31 Aug
€509
includes taxes & fees
20 Sept - 21 Sept
€471
includes taxes & fees
23 Aug - 24 Aug
€568
includes taxes & fees
30 Aug - 31 Aug
Save an average of 15% on thousands of hotels when you're signed in
Explore similar 4-star hotels
Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Southwest Side.
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
€247
12 Sept - 13 Sept
includes taxes & fees
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr Chicago IL
€216
2 Sept - 3 Sept
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
€146
9 Sept - 10 Sept
includes taxes & fees
8/10 Very good! (2,046 reviews)
Still don't see what you're looking for?
See all properties in Southwest Side.
You can also use these popular filters to refine your search.
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.
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
Explore a world of travel with Expedia
- 3 Star Hotels in Chicago
- 3 Star Hotels in Country Club Hills
- 3 Star Hotels in Lincoln Park
- 3 Star Hotels in Lombard
- 3 Star Hotels in North Side
- 4 Star Hotels in Chicago
- 4 Star Hotels in Far Southeast Side
- 4 Star Hotels in Magnificent Mile
- 4 Star Hotels in Northwest Side
- 4 Star Hotels in Southwest Side
- 5 Star Hotels in Belmont Cragin
- 5 Star Hotels in Brookfield
- 5 Star Hotels in Chicago
- 5 Star Hotels in Elmhurst
- 5 Star Hotels in Hyde Park
- 5 Star Hotels in Lincoln Park
- 5 Star Hotels in Magnificent Mile
- 5 Star Hotels in Northwest Side
- 5 Star Hotels in River Forest
- 5 Star Hotels in The Loop
- 5 Star Hotels in Willow Springs
- Hotels near Abbott Park
- Archer Heights Hotels
- Bronzeville Hotels
- B&B in Burbank
- B&B in Chicago
- Cheap Hotels in Chicago
- Motel 6 Hotels in Chicago
- Red Roof Inn Hotels in Chicago
- Chicago Hotels
- Motels in Chicago
- Hotels with Pool in Chinatown
- Chinatown Hotels
- Beach Hotels in Cicero
- Clearing Hotels
- Hotels near Credit Union 1 Arena
- Englewood Hotels
- Evergreen Park Hotels
- Apartments in Far Southwest Side
- Oakwood Hotels in Grace Abbott Homes
- Hometown Hotels
- Club Quarters Hotels in Hyde Park
- Hotels with Spa in Hyde Park
- Hotels near Hyde Park Hair Salon
- Little Italy Hotels
- Little Village Hotels
- Lower West Side Hotels
- Hotels near Midway Intl.
- Hotels near Midway Station
- Near South Side Hotels
- North Lawndale Hotels
- Hotels near Oak Woods Cemetery
- Hotels near Soldier Field
- Lgbt-Friendly Hotels in South Loop
- B&B in South Side
- Hyatt Hotels in South Side
- Marriott Hotels & Resorts in South Side
- Extended Stay America Hotels in Southwest Side
- Extended Stay America Hotels in The Loop
- Romantic Hotels in The Loop
- West Englewood Hotels
- Cheap Hotels in West Loop
- Hostels in West Side
- 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)