Southwest Side 5 Stars Hotels
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check availability on Southwest Side 5 Star Hotels
Our top choices for Southwest Side 5-star hotels
9.4 out of 10, Exceptional, (1,001 reviews)
"Liked the layout of our suite and that the hotel was right inside the shopping Mall & Bloomingdales."
August
The price is HK$4,156
HK$4,942 total
includes taxes & fees
16 Aug - 17 Aug
2. Trump International Hotel & Tower Chicago
Trump International Hotel & Tower ChicagoDowntown Chicago
9.6 out of 10, Exceptional, (1,957 reviews)
"Great location and wonderful staff."
Ryan
The price is HK$3,676
HK$4,370 total
includes taxes & fees
9 Aug - 10 Aug
9.8 out of 10, Exceptional, (1,000 reviews)
"Wonderful hotel stay"
Robert
The price is HK$4,235
HK$5,035 total
includes taxes & fees
16 Aug - 17 Aug
9.4 out of 10, Exceptional, (1,000 reviews)
"Beautiful property with great location in Chicago. Can’t wait to stay again."
Steve
The price is HK$4,200
HK$4,993 total
includes taxes & fees
23 Aug - 24 Aug
9.8 out of 10, Exceptional, (1,000 reviews)
"Welcoming and attentive staff throughout the hotel made my stay an enjoyable and memorable experience."
Charles
The price is HK$4,901
HK$5,827 total
includes taxes & fees
9 Aug - 10 Aug
9.2 out of 10, Wonderful, (1,001 reviews)
"I have stayed at this hotel a few times and each time it is better than the last. Great service, great location. Can’t wait to come back again."
Caryn
The price is HK$3,733
HK$4,438 total
includes taxes & fees
23 Aug - 24 Aug
9.4 out of 10, Exceptional, (895 reviews)
"The breakfast is a must try there."
Yidong
The price is HK$3,471
HK$4,322 total
includes taxes & fees
30 Aug - 31 Aug
9.6 out of 10, Exceptional, (1,000 reviews)
"Our room was wonderful"
Jennifer
The price is HK$4,341
HK$5,161 total
includes taxes & fees
9 Aug - 10 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.
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
The price is HK$1,325 per night from 30 Aug to 31 Aug
HK$1,325
HK$1,511 total
30 Aug - 31 Aug
includes taxes & fees
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.
Photo by by Midway Intl Airport
Open Photo by by Midway Intl Airport
Top Southwest Side Hotel Reviews
Explore a world of travel with Expedia
- Fairmont Hotels in Chatham Fields
- 3 Star Hotels in Old Town Chicago
- Trump International Hotels in West Lawn
- Fairmont Hotels in Fuller Park
- 5 Star Hotels in Magnificent Mile
- Hotels near Midway Station
- 5 Star Hotels in Hyde Park
- 5 Star Hotels in Bucktown
- 3 Star Hotels in Hyde Park
- Hotels near 87th Station
- Marriott Hotels & Resorts in Hyde Park
- 4 Star Hotels in Central Station
- 5 Star Hotels in Pullman
- Clubhouse Hotels in Ducktown
- Extended Stay America Hotels in Southwest Side
- B&B in 35th-Archer Station
- Hyatt Hotels in Oakland
- Independent Hotels in Sleepy Hollow
- 5 Star Hotels in The Loop
- Accor Hotels in Chicago Museum Campus
- Hotels near University of Chicago
- Hard Rock Hotels in Garfield Manor
- Hotels near Cottage Grove Station
- 4 Star Hotels in Clearing
- Hotels near Midway Intl.
- Pet-Friendly Hotel Hotels in Hyde Park
- Hotels near Ashland-63rd Station
- Omni Hotels in McKinley Park
- Hilton Hotels in Central Station
- 5 Star Hotels in Downtown Chicago
- Omni Hotels in Sleepy Hollow
- The Peninsula Group Hotels in South Commons
- Hotels near Kam Isaiah Israel Congregation
- 5 Star Hotels in Berwyn
- Hotels near Court Theatre
- 5 Star Hotels in Forest View
- 4 Star Hotels in Washington Heights
- 5 Star Hotels in Dearborn Homes
- Sage Hospitality Hotels in Garfield Manor
- 4 Star Hotels in Downtown Chicago
- 4 Star Hotels in East Garfield Park
- Kenwood Hotels
- Accor Hotels in Grace Abbott Homes
- Marriott Hotels & Resorts in Garfield Manor
- 5 Star Hotels in Near South Side
- Budgetel Hotels in West Elsdon
- Destination Hotels in Southwest Side
- 5 Star Hotels in Summit
- B&B in Chicago Wrightwood Station
- Hotel with Pool Hotels in Hyde Park
- Independent Hotels in Greater Grand Crossing
- B&B in Halsted Station
- 3 Star Hotels in Chicago
- Hotels near Kedzie Station
- 4 Star Hotels in Chicago
- 5 Star Hotels in Grace Abbott Homes
- Red Roof Inn Hotels in Kenwood
- Gage Park Hotels
- La Quinta Inn & Suites Hotels in Garfield Manor
- 3 Star Hotels in The Loop
- 5 Star Hotels in Hometown
- Club Quarters Hotels in Grace Abbott Homes
- Swissotel Hotels in Hometown
- Spa Hotel Hotels in Armour Square
- Best Western Hotels in Glendale
- 3 Star Hotels in Downtown Chicago
- Swissotel Hotels in Ducktown
- Club Quarters Hotels in Glendale
- La Quinta Inn & Suites Hotels in Sleepy Hollow
- 5 Star Hotels in Logan Square
- 5 Star Hotels in Little Village
- 5 Star Hotels in Near West Side
- Accor Hotels in Washington Park Court
- 5 Star Hotels in Chicago
- Marriott Hotels & Resorts in South Loop
- 5 Star Hotels in Cicero
- Hotels near University of Chicago Medicine
- 4 Star Hotels in South Loop
- The Loop Hotels
- Destination Hotels in Kenwood
- Hyatt Hotels in Dearborn Homes
- Flights from Miami (MIA) to Chicago (MDW)
- Flights from Kansas City (MCI) to Chicago (MDW)
- Flights from Oklahoma City (OKC) to Chicago (MDW)
- Flights from Baltimore (BWI) to Chicago (MDW)
- Flights to Cicero
- Flights from Hong Kong (HKG) to Chicago (MDW)
- Flights from New York (JFK) to Chicago (MDW)
- Flights from San Francisco (SFO) to Chicago (MDW)