Photo by by Midway Intl Airport
Luxury Hotels & Resorts in Southwest Side from AU$140
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check availability on Southwest Side Luxury Hotels
Our top choices for Southwest Side luxury hotels
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, (2,495 reviews)
"Perfect stay for families visiting Chicago "
Casey
The price is AU$383
includes taxes & fees
25 May - 26 May
9.0 out of 10, Wonderful, (3,326 reviews)
"It’s walking distance from the hotel to go to almost every tourists place. Hotel is clean and staffs are nice. The hotel doesn’t have swimming pools if you are looking for swimming pool. For us not a big deal. Overall, great hotel for family with small kids and everyone’s."
Sharifah
The price is AU$391
includes taxes & fees
24 May - 25 May
9.4 out of 10, Exceptional, (3,516 reviews)
"10/10. Feels like a luxury hotel for 225 a night! "
Griffin
The price is AU$439
includes taxes & fees
25 May - 26 May
8.8 out of 10, Excellent, (2,154 reviews)
"The massage downstairs at the spa was the absolute best!"
Sharefree
The price is AU$342
includes taxes & fees
25 May - 26 May
9.2 out of 10, Wonderful, (1,126 reviews)
- Indulge in architectural splendour and upscale amenities at this Art Deco Chicago hotel, where luxury meets city centre convenience.
"Our family had 3 rooms in VIP area. Murriell was our assistant when we checked in and she was super observant! She recommended the upgrade and we accepted. That made our stay the best!! A great family area to enjoy time together!
She sent us a special note and gift! What a wonder person!
The hotel was the best location too. We enjoyed the hotel and our trip very much! Thank you for Murriell for bringing joy!!"
Margaret
The price is AU$515
includes taxes & fees
26 May - 27 May
8.6 out of 10, Excellent, (1,623 reviews)
"We enjoyed our stay and location of hotel. Pool area was amazing and family friendly. However, our mattress was awful for adult. Our kids didn’t complain though 😊"
Kelly
The price is AU$408
includes taxes & fees
25 May - 26 May
8.6 out of 10, Excellent, (1,002 reviews)
- Art Deco elegance meets beachfront luxury with casino thrills, fine dining, and marina views.
"The room was honestly one of the best I have ever stayed in — incredibly spacious, spotless, and so comfortable that it felt like a luxury retreat."
Katrina
The price is AU$220
includes taxes & fees
18 May - 19 May
8.6 out of 10, Excellent, (2,448 reviews)
- Historic Chicago luxury hotel offers spa, pillowtop beds, and prime location near Millennium Park.
"Beautiful property, great resturant on site, an the pool and spa was amazing."
Tim
The price is AU$292
includes taxes & fees
25 May - 26 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.
Top Southwest Side Hotel Reviews
Hilton Chicago/Magnificent Mile Suites
8/10 Good
Explore a world of travel with Expedia
- Hotels near Anna and Frederick Douglass Park
- Beverly Hotels
- Brighton Park Hotels
- B&B in Burbank
- Luxury Hotels in Burbank
- Burbank Hotels
- Hotels near Chicago 59th Street Station
- Apartments in Chicago 63rd Street Station
- B&B in Chicago Halsted Station
- Cheap Hotels in Chicago
- Chicago Hotels
- Boutique Hotels in Chicago Lawn
- Family Hotels in Chicago Lawn
- Historic Hotels in Chicago Lawn
- Hotels with Pool in Chicago Lawn
- Romantic Hotels in Chicago Lawn
- Hotels near Chicago McCormick Place Station
- Inns in Chicago McCormick Place Station
- Business Hotels in Chicago Museum Campus
- Cheap Hotels in Chicago Museum Campus
- Historic Hotels in Chicago Museum Campus
- Chinatown Hotels
- Cicero Hotels
- Hotels near Damen Station
- Cook County Hotels
- Luxury Hotels in East Garfield Park
- Boutique Hotels in Englewood
- Englewood Hotels
- Cheap Hotels in Essex
- Family Hotels in Essex
- Evergreen Park Hotels
- Lgbt Welcoming Hotels in Forest View
- Fuller Park Hotels
- Four Seasons Hotels in Gold Coast
- Grace Abbott Homes Hotels
- Greater Grand Crossing Hotels
- Hotels near Halsted Station
- All Inclusive Hotels in Hometown
- Hometown Hotels
- Boutique Hotels in Hyde Park
- Cheap Hotels in Hyde Park
- Green Hotels in Hyde Park
- Luxury Hotels in Hyde Park
- Spa Hotels in Hyde Park
- Hyde Park Hotels
- Hotels near Hyde Park Hair Salon
- Hotels near Illinois Institute of Technology
- Hotels near Lakefront Trail
- Cheap Hotels in Little Italy
- Little Italy Hotels
- Lower West Side Hotels
- Hotels near McCormick Place
- Hotels near Midway Intl.
- Lgbt Welcoming Hotels in Near South Side
- Family Hotels in North Lawndale
- Lgbt Welcoming Hotels in Oak Lawn
- Luxury Hotels in Oakland
- Cheap Hotels in Pilsen
- Hotels near SR Crown Hall
- Sleepy Hollow Hotels
- Adults Only Hotels in South Side
- Business Hotels in South Side
- Hotels near University of Chicago
- Boutique Hotels in Washington Park
- Washington Park Hotels
- West Englewood Hotels
- Flights to Burbank
- Flights to Chicago
- Flights to South Side
- Flights from Midway Intl.
- Flights from Belleville (BLV) to Chicago (MDW)
- Flights from Burbank (BUR) to Chicago (MDW)
- Flights from Baltimore (BWI) to Chicago (MDW)
- Flights from Champaign (CMI) to Chicago (MDW)
- Flights from Charleston (CRW) to Chicago (MDW)
- Flights from Denver (DEN) to Chicago (MDW)
- Flights from Newark Liberty Intl. Airport (EWR) to Chicago (MDW)
- Flights from Hermiston (HES) to Chicago (MDW)
- Flights from Hibbing (HIB) to Chicago (MDW)
- Flights from New York (JFK) to Chicago (MDW)
- Flights from Mildura (MQL) to Chicago (MDW)