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
6.4 out of 10, (1,005 reviews)
- Enjoy a comfortable stay with airport shuttle and easy Orange Line access.
"It is a good place to stay."
Paul Adrian
The price is €97
includes taxes & fees
18 Feb - 19 Feb
Holiday Inn Chicago – Midway Airport S by IHG
Holiday Inn Chicago – Midway Airport S by IHGWest Lawn
8.4 out of 10, Very good, (1,006 reviews)
"Staff very friendly "
Kali
The price is €96
includes taxes & fees
17 Mar - 18 Mar
Skylark Motel
Skylark MotelGarfield Ridge
4.6 out of 10, (119 reviews)
- Convenient Chicago motel with free parking and WiFi, minutes from McCormick Place.
"Easily one of the worst places ever. Slightly better than spending the night in Chicago Midway terminal."
Stephen
The price is €88
includes taxes & fees
2 Mar - 3 Mar
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, (2,377 reviews)
- Luxurious getaway on Navy Pier with stunning Lake Michigan views and Latin cuisine.
"Great stay"
Blake
The price is €150
includes taxes & fees
23 Feb - 24 Feb
Freehand Chicago
Freehand ChicagoDowntown Chicago
8.0 out of 10, Very good, (2,761 reviews)
- Stylish Art Deco hotel just steps from Michigan Avenue and vibrant city centre Chicago.
"I enjoyed my stay"
Emily
The price is €72
includes taxes & fees
22 Feb - 23 Feb
FOUND Hotel Chicago River North
FOUND Hotel Chicago River NorthDowntown Chicago
8.4 out of 10, Very good, (461 reviews)
- Stylish city centre hotel near State Street offers access to Michigan Avenue and River.
"Amazing staff and very clean, modern rooms!"
genevieve
The price is €63
includes taxes & fees
1 Mar - 2 Mar
The Whitehall Hotel, BW Premier Collection
The Whitehall Hotel, BW Premier CollectionDowntown Chicago
8.4 out of 10, Very good, (3,967 reviews)
- Stroll from Michigan Avenue to Chicago's top attractions, dining, and subway access.
"Great location, the room was nice and the breakfast was good. Overall great value for this property"
Jorge
The price is €73
includes taxes & fees
24 Feb - 25 Feb
Hotel Riu Plaza Chicago
Hotel Riu Plaza ChicagoDowntown Chicago
9.4 out of 10, Exceptional, (3,356 reviews)
"Amazing place, breakfast is great , location is great - honestly great hotel! "
Brisa
The price is €136
includes taxes & fees
4 Mar - 5 Mar
Aloft Chicago Mag Mile
Aloft Chicago Mag MileDowntown Chicago
8.6 out of 10, Excellent, (3,098 reviews)
- Stylish hotel near Michigan Ave with an indoor pool and American dining options.
"Great location and friendly staff. "
Pablo
The price is €96
includes taxes & fees
18 Feb - 19 Feb
Swissotel - Chicago
Swissotel - ChicagoDowntown Chicago
9.0 out of 10, Wonderful, (3,211 reviews)
- Luxurious stay in the heart of Chicago, steps from Michigan Avenue and parks.
"Place is always top notch..stay here anytime we stay in Chicago."
Jon
The price is €150
includes taxes & fees
22 Feb - 23 Feb
Best Western Grant Park Hotel
Best Western Grant Park HotelDowntown Chicago
8.2 out of 10, Very good, (2,681 reviews)
"Clean room and the staff are great. "
Doug
The price is €71
includes taxes & fees
22 Feb - 23 Feb
Sofitel Chicago Magnificent Mile
Sofitel Chicago Magnificent MileDowntown Chicago
9.4 out of 10, Exceptional, (2,323 reviews)
- Luxurious retreat steps from Michigan Avenue with 24-hour fitness centre.
"Staff was friendly and helpful! Great stay!"
Kristin
The price is €200
includes taxes & fees
4 Mar - 5 Mar
Congress Plaza Hotel
Congress Plaza HotelDowntown Chicago
8.0 out of 10, Very good, (9,902 reviews)
- Lakeside elegance in Chicago with historic charm and stunning views of the water from select rooms.
"Great location, beautiful historic hotel with clean, updated rooms. "
Jennifer
The price is €188
includes taxes & fees
13 Mar - 14 Mar
Hyatt Regency Chicago
Hyatt Regency ChicagoDowntown Chicago
9.4 out of 10, Exceptional, (3,476 reviews)
- Centrally located hotel with stunning city and lake views only steps from Michigan Avenue.
"Clean room, great staff, great location "
Tiffany
The price is €202
includes taxes & fees
22 Feb - 23 Feb
Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown ChicagoDowntown Chicago
7.4 out of 10, Good, (2,518 reviews)
- City centre Chicago escape near art and park attractions.
"Always a good stay"
Domenic
The price is €75
includes taxes & fees
25 Feb - 26 Feb
The Chicago Hotel Collection Ambassador Gold Coast
The Chicago Hotel Collection Ambassador Gold CoastDowntown Chicago
8.2 out of 10, Very good, (1,286 reviews)
- Experience lakeside elegance with easy access to Michigan Avenue and Oak Street Beach.
"Great hotel with great location. Would definitely stay here again. "
Sheila
The price is €105
includes taxes & fees
23 Feb - 24 Feb
LondonHouse Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by HiltonDowntown Chicago
9.4 out of 10, Exceptional, (3,618 reviews)
- Enjoy the riverside elegance of city centre Chicago, steps from Michigan Avenue.
"Staff was friendly and loved the decor at this hotel…will definitely be staying again"
Osama
The price is €178
includes taxes & fees
23 Feb - 24 Feb
Sports Illustrated Resorts Chicago
Sports Illustrated Resorts ChicagoDowntown Chicago
9.2 out of 10, Wonderful, (1,398 reviews)
- Stay steps away from the Chicago Riverwalk at this luxurious hotel with nightclub.
"Staff was super friendly and rooms were clean. Definitely will come back "
Daisy
The price is €183
includes taxes & fees
22 Feb - 23 Feb
Pendry Chicago
Pendry ChicagoDowntown Chicago
9.4 out of 10, Exceptional, (1,150 reviews)
- Elegant historical landmark in city centre Chicago with rooftop views of the city.
"Excellent hotel and location."
Marcelo
The price is €223
includes taxes & fees
15 Mar - 16 Mar
Staypineapple, An Iconic Hotel, The Loop
Staypineapple, An Iconic Hotel, The LoopDowntown Chicago
9.4 out of 10, Exceptional, (1,009 reviews)
"Location was great, staff was very friendly, and the rooms were clean. "
Lori
The price is €144
includes taxes & fees
1 Mar - 2 Mar
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 Great Lakes attractions
Learn more about Southwest Side
Explore attractions like Balzekas Museum of Lithuanian Culture and Union Stock Yard Gate 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
Palmer House a Hilton Hotel
10/10 Excellent
More cheap stays in Southwest Side
Motel 6 Naperville, IL
1585 Naperville Wheaton Road Naperville IL
The price is €44 per night from 22 Feb to 23 Feb
€44
22 Feb - 23 Feb
includes taxes & fees
7.8/10 Good! (1,238 reviews)
5 Star Hotels
10 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
