Southwest Side Hotels

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Southwest Side hotels

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG
2.5 star property
West Lawn
8.4 out of 10, Very Good, (1,004 reviews)
"Staff very friendly "
United States
Kali
The price is P4,990
P6,439 total
includes taxes & fees
Feb 18 - Feb 19
Holiday Inn Chicago – Midway Airport S by IHG

Carlton Inn Midway

Carlton Inn Midway
2.0 star property
Archer Heights
6.4 out of 10, (1,003 reviews)
  • cleanliness
    Enjoy a comfortable stay with airport shuttle and easy Orange Line access.
"It is a good place to stay."
United States
Paul Adrian
The price is P5,123
P6,014 total
includes taxes & fees
Feb 16 - Feb 17
Carlton Inn Midway

Skylark Motel

Skylark Motel
2.0 star property
Garfield Ridge
4.6 out of 10, (119 reviews)
  • cleanliness
    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."
United States
Stephen
The price is P5,164
P6,063 total
includes taxes & fees
Feb 16 - Feb 17
Skylark Motel

Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,527 reviews)
  • cleanliness
    Serene spa hotel near Lake Michigan offers relaxation in the heart of Chicago.
"Great location, friendly staff and nice room"
United States
Srinivasa
The price is P3,283
P5,557 total
includes taxes & fees
Feb 22 - Feb 23
Claridge House Chicago, Tapestry Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2,371 reviews)
  • cleanliness
    Luxurious getaway on Navy Pier with stunning Lake Michigan views and Latin cuisine.
"Great stay"
United States
Blake
The price is P7,103
P10,314 total
includes taxes & fees
Feb 22 - Feb 23
Sable at Navy Pier Chicago, Curio Collection by Hilton

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,317 reviews)
  • cleanliness
    Experience Chicago in Gold Coast, near Michigan Avenue and Lake Michigan shores.
"Great hotel!"
United States
Julie
The price is P7,834
P10,908 total
includes taxes & fees
Mar 1 - Mar 2
Thompson Chicago, by Hyatt

Moxy Chicago Downtown

Moxy Chicago Downtown
3.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (888 reviews)
  • cleanliness
    Modern hotel in downtown Chicago offers chic accommodations near Michigan Avenue.
"Clean, friendly staff, and excellent location "
United States
Paulina
The price is P6,267
P7,357 total
includes taxes & fees
Feb 22 - Feb 23
Moxy Chicago Downtown

Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2,316 reviews)
  • cleanliness
    Luxurious retreat steps from Michigan Avenue with 24-hour fitness center.
"Staff was friendly and helpful! Great stay!"
United States
Kristin
The price is P10,309
P13,804 total
includes taxes & fees
Feb 16 - Feb 17
Sofitel Chicago Magnificent Mile

Level Chicago Fulton Market

Level Chicago Fulton Market
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (403 reviews)
  • cleanliness
    Trendy Fulton Market hotel with pool, close to Michigan Avenue and the Riverwalk.
"The hotel in it’s entirety was better than advertised "
United States
Eric
Level Chicago Fulton Market

Springhill Suites by Marriott Chicago Downtown/ River North

Springhill Suites by Marriott Chicago Downtown/ River North
3.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,051 reviews)
  • cleanliness
    Stylish downtown Chicago hotel offers free breakfast and fitness close to Riverwalk.
"Great hotel, good food and great service ! "
United States
Fernando
The price is P6,673
P7,834 total
includes taxes & fees
Feb 22 - Feb 23
Springhill Suites by Marriott Chicago Downtown/ River North

The Hoxton Chicago

The Hoxton Chicago
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,003 reviews)
  • cleanliness
    Stylish Chicago hotel near Riverwalk with rooftop pool and Mediterranean dining.
"Amazing, I loved my stay"
United States
Valerie
The Hoxton Chicago

citizenM Chicago Downtown

citizenM Chicago Downtown
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (4,214 reviews)
  • cleanliness
    Modern hotel in downtown Chicago with 24-hour dining and stylish accommodations.
"Friendly staff, cozy room, good location. "
United States
Andrew
The price is P6,209
P7,289 total
includes taxes & fees
Feb 22 - Feb 23
citizenM Chicago Downtown

Hyatt House Chicago West Loop

Hyatt House Chicago West Loop
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,188 reviews)
  • cleanliness
    Enjoy a comfy stay with easy access to United Center and Millennium Park.
"Great location, friendly staff, spacious room"
United States
Mary
The price is P8,356
P9,809 total
includes taxes & fees
Feb 22 - Feb 23
Hyatt House Chicago West Loop

Hampton Inn Chicago West Loop Fulton Market Area

Hampton Inn Chicago West Loop Fulton Market Area
2.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Enjoy Chicago's West Loop with an indoor pool and rooftop terrace minutes away.
"Nice hotel and staff. "
United States
Wendy
The price is P7,349
P8,627 total
includes taxes & fees
Feb 21 - Feb 22
Hampton Inn Chicago West Loop Fulton Market Area

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,606 reviews)
  • cleanliness
    Enjoy the riverside elegance of downtown Chicago, steps from Michigan Avenue.
"Staff was friendly and loved the decor at this hotel…will definitely be staying again"
Canada
Osama
The price is P9,469
P11,116 total
includes taxes & fees
Feb 22 - Feb 23
LondonHouse Chicago, Curio Collection by Hilton

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (4,363 reviews)
  • cleanliness
    Experience downtown Chicago steps from Michigan Avenue with an indoor pool.
"Great staff, great room, and close to everything "
United States
George
The price is P4,758
P5,586 total
includes taxes & fees
Feb 22 - Feb 23
Hilton Garden Inn Chicago Downtown/Magnificent Mile

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Downtown Chicago
8.2 out of 10, Very Good, (1,284 reviews)
  • cleanliness
    Experience lakeside elegance with easy access to Michigan Avenue and Oak Street Beach.
"Great hotel with great location. Would definitely stay here again. "
United States
Sheila
The price is P6,134
P7,201 total
includes taxes & fees
Feb 16 - Feb 17
The Chicago Hotel Collection Ambassador Gold Coast

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,855 reviews)
  • cleanliness
    Luxury Chicago escape with lakeside pools, steps from Millennium Park.
"Room was very nice, views were fantastic and the restaurant was excellent "
United States
Michael
The price is P9,868
P13,092 total
includes taxes & fees
Feb 22 - Feb 23
Radisson Blu Aqua Hotel Chicago

ACME Hotel Chicago, Outset Collection by Hilton

ACME Hotel Chicago, Outset Collection by Hilton
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,955 reviews)
  • cleanliness
    Quirky boutique escape near Michigan Avenue with close access to Red Line transit.
"Very convenient place to stay friendly and helpful staff."
United States
Rick
The price is P4,711
P5,530 total
includes taxes & fees
Feb 22 - Feb 23
ACME Hotel Chicago, Outset Collection by Hilton

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,313 reviews)
  • cleanliness
    Enjoy a rooftop pool oasis steps from Michigan Avenue and Chicago's attractions.
"Great staff, room spotless, great price."
United States
Robert
The price is P5,424
P6,368 total
includes taxes & fees
Feb 22 - Feb 23
DoubleTree by Hilton Chicago - Magnificent Mile
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.

Chicago, IL which includes landscape views and an airport
Photo by by Midway Intl Airport
Open Photo by by Midway Intl Airport

Top Southwest Side Hotel Reviews

More cheap stays in Southwest Side