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Check availability on South Side Hotels with Free Wifi

Our top choices for South Side hotels with free wifi

Free daily buffet breakfast
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

2.5 star property
Bedford Park
9.0 out of 10, Wonderful, (1229)
"Will definitely stay there again ."
United States
Jose Remedios
$116 nightly
The price is $136
Dec 25 - Dec 26
Total with taxes and fees
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
View from property
Hyatt Place Chicago-South/University Medical Center

Hyatt Place Chicago-South/University Medical Center

3.0 star property
Hyde Park
8.8 out of 10, Excellent, (1003)
"Great stay"
United States
Nikhil
$127 nightly
The price is $149
Dec 14 - Dec 15
Total with taxes and fees
Hyatt Place Chicago-South/University Medical Center
Free WiFi, bed sheets
Motel 6 - Chicago, IL

Motel 6 - Chicago, IL

2.0 star property
Washington Heights
7.0 out of 10, Good, (199)
"Everything was very nice even staff"
United States
Maurice
$80 nightly
The price is $94
Dec 10 - Dec 11
Total with taxes and fees
Motel 6 - Chicago, IL
Reception
Saratoga Motel By Capital O Near Midway Airport Chicago IL

Saratoga Motel By Capital O Near Midway Airport Chicago IL

2.5 star property
Ashburn
7.0 out of 10, Good, (28)
"Clean room friendly staff "
United States
Christian
$79 nightly
The price is $91
Dec 10 - Dec 11
Total with taxes and fees
Saratoga Motel By Capital O Near Midway Airport Chicago IL
View from room
Jaslin Hotel

Jaslin Hotel

3.0 star property
Chinatown
9.0 out of 10, Wonderful, (1182)
"Excellent service, clean room, great location"
United States
Stefan
$116 nightly
The price is $137
Jan 1 - Jan 2, 2026
Total with taxes and fees
Jaslin Hotel
Lobby
SpringHill Suites by Marriott Chicago Chinatown

SpringHill Suites by Marriott Chicago Chinatown

3.5 star property
Chinatown
9.6 out of 10, Exceptional, (1008)
"Clean, good staff"
Canada
Veronique E
$112 nightly
The price is $131
Jan 1 - Jan 2, 2026
Total with taxes and fees
SpringHill Suites by Marriott Chicago Chinatown
Interior
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10

Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10

Brighton Park
10.0 out of 10, Exceptional, (1)
"Family-friendly, quiet, perfect for a family or friends vacationing in Chicago. The apartment is very clean and the host was always available and responded quickly. The next time I come to Chicago, i will definitely stay at the apartment [if available]. "
United States
Fabian H.
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
Classic Apartment | Private kitchen
Stylish Apartment near Chicago Downtown

Stylish Apartment near Chicago Downtown

2.0 star property
Bridgeport
$400 nightly
The price is $469
Dec 10 - Dec 11
Total with taxes and fees
Stylish Apartment near Chicago Downtown
Iron/ironing board, travel crib, WiFi, bed sheets
Modern Studio Near UChicago

Modern Studio Near UChicago

Hyde Park
9.4 out of 10, Exceptional, (10)
"Clean room and convenient location! "
United States
Gabriela
$140 nightly
The price is $155
Dec 10 - Dec 11
Total with taxes and fees
Modern Studio Near UChicago
Fridge, microwave, oven, stovetop
W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade

W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade

Brighton Park
9.2 out of 10, Wonderful, (7)
"Great location, spacious, and family friendly. Had cousins over and they had a blast playing the video games. "
United States
Jessica H.
$260 nightly
The price is $291
Jan 1 - Jan 2, 2026
Total with taxes and fees
W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade
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.
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Top South Side Hotel Reviews

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

10/10 Excellent
"The definition of a perfect stay!"
Gerardo 1-night trip
Posted 1 day ago
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

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