Find Business Hotels in South Side, IL

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Our top choices for South Side business-friendly hotels

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
8.8 out of 10, Excellent, (1249)
"Will definitely stay there again ."
United States
Jose Remedios
The price is ¥17,536
¥20,601 total
includes taxes & fees
Dec 30 - Dec 31
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

SpringHill Suites by Marriott Chicago Chinatown

SpringHill Suites by Marriott Chicago Chinatown
3.5 star property
Chinatown
9.6 out of 10, Exceptional, (1000)
"Clean room, nice staff and perfect spot to enjoy the city "
United States
Alexis
The price is ¥15,814
¥18,563 total
includes taxes & fees
Jan 1 - Jan 2, 2026
SpringHill Suites by Marriott Chicago Chinatown

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, (1001)
"They held my credit card for over 30 minutes because something was going on with their cash register. I was really upset because it was ruining my evening and I needed my card. Is there anyway I could be compensated for all of this negative energy that I received from not getting my credit card Back one time "
United States
Michael
The price is ¥15,970
¥20,314 total
includes taxes & fees
Dec 30 - Dec 31
Holiday Inn Chicago – Midway Airport S by IHG

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)
"The staff was super friendly, and the room was clean! Great location."
United States
Marie
The price is ¥21,137
¥24,811 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Hyatt Place Chicago-South/University Medical Center

Chicago Marriott Midway

Chicago Marriott Midway
3.5 star property
Bedford Park
8.4 out of 10, Very Good, (912)
"The property was excellent the rooms fantastic and the staff were equally wonderful and helpful. "
United States
Leilani
The price is ¥20,855
¥24,501 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Chicago Marriott Midway

Sophy Hyde Park

Sophy Hyde Park
4.0 star property
Hyde Park
9.6 out of 10, Exceptional, (1003)
"Great staff, location and ambience."
United States
Jaison
The price is ¥28,041
¥37,146 total
includes taxes & fees
Dec 30 - Dec 31
Sophy Hyde Park

Carlton Inn Midway

Carlton Inn Midway
2.0 star property
Archer Heights
6.4 out of 10, (1002)
"The room was clean and satisfied our needs. Was handy using their shuttle to Midway Airport."
United States
Charles
The price is ¥16,440
¥19,299 total
includes taxes & fees
Dec 29 - Dec 30
Carlton Inn Midway

Best Western Inn & Suites - Midway Airport

Best Western Inn & Suites - Midway Airport
2.5 star property
Burbank
6.6 out of 10, (1002)
" Clean and quiet with a variety of restaurants nearby. "
United States
Rachel
The price is ¥15,018
¥16,668 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Best Western Inn & Suites - Midway Airport

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, (2277)
"Great staff and restaurants!!"
United States
Abigale
The price is ¥13,224
¥20,856 total
includes taxes & fees
Jan 20 - Jan 21, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton

River Hotel

River Hotel
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (4868)
"Clean friendly hotel "
United States
maria
The price is ¥12,776
¥14,998 total
includes taxes & fees
Jan 10 - Jan 11, 2026
River Hotel
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 South Side Hotel Reviews

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