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Check availability on South Side Hotels with Airport Transfers

Our top choices for South Side hotels with free airport shuttle

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

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, (1232)
"Will definitely stay there again ."
United States
Jose Remedios
The price is ₹10,076
₹11,837 total
includes taxes & fees
21 Dec - 22 Dec
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
Traditional Room, 2 Queen Beds, Non Smoking | Premium bedding, desk, laptop workspace, soundproofing
Carlton Inn Midway

Carlton Inn Midway

Carlton Inn Midway
2.0 star property
Archer Heights
6.4 out of 10, (1001)
"The room was clean and satisfied our needs. Was handy using their shuttle to Midway Airport."
United States
Charles
The price is ₹8,898
₹10,446 total
includes taxes & fees
1 Jan - 2 Jan 2026
Carlton Inn Midway
Restaurant
Holiday Inn Chicago – Midway Airport S by IHG

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, (1000)
"Great stay"
United States
Maria
The price is ₹10,166
₹12,833 total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Chicago – Midway Airport S by IHG
Serves lunch, dinner and happy hour
Chicago Marriott Midway

Chicago Marriott Midway

Chicago Marriott Midway
3.5 star property
Bedford Park
8.4 out of 10, Very good, (910)
"The property was excellent the rooms fantastic and the staff were equally wonderful and helpful. "
United States
Leilani
The price is ₹13,024
₹15,301 total
includes taxes & fees
1 Jan - 2 Jan 2026
Chicago Marriott Midway
Free daily buffet breakfast
Hampton Inn Chicago-O'Hare International Airport

Hampton Inn Chicago-O'Hare International Airport

Hampton Inn Chicago-O'Hare International Airport
2.5 star property
Schiller Park
9.2 out of 10, Wonderful, (2126)
"Great and clean - shuttle service to the airport was really nice"
Canada
Amanda
The price is ₹8,456
₹9,639 total
includes taxes & fees
21 Dec - 22 Dec
Hampton Inn Chicago-O'Hare International Airport
Exterior
Hyatt Place Chicago/O'Hare Airport

Hyatt Place Chicago/O'Hare Airport

Hyatt Place Chicago/O'Hare Airport
3.0 star property
Rosemont
8.4 out of 10, Very good, (3271)
"Excellent place to stay with great staff and service!"
United States
Gabriela
The price is ₹9,627
₹10,972 total
includes taxes & fees
11 Jan - 12 Jan 2026
Hyatt Place Chicago/O'Hare Airport
Lobby
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago
4.0 star property
Rosemont
8.8 out of 10, Excellent, (2193)
"Very nice place to stay "
United States
Ramon
The price is ₹10,629
₹12,115 total
includes taxes & fees
15 Dec - 16 Dec
Hyatt Regency O'Hare Chicago
Lobby sitting area
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG
3.0 star property
Rosemont
9.0 out of 10, Wonderful, (2656)
"great place to stay"
Canada
Justine
The price is ₹9,626
₹11,129 total
includes taxes & fees
11 Jan - 12 Jan 2026
Holiday Inn Chicago O'Hare – Rosemont by IHG
Reception hall
Loews Chicago O'Hare Hotel

Loews Chicago O'Hare Hotel

Loews Chicago O'Hare Hotel
4.5 star property
Rosemont
9.4 out of 10, Exceptional, (1910)
"Great theater location. "
United States
Stephen
The price is ₹12,505
₹14,253 total
includes taxes & fees
13 Dec - 14 Dec
Loews Chicago O'Hare Hotel
Exterior
Holiday Inn Express & Suites Bensenville - O'Hare by IHG

Holiday Inn Express & Suites Bensenville - O'Hare by IHG

Holiday Inn Express & Suites Bensenville - O'Hare by IHG
3.0 star property
Bensenville
8.8 out of 10, Excellent, (1001)
"Stayed there a few days the staff was nice breakfast was good and area was safe!"
United States
Bertha A
The price is ₹10,157
₹11,577 total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express & Suites Bensenville - O'Hare by IHG
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 staff were helpful in explaining the free shuttle to Midway airport.The shuttle picks you up at a point outside the third level. There is a sign indicating the correct spot. You have to tell the staff when you want to get taken back to Midway and they tell you what time to come to the lobby "
Joseph 1-night trip
Posted 3 days ago
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

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