Book Hotels in South Side, IL
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Top South Side hotels
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
6500 S Cicero Ave Chicago IL
Fully refundable
$135 nightly
The price is $159 total per night from Nov 15 to Nov 16
$159 total
Nov 15 - Nov 16
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and a free airport shuttle. Traveling for business? Take advantage of ...
"I have stayed here several times before flying out the next morning from Midway Airport and it's always been spotless however it looked like somebody had spilled coffee or a brown liquid down the wall behind the bed and on the baseboard. Also the lights on the awning were off so it was pitch dark ..."
Reviewed on Oct 15, 2026
Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
Fully refundable
$145 nightly
The price is $168 total per night from Nov 1 to Nov 2
$168 total
Nov 1 - Nov 2
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public ...
"The shuttle is an issue. Waited an hour for pickup at the Midway train station. The driver lied and said that he arrived and there was no one to pick up. Complete lie."
Reviewed on Oct 15, 2026
Villa Dubois Guest House
3722 S Calumet Ave Chicago IL
$141 nightly
The price is $166 total per night from Nov 15 to Nov 16
$166 total
Nov 15 - Nov 16
Total with taxes and fees
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, a communal living room, and express check-in are also on ...
"No staff on site, property will ask for a "refundable" security deposit before sending door access code even after paying through Expedia. After stay they will not respond to request of the refundable security deposit. They rejected 2 request then blocked me."
Reviewed on Oct 15, 2026
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
$159 nightly
The price is $187 total per night from Nov 1 to Nov 2
$187 total
Nov 1 - Nov 2
Total with taxes and fees
Free self parking is available and the hotel's multilingual staff can provide around-the-clock assistance. WiFi in public areas is free. Luggage storage is also ...
Jaslin Hotel
261 West Cermak Rd Chicago IL
$149 nightly
The price is $177 total per night from Nov 11 to Nov 12
$177 total
Nov 11 - Nov 12
Total with taxes and fees
A 24-hour gym is featured at this hotel, along with free WiFi in public areas and luggage storage. Multilingual staff at the 24-hour front desk can provide around-the-clock ...
Motel 6 - Chicago, IL
10022 South Halsted Street Chicago IL
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $117 total per night from Oct 18 to Oct 19
$117 total
Oct 18 - Oct 19
Total with taxes and fees
Free self parking is available and the motel's front desk is staffed around-the-clock. Laundry facilities are provided for your convenience.
Chinatown Hotel Chicago
214 West 22nd Place Chicago IL
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $119 total per night from Nov 1 to Nov 2
$119 total
Nov 1 - Nov 2
Total with taxes and fees
Free WiFi in public areas, a communal living room, and express check-out are available at this hotel. Luggage storage and a safe deposit box are also ...
SpringHill Suites by Marriott Chicago Chinatown
2357 S WENTWORTH AVE Chicago IL
Fully refundableReserve now, pay when you stay
$188 nightly
The price is $224 total per night from Nov 1 to Nov 2
$224 total
Nov 1 - Nov 2
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast and free WiFi. Business travelers can take advantage of the 24-hour business center. ...
Carlton Inn Midway
4944 S Archer Ave Chicago IL
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $126 total per night from Oct 18 to Oct 19
$126 total
Oct 18 - Oct 19
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free continental breakfast, free self parking, and a free airport shuttle. Traveling on business? Take ...
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.
Cheap South Side hotels
Chinatown Hotel Chicago
214 West 22nd Place Chicago IL
$101 nightly
The price is $119 total per night from Nov 1 to Nov 2
$119 total
Nov 1 - Nov 2
Total with taxes and fees
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.
Hotels in South Side with star-rating
Check South Side Hotels by Star Rating
4 Star Hotels
1 properties
Recent South Side hotel reviews by fellow wanderers
Holiday Inn Chicago – Midway Airport S by IHG
4 out of 5
Posted 1 hour ago
Travelocity Verified Review
"The shuttle is an issue. Waited an hour for pickup at the Midway train station. The driver lied and said that he arrived and there was no one to pick up. Complete lie."
A verified traveler stayed at Holiday Inn Chicago – Midway Airport S by IHG
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