Photo by by Midway Intl Airport

South Side Hotels

Start date: Check-in selected.
To Date
End date: Check-out
  • 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

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Star rating

Top 10 trending South Side hotels

Motel 6 - Chicago, IL
2.0 star property
6.8 out of 10, (157)
"Overall just what i needed, not really a vacation destination, but worked for what i needed."
United States
Francis X.
The price is P3,950
P4,637 total
includes taxes & fees
Nov 21 - Nov 22
Motel 6 - Chicago, IL
Saratoga Motel By Capital O Near Midway Airport Chicago IL
2.5 star property
6.0 out of 10, (11)
"Nice place "
United States
Albert
The price is P5,033
P5,909 total
includes taxes & fees
Nov 9 - Nov 10
Saratoga Motel By Capital O Near Midway Airport Chicago IL
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
2.5 star property
9.0 out of 10, Wonderful, (1173)
"Room was spacious and clean. Breakfast was nice and convenient. Will stay again."
United States
Esther
The price is P6,555
P7,701 total
includes taxes & fees
Nov 23 - Nov 24
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
Villa Dubois Guest House
2.0 star property
8.6 out of 10, Excellent, (76)
"My stay was very pleasant. The accommodation was comfortable, easily accessible, and well connected to public transport. I highly recommend it to anyone visiting the area."
United States
Lizeth
The price is P4,390
P5,153 total
includes taxes & fees
Nov 9 - Nov 10
Villa Dubois Guest House
Jaslin Hotel
3.0 star property
9.0 out of 10, Wonderful, (1169)
"parking was kind of sketchy but doable. would stay here again "
United States
Mia
The price is P7,550
P8,864 total
includes taxes & fees
Nov 11 - Nov 12
Jaslin Hotel
Chinatown Hotel Chicago
1.5 star property
5.4 out of 10, (1000)
"Clean room."
United States
Claudio Andrés
The price is P3,951
P4,638 total
includes taxes & fees
Nov 9 - Nov 10
Chinatown Hotel Chicago
Capital O Empire Motel Chicago I-94
2.5 star property
3.4 out of 10, (22)
"False advertisement: they are no longer associated with OYO so the use of the "Capital O" name is misleading. Under new ownership of arabs and Africans and it looks like it. Holes in the walls from maintenece AND mice, no wifi, homeless folks sleeping in and around the place, maintenace leaves trash in the center of the parking lot for the hobos to rummage through. "
United States
Savon
The price is P3,395
P4,395 total
includes taxes & fees
Nov 30 - Dec 1
Capital O Empire Motel Chicago I-94
SpringHill Suites by Marriott Chicago Chinatown
3.5 star property
9.6 out of 10, Exceptional, (1031)
"Variety of good restaurants around. Great service "
United States
Jon-Anthony
The price is P6,789
P7,970 total
includes taxes & fees
Nov 23 - Nov 24
SpringHill Suites by Marriott Chicago Chinatown
Carlton Inn Midway
2.0 star property
6.4 out of 10, (1002)
"Very friendly! With airport shuttle!"
United States
Guochong
The price is P6,965
P8,177 total
includes taxes & fees
Nov 7 - Nov 8
Carlton Inn Midway
Rainbow Motel
2.0 star property
6.2 out of 10, (14)
"This property is just old and needs some repairs. Some effort has been put forward in this regard, but more would be nicer. There are wall defects and paint on the bathroom tiles."
United States
Steven
The price is P5,677
P6,665 total
includes taxes & fees
Nov 11 - Nov 12
Rainbow Motel
Mccormick Place Guest House
3.0 star property
8.8 out of 10, Excellent, (41)
"Very good place,nice host "
Canada
Qiang
The price is P3,839
P4,507 total
includes taxes & fees
Nov 10 - Nov 11
Mccormick Place Guest House
Chicago Marriott Midway
3.5 star property
8.4 out of 10, Very Good, (903)
"Great service, love the amenities, easy to get to"
United States
Luna
The price is P8,481
P9,963 total
includes taxes & fees
Nov 13 - Nov 14
Chicago Marriott Midway
Hyatt Place Chicago-South/University Medical Center
3.0 star property
8.8 out of 10, Excellent, (1032)
"Great hotel, great friendly staff"
United States
Hope
The price is P7,901
P9,275 total
includes taxes & fees
Dec 6 - Dec 7
Hyatt Place Chicago-South/University Medical Center
Admiral Motel By Oyo Chicago I-94
2.5 star property
4.0 out of 10, (38)
"Fine stay "
United States
Sharmaine
The price is P3,278
P4,257 total
includes taxes & fees
Dec 2 - Dec 3
Admiral Motel By Oyo Chicago I-94
Stylish Apartment near Chicago Downtown
2.0 star property
The price is P14,574
P23,154 total
includes taxes & fees
Nov 9 - Nov 10
Stylish Apartment near Chicago Downtown
Sophy Hyde Park
4.0 star property
9.6 out of 10, Exceptional, (1003)
"Loved my stay!"
United States
Dawnielle
The price is P11,067
P14,580 total
includes taxes & fees
Nov 23 - Nov 24
Sophy Hyde Park
Best Motel By OYO Chicago I-90
2.0 star property
3.4 out of 10, (47)
"Easy, safe parking "
United States
Ramon
The price is P3,278
P4,316 total
includes taxes & fees
Dec 7 - Dec 8
Best Motel By OYO Chicago I-90
Best Western Inn & Suites - Midway Airport
2.5 star property
6.6 out of 10, (1005)
"Room was very clean and staff did a great job at upkeeping. Not too far from Midway airport where you can use the CTA to get downtown if needed. "
United States
Markus
The price is P6,644
P7,374 total
includes taxes & fees
Nov 17 - Nov 18
Best Western Inn & Suites - Midway Airport
Skylark Motel
2.0 star property
4.6 out of 10, (119)
"The proximity to Midway was great. Other than that, it was pretty bad, holes in the floor, scarry shower. However, I didn't have to sleep on the floor at the airport, so I guess there is that."
United States
Brian
The price is P5,209
P6,115 total
includes taxes & fees
Nov 9 - Nov 10
Skylark Motel
Eurostars Magnificent Mile
4.0 star property
9.0 out of 10, Wonderful, (3080)
"Awesome location and excellent service, the staff was great!"
United States
Salvador
The price is P6,354
P7,459 total
includes taxes & fees
Dec 7 - Dec 8
Eurostars 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 South Side

Discover the metropolitan area of South Side—museums, skyscrapers, and top sights like Lake Michigan.

Chicago, IL featuring interior views and an airport as well as a couple
Photo by by Midway Intl Airport
Open Photo by by Midway Intl Airport

Top South Side Hotel Reviews

More cheap stays in South Side

Explore a world of travel with Expedia