A cityscape with a prominent building with a green dome, surrounded by greenery and a body of water.

South Side Hotels

  • 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

Property class

Guest rating

Selecting then applying a filter from this group will update the results on a new page

Our top choices for South Side hotels

1. 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, (1,384 reviews)
"Enjoyed my stay."
United States
Ambreauna
The price is P8,079
P9,491 total
includes taxes & fees
Dec 4 - Dec 5
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

2. 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, (1,006 reviews)
"Rooms were very clean and breakfast was actually pretty good."
United States
Kelley
The price is P11,387
P13,538 total
includes taxes & fees
Nov 22 - Nov 23
Hyatt Place Chicago-South/University Medical Center

3. SpringHill Suites by Marriott Chicago Chinatown

SpringHill Suites by Marriott Chicago Chinatown
3.5 star property
Chinatown
9.6 out of 10, Exceptional, (1,004 reviews)
"Nice and convenient location, with nice breakfast and friendly staff."
United States
Shouan
The price is P7,958
P9,462 total
includes taxes & fees
Dec 3 - Dec 4
SpringHill Suites by Marriott Chicago Chinatown

4. Sophy Hyde Park

Sophy Hyde Park
4.0 star property
Hyde Park
9.4 out of 10, Exceptional, (1,004 reviews)
"Nice bed and shower. Staff friendly"
United States
Trinette
The price is P14,256
P18,603 total
includes taxes & fees
Nov 24 - Nov 25
Sophy Hyde Park

5. Jaslin Hotel

Jaslin Hotel
3.0 star property
Chinatown
9.0 out of 10, Wonderful, (1,429 reviews)
"Great stay"
United States
Myangel
The price is P8,341
P9,918 total
includes taxes & fees
Dec 2 - Dec 3
Jaslin Hotel

6. Chicago Marriott Midway

Chicago Marriott Midway
3.5 star property
Bedford Park
8.4 out of 10, Very good, (1,004 reviews)
"Overall great stay"
United States
Cynitha
The price is P9,115
P10,708 total
includes taxes & fees
Nov 25 - Nov 26
Chicago Marriott Midway

7. Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG
2.5 star property
West Lawn
8.2 out of 10, Very good, (1,011 reviews)
"The staff was really kind and helpful!"
United States
Dorsy
The price is P7,252
P9,150 total
includes taxes & fees
Nov 23 - Nov 24
Holiday Inn Chicago – Midway Airport S by IHG

8. Best Western Inn & Suites - Midway Airport

Best Western Inn & Suites - Midway Airport
3.0 star property
Burbank
7.0 out of 10, Good, (1,000 reviews)
"Perfect setting"
United States
Angel
The price is P7,222
P8,015 total
includes taxes & fees
Nov 17 - Nov 18
Best Western Inn & Suites - Midway Airport

9. Chicago Lake Shore Hotel

Chicago Lake Shore Hotel
3.0 star property
Kenwood
7.0 out of 10, Good, (1,007 reviews)
"Great hotel. Very clean and we loved the free parking and that they gave you a parking pass. Will definitely be my go to hotel"
United States
Suzanne
The price is P9,120
P10,706 total
includes taxes & fees
Nov 4 - Nov 5
Chicago Lake Shore Hotel

10. Motel 6 - Chicago, IL

Motel 6 - Chicago, IL
2.0 star property
Washington Heights
7.0 out of 10, Good, (530 reviews)
"Secure parking"
United States
Ingrid
The price is P5,725
P6,720 total
includes taxes & fees
Nov 17 - Nov 18
Motel 6 - Chicago, IL

11. Imperial Motel Chicago I-57/I-94

Imperial Motel Chicago I-57/I-94
2.5 star property
Roseland
6.0 out of 10, (2 reviews)
"😂👍"
United States
Antyon
The price is P5,354
P6,285 total
includes taxes & fees
Nov 4 - Nov 5
Imperial Motel Chicago I-57/I-94

12. Villa Dubois Guest House

Villa Dubois Guest House
2.0 star property
Bronzeville
8.2 out of 10, Very good, (133 reviews)
"Wonderful place"
United States
Yohannes
The price is P7,458
P8,754 total
includes taxes & fees
Nov 4 - Nov 5
Villa Dubois Guest House

13. Carlton Inn Midway

Carlton Inn Midway
2.0 star property
Archer Heights
5.8 out of 10, (1,008 reviews)
"good location for access to the city"
United States
stephen T
The price is P6,813
P7,999 total
includes taxes & fees
Nov 8 - Nov 9
Carlton Inn Midway

14. Mccormick Place Guest House

Mccormick Place Guest House
3.0 star property
Bronzeville
8.4 out of 10, Very good, (81 reviews)
"Great parking and big living room."
United States
Jasmine
The price is P6,096
P7,157 total
includes taxes & fees
Nov 17 - Nov 18
Mccormick Place Guest House

15. Chinatown Hotel Chicago

Chinatown Hotel Chicago
1.5 star property
Chinatown
5.6 out of 10, (1,002 reviews)
"It was not dirty, nor spotless, overall great value for the location. This place is perfect for someone looking for a room to sleep while exploring Chinatown."
United States
michael
The price is P4,988
P5,855 total
includes taxes & fees
Nov 4 - Nov 5
Chinatown Hotel Chicago

16. Rainbow Motel

Rainbow Motel
2.0 star property
Garfield Ridge
5.4 out of 10, (74 reviews)
"Great value for the price. Staff was very friendly."
United States
Jerry
The price is P6,550
P7,689 total
includes taxes & fees
Nov 4 - Nov 5
Rainbow Motel

17. 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
5.6 out of 10, (114 reviews)
"Its a hotel owned and operated by the family rooms smell like pee bathrooms are nasty"
United States
Pedro
The price is P5,471
P6,969 total
includes taxes & fees
Nov 4 - Nov 5
Saratoga Motel By Capital O Near Midway Airport Chicago IL

18. Best Motel By OYO Chicago I-90

Best Motel By OYO Chicago I-90
2.5 star property
Woodlawn
3.4 out of 10, (159 reviews)
"The motel smell like rats. And i stay there no more 30 minutes and chek out i pay $130"
United States
Rifki
The price is P5,243
P6,154 total
includes taxes & fees
Nov 16 - Nov 17
Best Motel By OYO Chicago I-90

19. Admiral Motel By Oyo Chicago I-94

Admiral Motel By Oyo Chicago I-94
2.5 star property
Chatham
4.2 out of 10, (83 reviews)
"Better than ever"
United States
Dawn
The price is P5,243
P6,154 total
includes taxes & fees
Nov 16 - Nov 17
Admiral Motel By Oyo Chicago I-94

20. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1,218 reviews)
"Great location from both airports. Lovely hotel clean and convenient"
United Kingdom
Kanokkan
The price is P10,218
P12,147 total
includes taxes & fees
Nov 22 - Nov 23
Hilton Vacation Club Hotel Blake Chicago
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.

Compare top hotels in South Side

2.5 star property
Bedford Park
3.0 star property
Hyde Park
3.5 star property
Chinatown
4.0 star property
Hyde Park
3.0 star property
Chinatown
9.0
Wonderful
1,384 reviews
8.8
Excellent
1,006 reviews
9.6
Exceptional
1,004 reviews
9.4
Exceptional
1,004 reviews
9.0
Wonderful
1,429 reviews
The price is P8,079
P9,491 total
includes taxes & fees
Dec 4 - Dec 5
The price is P11,387
P13,538 total
includes taxes & fees
Nov 22 - Nov 23
The price is P7,958
P9,462 total
includes taxes & fees
Dec 3 - Dec 4
The price is P14,256
P18,603 total
includes taxes & fees
Nov 24 - Nov 25
The price is P8,341
P9,918 total
includes taxes & fees
Dec 2 - Dec 3
  • Yes, Breakfast included
  • No Pool
  • No Spa
  • No Pet-friendly
  • Yes, WiFi included
  • Yes, Parking
  • Yes, Breakfast included
  • Yes, Pool
  • No Spa
  • Yes, Pet-friendly
  • Yes, WiFi included
  • Yes, Parking
  • Yes, Breakfast included
  • No Pool
  • No Spa
  • No Pet-friendly
  • No WiFi included
  • Yes, Parking
  • No Breakfast included
  • No Pool
  • No Spa
  • Yes, Pet-friendly
  • Yes, WiFi included
  • No Parking
  • No Breakfast included
  • No Pool
  • No Spa
  • No Pet-friendly
  • Yes, WiFi included
  • No Parking
Save an average of 15% on thousands of hotels when you're signed in

Stay near popular South Side attractions

Learn more about South Side

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

A cityscape with a prominent building with a green dome, surrounded by greenery and a body of water.

Top South Side Hotel Reviews

More cheap stays in South Side