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

Luxury Hotels & Resorts in South Side from NZ$210

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Check availability on South Side Luxury Hotels

Our top choices for South Side luxury hotels

A modern living room with a dark blue sofa, a glass coffee table, and a wooden log wall.

1. Mccormick Place Guest House

Mccormick Place Guest House
3.0 star property
Bronzeville
8.8 out of 10, Excellent, (77 reviews)
"Great parking and big living room."
United States
Jasmine
The price is NZ$202
includes taxes & fees
16 Nov - 17 Nov
Mccormick Place Guest House
An outdoor café with tables and chairs, a red umbrella, and a flower-lined walkway.

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, (1,000 reviews)
"Will stay here again"
United States
RENE
The price is NZ$275
includes taxes & fees
23 Nov - 24 Nov
Hyatt Place Chicago-South/University Medical Center
A metallic sculpture of a deer on a shelf, a potted plant, and a vintage mailbox.

3. Villa Dubois Guest House

Villa Dubois Guest House
2.0 star property
Bronzeville
8.4 out of 10, Very good, (132 reviews)
"Our stay was great! The staff answered all of my questions promptly, it was easy to find and not having to pay for parking was a nice bonus."
United States
Allie
The price is NZ$192
includes taxes & fees
16 Nov - 17 Nov
Villa Dubois Guest House
Interior entrance

4. Chicago Lake Shore Hotel

Chicago Lake Shore Hotel
3.0 star property
Kenwood
7.2 out of 10, Good, (1,000 reviews)
"The bath was amazing to shower in!"
United States
Britany
The price is NZ$303
includes taxes & fees
24 Nov - 25 Nov
Chicago Lake Shore Hotel
A modern living room with a sofa, two blue chairs, a round coffee table, and a unique ceiling design.

5. SpringHill Suites by Marriott Chicago Chinatown

SpringHill Suites by Marriott Chicago Chinatown
3.5 star property
Chinatown
9.6 out of 10, Exceptional, (1,000 reviews)
"Nice and convenient location, with nice breakfast and friendly staff."
United States
Shouan
The price is NZ$210
includes taxes & fees
14 Dec - 15 Dec
SpringHill Suites by Marriott Chicago Chinatown
The exterior of Jaslin Hotel with a prominent sign, large windows, and a modern facade.

6. Jaslin Hotel

Jaslin Hotel
3.0 star property
Chinatown
9.0 out of 10, Wonderful, (1,439 reviews)
"Great stay"
United States
Myangel
The price is NZ$280
includes taxes & fees
6 Dec - 7 Dec
Jaslin Hotel
A modern interior with a staircase, green upholstered seating, and artwork on the walls.

7. 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, (1,390 reviews)
"Really enjoyed my stay. Will definitely stay there again"
United States
RENE
The price is NZ$261
includes taxes & fees
11 Dec - 12 Dec
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
Lobby lounge

8. Chicago Marriott Midway

Chicago Marriott Midway
3.5 star property
Bedford Park
8.4 out of 10, Very good, (1,007 reviews)
"Overall great stay"
United States
Cynitha
The price is NZ$303
includes taxes & fees
22 Nov - 23 Nov
Chicago Marriott Midway
A modern bar area with a curved counter, multiple stools, and pendant lighting. A menu board is visible on the wall, and a coffee machine is on the counter.

9. Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG
2.5 star property
West Lawn
8.0 out of 10, Very good, (1,004 reviews)
"The staff was really kind and helpful!"
United States
Dorsy
The price is NZ$226
includes taxes & fees
13 Dec - 14 Dec
Holiday Inn Chicago – Midway Airport S by IHG
A modern hotel room with a large bed, a nightstand, a wall-mounted lamp, and a door.

10. Motel 6 - Chicago, IL

Motel 6 - Chicago, IL
2.0 star property
Washington Heights
7.0 out of 10, Good, (538 reviews)
"great"
United States
Darren
The price is NZ$191
includes taxes & fees
29 Nov - 30 Nov
Motel 6 - Chicago, IL
A spacious lobby with a modern design, featuring a large sofa, multiple chairs, a coffee table, and a mural of an airplane.

11. Best Western Inn & Suites - Midway Airport

Best Western Inn & Suites - Midway Airport
3.0 star property
Burbank
7.0 out of 10, Good, (1,001 reviews)
"Always visit this location when we’re in the city. Can’t help but love them , especially the breakfast!! Best bacon ever"
United States
William
The price is NZ$210
includes taxes & fees
1 Dec - 2 Dec
Best Western Inn & Suites - Midway Airport
A modern reception area with a sofa, a round coffee table, and a reception desk.

12. Carlton Inn Midway

Carlton Inn Midway
2.0 star property
Archer Heights
5.8 out of 10, (1,002 reviews)
"good location for access to the city"
United States
stephen T
The price is NZ$226
includes taxes & fees
20 Nov - 21 Nov
Carlton Inn Midway
A hotel lobby with a black leather sofa, a white armchair, a large vase, and a potted plant.

13. Chinatown Hotel Chicago

Chinatown Hotel Chicago
1.5 star property
Chinatown
5.6 out of 10, (1,003 reviews)
"Cheap and very close to train station. 2miles away from the city."
United States
Jonna
The price is NZ$126
includes taxes & fees
14 Dec - 15 Dec
Chinatown Hotel Chicago
A hotel room with a bed, a desk, a chair, a lamp, and a window with curtains.

14. 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, (121 reviews)
"Staff was great"
United States
Regina
The price is NZ$198
includes taxes & fees
26 Nov - 27 Nov
Saratoga Motel By Capital O Near Midway Airport Chicago IL
A brick building with a sign for the Imperial Motel.

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

Imperial Motel Chicago I-57/I-94
2.5 star property
Roseland
6.8 out of 10, (3 reviews)
"😂👍"
United States
Antyon
The price is NZ$182
includes taxes & fees
14 Dec - 15 Dec
Imperial Motel Chicago I-57/I-94
A hallway with a glass door, a window with a view of the outside, and a ceiling-mounted air conditioning unit.

16. 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 NZ$174
includes taxes & fees
14 Dec - 15 Dec
Admiral Motel By Oyo Chicago I-94
A room with large windows, a wooden floor, and a built-in air conditioning unit.

17. Best Motel By OYO Chicago I-90

Best Motel By OYO Chicago I-90
2.5 star property
Woodlawn
3.4 out of 10, (163 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 NZ$174
includes taxes & fees
29 Nov - 30 Nov
Best Motel By OYO Chicago I-90
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

Best Western Inn & Suites - Midway Airport

Best Western Inn & Suites - Midway Airport

10/10 Excellent
"Amazing"
Mohamed 2-night trip
Posted 2 hours ago
Best Western Inn & Suites - Midway Airport

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