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

Villas in South Side

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan
No exact matches found, but these alternatives could be just right

Recommended hotels in South Side

A modern building with a glass facade, a red and white sign for 'Red Menopolo Cafe', and a 'SHARK' sign.

1. 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, (1,005 reviews)
"location is fantastic, staff very helpful, traveled with my pet and no issues whatsoever."
United States
Denise
The price is S$417
includes taxes & fees
23 Oct - 24 Oct
Hyatt Place Chicago-South/University Medical Center
A multi-story hotel with a modern design, featuring a prominent entrance with a marquee and outdoor seating area.

2. Sophy Hyde Park

Sophy Hyde Park
4.0 star property
Hyde Park
9.4 out of 10, Exceptional, (1,010 reviews)
"Beautiful property and great location."
United States
amy
The price is S$501
includes taxes & fees
24 Oct - 25 Oct
Sophy Hyde Park
A Holiday Inn Express hotel with a covered entrance and multiple windows.

3. 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, (1,369 reviews)
"Everything about the property was great"
United States
Beatrice
The price is S$270
includes taxes & fees
27 Sept - 28 Sept
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
A hotel with a brick facade, a marquee sign, and a visible entrance.

4. SpringHill Suites by Marriott Chicago Chinatown

SpringHill Suites by Marriott Chicago Chinatown
3.5 star property
Chinatown
9.6 out of 10, Exceptional, (1,003 reviews)
"Good location, safe, convenient, clean"
United States
Wenli
The price is S$340
includes taxes & fees
23 Oct - 24 Oct
SpringHill Suites by Marriott Chicago Chinatown

5. Chicago Lake Shore Hotel

Chicago Lake Shore Hotel
3.0 star property
Kenwood
7.0 out of 10, Good, (1,006 reviews)
"clean room and friendly staff"
United States
John
The price is S$253
includes taxes & fees
4 Oct - 5 Oct
Chicago Lake Shore Hotel
A hotel with multiple floors, large windows, and a prominent sign for the Jaslin Hotel.

6. Jaslin Hotel

Jaslin Hotel
3.0 star property
Chinatown
9.0 out of 10, Wonderful, (1,382 reviews)
"We enjoyed our stay"
United States
Jeffrey
The price is S$255
includes taxes & fees
13 Oct - 14 Oct
Jaslin Hotel
A multi-story motel with a parking lot.

7. Motel 6 - Chicago, IL

Motel 6 - Chicago, IL
2.0 star property
Washington Heights
7.0 out of 10, Good, (496 reviews)
"It was close to high way so it could ease if you would like to go to downtown, the staff were helpful, room was clean enough."
Canada
Nazli
The price is S$135
includes taxes & fees
19 Oct - 20 Oct
Motel 6 - Chicago, IL
A Holiday Inn hotel with a parking lot and several cars parked in front.

8. 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, (1,014 reviews)
"The room was clean, the hotel is conveniently located, and super close to the airport."
United States
Fabian
The price is S$241
includes taxes & fees
27 Sept - 28 Sept
Holiday Inn Chicago – Midway Airport S by IHG
A Marriott hotel with a brick facade, a covered entrance, and landscaped areas with trees and shrubs.

9. Chicago Marriott Midway

Chicago Marriott Midway
3.5 star property
Bedford Park
8.4 out of 10, Very good, (1,003 reviews)
"Beautiful hotel. Very quiet. Conveniently located."
United States
Carolyn
The price is S$341
includes taxes & fees
26 Sept - 27 Sept
Chicago Marriott Midway
A van parked in front of a building with a balcony and a sign indicating a parking area.

10. Carlton Inn Midway

Carlton Inn Midway
2.0 star property
Archer Heights
6.0 out of 10, (1,010 reviews)
"It’s very Good, good location, good parking, good room and good employees"
United States
Icaro
The price is S$157
includes taxes & fees
27 Sept - 28 Sept
Carlton Inn Midway
A Best Western hotel with a brick facade, multiple windows, and a covered parking area.

11. Best Western Inn & Suites - Midway Airport

Best Western Inn & Suites - Midway Airport
3.0 star property
Burbank
7.0 out of 10, Good, (1,008 reviews)
"CLEAN ROOMS, 5 STAR STAFF, GOOD BREAKFAST AND PARKING"
United States
David L
The price is S$198
includes taxes & fees
29 Sept - 30 Sept
Best Western Inn & Suites - Midway Airport
A hallway with wooden flooring, a dining area with a table and chairs, and a blue sofa.

12. Villa Dubois Guest House

Villa Dubois Guest House
2.0 star property
Bronzeville
7.6 out of 10, Good, (142 reviews)
"Great place to stay. Quiet, clean and tastefully furnished. Good location for Southside destinations and good access to public transportation."
United States
Robert
The price is S$183
includes taxes & fees
24 Sept - 25 Sept
Villa Dubois Guest House
A brick building with a sign for Chicagochinatownhotel.com.

13. Chinatown Hotel Chicago

Chinatown Hotel Chicago
1.5 star property
Chinatown
5.6 out of 10, (1,002 reviews)
"Bare bones. Good for cheap last minute short stays."
United States
Celina
The price is S$152
includes taxes & fees
24 Sept - 25 Sept
Chinatown Hotel Chicago
A motel with a two-story structure, numbered rooms, and a parking area with a car.

14. Rainbow Motel

Rainbow Motel
2.0 star property
Garfield Ridge
5.4 out of 10, (60 reviews)
"Great value for the price. Staff was very friendly."
United States
Jerry
The price is S$115
includes taxes & fees
24 Sept - 25 Sept
Rainbow Motel
A mural on a building's side, depicting a person holding a clapperboard and a film reel, with text 'DUBOIS FOREST WOLF KELL' and '2015 VILE'.

15. Mccormick Place Guest House

Mccormick Place Guest House
3.0 star property
Bronzeville
6.6 out of 10, (99 reviews)
"Overall I like the place. If you are looking for a place that is"
United States
Tyler
The price is S$144
includes taxes & fees
29 Sept - 30 Sept
Mccormick Place Guest House

16. Best Motel By OYO Chicago I-90

Best Motel By OYO Chicago I-90
2.5 star property
Woodlawn
3.6 out of 10, (142 reviews)
"A/c working, friendly staff, free parking but messy sheets and a baby mouse in the room"
United States
Saul
The price is S$123
includes taxes & fees
19 Oct - 20 Oct
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top South Side Hotel Reviews

Best Western Inn & Suites - Midway Airport

Best Western Inn & Suites - Midway Airport

10/10 Excellent
"Rooms very clean. Staff very friendly and helpful… will definitely stay here again"
susan 1-night trip
Posted less than an hour ago
Best Western Inn & Suites - Midway Airport

Find out more about South Side

South Side Villas information

Number of reviews
9,729
Accommodation
0 Villas
Lowest Price
S$115
Highest Price
S$501

Explore a world of travel with Expedia