South Side Villas ￥14,502

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

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

In two months

In three months

In four months

No exact matches found, but these alternatives could be just right

Recommended hotels in South Side

An outdoor café with tables and chairs, a red umbrella, and a flower-lined walkway.

1. Hyatt Place Chicago-South/University Medical Center

Hyde Park

Kelley

￥27,571 total

includes taxes & fees

Nov 24 - Nov 25

A hotel with a covered entrance, multiple windows, and a clear sky.

2. Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

Bedford Park

Ambreauna

￥23,540 total

includes taxes & fees

Nov 28 - Nov 29

A hotel with a brick facade, a marquee sign, and a visible entrance.

3. SpringHill Suites by Marriott Chicago Chinatown

Chinatown

Sckilar

￥23,466 total

includes taxes & fees

Nov 24 - Nov 25

A Holiday Inn hotel with a parking lot and several cars parked in front.

4. Holiday Inn Chicago – Midway Airport S by IHG

West Lawn

Laura

￥23,432 total

includes taxes & fees

Nov 24 - Nov 25

A Marriott hotel with a brick facade, a covered entrance, and landscaped areas with trees and shrubs.

5. Chicago Marriott Midway

Bedford Park

Cynitha

￥26,505 total

includes taxes & fees

Nov 3 - Nov 4

A Best Western hotel with a brick facade, multiple windows, and a covered parking area.

6. Best Western Inn & Suites - Midway Airport

Burbank

Angel

￥19,876 total

includes taxes & fees

Nov 4 - Nov 5

7. Motel 6 - Chicago, IL

Washington Heights

Ingrid

￥16,667 total

includes taxes & fees

Nov 16 - Nov 17

A modern hotel room with large windows, a sofa, chairs, a dining table, and a coffee table.

8. Sophy Hyde Park

Hyde Park

Brent

￥42,815 total

includes taxes & fees

Nov 24 - Nov 25

A building with a red awning, a brick facade, and a parking lot with marked spaces.

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

Roseland

Antyon

￥15,557 total

includes taxes & fees

Nov 3 - Nov 4

A hotel with multiple floors, large windows, and a prominent sign for the Jaslin Hotel.

10. Jaslin Hotel

Chinatown

Myangel

￥26,245 total

includes taxes & fees

Nov 4 - Nov 5

A van parked in front of a building with a balcony and a sign indicating a parking area.

11. Carlton Inn Midway

Archer Heights

stephen T

￥18,220 total

includes taxes & fees

Nov 10 - Nov 11

A neatly arranged bedroom with a bed, bedside tables, and abstract wall art.

12. Hyde Park Trendy Studio Apartment in Good Spot

Hyde Park

Angelina

￥28,184 total

includes taxes & fees

Nov 16 - Nov 17

A wooden deck with a table and two white chairs, a lamp, and a brick wall with hanging planters.

13. Mccormick Place Guest House

Bronzeville

Jasmine

￥17,749 total

includes taxes & fees

Nov 3 - Nov 4

A hallway with wooden flooring, a dining area with a table and chairs, and a blue sofa.

14. Villa Dubois Guest House

Bronzeville

Yohannes

￥19,980 total

includes taxes & fees

Nov 10 - Nov 11

15. Chicago Lake Shore Hotel

Kenwood

Suzanne

￥26,500 total

includes taxes & fees

Nov 4 - Nov 5

16. Chinatown Hotel Chicago

Chinatown

michael

￥14,502 total

includes taxes & fees

Nov 10 - Nov 11

A modern living room with a sofa, coffee table, and TV. There are windows with blinds, a radiator, and a plant.

17. Sleek & Functional 2-Bedroom Apt

Hyde Park

Lisa T.

￥40,182 total

includes taxes & fees

Nov 15 - Nov 16

A motel with a two-story structure, numbered rooms, and a parking area with a car.

18. Rainbow Motel

Garfield Ridge

Jerry

￥15,181 total

includes taxes & fees

Nov 11 - Nov 12

A multi-story building with a uniform facade, large windows, and a flat roof.

19. Relaxed City Stay in Hyde Park | Cozy Studio Unit

Kenwood

￥43,079 total

includes taxes & fees

Nov 9 - Nov 10

A multi-story brick building with a traditional architectural style, featuring a mix of brick and timber framing.

20. Trendy Studio Apartment in Chicago

Hyde Park

￥37,244 total

includes taxes & fees

Nov 11 - Nov 12

View all properties

Find vacation rentals that suit your style

Apartments

Aparthotels

Save an average of 15% on thousands of hotels when you're signed in

Top South Side Hotel Reviews

Holiday Inn Chicago – Midway Airport S by IHG

8/10 Good

"The bar seems no one showing"

Hyatt Place Chicago-South/University Medical Center

8/10 Good

"Our overall experience was good. The staff was courteous and helpful. The room was clean and comfortable, but with one slight problem. The air conditioning/heating vent blew air right onto the bed ... had to turn it off at night. I had anticipated using the indoor pool, but it was drained and closed. I had asked for additional packets of decaf coffee for the in-room coffee maker ... never got them. On our day of departure, we had a 7:15 Uber pickup scheduled and planned for an early breakfast, but the hot breakfast items weren't brought out until after 6:30 ... kind of cutting it close."