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

South Side Hotel Guide - Hotels with Air Conditioning in South Side, Chicago

  • 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 availability on South Side Hotels with Air Conditioning

Tonight
17 Sept - 18 Sept
Tomorrow
18 Sept - 19 Sept
This weekend
18 Sept - 20 Sept
Next weekend
25 Sept - 27 Sept

Our top choices for South Side hotels with air conditioning

An outdoor café with tables and chairs, a red umbrella, and a flower-lined walkway.
A modern multi-story building with a prominent central tower, large windows, and a pedestrian walkway.
A hotel room with a bed, a desk, a chair, a sofa, a coffee table, and a painting on the wall.
A restaurant with a bar area, seating, and a television screen displaying a sports event.

1. Hyatt Place Chicago-South/University Medical Center

Hyatt Place Chicago-South/University Medical Center
Hyde Park
United States
Gladys
€272
includes taxes & fees
4 Oct - 5 Oct
Hyatt Place Chicago-South/University Medical Center
A hotel room with a large window offering a city view, two armchairs, a bed, and a lamp.
A hotel with multiple floors, large windows, and a prominent sign for the Jaslin Hotel.
A modern lobby with a glass partition, a fireplace, and a seating area.
A hotel room with a sofa, two armchairs, a coffee table, a TV, and a city view.

2. Jaslin Hotel

Jaslin Hotel
Chinatown
United States
Shaun
€177
includes taxes & fees
29 Sept - 30 Sept
Jaslin Hotel
A modern hotel room with large windows, a sofa, chairs, a dining table, and a coffee table.
A spacious living area with a modern chandelier, comfortable seating, and a fireplace.
An outdoor seating area with sofas, chairs, and tables, surrounded by trees and string lights.
A bar area with a marble countertop, multiple shelves of bottles, and a large TV screen. There are several bar stools and a round table with a vase of flowers.

3. Sophy Hyde Park

Sophy Hyde Park
Hyde Park
United States
Latricia
€409
includes taxes & fees
2 Oct - 3 Oct
Sophy Hyde Park
A hallway with wooden flooring, a dining area with a table and chairs, and a blue sofa.
A room with a wooden herringbone ceiling, a wall clock, and shelves with various decorative items and books.
A modern kitchen with white cabinets, stainless steel appliances, and patterned wallpaper.
A dining area with a wooden table and chairs, a rock sculpture centerpiece, and a large green wall art piece.

4. Villa Dubois Guest House

Villa Dubois Guest House
Bronzeville
United States
Robert
€124
includes taxes & fees
21 Sept - 22 Sept
Villa Dubois Guest House
A row of parked cars along a tree-lined street with multi-story buildings in the background.
A hotel room with a large bed, a desk, a chair, a nightstand, a lamp, and a mirror.

5. Chicago Lake Shore Hotel

Chicago Lake Shore Hotel
Kenwood
United States
John
€172
includes taxes & fees
20 Sept - 21 Sept
Chicago Lake Shore Hotel
A modern living room with a sofa, two blue chairs, a round coffee table, and a unique ceiling design.
A modern lobby with a sofa, a coffee table, and a large digital art display.
A modern kitchen with built-in appliances, wooden cabinets, and a variety of food items on shelves.
A modern hotel room with a bed, a sofa, a desk, and artwork on the walls.

6. SpringHill Suites by Marriott Chicago Chinatown

SpringHill Suites by Marriott Chicago Chinatown
Chinatown
United States
Laura
€260
includes taxes & fees
15 Oct - 16 Oct
SpringHill Suites by Marriott Chicago Chinatown
A modern bar area with a bar counter, seating, and large windows offering a view of the street.
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.
A modern lobby with a vending machine, a statue, and an exit sign.
A hotel room with a bed, a seating area with a table and a plant, a window with a city view, and a radiator.

7. Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG
West Lawn
United States
Fabian
€164
includes taxes & fees
27 Sept - 28 Sept
Holiday Inn Chicago – Midway Airport S by IHG
A hotel room with a bed, a desk, a chair, a TV, and a colorful rug.
A hotel room with a blue sofa, a small table, a TV, a desk with a chair, and a large window.
A conference room with a long table, yellow chairs, and water bottles.
A coffee station with two coffee machines, a coffee press, and various coffee pods and cups.

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

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
Bedford Park
United States
Beatrice
€192
includes taxes & fees
4 Oct - 5 Oct
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
A modern kitchen with a stainless steel refrigerator, a wooden floor, and a beige chair with a cushion.
A bedroom with a bed, bedside tables, a nightstand, a bench, and a lamp.
A modern living room with a sofa, a small table, and a decorative vase with red flowers.
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

9. 2MI to Obama Center - Pet-Friendly near UOC!

2MI to Obama Center - Pet-Friendly near UOC!
Woodlawn
United States
Kali P.
€304
includes taxes & fees
27 Sept - 28 Sept
2MI to Obama Center - Pet-Friendly near UOC!
A modern living room with a dark blue sofa, a glass coffee table, and a wooden log wall.
A bedroom with a large bed, a headboard, a wall-mounted artwork, and a window with curtains.
A modern living room with a fireplace, two armchairs, a sofa, and a large plant.
A modern kitchen with dark cabinetry, a stainless steel stove, and a glass-fronted upper cabinet.

10. Mccormick Place Guest House

Mccormick Place Guest House
Bronzeville
United States
Robert
€98
includes taxes & fees
29 Sept - 30 Sept
Mccormick Place Guest House
View all properties

Top South Side Hotel Reviews

Best Western Inn & Suites - Midway Airport

Best Western Inn & Suites - Midway Airport

10/10 Excellent
"The Staff was very accommodating. Very nice and helpful. They were very professional. I used this location regularly I feel comfortable and safe. Very convenient for me. I appreciate the staff."
Melba 3-night trip
Posted 3 hours ago
Best Western Inn & Suites - Midway Airport
Carlton Inn Midway

Carlton Inn Midway

10/10 Excellent
"Excellent breakfast, best shuttle service, Excellent hospitality."
Amit 1-night trip
Posted 14 hours ago
Carlton Inn Midway
Hyatt Place Chicago-South/University Medical Center

Hyatt Place Chicago-South/University Medical Center

10/10 Excellent
"Breakfast was a great start to the day. The staff was very friendly and helpful. Wish the pool would have been open, but also glad they commit to shutting down at times to take care of it. Great stay."
Bridget 1-night trip
Posted 14 hours ago
Hyatt Place Chicago-South/University Medical Center
Jaslin Hotel

Jaslin Hotel

10/10 Excellent
"Room cleaned and well maintained"
Jonathan 2-night trip
Posted 20 hours ago
Jaslin Hotel
Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

10/10 Excellent
"Na"
Marlon 3-night trip
Posted 22 hours ago
Holiday Inn Chicago – Midway Airport S by IHG
Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

10/10 Excellent
"Great location. Very clean-looks refurbished. The staff is amazing-very helpful & they try to help you have a good experience!"
Theodore 3-night trip
Posted 2 days ago
Chicago Lake Shore Hotel

Explore a world of travel with Expedia