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Hotels with connecting rooms in South Side, Chicago

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Check availability on South Side Hotels with connecting rooms

Tonight
Oct 15 - Oct 16
Tomorrow
Oct 16 - Oct 17
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Our top choices for South Side hotels with connecting rooms

A hotel room with a bed, a desk, a chair, a TV, and a colorful rug.
A modern interior with a staircase, green upholstered seating, and artwork on the walls.
A hotel room with a blue sofa, a small table, a TV, a desk with a chair, and a large window.
A breakfast bar with labeled sections for cereal and fruit, a blue oatmeal container, and a variety of condiments and utensils.

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

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
Bedford Park
United States
Roberto
P8,512
P10,000 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
An outdoor café with tables and chairs, a red umbrella, and a flower-lined walkway.
A hotel room with a bed, a desk, a chair, a sofa, a coffee table, and a painting on the wall.
A modern multi-story building with a prominent central tower, large windows, and a pedestrian walkway.
A modern lounge area with a fireplace, comfortable seating, and a large window.

2. Hyatt Place Chicago-South/University Medical Center

Hyatt Place Chicago-South/University Medical Center
Hyde Park
United States
Gladys
P11,194
P13,308 total
includes taxes & fees
Nov 1 - Nov 2
Hyatt Place Chicago-South/University Medical Center
A modern bar area with a bar counter, seating, and large windows offering a view of the street.
A hotel room with a bed, a seating area with a table and a plant, a window with a city view, and a radiator.
A modern lobby with a vending machine, a statue, and an exit sign.
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.

3. Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG
West Lawn
United States
Paulina
P8,489
P10,595 total
includes taxes & fees
Nov 1 - Nov 2
Holiday Inn Chicago – Midway Airport S by IHG
A modern hotel room with large windows, a sofa, chairs, a dining table, and a coffee table.
A multi-story hotel with a modern design, featuring a prominent entrance with a marquee and outdoor seating area.
A spacious living area with a modern chandelier, comfortable seating, and a fireplace.
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.

4. Sophy Hyde Park

Sophy Hyde Park
Hyde Park
United States
Mary Kay
P15,492
P20,037 total
includes taxes & fees
Nov 16 - Nov 17
Sophy Hyde Park
Lobby lounge
A modern living room with two grey armchairs, a round coffee table, and a large potted plant.
A Marriott hotel with a brick facade, a covered entrance, and landscaped areas with trees and shrubs.
A bar area with a black marble countertop, wicker bar stools, and a variety of bottles and glasses on shelves.

5. Chicago Marriott Midway

Chicago Marriott Midway
Bedford Park
United States
Carolyn
P10,690
P12,559 total
includes taxes & fees
Nov 15 - Nov 16
Chicago Marriott Midway
A modern living room with a sofa, two blue chairs, a round coffee table, and a unique ceiling design.
A modern hotel room with a bed, a sofa, a desk, and artwork on the walls.
A modern kitchen with built-in appliances, wooden cabinets, and a variety of food items on shelves.
A modern restaurant with a bar area, multiple seating options, and a contemporary design.

6. SpringHill Suites by Marriott Chicago Chinatown

SpringHill Suites by Marriott Chicago Chinatown
Chinatown
United States
Cayci
P11,829
P14,063 total
includes taxes & fees
Nov 1 - Nov 2
SpringHill Suites by Marriott Chicago Chinatown
A spacious lobby with a wooden floor, a staircase with a green accent, and a reception area with a sign reading "Welcome".
A hotel reception area with a staircase, reception desk, and a large potted plant.
A Sleep Inn hotel with a prominent tower, a covered entrance, and a landscaped front yard.
A buffet setup with coffee machines, milk dispensers, and food containers.

7. Sleep Inn Midway Airport Bedford Park

Sleep Inn Midway Airport Bedford Park
Bedford Park
United States
Diane
P5,725
P6,725 total
includes taxes & fees
Nov 8 - Nov 9
Sleep Inn Midway Airport Bedford Park
A modern lobby with sofas, tables, and a reception desk.
A modern bar area with stools, a large TV, and a decorative plant.
A modern interior with a flat-screen TV displaying a menu, decorative golden star-shaped objects on mirrored stands, and a tiled floor.
A hotel room with a bed, a sofa, a desk with a computer, a TV, and a window with curtains.

8. Baymont by Wyndham Chicago/Alsip

Baymont by Wyndham Chicago/Alsip
Alsip
United States
James
P5,826
P6,583 total
includes taxes & fees
Oct 25 - Oct 26
Baymont by Wyndham Chicago/Alsip
A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."
A lobby with two green armchairs, a glass coffee table, a chandelier, and a fireplace.
A bar area with a checkered floor, wooden chairs, a bar counter, and two televisions mounted on the wall.
A residential street with a sidewalk, houses, and greenery.

9. Carleton of Oak Park

Carleton of Oak Park
Oak Park
United States
Brad
P7,697
P8,542 total
includes taxes & fees
Oct 27 - Oct 28
Carleton of Oak Park
A modern hotel lobby with a curved white sofa, two side tables with lamps, a black coffee table, and a large chandelier.
A restaurant interior with wooden tables and chairs, a carpeted floor, and framed pictures on the walls.
A hotel room with two beds, a desk with a television, a chair, a desk lamp, and a painting on the wall.
A conference room with a long table, chairs, and a large screen.

10. Hilton Chicago

Hilton Chicago
Downtown Chicago
Canada
Anna
P10,459
P14,285 total
includes taxes & fees
Oct 30 - Oct 31
Hilton Chicago
View all properties

Top South Side Hotel Reviews

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

10/10 Excellent
"Excellent service"
Carlos 3-night trip
Posted 6 hours ago
Holiday Inn Chicago – Midway Airport S by IHG
Chicago Marriott Midway

Chicago Marriott Midway

10/10 Excellent
"Love"
Ananada 3-night trip
Posted 17 hours ago
Chicago Marriott Midway

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