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Hotels with connecting rooms in South Side

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Check availability on South Side Hotels with connecting rooms

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

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 coffee station with two espresso machines, a coffee grinder, and various coffee-related items.
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
S$204
includes taxes & fees
15 Nov - 16 Nov
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 modern lounge area with a fireplace, comfortable seating, and a large window.
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.

2. Hyatt Place Chicago-South/University Medical Center

Hyatt Place Chicago-South/University Medical Center
Hyde Park
United States
Gladys
S$272
includes taxes & fees
1 Nov - 2 Nov
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 reception desk with a mosaic wall, a digital display, and a sign indicating amenities like restrooms and a meeting room.
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.

3. Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG
West Lawn
United States
Paulina
S$216
includes taxes & fees
1 Nov - 2 Nov
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 spacious living area with a modern chandelier, comfortable seating, and a fireplace.
A multi-story hotel with a modern design, featuring a prominent entrance with a marquee and outdoor seating area.
An outdoor seating area with sofas, chairs, and tables, surrounded by trees and string lights.

4. Sophy Hyde Park

Sophy Hyde Park
Hyde Park
United States
Mary Kay
S$407
includes taxes & fees
31 Oct - 1 Nov
Sophy Hyde Park
Lobby lounge
A modern living room with two grey armchairs, a round coffee table, and a large potted plant.
A bar area with a black marble countertop, wicker bar stools, and a variety of bottles and glasses on shelves.
A Marriott hotel with a brick facade, a covered entrance, and landscaped areas with trees and shrubs.

5. Chicago Marriott Midway

Chicago Marriott Midway
Bedford Park
United States
Carolyn
S$257
includes taxes & fees
15 Nov - 16 Nov
Chicago Marriott Midway
A modern living room with a sofa, two blue chairs, a round coffee table, and a unique ceiling design.
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.
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
S$287
includes taxes & fees
1 Nov - 2 Nov
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
S$137
includes taxes & fees
8 Nov - 9 Nov
Sleep Inn Midway Airport Bedford Park
A modern lobby with sofas, tables, and a reception desk.
A hotel with a flat facade, a parking lot, and a well-lit entrance.
A hotel room with a bed, a sofa, a desk with a computer, a TV, and a window with curtains.
A modern bar area with stools, a large TV, and a decorative plant.

8. Baymont by Wyndham Chicago/Alsip

Baymont by Wyndham Chicago/Alsip
Alsip
United States
James
S$134
includes taxes & fees
28 Oct - 29 Oct
Baymont by Wyndham Chicago/Alsip
A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."
A bar area with a checkered floor, wooden chairs, a bar counter, and two televisions mounted on the wall.
A dimly lit restaurant with booths and tables, featuring a large clock and a television screen 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
S$174
includes taxes & fees
28 Oct - 29 Oct
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 marina with numerous boats docked, surrounded by a cityscape with high-rise buildings and a stadium.
A conference room with a long table, chairs, and a large screen.

10. Hilton Chicago

Hilton Chicago
Downtown Chicago
Canada
Anna
S$291
includes taxes & fees
30 Oct - 31 Oct
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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