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

South Side Hotel Guide - Hotels with Connecting Rooms in South Side, Chicago

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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 hotel room with a blue sofa, a small table, a TV, a desk with a chair, and a large window.
A coffee station with two espresso machines, a coffee grinder, and various coffee-related items.
A modern interior with a staircase, green upholstered seating, and artwork on the walls.

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
€142
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 restaurant with a bar area, seating, and a television screen displaying a sports event.
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.

2. Hyatt Place Chicago-South/University Medical Center

Hyatt Place Chicago-South/University Medical Center
Hyde Park
United States
Gladys
€189
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 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 reception desk with a mosaic wall, a digital display, and a sign indicating amenities like restrooms and a meeting room.
A hotel room with a bed, a seating area with a table and a plant, a window with a city view, and a radiator.

3. Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG
West Lawn
United States
Paulina
€151
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 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.
A spacious living area with a modern chandelier, comfortable seating, and a fireplace.

4. Sophy Hyde Park

Sophy Hyde Park
Hyde Park
United States
Mary Kay
€309
includes taxes & fees
31 Oct - 1 Nov
Sophy Hyde Park
Lobby lounge
A Marriott hotel with a brick facade, a covered entrance, and landscaped areas with trees and shrubs.
A hotel room with two beds, a desk, and a chair.
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
€179
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 lobby with a sofa, a coffee table, and a large digital art display.
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.

6. SpringHill Suites by Marriott Chicago Chinatown

SpringHill Suites by Marriott Chicago Chinatown
Chinatown
United States
Cayci
€200
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 Sleep Inn hotel with a prominent tower, a covered entrance, and a landscaped front yard.
A modern living room with sofas, a coffee table, and a fireplace.
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
€96
includes taxes & fees
8 Nov - 9 Nov
Sleep Inn Midway Airport Bedford Park
A modern lobby with sofas, tables, and a reception desk.
A modern interior with a flat-screen TV displaying a menu, decorative golden star-shaped objects on mirrored stands, and a tiled floor.
A modern bar area with stools, a large TV, and a decorative plant.
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
€94
includes taxes & fees
25 Oct - 26 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
€122
includes taxes & fees
21 Oct - 22 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 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
€203
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 16 hours ago
Chicago Marriott Midway

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