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

Find South Side Business Hotels from S$140

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Check availability on South Side Business Hotels

Tonight
9 Oct - 10 Oct
Tomorrow
10 Oct - 11 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for South Side business-friendly hotels

A hotel room with a bed, a desk, a chair, a TV, and a colorful rug.
A coffee station with two espresso machines, a coffee grinder, and various coffee-related items.
A Holiday Inn Express & Suites hotel with a modern facade, multiple parking spaces, and a well-lit entrance.
A hotel reception desk with a modern design, including a digital display and a sign indicating it is a non-smoking property.

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$203
includes taxes & fees
8 Nov - 9 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 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 restaurant with a bar area, seating, and a television screen displaying a sports event.

2. Hyatt Place Chicago-South/University Medical Center

Hyatt Place Chicago-South/University Medical Center
Hyde Park
United States
Gladys
S$271
includes taxes & fees
1 Nov - 2 Nov
Hyatt Place Chicago-South/University Medical Center
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 lobby with a sofa, a coffee table, and a large digital art display.
A modern restaurant with a bar area, multiple seating options, and a contemporary design.

3. SpringHill Suites by Marriott Chicago Chinatown

SpringHill Suites by Marriott Chicago Chinatown
Chinatown
United States
Cayci
S$286
includes taxes & fees
1 Nov - 2 Nov
SpringHill Suites by Marriott Chicago Chinatown
A hotel lobby with a reception desk, seating area, and a cityscape mural on the ceiling.
A spacious hotel lobby with seating areas, a reception desk, and a large window offering a view.
A hotel room with a large bed, two bedside tables with lamps, a leather armchair, a sofa, and a small table.
A Best Western hotel with a brick facade, multiple windows, and a covered parking area.

4. Best Western Inn & Suites - Midway Airport

Best Western Inn & Suites - Midway Airport
Burbank
United States
David L
S$161
includes taxes & fees
2 Nov - 3 Nov
Best Western Inn & Suites - Midway Airport
A modern bar area with a bar counter, seating, and large windows offering a view of the street.
A modern lobby with a vending machine, a statue, and an exit sign.
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.

5. Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG
West Lawn
United States
Paulina
S$210
includes taxes & fees
8 Nov - 9 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 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.
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.

6. Sophy Hyde Park

Sophy Hyde Park
Hyde Park
United States
Brent
S$442
includes taxes & fees
31 Oct - 1 Nov
Sophy Hyde Park
Lobby
A hotel room with two beds, a desk, and a chair.
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.

7. Chicago Marriott Midway

Chicago Marriott Midway
Bedford Park
United States
Carolyn
S$269
includes taxes & fees
26 Oct - 27 Oct
Chicago Marriott Midway
A hotel room with two beds, a desk, a chair, a dresser, and a bathroom visible through an open door.
A modern living room with a flat-screen TV mounted above a fireplace, flanked by two potted plants.
A modern living room with a grey sofa, a round coffee table, and a chair. There are framed pictures on the wall and a window providing natural light.
A breakfast bar with coffee makers, a toaster, and a variety of pastries.

8. Carlton Inn Midway

Carlton Inn Midway
Archer Heights
United States
Icaro
S$157
includes taxes & fees
25 Oct - 26 Oct
Carlton Inn Midway
A hotel room with a bed, a desk, a chair, a lamp, and a window with curtains.
A room with a microwave on a counter, a door with a 'No Smoking' sign, and a window with a view of cars and trees.
A reception desk with various notices and a security camera.
A motel with a row of parking spaces and a building with a red roof and beige walls.

9. Saratoga Motel By Capital O Near Midway Airport Chicago IL

Saratoga Motel By Capital O Near Midway Airport Chicago IL
Ashburn
United States
Aniya
S$140
includes taxes & fees
12 Oct - 13 Oct
Saratoga Motel By Capital O Near Midway Airport Chicago IL
A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."
A residential street with a sidewalk, houses, and greenery.
A dimly lit restaurant with booths and tables, featuring a large clock and a television screen on the wall.
A bar area with a checkered floor, wooden chairs, a bar counter, and two televisions mounted on the wall.

10. Carleton of Oak Park

Carleton of Oak Park
Oak Park
United States
Brad
S$174
includes taxes & fees
12 Oct - 13 Oct
Carleton of Oak Park
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Top South Side Hotel Reviews

Chinatown Hotel Chicago

Chinatown Hotel Chicago

8/10 Good
"The location is wonderful, and if you're looking for a no-frills place to stay and you plan to be out and about all day, this is a great option. The building has seen better days, but it's everything we needed it to be. Also, it was very quiet for sleeping at night, very little traffic noise, etc. Would definitely stay here again."
Jennifer 2-night trip
Posted 2 days ago
Chinatown Hotel Chicago
Hyatt Place Chicago-South/University Medical Center

Hyatt Place Chicago-South/University Medical Center

10/10 Excellent
"Breakfast buffet was excellent, rooms spacious and comfortable. Only bummer was the pool was closed for renovations when we were there and the listing didn't say so. Also the parking fee is HIGH so be prepared!"
Cristeta 2-night trip
Posted 2 days ago
Hyatt Place Chicago-South/University Medical Center
Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

10/10 Excellent
"Definitely a motel vibe, no elevator. Nice staff and clean rooms."
William 1-night trip
Posted 4 days ago
Chicago Lake Shore Hotel

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