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

Hotels with Restaurants in South Side

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Check availability on South Side Hotels with Restaurants

Tonight
7 Oct - 8 Oct
Tomorrow
8 Oct - 9 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for South Side hotels with a restaurant

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 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.

1. Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG
West Lawn
United States
Paulina
S$221
includes taxes & fees
25 Oct - 26 Oct
Holiday Inn Chicago – Midway Airport S by IHG
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.

2. Chicago Marriott Midway

Chicago Marriott Midway
Bedford Park
United States
Carolyn
S$263
includes taxes & fees
7 Nov - 8 Nov
Chicago Marriott Midway
A modern hotel room with large windows, a sofa, chairs, a dining table, and a coffee table.
An outdoor seating area with sofas, chairs, and tables, surrounded by trees and string lights.
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.

3. Sophy Hyde Park

Sophy Hyde Park
Hyde Park
United States
Mary Kay
S$409
includes taxes & fees
1 Nov - 2 Nov
Sophy Hyde Park
A hotel room with a large bed, a nightstand with a lamp, a wall clock, and a window with curtains.
A reception area with a desk, a seating area with a blue sofa, and a bookshelf filled with books.
A restaurant with booths and tables, a television on the wall, and a view of the street outside.
Front of property

4. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
Downtown Chicago
United States
John
S$261
includes taxes & fees
3 Nov - 4 Nov
Hilton Vacation Club Hotel Blake Chicago
A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.
Outdoor seating with yellow umbrellas labeled "Twisted Tea," wicker chairs, and tables.
A grand ballroom with ornate ceiling decorations, multiple chandeliers, and a central table with a white tablecloth.
A spacious bar area with a central bar, multiple seating options including bar stools and tables, and a well-lit ceiling with recessed lighting.

5. Congress Plaza Hotel

Congress Plaza Hotel
Downtown Chicago
United States
Katimah
S$178
includes taxes & fees
1 Nov - 2 Nov
Congress Plaza Hotel
A large, historic building with a central courtyard surrounded by trees.
A marina with numerous boats docked, surrounded by a cityscape with high-rise buildings and a stadium.
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.

6. Hilton Chicago

Hilton Chicago
Downtown Chicago
Canada
Anna
S$289
includes taxes & fees
30 Oct - 31 Oct
Hilton Chicago
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 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.

7. Carleton of Oak Park

Carleton of Oak Park
Oak Park
United States
Brad
S$160
includes taxes & fees
28 Oct - 29 Oct
Carleton of Oak Park
A bakery display with various types of bread and packaged goods.
A modern interior with a bar area, seating, and decorative wooden panels.
A reception area with a marble counter, decorative Buddha statues, and a wall with a quote.
A hotel room with a large bed, a flat-screen TV, a desk with a lamp, and a chair.

8. Best Western Grant Park Hotel

Best Western Grant Park Hotel
Downtown Chicago
United States
Shelby Ryann
S$245
includes taxes & fees
25 Oct - 26 Oct
Best Western Grant Park Hotel
A modern hotel lobby with large windows, leather sofas, and a view of the cityscape.
A compact kitchen with a microwave, coffee maker, and sink.
A restaurant with booths, tables, and a green wall in the background.
A hotel room with a bed, a desk with a chair, a sofa, and a view of a building through the window.

9. Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
Downtown Chicago
United States
Sandra
S$170
includes taxes & fees
2 Nov - 3 Nov
Travelodge by Wyndham Downtown Chicago
An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.
A spacious outdoor dining area with large windows overlooking the sea, featuring multiple tables and stools.
A waterfront cityscape with modern buildings, a Ferris wheel, and several cruise ships docked.
A modern living room with a large window overlooking a body of water, a tripod, and a sofa.

10. Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
United States
Shanequa
S$392
includes taxes & fees
1 Nov - 2 Nov
Sable at Navy Pier Chicago, Curio Collection by Hilton
View all properties

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 21 hours 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 22 hours ago
Hyatt Place Chicago-South/University Medical Center
Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

10/10 Excellent
"clean room."
Francis 1-night trip
Posted 1 day ago
Holiday Inn Chicago – Midway Airport S by IHG
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 2 days ago
Chicago Lake Shore Hotel
Chicago Marriott Midway

Chicago Marriott Midway

8/10 Good
"The hotel is clean and safe. I was disappointed that they only had 5 handicapped parking spaces and the parking lot was so full. It was difficult for me to have to park in the back of the parking lot and all of the handicapped parking spaces was full."
Anna 1-night trip
Posted 3 days ago
Chicago Marriott Midway

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