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

Hotels with Bars / Lounges in South Side

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Check availability on South Side Hotels with Bars / Lounges

Tonight
2 Oct - 3 Oct
Tomorrow
3 Oct - 4 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for South Side hotels with a bar

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 reception desk with a mosaic wall, a digital display, and a sign indicating amenities like restrooms and a meeting room.

1. Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG
West Lawn
United States
Allen
S$209
includes taxes & fees
1 Nov - 2 Nov
Holiday Inn Chicago – Midway Airport S 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 modern lounge area with a fireplace, comfortable seating, and a large window.
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
Denise
S$317
includes taxes & fees
2 Nov - 3 Nov
Hyatt Place Chicago-South/University Medical Center
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 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.

3. Sophy Hyde Park

Sophy Hyde Park
Hyde Park
United States
amy
S$410
includes taxes & fees
1 Nov - 2 Nov
Sophy Hyde Park
Lobby
A hotel room with two beds, a desk, and a chair.
A Marriott hotel with a brick facade, a covered entrance, and landscaped areas with trees and shrubs.
A modern living room with two grey armchairs, a round coffee table, and a large potted plant.

4. Chicago Marriott Midway

Chicago Marriott Midway
Bedford Park
United States
Carolyn
S$242
includes taxes & fees
2 Nov - 3 Nov
Chicago Marriott Midway
A modern bar area with wooden furniture, a beverage display, and a Starbucks logo.
A modern reception area with a wooden reception desk, a seating area with sofas and a coffee table, and a large wall-mounted artwork.
A modern lobby with a sofa set, a coffee table, and a large abstract wall art piece.
A hotel room with two beds, a sofa, a desk, and a chair.

5. Hyatt Place Chicago Midway Airport

Hyatt Place Chicago Midway Airport
Bedford Park
United States
Veronica
S$228
includes taxes & fees
1 Nov - 2 Nov
Hyatt Place Chicago Midway Airport
A large, historic building with a central courtyard surrounded by trees.
A hotel room with two beds, a desk with a television, a chair, a desk lamp, and a painting on the wall.
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
United States
Alan
S$289
includes taxes & fees
30 Oct - 31 Oct
Hilton Chicago
A modern dining area with round tables and white chairs, a kitchen area with a coffee machine, and a view of the outdoors through large windows.
A bar area with a long counter, multiple liquor bottles, and a variety of glasses.
Front of property
A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

7. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
Downtown Chicago
United States
John
S$276
includes taxes & fees
29 Oct - 30 Oct
Hilton Vacation Club Hotel Blake Chicago
An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.
A waterfront cityscape with modern buildings, a Ferris wheel, and several cruise ships docked.
A view from a room with a large window overlooking a cityscape at night, featuring a river and illuminated buildings.
A spacious outdoor dining area with large windows overlooking the sea, featuring multiple tables and stools.

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

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
United States
Shanequa
S$365
includes taxes & fees
4 Oct - 5 Oct
Sable at Navy Pier Chicago, Curio Collection by Hilton
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 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.

9. Carleton of Oak Park

Carleton of Oak Park
Oak Park
United States
Brad
S$160
includes taxes & fees
5 Oct - 6 Oct
Carleton of Oak Park
A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.
A grand ballroom with ornate ceiling decorations, multiple chandeliers, and a central table with a white tablecloth.
A cityscape with various buildings, including a prominent skyscraper and a classical building with arched windows.
A spacious bar area with a central bar, multiple seating options including bar stools and tables, and a well-lit ceiling with recessed lighting.

10. Congress Plaza Hotel

Congress Plaza Hotel
Downtown Chicago
United States
Guadalupe
S$194
includes taxes & fees
1 Nov - 2 Nov
Congress Plaza Hotel
View all properties

Top South Side Hotel Reviews

Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

10/10 Excellent
"Everything was clean they are busy updating this hotel. I like to location close to the hospital and free parking."
David 2-night trip
Posted 14 hours ago
Chicago Lake Shore Hotel
Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

8/10 Good
"The hotel was nice. I loved the restaurant. The location though was a bit much. Will stay again, but definitely plan time to get to where u need to be."
Miaya 3-night trip
Posted 17 hours ago
Holiday Inn Chicago – Midway Airport S by IHG
Carlton Inn Midway

Carlton Inn Midway

10/10 Excellent
"The room was lovely and clean, breakfast was good, staff was very pleasant"
Elaine 2-night trip
Posted 3 days ago
Carlton Inn Midway

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