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

South Side Hotel Guide - Hotels with Bar in South Side, Chicago

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Check availability on South Side Hotels with Bar

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 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.

1. Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG
West Lawn
United States
Allen
€146
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 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.
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
Denise
€220
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.
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.
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
€307
includes taxes & fees
31 Oct - 1 Nov
Sophy Hyde Park
Lobby
A Marriott hotel with a brick facade, a covered entrance, and landscaped areas with trees and shrubs.
A bar area with a black marble countertop, wicker bar stools, and a variety of bottles and glasses on shelves.
A hotel room with two beds, a desk, and a chair.

4. Chicago Marriott Midway

Chicago Marriott Midway
Bedford Park
United States
Carolyn
€168
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 lobby with a sofa set, a coffee table, and a large abstract wall art piece.
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 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
€159
includes taxes & fees
1 Nov - 2 Nov
Hyatt Place Chicago Midway Airport
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 hotel room with two beds, a desk with a television, a chair, a desk lamp, and a painting on the wall.

6. Hilton Chicago

Hilton Chicago
Downtown Chicago
United States
Alan
€200
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.
A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.
A hotel room with two beds, a nightstand, a telephone, and a wall with printed text.

7. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
Downtown Chicago
United States
John
€192
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 spacious outdoor dining area with large windows overlooking the sea, featuring multiple tables and stools.
A modern living room with a large window overlooking a body of water, a tripod, and a sofa.
A waterfront cityscape with modern buildings, a Ferris wheel, and several cruise ships docked.

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

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
United States
Shanequa
€273
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 bar area with a checkered floor, wooden chairs, a bar counter, and two televisions mounted on the wall.
A lobby with two green armchairs, a glass coffee table, a chandelier, and a fireplace.
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
€120
includes taxes & fees
4 Oct - 5 Oct
Carleton of Oak Park
A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.
A spacious bar area with a central bar, multiple seating options including bar stools and tables, and a well-lit ceiling with recessed lighting.
A grand ballroom with ornate ceiling decorations, multiple chandeliers, and a central table with a white tablecloth.
Outdoor seating with yellow umbrellas labeled "Twisted Tea," wicker chairs, and tables.

10. Congress Plaza Hotel

Congress Plaza Hotel
Downtown Chicago
United States
Guadalupe
€134
includes taxes & fees
1 Nov - 2 Nov
Congress Plaza Hotel
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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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