TOP Hotels with a Bar in South Side, IL for 2026

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

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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 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.

1. Holiday Inn Chicago – Midway Airport S by IHG

West Lawn

Allen

₹12,616

₹15,774 total

includes taxes & fees

1 Nov - 2 Nov

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 modern lounge area with a fireplace, comfortable seating, and a large window.

2. Hyatt Place Chicago-South/University Medical Center

Hyde Park

Denise

₹20,032

₹23,816 total

includes taxes & fees

2 Nov - 3 Nov

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 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.

An outdoor seating area with sofas, chairs, and tables, surrounded by trees and string lights.

3. Sophy Hyde Park

Hyde Park

amy

₹23,843

₹30,816 total

includes taxes & fees

1 Nov - 2 Nov

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.

A bar area with a black marble countertop, wicker bar stools, and a variety of bottles and glasses on shelves.

4. Chicago Marriott Midway

Bedford Park

Carolyn

₹15,506

₹18,216 total

includes taxes & fees

2 Nov - 3 Nov

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 hotel with a glass facade, a covered entrance, and an American flag.

A hotel room with two beds, a sofa, a desk, and a chair.

5. Hyatt Place Chicago Midway Airport

Bedford Park

Veronica

₹14,639

₹17,198 total

includes taxes & fees

1 Nov - 2 Nov

A large, historic building with a central courtyard surrounded by trees.

A modern hotel lobby with a curved white sofa, two side tables with lamps, a black coffee table, and a large chandelier.

A marina with numerous boats docked, surrounded by a cityscape with high-rise buildings and a stadium.

A restaurant interior with wooden tables and chairs, a carpeted floor, and framed pictures on the walls.

6. Hilton Chicago

Downtown Chicago

Alan

₹15,963

₹21,805 total

includes taxes & fees

30 Oct - 31 Oct

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.

7. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

John

₹17,474

₹20,774 total

includes taxes & fees

29 Oct - 30 Oct

An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.

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.

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

Downtown Chicago

Shanequa

₹20,290

₹27,444 total

includes taxes & fees

4 Oct - 5 Oct

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Top South Side Hotel Reviews

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."

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."

Carlton Inn Midway

10/10 Excellent

"The room was lovely and clean, breakfast was good, staff was very pleasant"

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Check availability on South Side Hotels with a Bar

Our top choices for South Side hotels with a bar

1. Holiday Inn Chicago – Midway Airport S by IHG