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

Boutique Hotels in South Side

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Check availability on South Side Boutique Hotels

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

Our top choices for South Side boutique hotels

A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."
A dimly lit restaurant with booths and tables, featuring a large clock and a television screen on the wall.
A residential street with a sidewalk, houses, and greenery.
A lobby with two green armchairs, a glass coffee table, a chandelier, and a fireplace.

1. Carleton of Oak Park

Carleton of Oak Park
Oak Park
United States
Brad
S$174
includes taxes & fees
27 Oct - 28 Oct
Carleton of Oak Park
A hotel room with a large bed, a nightstand with a lamp, a wall clock, and a window with curtains.
Front of property
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.

2. 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
The CL Champagne Lodge with a prominent tower and a signboard.
A reception area with a wooden counter, a computer, and framed pictures on the wall.
A spa room with a wooden ceiling, a large hot tub, and glass walls.
A modern bathroom with a large bathtub, a glass-enclosed shower, and a fireplace with two potted plants.

3. The Champagne Lodge & Luxury Suites

The Champagne Lodge & Luxury Suites
Willowbrook
United States
Lamarr
S$184
includes taxes & fees
28 Oct - 29 Oct
The Champagne Lodge & Luxury Suites
A rooftop lounge with a fire feature, seating, and a city view.
The entrance of Hotel Lincoln with a clear sign above the doors and a cyclist passing by.
A staircase with a red wall adorned with various framed artworks.
A hotel lobby with a reception desk, leather seating, a patterned rug, and a wall with various artworks.

4. Hotel Lincoln

Hotel Lincoln
Lincoln Park
United States
Daniel
S$249
includes taxes & fees
25 Oct - 26 Oct
Hotel Lincoln
A room with a brick wall, a large wooden door, a flat-screen TV, and a grey armchair.
A white door with a glass panel and a brass handle.
A narrow alleyway with a brick building, a wooden door with glass panels, and a potted plant.
A bedroom with a large bed, a bench, a chair, and a mirror.

5. The Golden Arm

The Golden Arm
West Town
United States
John
S$299
includes taxes & fees
25 Oct - 26 Oct
The Golden Arm
A hotel room with a bed, a desk, a television, and a window with a view of buildings.
A lobby with a reception desk, a green counter, a bar area, and a seating area with leather chairs.
The Willows Hotel with a classical facade, arched windows, and a signboard.
A well-appointed lounge area with a fireplace, leather armchairs, and a checkered floor.

6. The Willows Hotel

The Willows Hotel
Lakeview
United States
John S
S$180
includes taxes & fees
3 Nov - 4 Nov
The Willows Hotel
A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.
A modern living room with a fireplace, leather sofas, and a wooden floor.
A hotel room with a large bed, a TV, a desk, and a chair.
A person sitting on a couch with a laptop, reading a book, in a room with a large window and a framed picture on the wall.

7. Central Loop Hotel

Central Loop Hotel
Downtown Chicago
United States
Nathan
S$193
includes taxes & fees
2 Nov - 3 Nov
Central Loop Hotel
A bar area with a long counter, bar stools, and a mirrored wall.
A luxurious bathroom with a large oval bathtub, a chandelier, and two large mirrors with floral arrangements.
A luxurious lobby with a grand fireplace, elegant seating arrangements, and classic wood paneling.
A restaurant with wooden flooring, long tables, and chairs with patterned upholstery.

8. The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
Downtown Chicago
United States
KURT
S$175
includes taxes & fees
3 Nov - 4 Nov
The Whitehall Hotel, BW Premier Collection
A room with two chairs and a small table, a large window with a city view at night.
A modern hotel lobby with a large window, seating area, and a reception desk.
A modern bar area with a circular seating arrangement, a staircase leading to an upper level, and a view of the city through large windows.
A modern living room with a sectional sofa, a round ottoman, a dining area with chairs and a table, and a large mirror on the wall.

9. Eurostars Magnificent Mile

Eurostars Magnificent Mile
Downtown Chicago
United States
Will
S$219
includes taxes & fees
1 Nov - 2 Nov
Eurostars Magnificent Mile
A bar area with a checkered floor, leather seating, and a bar counter with a visible liquor selection.
A hotel room with a bed, desk, lamp, and a wall with a handprint design.
A lounge area with a checkered floor, blue sofas, a bench, and a patterned coffee table.
A modern lounge with a green sofa, armchairs, a coffee table, and a piano.

10. ACME Hotel Chicago, Outset Collection by Hilton

ACME Hotel Chicago, Outset Collection by Hilton
Downtown Chicago
United States
alex
S$178
includes taxes & fees
1 Nov - 2 Nov
ACME Hotel Chicago, Outset Collection by Hilton
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Top South Side Hotel Reviews

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