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
22 Aug - 23 Aug
Tomorrow
23 Aug - 24 Aug
Next weekend
28 Aug - 30 Aug
In two weeks
4 Sept - 6 Sept

Our top choices for South Side boutique hotels

A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.
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.
A hotel room with a large bed, a TV, a desk, and a chair.
A modern living room with a fireplace, leather sofas, and a wooden floor.

1. Central Loop Hotel

Central Loop Hotel
Downtown Chicago
United States
Ethan
S$184
includes taxes & fees
23 Aug - 24 Aug
Central Loop Hotel
A hotel room with a large bed, two armchairs, a desk, and a view of a cityscape through large windows.
A hotel room with a city view, a dining area, a sofa, and a TV.
A modern hotel room with a city view, a dining area with a table and chairs, and a large potted plant.
A spacious lobby with a glass entrance, escalators, and a tiled floor.

2. The Buckingham Hotel

The Buckingham Hotel
Downtown Chicago
United States
Dominique
S$253
includes taxes & fees
30 Aug - 31 Aug
The Buckingham Hotel
A hotel bathroom with a large mirror, a sink, and a vanity.
A hotel room with a view of a cityscape through a large window, a floor lamp, a sofa with cushions, and a small table with a plant.
A bakery display with pastries and a coffee shop sign in the background.
A hotel with a classic facade, large windows, and a prominent entrance.

3. Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago
Downtown Chicago
United States
Marisela
S$296
includes taxes & fees
30 Aug - 31 Aug
Sports Illustrated Resorts Chicago
A corridor with ornate black metal railings and a patterned carpet.
A modern hotel room with a sofa, a small table, a bench, a TV, and a cabinet.
A multi-story building with a grid of windows, surrounded by other high-rise buildings.
A dining area with tables and chairs, a hanging light fixture, and a view of the street through a window.

4. Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
United States
Beth
S$271
includes taxes & fees
30 Aug - 31 Aug
Staypineapple, An Iconic Hotel, The Loop
A bar area with a checkered floor, leather seating, and a bar counter with a visible liquor selection.
A modern lounge with a green sofa, armchairs, a coffee table, and a piano.
A hotel room with a bed, desk, lamp, and a wall with a handprint design.
A building with a marquee sign reading 'ACME HOTEL COMPANY' and a 'VACANCY' sign.

5. ACME Hotel Chicago, Outset Collection by Hilton

ACME Hotel Chicago, Outset Collection by Hilton
Downtown Chicago
United States
Dylan
S$222
includes taxes & fees
30 Aug - 31 Aug
ACME Hotel Chicago, Outset Collection by Hilton
A bar area with a long counter, bar stools, and a mirrored wall.
A tall red brick building with a classic architectural style, surrounded by modern skyscrapers.
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.

6. The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
Downtown Chicago
United States
nancy
S$222
includes taxes & fees
30 Aug - 31 Aug
The Whitehall Hotel, BW Premier Collection
An outdoor rooftop lounge with seating, a fire feature, and a view of the city skyline at night.
A modern lobby with a wooden ceiling, leather sofas, and a coffee bar.
A rooftop venue with white chairs and a sofa, draped with white fabric and floral arrangements, overlooking a cityscape.
A modern lounge area with leather sofas, wooden coffee tables, and ambient lighting.

7. The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
Downtown Chicago
United States
TaShandra
S$195
includes taxes & fees
30 Aug - 31 Aug
The Chicago Hotel Collection - Magnificent Mile
A modern bar area with a marble countertop, leather bar stools, a chandelier, and a wall-mounted TV.
A hotel room with a large bed, a desk with a lamp, a TV, and a bathroom visible through an open door.
A modern lobby with a sofa, armchairs, and a table. A large window offers a view of the street.
A modern hotel with a glass facade, multiple floors, and a prominent entrance with a purple-lit canopy.

8. Ivy Boutique Hotel

Ivy Boutique Hotel
Downtown Chicago
United States
Adam
S$193
includes taxes & fees
30 Aug - 31 Aug
Ivy Boutique Hotel
A person relaxing on a sofa with a laptop, a glass of red wine, and a small table with a vase of flowers and a telephone.
A room with a bed against a window overlooking a cityscape. There is a small table with a book, a vase with flowers, and a cup.
A modern hotel lobby with leather sofas, a coffee table, and a floor lamp.
A bar area with a long counter, multiple shelves of bottles, and four bar stools.

9. L7 Chicago by LOTTE

L7 Chicago by LOTTE
Downtown Chicago
United States
Girivasan
S$325
includes taxes & fees
30 Aug - 31 Aug
L7 Chicago by LOTTE
A room with two chairs and a small table, a large window with a city view at night.
A bar area with a long counter, multiple stools, and a television screen.
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.
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.

10. Eurostars Magnificent Mile

Eurostars Magnificent Mile
Downtown Chicago
United States
Matthew
S$266
includes taxes & fees
30 Aug - 31 Aug
Eurostars Magnificent Mile
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Top South Side Hotel Reviews

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