Boutique Hotels in South Side
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A cityscape with a prominent building with a green dome, surrounded by greenery and a body of water.

Best Boutique Hotels in South Side

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your current months are November, 2026 and December, 2026.

November 2026

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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 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.

A lobby with two green armchairs, a glass coffee table, a chandelier, and a fireplace.

1. Carleton of Oak Park

Carleton of Oak Park

3.0 star property

Oak Park

9.2 out of 10, Wonderful, (1,218 reviews)

9.2/10

Wonderful

(1,218 reviews)

"Very nice efficient charming old hotel. I would stay again and I would try the restaurants for dinner and breakfast."

Thomas

The price is RM497

RM497

RM552 total

includes taxes & fees

8 Nov - 9 Nov

Carleton of Oak Park

A rooftop terrace with a fire feature, seating, and a cityscape view.

A row of brick townhouses with a black metal staircase leading to the entrance.

A hotel lobby with a reception desk, a staircase, and a wall adorned with various artworks.

A staircase with a railing leading to a gallery of framed artworks on a red wall.

2. Hotel Lincoln

Hotel Lincoln

4.0 star property

Lincoln Park

8.0 out of 10, Very good, (1,159 reviews)

8.0/10

Very good

(1,159 reviews)

"Good stay and amenities."

Charles

The price is RM411

RM411

RM588 total

includes taxes & fees

22 Nov - 23 Nov

Hotel Lincoln

A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

A hotel entrance with a marquee sign, a glass awning, and a blue carpet leading to the door.

A bar area with a long counter, multiple liquor bottles, and a variety of glasses.

A modern conference room with a wooden table, white chairs, a potted plant, and a large window with decorative plants.

3. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago

4.0 star property

Downtown Chicago

9.6 out of 10, Exceptional, (1,216 reviews)

9.6/10

Exceptional

(1,216 reviews)

"Great location from both airports. Lovely hotel clean and convenient"

Kanokkan

The price is RM653

RM653

RM777 total

includes taxes & fees

22 Nov - 23 Nov

Hilton Vacation Club Hotel Blake Chicago

The CL Champagne Lodge with a prominent tower and a signboard.

A spa room with a wooden ceiling, a large hot tub, and glass walls.

A hotel room with two beds, a large bathtub, a desk with a computer, and a microwave.

A reception area with a wooden counter, a computer, and framed pictures on the wall.

4. The Champagne Lodge & Luxury Suites

The Champagne Lodge & Luxury Suites

3.5 star property

Willowbrook

8.6 out of 10, Excellent, (1,658 reviews)

8.6/10

Excellent

(1,658 reviews)

"Great place for anniversary!"

Vrisa

The price is RM500

RM500

RM631 total

includes taxes & fees

30 Nov - 1 Dec

The Champagne Lodge & Luxury Suites

A room with a brick wall, a large wooden door, a flat-screen TV, and a grey armchair.

A modern kitchen with dark wood cabinets, a white countertop, and a built-in oven. There are two windows with patterned curtains, a stone accent wall, and a coffee maker on the counter.

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

2.5 star property

West Town

8.2 out of 10, Very good, (711 reviews)

8.2/10

Very good

(711 reviews)

"I had a great experience. The room was peaceful and clean. The location was perfect."

Freda

The price is RM524

RM524

RM615 total

includes taxes & fees

8 Nov - 9 Nov

The Golden Arm

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.

6. Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 star property

Downtown Chicago

9.0 out of 10, Wonderful, (1,549 reviews)

9.0/10

Wonderful

(1,549 reviews)

"Great resort and clean.. very good location"

Christopher

The price is RM496

RM496

RM706 total

includes taxes & fees

23 Nov - 24 Nov

Sports Illustrated Resorts Chicago

The Willows Hotel with a classical facade, arched windows, and a signboard.

A lobby with a reception desk, a green counter, a bar area, and a seating area with leather chairs.

A well-appointed lounge area with a fireplace, leather armchairs, and a checkered floor.

A hotel room with a bed, a desk, a television, and a window with a view of buildings.

7. The Willows Hotel

The Willows Hotel

3.0 star property

Lakeview

8.6 out of 10, Excellent, (1,005 reviews)

8.6/10

Excellent

(1,005 reviews)

"Great staff and cute hotel. Everything was walking distance from hotel and highly recommend the hotel and neighborhood area."

Cynthia

The price is RM373

RM373

RM437 total

includes taxes & fees

30 Nov - 1 Dec

The Willows 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 restaurant with wooden flooring, long tables, and chairs with patterned upholstery.

A luxurious lobby with a grand fireplace, elegant seating arrangements, and classic wood paneling.

8. The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 star property

Downtown Chicago

8.4 out of 10, Very good, (3,950 reviews)

8.4/10

Very good

(3,950 reviews)

"Friendly staff and great location"

Alexis

The price is RM346

RM346

RM411 total

includes taxes & fees

23 Nov - 24 Nov

The Whitehall Hotel, BW Premier Collection

A building with a marquee reading 'ACME HOTEL COMPANY' and a sign stating 'ACME HOTEL NOT VACANCY'.

A hotel room with a bed, bedside table, lamp, desk with laptop, and a door leading to a bathroom.

9. ACME Hotel Chicago, Outset Collection by Hilton

ACME Hotel Chicago, Outset Collection by Hilton

3.5 star property

Downtown Chicago

9.0 out of 10, Wonderful, (1,957 reviews)

9.0/10

Wonderful

(1,957 reviews)

"Hotel is great for the price."

alex

The price is RM368

RM368

RM437 total

includes taxes & fees

6 Dec - 7 Dec

ACME Hotel Chicago, Outset Collection by Hilton

A multi-story building with a brick facade, a well-maintained lawn, and a black metal fence.

A cozy lounge area with leather sofas, a central coffee table, and a fireplace.

A cozy lounge area with green walls, wooden floors, and leather seating. There are tables and chairs arranged for dining and socializing.

A bar area with a dark blue brick wall, wooden slats, and a counter with two chairs.

10. The Majestic Hotel

The Majestic Hotel

3.0 star property

Lakeview

9.0 out of 10, Wonderful, (1,039 reviews)

9.0/10

Wonderful

(1,039 reviews)

"It’s a charming hotel. Well located, and it was nice to have parking available."

Sarah

The price is RM435

RM435

RM511 total

includes taxes & fees

9 Nov - 10 Nov

The Majestic Hotel

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Best Boutique Hotels in South Side

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for South Side boutique hotels

1. Carleton of Oak Park

2. Hotel Lincoln

3. Hilton Vacation Club Hotel Blake Chicago

4. The Champagne Lodge & Luxury Suites

5. The Golden Arm

6. Sports Illustrated Resorts Chicago

7. The Willows Hotel

8. The Whitehall Hotel, BW Premier Collection

9. ACME Hotel Chicago, Outset Collection by Hilton

10. The Majestic Hotel

Explore a world of travel with Expedia