Boutique Hotels in South Side
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South Side Hotel Guide - Boutique Hotels in South Side, Chicago

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your current months are November, 2026 and December, 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 €121

€121

includes taxes & fees

18 Nov - 19 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 €129

€129

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 €170

€170

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, (1,661 reviews)

8.6/10

Excellent

(1,661 reviews)

"Great place for anniversary!"

Vrisa

The price is €138

€138

includes taxes & fees

10 Nov - 11 Nov

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 €135

€135

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)

"Loved this stay as a solo traveler!"

Macie

The price is €163

€163

includes taxes & fees

6 Dec - 7 Dec

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 €96

€96

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, (3,951 reviews)

8.4/10

Very good

(3,951 reviews)

"Friendly staff and great location"

Alexis

The price is €90

€90

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 €95

€95

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 €112

€112

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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Top South Side Hotel Reviews

Hotel Lincoln

Lincoln Park

8/10 Good

Stayed in this hotel for family living in Old Town

Susan

Reviewed October 6, 2025Reviewed October 6, 2025

Hotel Lincoln

A modern restaurant interior with a green wall, hanging lights, and a long dining area.

A modern indoor pool area with clear glass walls, lounge chairs, and a view of city buildings.

A rooftop lounge with green cushioned seating, a small round table, and a view of city buildings.

A modern interior with wooden flooring, black furniture, and large windows offering city views.

Hotel 505 River North

Downtown Chicago

10/10 Excellent

Really enjoyed our stay here, very central location, property in good condition, comfortable rooms & beds with good toiletries and restaurant and bar were good. Used the gym which although small had everything I’d want. Only thing that was disappointing was I had booked here for the pool and two days before arrival we were told the pool was closed for the time being.

Aisling

Reviewed June 27, 2025Reviewed June 27, 2025

Hotel 505 River North

A room with two chairs and a small table, a large window with a city view at night.

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 hotel lobby with a large window, seating area, and a reception desk.

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.

Eurostars Magnificent Mile

Downtown Chicago

10/10 Excellent

nicholas

Reviewed October 8, 2026Reviewed October 8, 2026

Eurostars Magnificent Mile

A modern bar area with a marble countertop, leather bar stools, a chandelier, and a wall-mounted TV.

A modern hotel with a glass facade, multiple floors, and a prominent entrance with a purple-lit canopy.

A hotel lobby with a curved floor design, a glass entrance, and a large mural on the wall.

A hotel room with a large bed, a desk with a lamp, a TV, and a bathroom visible through an open door.

Ivy Boutique Hotel

Downtown Chicago

10/10 Excellent

Excellent rooms, very helpful staff

Anthony

Reviewed April 30, 2026Reviewed April 30, 2026

Ivy Boutique Hotel

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South Side Hotel Guide - Boutique Hotels in South Side, Chicago

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

Top South Side Hotel Reviews

Hotel Lincoln

8/10 Good

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