B&B in Southwest Side
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your current months are November, 2026 and December, 2026.

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Our top choices for Southwest Side bed & breakfast

A modern living room with a sofa, a coffee table, and a dining area with a table and chairs.

A kitchen with a dining table set for a meal, a dog sitting at the table, and various kitchen appliances and utensils.

A bedroom with a bed, pillows, a painting, wall-mounted candelabras, and a window with curtains.

A living room with a black patterned rug, a glass coffee table, a wooden dining table with chairs, a small bench, and a cityscape painting on the wall.

1. Dorothy's

Dorothy's

2.0 star property

Lakeview

8.6 out of 10, Excellent, (197 reviews)

8.6/10

Excellent

(197 reviews)

"I enjoyed my stay"

Kellen

The price is €62

€62

includes taxes & fees

7 Dec - 8 Dec

Dorothy's

A spacious kitchen with white cabinetry, a central island with bar stools, pendant lighting, and a large window with a view.

A living room with a fireplace, a sofa, a coffee table, and a TV mounted on the wall.

A modern kitchen with white cabinetry, stainless steel appliances, and a wooden dining table.

A modern kitchen with white cabinetry, stainless steel appliances, and a wooden dining table with benches.

2. The Sono Chicago

The Sono Chicago

3.5 star property

Near North Side

9.8 out of 10, Exceptional, (575 reviews)

9.8/10

Exceptional

(575 reviews)

"I like that it had a balcony food choice wasn’t my type of style end up ordering food off of site but definitely had all the amenities for you to be ready for the next day. Will be staying again little bit pricey for a short weekend stay but I will definitely be coming back. Very great part of the town hope to own my own own home in this place one day."

Tavarion

The price is €139

€139

includes taxes & fees

23 Nov - 24 Nov

The Sono Chicago

A narrow stone pathway leading to a house with a green porch and a large tree overhanging the path.

A fire pit surrounded by glass pebbles, with a television displaying a football game in the background.

A narrow brick alley with a tree in the center, surrounded by potted plants and greenery.

A staircase with a wooden handrail and a mirror above it.

3. The Villa Toscana

The Villa Toscana

2.5 star property

Lakeview

8.2 out of 10, Very good, (690 reviews)

8.2/10

Very good

(690 reviews)

"Nice house set back from the street. Clean room. Nice atmosphere. Would stay again."

John

The price is €85

€85

includes taxes & fees

10 Nov - 11 Nov

The Villa Toscana

A patio with a grill, outdoor seating, and potted plants.

A building with a large window, a bench, and a sign that reads "RAY'S BUCKTOWN BED & BREAKFAST".

A cozy interior with a wooden staircase, a seating area with chairs and a table, and shelves with various items.

A room with wooden flooring, a bookshelf filled with books and decorative items, two chairs, and a table with various objects.

4. Ray's Bucktown B&B

Ray's Bucktown B&B

3.5 star property

Bucktown

9.8 out of 10, Exceptional, (423 reviews)

9.8/10

Exceptional

(423 reviews)

"Thank you again for an amazing stay at Rays!"

Lora

The price is €187

€187

includes taxes & fees

10 Nov - 11 Nov

Ray's Bucktown B&B

A courtyard with brick arches, outdoor seating, and potted plants.

A stone entrance with a black metal gate, a black mat, and two lion statues.

A grand foyer with a wooden staircase, a chandelier, and a large window.

A spacious dining area with a long wooden table, ornate chairs, and a chandelier.

5. Villa D' Citta

Villa D' Citta

3.5 star property

Lincoln Park

9.4 out of 10, Exceptional, (129 reviews)

9.4/10

Exceptional

(129 reviews)

"Very elegant !"

Hernando

The price is €217

€217

includes taxes & fees

2 Dec - 3 Dec

Villa D' Citta

A wooden staircase with built-in seating and potted plants, leading to a modern interior with large windows and a mezzanine level.

A modern hotel interior with a glass railing, a neon sign, a bar area, and a patterned rug.

A spacious living area with a high ceiling, exposed brick walls, and a large window. A glass coffee table with books is in the center, and a fireplace with a framed picture above it is visible.

A kitchen with a large island, hanging kitchen tools, and a brick wall.

6. The Publishing House B&B

The Publishing House B&B

3.5 star property

Downtown Chicago

9.8 out of 10, Exceptional, (222 reviews)

9.8/10

Exceptional

(222 reviews)

"We enjoyed amazing breakfast. Everything was great. I enjoyed playing with 2 dogs. It was fun."

Nobue

The price is €273

€273

includes taxes & fees

10 Dec - 11 Dec

The Publishing House B&B

A brick building with a round metal table and chairs, a blue door, and a small garden area with plants and a bench.

A dark blue door with a small window above it, flanked by two potted plants.

A bedroom with a brick wall, a flat-screen TV, a bed with white bedding, a floral wall tapestry, and a small table with chairs.

A modern kitchen with white subway tiles, a stainless steel range hood, and a double oven. There are three yellow stools at the island.

7. Wicker Park Inn

Wicker Park Inn

3.5 star property

West Town

9.0 out of 10, Wonderful, (287 reviews)

9.0/10

Wonderful

(287 reviews)

"Loved the location"

Mary

The price is €221

€221

includes taxes & fees

16 Nov - 17 Nov

Wicker Park Inn

A well-lit hallway with a wooden dresser, a table with chairs, and a blue patterned rug.

A spacious living room with a fireplace, a piano, and a dining area with a table and chairs.

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a red coffee machine.

A neatly arranged bedroom with a large bed, bedside lamps, a nightstand, a dresser, and a built-in fireplace.

8. Harvey House Bed & Breakfast

Harvey House Bed & Breakfast

4.0 star property

Oak Park

9.8 out of 10, Exceptional, (138 reviews)

9.8/10

Exceptional

(138 reviews)

"We had a comfortable stay. Bed was great, host was very accommodating and location was great!"

Monica

The price is €257

€257

includes taxes & fees

10 Nov - 11 Nov

Harvey House Bed & Breakfast

A modern living room with leather sofas, a dining area, and large windows offering a view of greenery.

A crowded beach with people sunbathing and swimming, surrounded by tall buildings.

A modern living room with leather sofas, a coffee table, a TV, and a dining area with natural light.

A patio with a brick floor, metal chairs, a round table, and a blue umbrella.

9. House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast

3.5 star property

Edgewater

9.2 out of 10, Wonderful, (525 reviews)

9.2/10

Wonderful

(525 reviews)

"Honestly great, clean, and did not hear neighbors. Would stay again!"

Malena

The price is €175

€175

includes taxes & fees

10 Nov - 11 Nov

House 5863 - Chicago Bed and Breakfast

A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a gas stove.

A two-story building with a dark front door, a brick facade, and a metal fence in front.

A living room with a sofa, coffee table, and a dining area with chairs and a table.

A neatly made bed with a wooden headboard, a pillow, and a rolled towel on a plain wall with a single piece of artwork.

10. Pristine Apartment with Free Street Parking

Pristine Apartment with Free Street Parking

Humboldt Park

The price is €246

€246

includes taxes & fees

30 Nov - 1 Dec

Pristine Apartment with Free Street Parking

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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Learn more about Southwest Side

Explore attractions like Balzekas Museum of Lithuanian Culture and Ephraim Bajar Cultural Center as you discover things to see and do in Southwest Side.

See all hotels in Southwest Side

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Search Bed and Breakfast in Southwest Side

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Southwest Side bed & breakfast

1. Dorothy's

2. The Sono Chicago

3. The Villa Toscana

4. Ray's Bucktown B&B

5. Villa D' Citta

6. The Publishing House B&B

7. Wicker Park Inn

8. Harvey House Bed & Breakfast

9. House 5863 - Chicago Bed and Breakfast

10. Pristine Apartment with Free Street Parking

Learn more about Southwest Side

Explore a world of travel with Expedia