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Check prices for these dates

Next weekend
23 Oct - 25 Oct
In two weeks
30 Oct - 1 Nov
In one month
13 Nov - 15 Nov
In two months
11 Dec - 13 Dec

Our top choices for Far Southwest Side bed & breakfast

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

1. Dorothy's

Dorothy's
2.0 star property
Lakeview
8.6 out of 10, Excellent, (192 reviews)
"Fun unique apartment above a wonderful pizza place! Great location and the stay was just great!"
United States
Mick
The price is AU$118
includes taxes & fees
16 Nov - 17 Nov
Dorothy's
A bathroom with a glass-tiled wall, a sink, and a shower area.

2. Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (421 reviews)
"Thank you again for an amazing stay at Rays!"
United States
Lora
The price is AU$309
includes taxes & fees
25 Oct - 26 Oct
Ray's Bucktown B&B
A fire pit surrounded by glass pebbles, with a television displaying a football game in the background.

3. The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
8.0 out of 10, Very good, (683 reviews)
"Nice house set back from the street. Clean room. Nice atmosphere. Would stay again."
United States
John
The price is AU$160
includes taxes & fees
16 Nov - 17 Nov
The Villa Toscana
A well-lit hallway with a wooden dresser, a table with chairs, and a blue patterned rug.

4. Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (136 reviews)
"We had a comfortable stay. Bed was great, host was very accommodating and location was great!"
United States
Monica
The price is AU$412
includes taxes & fees
5 Nov - 6 Nov
Harvey House Bed & Breakfast
A spacious kitchen with white cabinetry, a central island with bar stools, pendant lighting, and a large window with a view.

5. The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (568 reviews)
"It was a very comfortable hotel. We loved the free street parking, easy access to public transportation, coffee, breakfast, bottled water, bubbly water and snacks. I will stay here again!"
United States
Christie
The price is AU$299
includes taxes & fees
29 Oct - 30 Oct
The Sono Chicago
A modern living room with leather sofas, a dining area, and large windows offering a view of greenery.

6. House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (523 reviews)
"Honestly great, clean, and did not hear neighbors. Would stay again!"
United States
Malena
The price is AU$289
includes taxes & fees
20 Oct - 21 Oct
House 5863 - Chicago Bed and Breakfast
A brick building with a sign for The Wicker Park Inn, including a phone number and website.

7. Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (285 reviews)
"Loved the location"
United States
Mary
The price is AU$447
includes taxes & fees
2 Nov - 3 Nov
Wicker Park Inn
A wooden staircase with built-in seating and potted plants, leading to a modern interior with large windows and a mezzanine level.

8. The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (221 reviews)
"We enjoyed amazing breakfast. Everything was great. I enjoyed playing with 2 dogs. It was fun."
Japan
Nobue
The price is AU$370
includes taxes & fees
25 Oct - 26 Oct
The Publishing House B&B
A grand foyer with a wooden staircase, a chandelier, and a large window.

9. Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (129 reviews)
"Very elegant !"
United States
Hernando
The price is AU$426
includes taxes & fees
26 Oct - 27 Oct
Villa D' Citta
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a gas stove.

10. Pristine Apartment with Free Street Parking

Pristine Apartment with Free Street Parking
Humboldt Park
The price is AU$560
includes taxes & fees
27 Oct - 28 Oct
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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Top Far Southwest Side Hotel Reviews

The Wade

The Wade

8/10 Good
"Convenient location and loved the room."
Ashaleigh 1-night trip
Posted less than an hour ago
The Wade

Find out more about Far Southwest Side

Far Southwest Side B&B information

Number of reviews
2,339
Accommodation
9 B&B
Lowest Price
AU$118
Highest Price
AU$560

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