Default HTG hotel image

Search B&B in Far Southwest Side

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct
In one month
30 Oct - 1 Nov
In two months
27 Nov - 29 Nov

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, (186 reviews)
"Space was so clean and modern. Breakfast was good also. Very nice stay."
United States
Steven
The price is 1.163.187 ₫
2.274.205 ₫ total
includes taxes & fees
1 Nov - 2 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, (416 reviews)
"The breakfast is fantastic!! Very unique and fun decor!"
United States
Susan
The price is 5.636.005 ₫
6.362.478 ₫ total
includes taxes & fees
13 Oct - 14 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, (678 reviews)
"Was a nice house the room we stayed in was cozy bed was really comfortable and in walking distance to wrigley field would definitely stay here again"
United States
John
The price is 1.692.074 ₫
3.024.546 ₫ total
includes taxes & fees
1 Nov - 2 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, (135 reviews)
"We had a comfortable stay. Bed was great, host was very accommodating and location was great!"
United States
Monica
The price is 7.599.144 ₫
8.433.627 ₫ total
includes taxes & fees
12 Oct - 13 Oct
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
9.8 out of 10, Exceptional, (560 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 6.309.252 ₫
7.406.491 ₫ total
includes taxes & fees
25 Oct - 26 Oct
The Sono Chicago
A wooden staircase with built-in seating and potted plants, leading to a modern interior with large windows and a mezzanine level.

6. The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (217 reviews)
"The best hotel breakfast I have ever had. I will return for the breakfast!"
United States
Kathryn
The Publishing House B&B
A modern living room with leather sofas, a dining area, and large windows offering a view of greenery.

7. House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (519 reviews)
"good"
United States
jiantao
The price is 3.271.464 ₫
5.442.314 ₫ total
includes taxes & fees
28 Oct - 29 Oct
House 5863 - Chicago Bed and Breakfast
A brick building with a sign for The Wicker Park Inn, including a phone number and website.

8. Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (284 reviews)
"Great location. Staff was very helpful.👍"
United States
Michael
The price is 7.098.558 ₫
8.332.887 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Wicker Park Inn
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, (126 reviews)
"What a pleasant stay, staff was welcoming and wanting to make sure our needs were met with our expectations. Meals were abundant and homemade. Rooms w/bath were clean with abundant towels. We will stay again."
United States
Jeffrey
The price is 6.539.033 ₫
7.676.256 ₫ total
includes taxes & fees
26 Oct - 27 Oct
Villa D' Citta
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Far Southwest Side Hotel Reviews

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Hotel was very clean, grateful housekeeping came in everyday and provided clean towels. Room view was very nice and as advertised."
Erica 4-night trip
Posted 9 hours ago
The Royal Sonesta Chicago Downtown

Find out more about Far Southwest Side

Far Southwest Side B&B information

Number of reviews
Accommodation
 B&B
Lowest Price
Highest Price