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Check prices for these dates

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

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.

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 ₩55,202
₩112,390 total
includes taxes & fees
Nov 2 - Nov 3
Dorothy's
A fire pit surrounded by glass pebbles, with a television displaying a football game in the background.

2. The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
8.0 out of 10, Very good, (679 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 ₩77,213
₩145,026 total
includes taxes & fees
Nov 2 - Nov 3
The Villa Toscana
A bathroom with a glass-tiled wall, a sink, and a shower area.

3. 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 ₩295,139
₩333,182 total
includes taxes & fees
Oct 13 - Oct 14
Ray's Bucktown B&B
A spacious kitchen with white cabinetry, a central island with bar stools, pendant lighting, and a large window with a view.

4. The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (561 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 ₩330,395
₩387,854 total
includes taxes & fees
Oct 25 - Oct 26
The Sono Chicago
A well-lit hallway with a wooden dresser, a table with chairs, and a blue patterned rug.

5. 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 ₩350,953
₩389,485 total
includes taxes & fees
Nov 2 - Nov 3
Harvey House Bed & Breakfast
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, (519 reviews)
"good"
United States
jiantao
The price is ₩171,316
₩284,996 total
includes taxes & fees
Oct 5 - Oct 6
House 5863 - Chicago Bed and Breakfast
A grand foyer with a wooden staircase, a chandelier, and a large window.

7. 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 ₩342,428
₩401,981 total
includes taxes & fees
Oct 7 - Oct 8
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.

8. 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 price is ₩328,437
₩370,772 total
includes taxes & fees
Nov 1 - Nov 2
The Publishing House B&B
A brick building with a sign for The Wicker Park Inn, including a phone number and website.

9. 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 ₩371,728
₩436,366 total
includes taxes & fees
Nov 1 - Nov 2
Wicker Park Inn
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 Southwest Side Hotel Reviews

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent
"The hotel is located in a prime Chicago Gold Coast location. A few blocks from Gibsons and Rush street and 2 blocks off the lake for beautiful walks. The rooms, although a bit dated, the cleaning staff did an amazing job ensuring everything was very clean. Customer service, the bar, valet and front desk staff were very accommodating. This hotel has everything you need without the outrageous price tags of other Chicago hotels. I will be staying here again. Wonderful trip!"
jenifer 1-night trip
Posted less than an hour ago
The Chicago Hotel Collection Ambassador Gold Coast

Find out more about Southwest Side

Southwest Side B&B information

Number of reviews
1,744
Accommodation
8 B&B
Lowest Price
₩112,390
Highest Price
₩436,366