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Search B&B in Southwest Side

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Check prices for these dates

Next weekend
2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct
In one month
23 Oct - 25 Oct
In two months
20 Nov - 22 Nov

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, (185 reviews)
"Space was so clean and modern. Breakfast was good also. Very nice stay."
United States
Steven
The price is Rp1.028.379
Rp1.834.274 total
includes taxes & fees
26 Oct - 27 Oct
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)
"Superb breakfast and very friendly staff. Great place to stay!"
United States
mary
The price is Rp3.308.548
Rp3.734.949 total
includes taxes & fees
27 Sept - 28 Sept
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, (675 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 Rp1.359.824
Rp2.312.938 total
includes taxes & fees
26 Oct - 27 Oct
The Villa Toscana
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, (557 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 Rp3.708.612
Rp4.353.767 total
includes taxes & fees
27 Sept - 28 Sept
The Sono Chicago
A modern living room with leather sofas, a dining area, and large windows offering a view of greenery.

5. 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 Rp2.245.068
Rp3.734.831 total
includes taxes & fees
5 Oct - 6 Oct
House 5863 - Chicago Bed and Breakfast
A grand foyer with a wooden staircase, a chandelier, and a large window.

6. Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (125 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 Rp4.487.463
Rp5.267.892 total
includes taxes & fees
5 Oct - 6 Oct
Villa D' Citta
A well-lit hallway with a wooden dresser, a table with chairs, and a blue patterned rug.

7. 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 Rp5.214.972
Rp5.787.643 total
includes taxes & fees
7 Oct - 8 Oct
Harvey House Bed & Breakfast
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 Rp4.451.947
Rp5.025.804 total
includes taxes & fees
25 Oct - 26 Oct
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, (283 reviews)
"Great location. Staff was very helpful.👍"
United States
Michael
The price is Rp5.291.670
Rp6.211.656 total
includes taxes & fees
26 Oct - 27 Oct
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

Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

8/10 Good
"The hotel and the room were very nice. It was right across from the hospital which was were my husband was at. I had a king size bed and it was quite spacious. The amenities in the room were okay but the bathroom had everything from the shampoo, bath wash and hair dryer to help so that you don't have to bring those for your visit. They also will supply you any bathroom amenities if you forget anything. The only thing that I didn't particular care for was that they only had a refrigerator but no microwave and the ice machine didn't work on my floor so I was forced to use one on the opposite elevator for any time that I wanted ice. Other than that I would recommend this hotel if you are in the area."
Sheena 2-night trip
Posted less than an hour ago
Hampton Inn Chicago Downtown/Magnificent Mile

Find out more about Southwest Side

Southwest Side B&B information

Number of reviews
1,829
Accommodation
9 B&B
Lowest Price
Rp1.834.274
Highest Price
Rp6.211.656