A greenhouse with a glass ceiling, various cacti, and a wooden structure in the center.

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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 West Side bed & breakfast

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

1. The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (216 reviews)
"Gorgeous building inside and out. Beautiful clean rooms. Amazing public spaces. Breakfast was by far one of the best meals of the whole trip."
United States
Mollie
The price is £266
includes taxes & fees
27 Sept - 28 Sept
The Publishing House B&B
A brick building with a sign for The Wicker Park Inn, including a phone number and website.

2. 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 £279
includes taxes & fees
27 Sept - 28 Sept
Wicker Park Inn
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a gas stove.

3. Pristine Apartment with Free Street Parking

Pristine Apartment with Free Street Parking
Humboldt Park
The price is £329
includes taxes & fees
20 Oct - 21 Oct
Pristine Apartment with Free Street Parking
A modern living room with a sofa, a coffee table, and a dining area with a table and chairs.

4. Dorothy's

Dorothy's
2.0 star property
Lakeview
8.6 out of 10, Excellent, (183 reviews)
"Space was so clean and modern. Breakfast was good also. Very nice stay."
United States
Steven
The price is £91
includes taxes & fees
30 Sept - 1 Oct
Dorothy's
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, (555 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 £198
includes taxes & fees
30 Sept - 1 Oct
The Sono Chicago
A bathroom with a glass-tiled wall, a sink, and a shower area.

6. Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (415 reviews)
"Superb breakfast and very friendly staff. Great place to stay!"
United States
mary
The price is £156
includes taxes & fees
28 Sept - 29 Sept
Ray's Bucktown B&B
A fire pit surrounded by glass pebbles, with a television displaying a football game in the background.

7. 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 £106
includes taxes & fees
30 Sept - 1 Oct
The Villa Toscana
A modern living room with leather sofas, a dining area, and large windows offering a view of greenery.

8. House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (518 reviews)
"The city was working on the water, so we were unable to shower for two mornings. I just wish we had been informed ahead of time that there would be little to no water pressure, as we would have made arrangements to shower at our daughter’s place. Other than that the place was really comfortable and we will stay here again."
United States
Lisa
The price is £156
includes taxes & fees
23 Sept - 24 Sept
House 5863 - Chicago Bed and Breakfast
A well-lit hallway with a wooden dresser, a table with chairs, and a blue patterned rug.

9. 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 £243
includes taxes & fees
23 Sept - 24 Sept
Harvey House Bed & Breakfast
A grand foyer with a wooden staircase, a chandelier, and a large window.

10. 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 £221
includes taxes & fees
5 Oct - 6 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.
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Top West Side Hotel Reviews

Chicago Parthenon Hostel

Chicago Parthenon Hostel

10/10 Excellent
"Stayed in the 8 female dorm for a few hrs before my early flight outta OHare. Room was clean, bed was comfy- decent sheets, comforter and pillows. Everyone was super respectful and quiet except for 1 girl who was taking on her phone pretty loud so that was annoying but other than that nice place. easy check in / out, front desk man was super nice. Would def stay again."
Maria 1-night trip
Posted 3 hours ago
Chicago Parthenon Hostel

Find out more about West Side

West Side B&B information

Number of reviews
2,246
Accommodation
3 B&B
Lowest Price
£91
Highest Price
£279

Frequently asked questions

What is the nightly rate for a B&B in West Side?
Prices for B&Bs in West Side often vary, but you can find a great deal from £91 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at West Side B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
What is the difference between a West Side Bed and Breakfast and a hotel?
Every West Side B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at West Side B&Bs.

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