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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Northwest 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, (197 reviews)
"I enjoyed my stay"
United States
Kellen
The price is ₩39,184
₩93,782 total
includes taxes & fees
Dec 7 - Dec 8
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
8.2 out of 10, Very good, (690 reviews)
"Nice house set back from the street. Clean room. Nice atmosphere. Would stay again."
United States
John
The price is ₩63,582
₩129,252 total
includes taxes & fees
Nov 10 - Nov 11
The Villa Toscana
A spacious kitchen with white cabinetry, a central island with bar stools, pendant lighting, and a large window with a view.

3. The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
9.8 out of 10, Exceptional, (575 reviews)
"I like that it had a balcony food choice wasn’t my type of style end up ordering food off of site but definitely had all the amenities for you to be ready for the next day. Will be staying again little bit pricey for a short weekend stay but I will definitely be coming back. Very great part of the town hope to own my own own home in this place one day."
United States
Tavarion
The price is ₩180,218
₩211,551 total
includes taxes & fees
Nov 23 - Nov 24
The Sono Chicago
A modern living room with leather sofas, a dining area, and large windows offering a view of greenery.

4. House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (525 reviews)
"Honestly great, clean, and did not hear neighbors. Would stay again!"
United States
Malena
The price is ₩155,643
₩265,795 total
includes taxes & fees
Nov 10 - Nov 11
House 5863 - Chicago Bed and Breakfast
A bathroom with a glass-tiled wall, a sink, and a shower area.

5. Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (423 reviews)
"Thank you again for an amazing stay at Rays!"
United States
Lora
The price is ₩252,128
₩284,622 total
includes taxes & fees
Nov 10 - Nov 11
Ray's Bucktown B&B
A courtyard with brick arches, outdoor seating, and potted plants.

6. 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 ₩281,045
₩329,922 total
includes taxes & fees
Dec 2 - Dec 3
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, (138 reviews)
"We had a comfortable stay. Bed was great, host was very accommodating and location was great!"
United States
Monica
The price is ₩352,409
₩391,101 total
includes taxes & fees
Nov 10 - Nov 11
Harvey House Bed & Breakfast
A brick building with a round metal table and chairs, a blue door, and a small garden area with plants and a bench.

8. Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (287 reviews)
"Loved the location"
United States
Mary
The price is ₩286,028
₩335,779 total
includes taxes & fees
Nov 16 - Nov 17
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.

9. The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (222 reviews)
"We enjoyed amazing breakfast. Everything was great. I enjoyed playing with 2 dogs. It was fun."
Japan
Nobue
The price is ₩367,946
₩415,374 total
includes taxes & fees
Dec 10 - Dec 11
The Publishing House B&B
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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Learn more about Northwest Side

Check out the local area in Northwest Side—home to attractions like Walt Disney House and Milwaukee Avenue.

See all hotels in Northwest Side
A curved pathway with a metal fence, flowering trees, and a street lamp.

Top reviews in Northwest Side

A spacious kitchen with white cabinetry, a central island with bar stools, pendant lighting, and a large window with a view.
The Sono Chicago

The Sono Chicago

The Sono Chicago
Near North Side

10/10 Excellent

Our stay at The Sono was great! We were only staying a night and booked a queen room, and they gave us a free upgrade to a king room since it was unoccupied. The room was fantastic & clean, the breakfast was delicious with lots of variety and the voucher for free street parking made this the best option for our stay. I would definitely stay again.
United States
Kathrine
Reviewed January 23, 2025
The Sono Chicago