A nighttime city skyline reflected in a calm body of water, with illuminated buildings and a bridge.

Search Bed and Breakfasts in North 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
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for North 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, (196 reviews)
"I enjoyed my stay"
United States
Kellen
The price is ₹3,209
₹7,088 total
includes taxes & fees
24 Nov - 25 Nov
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, (687 reviews)
"Nice house set back from the street. Clean room. Nice atmosphere. Would stay again."
United States
John
The price is ₹5,197
₹9,896 total
includes taxes & fees
24 Nov - 25 Nov
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, (423 reviews)
"Thank you again for an amazing stay at Rays!"
United States
Lora
The price is ₹19,575
₹22,098 total
includes taxes & fees
8 Nov - 9 Nov
Ray's Bucktown B&B
A grand foyer with a wooden staircase, a chandelier, and a large window.

4. 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 ₹19,535
₹22,933 total
includes taxes & fees
2 Dec - 3 Dec
Villa D' Citta
A brick building with a sign for The Wicker Park Inn, including a phone number and website.

5. Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (286 reviews)
"Loved the location"
United States
Mary
The price is ₹23,008
₹27,009 total
includes taxes & fees
16 Nov - 17 Nov
Wicker Park Inn
A spacious kitchen with white cabinetry, a central island with bar stools, pendant lighting, and a large window with a view.

6. The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
9.8 out of 10, Exceptional, (573 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 ₹15,374
₹18,048 total
includes taxes & fees
9 Nov - 10 Nov
The Sono Chicago
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, (524 reviews)
"Honestly great, clean, and did not hear neighbors. Would stay again!"
United States
Malena
The price is ₹11,256
₹19,012 total
includes taxes & fees
10 Nov - 11 Nov
House 5863 - Chicago Bed and 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, (222 reviews)
"We enjoyed amazing breakfast. Everything was great. I enjoyed playing with 2 dogs. It was fun."
Japan
Nobue
The price is ₹30,076
₹33,953 total
includes taxes & fees
2 Dec - 3 Dec
The Publishing House B&B
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, (138 reviews)
"We had a comfortable stay. Bed was great, host was very accommodating and location was great!"
United States
Monica
The price is ₹24,456
₹27,141 total
includes taxes & fees
10 Nov - 11 Nov
Harvey House Bed & Breakfast
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 North Side Hotel Reviews

Wrigleyville Suites

Wrigleyville Suites

10/10 Excellent
"Clean room"
Michael 1-night trip
Posted 22 hours ago
Wrigleyville Suites

Find out more about North Side

North Side B&B information

Number of reviews
611
Accommodation
4 B&B
Lowest Price
₹7,088
Highest Price
₹33,953

Explore a world of travel with Expedia