Photo by throwingsofas

Find the Best Northwest Side Bed and Breakfast

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    one key illustration
    Treat yourself
    Save instantly and earn perks with One Key
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Browse Select Northwest Side B&B

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (548)
"Super cute house! Very detailed directions on check in, super easy excellent neighbourhood!"
The price is £99
includes taxes & fees
4 May - 5 May
The Villa Toscana

The Publishing House B&B

3.5 star property
9.8 out of 10, Exceptional, (171)
"Amazing stay! Great location and beautiful hotel that made you feel cozy"
The price is £185
includes taxes & fees
26 May - 27 May
The Publishing House B&B

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (348)
"What a rad spot...great staff, A M A Z I N G breakfast (can I say Nutella and banana stuffed French toast?!), nice sauna on premise, clean rooms, so much to look at, and I parked in the garage! Will be back...daughters had a blast. "
The price is £143
includes taxes & fees
3 May - 4 May
Ray's Bucktown B&B

Dorothy's

3.0 star property
8.0 out of 10, Very good, (31)
"We love Dorothy's! This is such a great, inexpensive option for a stay in a fantastic neighborhood. Would recommend to anyone!"
The price is £68
includes taxes & fees
4 May - 5 May
Dorothy's

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (452)
"Was very warm and welcoming.. room was clean and updated… staff was friendly..! Had a great time…"
The price is £122
includes taxes & fees
11 May - 12 May
The Sono Chicago

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (242)
"The Wicker Park Inn was located close to many transportation options. The breakfast room was bright and sunny with good light breakfast options."
The price is £243
includes taxes & fees
5 May - 6 May
Wicker Park Inn

Villa D' Citta

3.5 star property
9.2 out of 10, Wonderful, (99)
"Wonderful place. "
The price is £202
includes taxes & fees
13 May - 14 May
Villa D' Citta

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (110)
"Awesome, comfortable stay good food options would recommend "
The price is £218
includes taxes & fees
12 May - 13 May
Harvey House Bed & Breakfast

House 5863 - Chicago Bed and Breakfast

3.5 star property
9.0 out of 10, Wonderful, (472)
"Erick was very friendly and responsive. The neighborhood around was wonderful. We walked everywhere we went and were able to park on the street with no problems. We would stay again. Thank you!"
The price is £216
includes taxes & fees
6 May - 7 May
House 5863 - Chicago Bed and Breakfast

Dubois Guest House Room 201

7.4 out of 10, Good, (3)
"We really enjoyed our stay. Cleanliness was top tier. "
The price is £220
includes taxes & fees
3 May - 4 May
Dubois Guest House Room 201

Villa Dubois Guest Room 6

The price is £184
includes taxes & fees
4 May - 5 May
Villa Dubois Guest Room 6

Villa Dubois Guest House Room 5

The price is £184
includes taxes & fees
4 May - 5 May
Villa Dubois Guest House Room 5

Dubois Guest House Room 101

The price is £220
includes taxes & fees
3 May - 4 May
Dubois Guest House Room 101

Dubois Guest House Room 202

The price is £220
includes taxes & fees
3 May - 4 May
Dubois Guest House Room 202

Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!

9.8 out of 10, Exceptional, (134)
"Our family of 4 enjoyed our short stay here. Great location that has everything you need a walking distance away. Jon was great to communicate with."
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
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.
Don't see what you're looking for?
See all available properties in Northwest Side
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Northwest Side

Charming Home in Portage Park

10.0 out of 10, Exceptional, (1)
"My family and stayed 2 nights at Alex's place. For us it was a great location equidistant from family events in the city. The 4 bedrooms were all very cozy and comfortable with easy access to bathrooms. The kitchen likewise was super clean and had everything that we needed. As an added bonus the house was only about 200 yards from a great breakfast restaurant call Eggselent. I would not hesitate to book Alex's house again on any return trip to Chicago. "
Charming Home in Portage Park

Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!

10.0 out of 10, Exceptional, (97)
"We had a great stay here in December. Communication was great and the property owner was very nice and helpful! Would definitely recommend this location. We will definitely return on our next trip if it’s available. "
Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (739)
"Great family place to stay. "
The price is £149
includes taxes & fees
26 May - 27 May
Sentral Michigan Avenue
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.