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

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Check prices for these dates

Next weekend
Aug 14 - Aug 16
In two weeks
Aug 21 - Aug 23
In one month
Sep 4 - Sep 6
In two months
Oct 2 - Oct 4

Our top choices for North Side bed & breakfast

Spa

1. Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (408 reviews)
"Superb breakfast and very friendly staff. Great place to stay!"
United States
mary
The price is ￥34,149
￥38,551 total
includes taxes & fees
Aug 9 - Aug 10
Ray's Bucktown B&B
Living area

2. Dorothy's

Dorothy's
2.0 star property
Lakeview
8.6 out of 10, Excellent, (162 reviews)
"Great location, just what we needed."
United States
Stephanie
The price is ￥12,466
￥20,143 total
includes taxes & fees
Aug 10 - Aug 11
Dorothy's
Double Room, Private Bathroom (Venetian) | Terrace/patio

3. The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
8.0 out of 10, Very Good, (660 reviews)
"Clean room, self serve breakfast, free street parking permit, cute cats!"
United States
Shu-Ting
The price is ￥14,640
￥23,480 total
includes taxes & fees
Aug 10 - Aug 11
The Villa Toscana
Lobby sitting area

4. Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (122 reviews)
"Wonderful! Will stay here again."
United States
Elsa
The price is ￥46,858
￥55,007 total
includes taxes & fees
Aug 10 - Aug 11
Villa D' Citta
TV

5. Five bedroom - 3 bath - Sleeps 12

Five bedroom - 3 bath - Sleeps 12
Lakeview
The price is ￥136,938
￥255,322 total
includes taxes & fees
Aug 24 - Aug 25
Five bedroom - 3 bath - Sleeps 12
Property entrance

6. Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (276 reviews)
"clean room, staff was helpful. We enjoyed our stay."
United States
Maggie
The price is ￥47,686
￥55,981 total
includes taxes & fees
Aug 31 - Sep 1
Wicker Park Inn
Private kitchen

7. The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (537 reviews)
"Close to some great places to eat locally and about an hour walk to river and central business activities......and a very comfy bed!"
United States
Bronwyn
The price is ￥29,576
￥34,719 total
includes taxes & fees
Aug 10 - Aug 11
The Sono Chicago
Staircase

8. The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (209 reviews)
"Outstanding! Staff, food, bed…everything was superb We’ll be back soon for sure"
United States
Sigfredo
The price is ￥36,746
￥41,482 total
includes taxes & fees
Aug 30 - Aug 31
The Publishing House B&B
Presidential Studio Suite, 2 Bedrooms (1st Floor) | Living area | 51-inch flat-screen TV with cable channels, TV, Netflix

9. House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (511 reviews)
"I love the location of this B&B. Right across from a beautiful park, walkable to some fabulous restaurants and shops - and the red line is so close! My room was clean, quiet, cutely decorated. The kitchen was well-stocked with breakfast options. My one recommendation would be - I wish the coffee was higher quality! The host was prompt, friendly, and responsive to my needs. I'll be back for sure!"
United States
Kimberly
The price is ￥20,577
￥33,916 total
includes taxes & fees
Aug 10 - Aug 11
House 5863 - Chicago Bed and Breakfast
Property entrance

10. Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (131 reviews)
"This was an amazing place to stay, highly recommended for something quiet and relaxing."
United States
Mia
The price is ￥42,634
￥47,316 total
includes taxes & fees
Aug 5 - Aug 6
Harvey House Bed & Breakfast
Coffee/tea maker, fridge, microwave, oven

11. Pristine Apartment with Free Street Parking

Pristine Apartment with Free Street Parking
Humboldt Park
The price is ￥73,490
￥85,728 total
includes taxes & fees
Aug 24 - Aug 25
Pristine Apartment with Free Street Parking
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 North Side Hotel Reviews

The Willows Hotel

The Willows Hotel

8/10 Good
"Clean Room nice stuff"
Lidia 2-night trip
Posted 13 hours ago
The Willows Hotel

Find out more about North Side

North Side B&B information

Number of reviews
2,854
Accommodation
7 B&B
Lowest Price
￥20,143
Highest Price
￥255,322

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