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
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct
In one month
30 Oct - 1 Nov
In two months
27 Nov - 29 Nov

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, (186 reviews)
"Space was so clean and modern. Breakfast was good also. Very nice stay."
United States
Steven
The price is AED 148
AED 302 total
includes taxes & fees
2 Nov - 3 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
8.0 out of 10, Very good, (679 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 AED 209
AED 392 total
includes taxes & fees
2 Nov - 3 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, (416 reviews)
"The breakfast is fantastic!! Very unique and fun decor!"
United States
Susan
The price is AED 797
AED 900 total
includes taxes & fees
19 Oct - 20 Oct
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, (126 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 AED 925
AED 1,086 total
includes taxes & fees
7 Oct - 8 Oct
Villa D' Citta
A modern living room with leather sofas, a dining area, and large windows offering a view of greenery.

5. House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (519 reviews)
"good"
United States
jiantao
The price is AED 463
AED 770 total
includes taxes & fees
5 Oct - 6 Oct
House 5863 - Chicago Bed and Breakfast
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
10.0 out of 10, Exceptional, (561 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 AED 893
AED 1,048 total
includes taxes & fees
25 Oct - 26 Oct
The Sono Chicago
A brick building with a sign for The Wicker Park Inn, including a phone number and website.

7. Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (284 reviews)
"Great location. Staff was very helpful.👍"
United States
Michael
The price is AED 1,004
AED 1,179 total
includes taxes & fees
1 Nov - 2 Nov
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.

8. The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (217 reviews)
"The best hotel breakfast I have ever had. I will return for the breakfast!"
United States
Kathryn
The price is AED 887
AED 1,002 total
includes taxes & fees
1 Nov - 2 Nov
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, (135 reviews)
"We had a comfortable stay. Bed was great, host was very accommodating and location was great!"
United States
Monica
The price is AED 948
AED 1,052 total
includes taxes & fees
2 Nov - 3 Nov
Harvey House Bed & Breakfast
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a gas stove.

10. Pristine Apartment with Free Street Parking

Pristine Apartment with Free Street Parking
Humboldt Park
The price is AED 1,233
AED 1,428 total
includes taxes & fees
27 Oct - 28 Oct
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
"The staff was friendly and attentive. Room was clean. Lots of food choices. It felt relatively safe, which is important to me. No complaints about the hotel or my stay. However, parking can be a bit tricky; the nearby garage does not have in and out privileges. You can park on the street, but spaces can be scarce. I got very lucky and was able to park on the street for zero dollars!"
Lisa 1-night trip
Posted less than an hour ago
The Willows Hotel

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