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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

B&B in Hillside

Dorothy's
1 bedroom, free WiFi, bed sheets

Dorothy's

3.0 star property
8.4 out of 10, Very Good, (58)
"Great to stay, close walk to many places. Cleaning lady was very helpful and friendly. Rooms a bit small but would definitely stay there again."
$121 nightly
The price is $135
Aug 12 - Aug 13
Total includes taxes and fees
Dorothy's
The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (588)
"Was a great stay!"
$133 nightly
The price is $149
Aug 12 - Aug 13
Total includes taxes and fees
The Villa Toscana
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (369)
"We had an amazing stay at Ray's. They made the entire process from start to finish simple and easy. They went above and beyond for us in many ways and we will definitely be back! "
$206 nightly
The price is $233
Aug 10 - Aug 11
Total includes taxes and fees
Ray's Bucktown B&B
House 5863 - Chicago Bed and Breakfast
Exterior

House 5863 - Chicago Bed and Breakfast

3.5 star property
9.0 out of 10, Wonderful, (476)
"Everything was taken care of! A wonderful stay. "
$180 nightly
The price is $212
Aug 11 - Aug 12
Total includes taxes and fees
House 5863 - Chicago Bed and Breakfast
The Publishing House B&B
Staircase

The Publishing House B&B

3.5 star property
9.8 out of 10, Exceptional, (181)
"What a lovely place to stay. This bnb was perect!"
$163 nightly
The price is $185
Sep 4 - Sep 5
Total includes taxes and fees
The Publishing House B&B
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (250)
"This was a great alternative to a typical hotel. The staff was extremely helpful and courteous. The room was very nice and the amenities were great. I would definitely stay again!"
$220 nightly
The price is $259
Sep 2 - Sep 3
Total includes taxes and fees
Wicker Park Inn
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (114)
"Large uniquely, decorated rooms,very comfortable ,great breakfast, great breakfast space, fun conversations at breakfast"
$262 nightly
The price is $300
Aug 11 - Aug 12
Total includes taxes and fees
Harvey House Bed & Breakfast
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (465)
"Excellent location. Beautiful property, extremely clean."
$196 nightly
The price is $230
Aug 12 - Aug 13
Total includes taxes and fees
The Sono Chicago
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (143)
"We were thrilled with the little neighborhood and options for food, drinks and shopping. Super easy to hop on bus to and from Wrigley!"
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Villa D' Citta
Lobby sitting area

Villa D' Citta

3.5 star property
9.4 out of 10, Exceptional, (105)
"Would stay again anytime!!"
$263 nightly
The price is $309
Aug 11 - Aug 12
Total includes taxes and fees
Villa D' Citta
Villa Dubois Guest Room 6
Fridge, microwave, oven, stovetop

Villa Dubois Guest Room 6

$206 nightly
The price is $238
Aug 10 - Aug 11
Total includes taxes and fees
Villa Dubois Guest Room 6
Wrigleyville Suites Room 1
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 1

2.0 star property
2.0 out of 10, (1)
"I would like to say that I was highly disappointed with the customer service, after already having the room booked for over a week I was contacted an hr and a half after check in on the day I was suppose to be there with additional requirements including a $200 fee (Hopefully I get that back) check in was at 3pm I wasnt able to get into my room till 6pm and I had a concert to attend at 8pm this rush caused more stress then it was worth but yes make sure the now $500 room is really worth it...
Wrigleyville Suites Room 1
Wrigleyville Suites Room 3
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 3

2.0 star property
Wrigleyville Suites Room 3
Dubois Guest House Room 101
TV, fireplace, books

Dubois Guest House Room 101

$249 nightly
The price is $290
Aug 8 - Aug 9
Total includes taxes and fees
Dubois Guest House Room 101
Dubois Guest House Room 201
Fridge, microwave, oven, stovetop

Dubois Guest House Room 201

7.4 out of 10, Good, (3)
"We really enjoyed our stay. Cleanliness was top tier. "
$249 nightly
The price is $290
Aug 8 - Aug 9
Total includes taxes and fees
Dubois Guest House Room 201
Villa Dubois Guest House Room 5
Fridge, oven, stovetop, coffee/tea maker

Villa Dubois Guest House Room 5

$211 nightly
The price is $244
Aug 8 - Aug 9
Total includes taxes and fees
Villa Dubois Guest House Room 5
Villa Dubois Guest House Room 2
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 2

$249 nightly
The price is $290
Aug 16 - Aug 17
Total includes taxes and fees
Villa Dubois Guest House Room 2
Dubois Guest House Room 202
Fridge, microwave, oven, stovetop

Dubois Guest House Room 202

2.0 out of 10, (1)
$249 nightly
The price is $290
Aug 8 - Aug 9
Total includes taxes and fees
Dubois Guest House Room 202
Wrigleyville Suites Room 2
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 2

2.0 star property
2.0 out of 10, (1)
Wrigleyville Suites Room 2
Villa Dubois Guest House Room 1
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 1

$284 nightly
The price is $331
Aug 10 - Aug 11
Total includes taxes and fees
Villa Dubois Guest House Room 1
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 Hillside Hotel Reviews

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

10/10 Excellent
"Great location"
Russell 1-night trip
Posted 12 hours ago
Fairmont Chicago at Millennium Park

Frequently asked questions

What is the nightly rate for a B&B in Hillside?
Prices for B&Bs in Hillside often vary, but you can find a great deal from $135 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Hillside B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a B&B in Hillside?
The best time to book a B&B in Hillside is during the vibrant spring months from April to June, when the area bursts into life with blooming flowers and mild weather. This period is ideal for travelers who appreciate outdoor activities, as temperatures range from the mid-50s to mid-70s Fahrenheit, creating a pleasant environment for hiking, biking, and exploring local attractions.

April marks the beginning of the tourist season and offers a fantastic opportunity for those seeking a tranquil getaway. The trails and parks are less crowded, allowing for a more intimate experience with nature. As you wander through the picturesque landscapes, you can enjoy the serenity of the surroundings, making it great for leisurely sightseeing.

If you're looking for more budget-friendly options, consider visiting in November, when the crowds have thinned out. This month showcases the beauty of the changing seasons, providing a different perspective of Hillside's charm. The crisp air and stunning autumn foliage create a serene backdrop for outdoor activities or cozy evenings at your B&B.
What is the difference between a Hillside Bed and Breakfast and a hotel?
Every Hillside B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Hillside B&Bs.