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Check prices for these dates

Next weekend
Nov 14 - Nov 16
In two weeks
Nov 21 - Nov 23
In one month
Dec 5 - Dec 7
In two months
Jan 2 - Jan 4

B&B in Hillside

Private kitchen
The Sono Chicago

The Sono Chicago

3.5 star property
Near North Side
10.0 out of 10, Exceptional, (479)
"Great location and hospitality! "
United States
Teresa
$136 nightly
The price is $159
Nov 13 - Nov 14
Total with taxes and fees
The Sono Chicago
Staircase
The Publishing House B&B

The Publishing House B&B

3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (187)
"Wonderful staff, beautiful hotel and great breakfast!"
United States
Veronica
$208 nightly
The price is $235
Nov 16 - Nov 17
Total with taxes and fees
The Publishing House B&B
Free WiFi, bed sheets
Dorothy's

Dorothy's

3.0 star property
Lakeview
8.4 out of 10, Very Good, (92)
"Halsted is a nice neibourhood. We liked the secondhand shops."
United States
Lisa
$73 nightly
The price is $79
Nov 11 - Nov 12
Total with taxes and fees
Dorothy's
Exterior
The Villa Toscana

The Villa Toscana

2.5 star property
Lakeview
7.8 out of 10, Good, (616)
"We "
United States
Brian
$81 nightly
The price is $89
Nov 10 - Nov 11
Total with taxes and fees
The Villa Toscana
Exterior
House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast

3.5 star property
Edgewater
9.0 out of 10, Wonderful, (490)
"I loved it was so close to busy Chicago but in the quiet subarbs where it was nice and quiet and felt very safe.The rooms were excellent and well equipped and the kitchen was full of snacks to eat when you wanted and a great selection of drinks. If I ever came to Chicago I would stay here again also the hosts were fantastic "
United Kingdom
Mark
$161 nightly
The price is $189
Nov 11 - Nov 12
Total with taxes and fees
House 5863 - Chicago Bed and Breakfast
Front of property
Ray's Bucktown B&B

Ray's Bucktown B&B

3.5 star property
Bucktown
9.8 out of 10, Exceptional, (381)
"Ray's is such a fun, quirky place to stay - tons of creativity has gone into making it a unique stay. The breakfast is fabulous, on-site parking is convenient, and there is excellent attention to safety and security. I thoroughly enjoyed my stay and look forward to visiting again!"
United States
Tala
$168 nightly
The price is $190
Nov 10 - Nov 11
Total with taxes and fees
Ray's Bucktown B&B
Property entrance
Wicker Park Inn

Wicker Park Inn

3.5 star property
West Town
9.0 out of 10, Wonderful, (256)
"My husband and I loved our stay. The room was beautiful, clean, and comfortable. Being able to stay in a neighborhood inn made our trip to Chicago memorable. We went to the Wicker Park Farmer's Market, ate at local restaurants, hung out at local bars, met cool people, and just enjoyed being part of the city. "
United States
Melissa
$199 nightly
The price is $233
Nov 10 - Nov 11
Total with taxes and fees
Wicker Park Inn
Lobby sitting area
Villa D' Citta

Villa D' Citta

3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (110)
"Would stay again anytime!!"
United States
Dominic
$206 nightly
The price is $242
Dec 1 - Dec 2
Total with taxes and fees
Villa D' Citta
Property entrance
Harvey House Bed & Breakfast

Harvey House Bed & Breakfast

4.0 star property
Oak Park
9.8 out of 10, Exceptional, (119)
"Beautiful home, welcoming host."
United States
scott
$231 nightly
The price is $256
Nov 10 - Nov 11
Total with taxes and fees
Harvey House Bed & Breakfast
5 bedrooms, free WiFi, bed sheets
Five bedroom - 3 bath - Sleeps 12

Five bedroom - 3 bath - Sleeps 12

Lakeview
$561 nightly
The price is $632
Nov 12 - Nov 13
Total with taxes and fees
Five bedroom - 3 bath - Sleeps 12
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

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"It's good"
Yingyi 3-night trip
Posted 20 hours ago
Congress Plaza Hotel

Find out more about Hillside

Hillside B&B information

Number of reviews
2,508
Accommodation
32 B&B
Lowest Price
$79
Highest Price
$632

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 $79 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.

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