A lush green valley with a winding road, steep mountains, and a misty atmosphere.

Book Hillside Bed & Breakfast

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Our top choices for Hillside bed & breakfast

The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (208 reviews)
"Outstanding! Staff, food, bed…everything was superb We’ll be back soon for sure"
United States
Sigfredo
$264 nightly
The price is $298
Jul 19 - Jul 20
Total with taxes and fees
The Publishing House B&B

The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (526 reviews)
"Great place! Easy street parking and within walking distance to shops and restaurants."
United States
Susan
$173 nightly
The price is $203
Jul 1 - Jul 2
Total with taxes and fees
The Sono Chicago

Dorothy's

Dorothy's
2.0 star property
Lakeview
8.6 out of 10, Excellent, (140 reviews)
"lots of clean rooms and clean bathrooms with products you can use. keep in mind however that not every room has its own private bathroom "
United States
Jia
$121 nightly
The price is $136
Jul 13 - Jul 14
Total with taxes and fees
Dorothy's

The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
7.8 out of 10, Good, (651 reviews)
"Small, but very convenient! Excellent location!"
Canada
Jeremy
$155 nightly
The price is $175
Jul 13 - Jul 14
Total with taxes and fees
The Villa Toscana

Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (402 reviews)
"The best breakfast I’ve ever had!!"
United States
Sixto
$212 nightly
The price is $239
Jun 22 - Jun 23
Total with taxes and fees
Ray's Bucktown B&B

Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (268 reviews)
"Very nice place and great location with a lot of restaurants and shops."
United States
Regina
$255 nightly
The price is $299
Jul 1 - Jul 2
Total with taxes and fees
Wicker Park Inn

Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (127 reviews)
"Spotless room and the best host! Breakfast was warm and delicious."
United States
Christine
$271 nightly
The price is $301
Jul 6 - Jul 7
Total with taxes and fees
Harvey House Bed & Breakfast

House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (507 reviews)
"The place is well run. The communal areas are clean and have what you need. The neighborhood is nice, everyone i took was gorgeous! And the perfect distance from the city."
United States
Joanna
$184 nightly
The price is $216
Jul 8 - Jul 9
Total with taxes and fees
House 5863 - Chicago Bed and Breakfast

Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (121 reviews)
"A fantastic stay yet again. I have stayed here the last few years while attending a conference. All the staff were great and amazing selection of food for breakfast and for late night snacks. I will be back again next year"
United Kingdom
Robert
$298 nightly
The price is $350
Jul 13 - Jul 14
Total with taxes and fees
Villa D' Citta

Pristine Apartment with Free Street Parking

Pristine Apartment with Free Street Parking
Humboldt Park
$454 nightly
The price is $466
Jun 30 - Jul 1
Total with taxes and fees
Pristine Apartment with Free Street Parking

Five bedroom - 3 bath - Sleeps 12

Five bedroom - 3 bath - Sleeps 12
Lakeview
$1,337 nightly
The price is $1,549
Jul 13 - Jul 14
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Hillside Hotel Reviews

Find out more about Hillside

Hillside B&B information

Number of reviews
2,950
Accommodation
13 B&B
Lowest Price
$136
Highest Price
$1,549

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 $136 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.

Explore a world of travel with Expedia