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

Book Hillside Bed & Breakfast

Check prices for these dates

Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11
In one month
Oct 23 - Oct 25
In two months
Nov 20 - Nov 22

Our top choices for Hillside bed & breakfast

Property entrance

1. 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
$293 nightly
The price is $325
Sep 22 - Sep 23
Total with taxes and fees
Harvey House Bed & Breakfast
Double Room, Private Bathroom (Venetian) | Terrace/patio

2. The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
8.0 out of 10, Very good, (675 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
$136 nightly
The price is $153
Sep 30 - Oct 1
Total with taxes and fees
The Villa Toscana
Living area

3. Dorothy's

Dorothy's
2.0 star property
Lakeview
8.6 out of 10, Excellent, (182 reviews)
"Space was so clean and modern. Breakfast was good also. Very nice stay."
United States
Steven
$113 nightly
The price is $127
Sep 30 - Oct 1
Total with taxes and fees
Dorothy's
Spa

4. Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (415 reviews)
"Superb breakfast and very friendly staff. Great place to stay!"
United States
mary
$185 nightly
The price is $208
Sep 28 - Sep 29
Total with taxes and fees
Ray's Bucktown B&B
Presidential Studio Suite, 2 Bedrooms (1st Floor) | Living area | 51-inch flat-screen TV with cable channels, TV, Netflix

5. House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (518 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
$179 nightly
The price is $210
Sep 22 - Sep 23
Total with taxes and fees
House 5863 - Chicago Bed and Breakfast
Private kitchen

6. The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (555 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
$226 nightly
The price is $265
Sep 30 - Oct 1
Total with taxes and fees
The Sono Chicago
Property entrance

7. Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (283 reviews)
"Great location. Staff was very helpful.👍"
United States
Michael
$353 nightly
The price is $414
Sep 28 - Sep 29
Total with taxes and fees
Wicker Park Inn
Staircase

8. The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (216 reviews)
"Gorgeous building inside and out. Beautiful clean rooms. Amazing public spaces. Breakfast was by far one of the best meals of the whole trip."
United States
Mollie
$360 nightly
The price is $407
Sep 27 - Sep 28
Total with taxes and fees
The Publishing House B&B
Lobby sitting area

9. Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (125 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
$252 nightly
The price is $296
Oct 5 - Oct 6
Total with taxes and fees
Villa D' Citta
Coffee/tea maker, fridge, microwave, oven

10. Pristine Apartment with Free Street Parking

Pristine Apartment with Free Street Parking
Humboldt Park
$430 nightly
The price is $441
Oct 20 - Oct 21
Total with taxes and fees
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 Hillside Hotel Reviews

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent
"Love this hotel, staff, pool and room quality are always excellent"
Iain 3-night trip
Posted less than an hour ago
InterContinental Chicago Magnificent Mile by IHG

Find out more about Hillside

Hillside B&B information

Number of reviews
2,245
Accommodation
13 B&B
Lowest Price
$127
Highest Price
$441

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 $127 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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