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

Find a Bed and Breakfast in Hillside from CA $157

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Check prices for these dates

Next weekend
Aug 14 - Aug 16
In two weeks
Aug 21 - Aug 23
In one month
Sep 4 - Sep 6
In two months
Oct 2 - Oct 4

Our top choices for Hillside bed & breakfast

Private kitchen

1. The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (539 reviews)
"Close to some great places to eat locally and about an hour walk to river and central business activities......and a very comfy bed!"
United States
Bronwyn
The price is CA $201
CA $236 total
includes taxes & fees
Aug 31 - Sep 1
The Sono Chicago
Living area

2. Dorothy's

Dorothy's
2.0 star property
Lakeview
8.6 out of 10, Excellent, (170 reviews)
"Great location, just what we needed."
United States
Stephanie
The price is CA $92
CA $157 total
includes taxes & fees
Aug 10 - Aug 11
Dorothy's
Property entrance

3. Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (132 reviews)
"This was an amazing place to stay, highly recommended for something quiet and relaxing."
United States
Mia
The price is CA $378
CA $419 total
includes taxes & fees
Aug 17 - Aug 18
Harvey House Bed & Breakfast
Staircase

4. The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (211 reviews)
"Outstanding! Staff, food, bed…everything was superb We’ll be back soon for sure"
United States
Sigfredo
The price is CA $326
CA $368 total
includes taxes & fees
Aug 30 - Aug 31
The Publishing House B&B
Double Room, Private Bathroom (Venetian) | Terrace/patio

5. The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
8.0 out of 10, Very good, (662 reviews)
"Clean room, self serve breakfast, free street parking permit, cute cats!"
United States
Shu-Ting
The price is CA $109
CA $183 total
includes taxes & fees
Aug 11 - Aug 12
The Villa Toscana
Spa

6. Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (412 reviews)
"Superb breakfast and very friendly staff. Great place to stay!"
United States
mary
The price is CA $242
CA $274 total
includes taxes & fees
Aug 10 - Aug 11
Ray's Bucktown B&B
Front of property

7. House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (513 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
The price is CA $176
CA $292 total
includes taxes & fees
Aug 18 - Aug 19
House 5863 - Chicago Bed and Breakfast
Lobby sitting area

8. Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (122 reviews)
"Wonderful! Will stay here again."
United States
Elsa
The price is CA $367
CA $431 total
includes taxes & fees
Aug 10 - Aug 11
Villa D' Citta
Property entrance

9. Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (279 reviews)
"clean room, staff was helpful. We enjoyed our stay."
United States
Maggie
The price is CA $430
CA $505 total
includes taxes & fees
Aug 31 - Sep 1
Wicker Park Inn
Coffee/tea maker, fridge, microwave, oven

10. Pristine Apartment with Free Street Parking

Pristine Apartment with Free Street Parking
Humboldt Park
The price is CA $651
CA $766 total
includes taxes & fees
Aug 24 - Aug 25
Pristine Apartment with Free Street Parking
TV

11. Five bedroom - 3 bath - Sleeps 12

Five bedroom - 3 bath - Sleeps 12
Lakeview
The price is CA $1,176
CA $2,169 total
includes taxes & fees
Aug 24 - Aug 25
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

Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

10/10 Excellent
"The location was great."
Jerry 4-night trip
Posted less than an hour ago
Hyatt Regency McCormick Place Chicago

Find out more about Hillside

Hillside B&B information

Number of reviews
2,222
Accommodation
13 B&B
Lowest Price
CA $157
Highest Price
CA $505

Frequently asked questions

Searching for B&Bs in Hillside?
Whether you're on a romantic vacation and want to stay somewhere quiet, or you're traveling solo and hoping to meet fellow tourists, a B&B might be the right choice for your trip. If you're interested in discovering some top attractions, United Center and Wrigley Field are worth a stop.
How do you know if a B&B is the best choice for your stay?
With attentive service, opportunities to meet guests from other places, and delectable breakfasts, B&Bs offer a unique environment.
What are the top B&Bs in Hillside?
Below are some B&Bs in the area: Dorothy's: 7 rooms. 13.8 mi (22.3 km) from the heart of Hillside.The Sono Chicago: 7 rooms. 13.6 mi (21.9 km) from the downtown core. Enjoy the rooftop terrace and fireplace in the lobby. House 5863 - Chicago Bed and Breakfast: 7 rooms. Situated 14.4 mi (23.2 km) from the heart of Hillside. Enjoy the designer toiletries and private yard. The Villa Toscana: 9 rooms. 13.9 mi (22.3 km) from the heart of downtown.Wicker Park Inn: 11 rooms. Located 12 mi (19.3 km) from the core of Hillside.
What's the best time of year to stay at a B&B in Hillside?
When you're dreaming of a trip to Hillside, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 71°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Hillside are January, November, February, and December, with each month seeing an average of 5 inches of snowfall.
What is there to do in Hillside?
Travelers enjoy Hillside for its restaurants and shopping. United Center and Wrigley Field are also some sites to visit if you want to see more of the area.
How can I get to and around Hillside?
You can plan your excursions in and around Hillside ahead of time with these transportation options. Fly into Chicago O'Hare Intl. Airport (ORD), which is located 6.9 mi (11 km) away from the heart of the city. You can also search for flights into Chicago Midway Airport (MDW), which is 10.4 mi (16.7 km) away. If you'd like to venture out around the area, consider renting a car to take in more sights.

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