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

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Check prices for these dates

Next weekend
31 July - 2 Aug
In two weeks
7 Aug - 9 Aug
In one month
21 Aug - 23 Aug
In two months
18 Sept - 20 Sept

Our top choices for Hillside bed & breakfast

Property entrance

Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (129 reviews)
"Spotless room and the best host! Breakfast was warm and delicious."
United States
Christine
The price is AU$430
includes taxes & fees
28 July - 29 July
Harvey House Bed & Breakfast
Private kitchen

The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (531 reviews)
"Really great spot , nice room and parking was easy :)"
United States
AnjolaOluwa
The price is AU$317
includes taxes & fees
28 July - 29 July
The Sono Chicago
Living area

Dorothy's

Dorothy's
2.0 star property
Lakeview
8.6 out of 10, Excellent, (156 reviews)
"Great location, just what we needed."
United States
Stephanie
The price is AU$203
includes taxes & fees
27 July - 28 July
Dorothy's
Staircase

The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (209 reviews)
"Outstanding! Staff, food, bed…everything was superb We’ll be back soon for sure"
United States
Sigfredo
The price is AU$458
includes taxes & fees
23 Aug - 24 Aug
The Publishing House B&B
Spa

Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (408 reviews)
"Superb breakfast and very friendly staff. Great place to stay!"
United States
mary
The price is AU$316
includes taxes & fees
27 July - 28 July
Ray's Bucktown B&B
Double Room, Private Bathroom (Venetian) | Terrace/patio

The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
8.0 out of 10, Very good, (659 reviews)
"Clean room, self serve breakfast, free street parking permit, cute cats!"
United States
Shu-Ting
The price is AU$260
includes taxes & fees
26 July - 27 July
The Villa Toscana
Presidential Studio Suite, 2 Bedrooms (1st Floor) | Living area

House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (509 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
The price is AU$308
includes taxes & fees
27 July - 28 July
House 5863 - Chicago Bed and Breakfast
Property entrance

Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (274 reviews)
"Nice place to stay in an historic neighborhood"
United States
Linda
The price is AU$455
includes taxes & fees
11 Aug - 12 Aug
Wicker Park Inn
Lobby sitting area

Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (121 reviews)
"Wonderful! Will stay here again."
United States
Elsa
The price is AU$481
includes taxes & fees
27 July - 28 July
Villa D' Citta
Coffee/tea maker, fridge, microwave, oven

Pristine Apartment with Free Street Parking

Pristine Apartment with Free Street Parking
Humboldt Park
The price is AU$763
includes taxes & fees
18 Aug - 19 Aug
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

Freehand Chicago

Freehand Chicago

10/10 Excellent
"The staff was very excellent!"
Damein 3-night trip
Posted less than an hour ago
Freehand Chicago

Find out more about Hillside

Hillside B&B information

Number of reviews
2,191
Accommodation
13 B&B
Lowest Price
AU$203
Highest Price
AU$481

Frequently asked questions

Searching for B&Bs in Hillside?
Whether you're on a romantic trip and want to stay somewhere quiet and intimate, or you're travelling solo and hoping to get some local recommendations, 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 visit.
How do you know if a B&B is a good option for your stay?
With attentive service, opportunities to socialise with other guests and of course a scrumptious breakfast, B&Bs all have a unique environment.
What are the top B&Bs in Hillside?
Here are some well-liked 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 city centre. Enjoy the rooftop terrace and fireplace in reception. 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 garden. The Villa Toscana: 9 rooms. 13.9 mi (22.3 km) from the city centre. Wicker Park Inn: 11 rooms. Located 12 mi (19.3 km) from the core of Hillside.
When is the best time to stay at a B&B in Hillside?
When you're dreaming of a escape to Hillside, make sure that you take the year-round temperatures into account. The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Hillside are January, November, February and December, with each month seeing an average of 13 cm of snowfall.
What is there to do in Hillside?
Travellers 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 International Airport (ORD), which is located 6.9 mi (11 km) from the city centre. Otherwise, you can search for flights to Chicago Midway Airport (MDW), which is 10.4 mi (16.7 km) away. If you'd like to venture out around the area, you may want a rental car for your journey.

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