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Check prices for these dates

Next weekend
24 Apr - 26 Apr
In two weeks
1 May - 3 May
In one month
15 May - 17 May
In two months
12 June - 14 June

Our top choices for Hillside bed & breakfast

Private kitchen

The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (502 reviews)
"Really happy with my choice of this lodging. Centrally located on a quiet street. Very new decor and bedding. Breakfast was good and adequate."
United States
Timothy
The price is AU$212
includes taxes & fees
16 Apr - 17 Apr
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, (200 reviews)
"Very clean room, friendly staff"
United States
STEVEN
The price is AU$294
includes taxes & fees
19 Apr - 20 Apr
The Publishing House B&B
Double Room, Private Bathroom (Venetian) | Terrace/patio

The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
7.8 out of 10, Good, (636 reviews)
"Overall the stay was fantastic looking forward to booking here again in the future "
United States
Rico
The price is AU$191
includes taxes & fees
27 Apr - 28 Apr
The Villa Toscana
Living area

Dorothy's

Dorothy's
3.0 star property
Lakeview
8.6 out of 10, Excellent, (112 reviews)
"cozy and close to cool places"
United States
Winter Fox
The price is AU$172
includes taxes & fees
4 May - 5 May
Dorothy's
Lobby sitting area

Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (116 reviews)
"Everything was perfect. The food was really yummy I would love the salsa recipe. "
United States
Earl
The price is AU$339
includes taxes & fees
20 Apr - 21 Apr
Villa D' Citta
Spa

Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (397 reviews)
"The breakfast alone was worth the trip! Warm, generous, eclectic, this place goes out of their way to welcome their guests. And they’re PET FRIENDLY. "
United States
Peter
The price is AU$258
includes taxes & fees
16 Apr - 17 Apr
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, (262 reviews)
"Everything was good."
United States
Michael
The price is AU$328
includes taxes & fees
26 Apr - 27 Apr
Wicker Park Inn
Courtyard

House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (499 reviews)
"Wonderful room, very good breakfast!"
United States
James
The price is AU$303
includes taxes & fees
19 Apr - 20 Apr
House 5863 - Chicago Bed and Breakfast
Property entrance

Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (124 reviews)
"The Property was beautiful! When we walked in, the first utterance out of our mouths was "Wow!" Street parking was easy. The room "The Chalet" that we stayed in was spacious with many amenities and was spotless. The bed was very comfortable as well! And being on the third story, we got our stair steps in for our trip! Haha."
United States
Timothy
The price is AU$360
includes taxes & fees
28 Apr - 29 Apr
Harvey House Bed & Breakfast
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

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

8/10 Good
"Staff is amazing. Pool is tiny and filled with children if it’s not like dawn. And then the heaters make a crazy amount of noise. "
Derrick 1-night trip
Posted 3 hours ago
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Find out more about Hillside

Hillside B&B information

Number of reviews
2,848
Accommodation
11 B&B
Lowest Price
AU$172
Highest Price
AU$360

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, Wrigley Field and Navy Pier 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 Villa Toscana: 9 rooms. 13.9 mi (22.3 km) from the city centre. The Sono Chicago: 7 rooms. Situated 13.6 mi (21.9 km) from the heart of Hillside. Enjoy the rooftop terrace and fireplace in reception. House 5863 - Chicago Bed and Breakfast: 7 rooms. 14.4 mi (23.2 km) from the city centre. Enjoy the designer toiletries and private garden. The Publishing House B&B: 11 rooms. Located 12.7 mi (20.5 km) from the core of Hillside. Enjoy the free full breakfast and winery.
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. Wrigley Field and Navy Pier 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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