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Check prices for these dates

Next weekend
21 Saf. - 23 Saf.
In two weeks
28 Saf. - 2 Rab. I
In one month
14 Rab. I - 16 Rab. I
In two months
11 Rab. II - 13 Rab. II

Compare B&B in Hillside with updated reviews, rates, and availability.

The Villa Toscana
Lounge

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (529)
" Pleasantly nastalgic decor in excellent location - electronic expectation to tip in a self-service and fee-for-every service establishment "
The price is SAR 115
SAR 285 total
includes taxes & fees
13 Feb - 14 Feb
The Villa Toscana
Dorothy's
Room

Dorothy's

3.0 star property
8.2 out of 10, Very Good, (21)
"Was having surgery but was canceled so I didn’t get to stay very long but would definitely stay again"
The price is SAR 118
SAR 270 total
includes taxes & fees
13 Feb - 14 Feb
Dorothy's
The Sono Chicago
Room

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (442)
"Our stay at The Sono was great! We were only staying a night and booked a queen room, and they gave us a free upgrade to a king room since it was unoccupied. The room was fantastic & clean, the breakfast was delicious with lots of variety and the voucher for free street parking made this the best option for our stay. I would definitely stay again."
The price is SAR 491
SAR 576 total
includes taxes & fees
18 Feb - 19 Feb
The Sono Chicago
The Publishing House B&B
Fireplace

The Publishing House B&B

3.5 star property
10.0 out of 10, Exceptional, (166)
"Was surprisingly excellent "
The price is SAR 531
SAR 599 total
includes taxes & fees
27 Feb - 28 Feb
The Publishing House B&B
Wicker Park Inn
Room

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (239)
"The Wicker Park Inn was located close to many transportation options. The breakfast room was bright and sunny with good light breakfast options."
The price is SAR 686
SAR 805 total
includes taxes & fees
25 Feb - 26 Feb
Wicker Park Inn
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (341)
"This B&B is a gem. Loved it. It’s like staying in someone’s huge, comfortable home with a fabulous hostess. Plenty of parking, creative decor, and the huge made to order breakfast is fabulous. They have snacks, homemade baked goods and all kinds of drinks in the kitchen. They serve breakfast until 11 for late risers. Laundry, sauna, steam room. Will definitely stay again."
The price is SAR 652
SAR 736 total
includes taxes & fees
13 Feb - 14 Feb
Ray's Bucktown B&B
House 5863 - Chicago Bed and Breakfast
Exterior

House 5863 - Chicago Bed and Breakfast

3.5 star property
9.0 out of 10, Wonderful, (472)
"Erick was very friendly and responsive. The neighborhood around was wonderful. We walked everywhere we went and were able to park on the street with no problems. We would stay again. Thank you!"
The price is SAR 838
SAR 1,219 total
includes taxes & fees
11 Mar - 12 Mar
House 5863 - Chicago Bed and Breakfast
Harvey House Bed & Breakfast
Interior

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (108)
"This is a beautiful little stay that feels like a walk back in time with a wonderful host Beth and delicious options for food and activities! We will be back "
The price is SAR 866
SAR 961 total
includes taxes & fees
18 Feb - 19 Feb
Harvey House Bed & Breakfast
Villa D' Citta
Front of property

Villa D' Citta

3.5 star property
9.2 out of 10, Wonderful, (99)
"Unique experience staying within a block of DePaul School of Music. Lovely property with open kitchen and great breakfast/coffee. Nice outdoor area with fire pit. Stayed in Capone suite which was comfortable but noisy as it was downstairs just below the kitchen. Note that private bath is down the hall as this wasn’t explained well when I booked. Would stay again and I do recommend."
The price is SAR 772
SAR 906 total
includes taxes & fees
26 Feb - 27 Feb
Villa D' Citta
Wrigleyville Suites Room 1
Bedroom with a queen-sized bed, patterned wallpaper, two windows with blinds, and a geometric rug on the floor.

Wrigleyville Suites Room 1

2.0 star property
2.0 out of 10, (1)
"I would like to say that I was highly disappointed with the customer service, after already having the room booked for over a week I was contacted an hr and a half after check in on the day I was suppose to be there with additional requirements including a $200 fee (Hopefully I get that back) check in was at 3pm I wasnt able to get into my room till 6pm and I had a concert to attend at 8pm this rush caused more stress then it was worth but yes make sure the now $500 room is really worth it...
The price is SAR 302
SAR 625 total
includes taxes & fees
13 Feb - 14 Feb
Wrigleyville Suites Room 1
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Dining Room

Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!

9.8 out of 10, Exceptional, (134)
"Our family of 4 enjoyed our short stay here. Great location that has everything you need a walking distance away. Jon was great to communicate with."
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Dubois Guest House Room 101
Cozy bedroom with a patterned wallpaper wall, a queen sized bed with grey linens, a ceiling fan, a vanity area with a mirror and chair,and a window with white curtains.

Dubois Guest House Room 101

The price is SAR 253
SAR 566 total
includes taxes & fees
13 Feb - 14 Feb
Dubois Guest House Room 101
Dubois Guest House Room 201
Cozy bedroom with a patterned wallpaper wall, a large mirror, a queen size bed with grey linens, a bedside table with a lamp and towels, and a window with white curtains.

Dubois Guest House Room 201

7.4 out of 10, Good, (3)
"We really enjoyed our stay. Cleanliness was top tier. "
Dubois Guest House Room 201
Villa Dubois Guest Room 6
A cozy bedroom with a patterned wallpaper wall, a large mirror, a queen size bed with grey linens, a bedside table with a lamp and towels, and a window with white curtains.

Villa Dubois Guest Room 6

Villa Dubois Guest Room 6
Villa Dubois Guest House Room 2
A simply furnished room with a plush armchair, a wooden table with and a framed painting on a blue ash paper wall.

Villa Dubois Guest House Room 2

Villa Dubois Guest House Room 2
Villa Dubois Guest House Room 5
A cozy and modern bedroom with brownish paper wall, a comfortable queen size bed, a large window with natural light, and stylish artwork.

Villa Dubois Guest House Room 5

Villa Dubois Guest House Room 5
Dubois Guest House Room 202
Cozy bedroom with a patterned wallpaper wall, a large mirror, a queen size bed with grey linens, a bedside table with a lamp and towels, and a window with white curtains.

Dubois Guest House Room 202

Dubois Guest House Room 202
Wrigleyville Suites Room 2
Bedroom with a metal bunk bed, patterned wallpaper, a wooden chair, and a window with blinds.

Wrigleyville Suites Room 2

2.0 star property
2.0 out of 10, (1)
The price is SAR 302
SAR 625 total
includes taxes & fees
13 Feb - 14 Feb
Wrigleyville Suites Room 2
Charming 3 bedrooms Apartment at the Medical District
Living area

Charming 3 bedrooms Apartment at the Medical District

2.0 star property
10.0 out of 10, Exceptional, (3)
"Great host, great place, great location."
Charming 3 bedrooms Apartment at the Medical District
Wrigleyville Suites Room 3
Cozy bedroom with a grey patterned wallpaper wall, a queen sized bed with grey linens and white towels, two bedside tables with lamps, and a window with natural light.

Wrigleyville Suites Room 3

2.0 star property
Wrigleyville Suites Room 3
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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Other property types in Hillside

Sentral Michigan Avenue
Pool

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (678)
"Perfect location, huge beautiful rooms, felt like a local. The pool was a huge plus!"
The price is SAR 411
SAR 593 total
includes taxes & fees
18 Feb - 19 Feb
Sentral Michigan Avenue
Sonder South Wabash
Living area

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (429)
"Property was convenient and clean. Overall great experience. Street meter parking could be a headache during parking hours but it’s a city thing. Also the incidental feee is a bit confusing with how it’s returned. "
The price is SAR 334
SAR 392 total
includes taxes & fees
9 Mar - 10 Mar
Sonder South Wabash
Sonder Market Hall
Living area

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (253)
"It was wonderful!"
The price is SAR 424
SAR 497 total
includes taxes & fees
6 Mar - 7 Mar
Sonder Market Hall
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.

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 playing some golf on your trip, Fresh Meadow Golf Club is a good spot to tee off.
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: The Villa Toscana: 9 rooms. 13.8 mi (22.3 km) from the heart of Hillside.Dorothy’s: 7 rooms. 13.8 mi (22.3 km) from the downtown core. The Sono Chicago: 7 rooms. Situated 13.6 mi (21.9 km) from the heart of Hillside. Enjoy the rooftop terrace and fireplace in the lobby. The Publishing House B&B: 11 rooms. 12.7 mi (20.5 km) from the heart of downtown. Enjoy the free full breakfast and winery. 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. If you want to check out some popular attractions in Hillside, you might enjoy a visit to Fresh Meadow Golf Club. Wrigley Field and Michigan Avenue 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.