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Compare 26 B&B in Hillside with updated reviews, rates, and availability.

Dorothy's
Room

Dorothy's

3.0 star property
8.6 out of 10, Excellent, (14)
"Cool place"
The price is SAR 169
SAR 330 total
includes taxes & fees
14 Jan - 15 Jan
Dorothy's
The Villa Toscana
Lounge

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (515)
"Great location. Great price. Comfortable room with private bathroom"
The price is SAR 122
SAR 293 total
includes taxes & fees
13 Jan - 14 Jan
The Villa Toscana
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (340)
"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 653
SAR 737 total
includes taxes & fees
12 Jan - 13 Jan
Ray's Bucktown B&B
The Publishing House B&B
Fireplace

The Publishing House B&B

3.5 star property
10.0 out of 10, Exceptional, (164)
"We absolutely loved our stay. The breakfast was amazing and the staff were great. We can’t wait to come back."
The price is SAR 562
SAR 634 total
includes taxes & fees
6 Feb - 7 Feb
The Publishing House B&B
The Sono Chicago
Room

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (441)
"Likely the best hotel experience we’ve had. Nice place in a good location. The breakfast was a great perk. Felt like we stumbled on a hidden gem spot. "
The price is SAR 505
SAR 592 total
includes taxes & fees
12 Jan - 13 Jan
The Sono Chicago
Harvey House Bed & Breakfast
Interior

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (107)
"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 867
SAR 962 total
includes taxes & fees
13 Jan - 14 Jan
Harvey House Bed & Breakfast
Wicker Park Inn
Room

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (238)
"This was the second time that I stayed at this property. The rooms are so beautiful and all the people are so friendly. I love the area and easy access to parking, would definitely stay here again and again! :)"
The price is SAR 686
SAR 806 total
includes taxes & fees
22 Jan - 23 Jan
Wicker Park Inn
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 532
SAR 838 total
includes taxes & fees
12 Jan - 13 Jan
House 5863 - Chicago Bed and 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 773
SAR 907 total
includes taxes & fees
11 Feb - 12 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 540
SAR 910 total
includes taxes & fees
12 Jan - 13 Jan
Wrigleyville Suites Room 1
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 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
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

The price is SAR 324
SAR 652 total
includes taxes & fees
12 Jan - 13 Jan
Villa Dubois Guest House Room 2
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 279
SAR 597 total
includes taxes & fees
12 Jan - 13 Jan
Dubois Guest House Room 101
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 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
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
Villa Dubois Guest House Room 4
A cozy and stylish bedroom with a comfortable bed, a patterned armchair, and a unique wall decoration.

Villa Dubois Guest House Room 4

Villa Dubois Guest House Room 4
Dubois Guest House Room 203
Close view of bedroom with a patterned accent wall, a queen size 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 203

Dubois Guest House Room 203
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)
"The entire experience associated with this VRBO rental was excellent. The location was great - 15 mins to downtown McCormack Center. The street had plenty of parking and very quiet at night. There are plenty of restaurants within walking distance. The rental was very clean and stocked with the necessary items you would need during a stay. The check in process was easy and the host was quick to respond to text messages. Unit provided parking. I would rent this unit again."
Charming 3 bedrooms Apartment at the Medical District
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, (650)
"Amazing view and the apartment space was perfect. There was some cabinets that were banged up pretty good and the garbage disposal/dishwasher were not working but it was such a beautiful place that it didn't even matter. The valet was super helpful as you have to walk around the block and with alot of luggage it wasn't easy. "
The price is SAR 412
SAR 593 total
includes taxes & fees
12 Jan - 13 Jan
Sentral Michigan Avenue
Kasa Magnificent Mile Chicago
Front of property

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (348)
"Kasa was a pleasant surprise. Based on previous reviews, we understood that this was not a traditional hotel with amenities and had a virtual front desk but we did have an onsite person that did help us check in and store luggage. The apartment style room was very spacious and clean. We enjoyed having the extra space to spread out and the full kitchen was so handy when storing food or leftovers. Also, when we didn’t get utensils with our to go orders- Kasa had us covered. It was a nice home...
Kasa Magnificent Mile Chicago
Sonder South Wabash
Living area

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (413)
"Beautiful Hotel with lots of amenities and entertainment in a walking distance "
The price is SAR 422
SAR 495 total
includes taxes & fees
30 Jan - 31 Jan
Sonder South Wabash
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. Ray’s Bucktown B&B: 11 rooms. Situated 11.7 mi (18.8 km) from the heart of Hillside. Enjoy the free cooked breakfast and rooftop terrace. 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. The Sono Chicago: 7 rooms. Located 13.6 mi (21.9 km) from the core of Hillside. Enjoy the rooftop terrace and fireplace in the lobby.
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. Michigan Avenue 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.