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Search B&B in Hillside

Compare 25 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, (499)
"Stayed here twice. Both times was problem free and just as I expected. Location is prime. "
The price is AED 180
AED 358 total
includes taxes & fees
24 Nov - 25 Nov
The Villa Toscana
Old Chicago Inn
Property entrance
Old Chicago Inn
2.0 star property
7.4 out of 10, Good, (762)
"Wonderful alternative to usual hotel properties at comparable prices. "
Old Chicago Inn
House 5863 - Chicago Bed and Breakfast
Exterior
House 5863 - Chicago Bed and Breakfast
3.5 star property
9.0 out of 10, Wonderful, (470)
"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 AED 473
AED 761 total
includes taxes & fees
26 Nov - 27 Nov
House 5863 - Chicago Bed and 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 AED 841
AED 987 total
includes taxes & fees
3 Dec - 4 Dec
Wicker Park Inn
The Sono Chicago
Room
The Sono Chicago
3.5 star property
10.0 out of 10, Exceptional, (435)
"We absolutely loved staying here. Everything was clean and comfortable. Breakfast was lovely, and there were beverages and snacks available. Easy check in and out, easy parking, everything was smooth and wonderful. "
The price is AED 485
AED 569 total
includes taxes & fees
25 Nov - 26 Nov
The Sono Chicago
Ray's Bucktown B&B
Front of property
Ray's Bucktown B&B
3.5 star property
9.8 out of 10, Exceptional, (331)
"Great place to stay for solo or couples. Breakfast service is incredible. "
The price is AED 528
AED 596 total
includes taxes & fees
3 Dec - 4 Dec
Ray's Bucktown B&B
Villa D' Citta
Front of property
Villa D' Citta
3.5 star property
9.4 out of 10, Exceptional, (97)
"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 AED 756
AED 888 total
includes taxes & fees
3 Dec - 4 Dec
Villa D' Citta
The Publishing House B&B
Fireplace
The Publishing House B&B
3.5 star property
9.8 out of 10, Exceptional, (160)
"This was the nicest stay I have had in years. Felt like a weekend with your best friend and they are an excellent host. Every amenity and design of the place is well intentioned and thought out. I will definitely be back!"
The price is AED 630
AED 721 total
includes taxes & fees
22 Dec - 23 Dec
The Publishing House B&B
Harvey House Bed & Breakfast
Interior
Harvey House Bed & Breakfast
4.0 star property
9.8 out of 10, Exceptional, (105)
"Surprisingly easy street parking for the Chicago area. This property is absolutely beautiful and immaculate. We stayed in the Chalet Suite. Be aware that the Chalet and Oak Park suites are on the third floor and you will have to hike up quite a lot of stairs, but the room is gorgeous if you're up to the hike. The innkeeper, Beth, is very kind and attentive to her guests. She puts a lot of thought into the breakfast as well. We had multigrain croissants imported from France, fresh squeezed orange...
The price is AED 848
AED 942 total
includes taxes & fees
25 Nov - 26 Nov
Harvey House Bed & Breakfast
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. "
The price is AED 273
AED 584 total
includes taxes & fees
23 Nov - 24 Nov
Dubois Guest House Room 201
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!
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 AED 273
AED 584 total
includes taxes & fees
23 Nov - 24 Nov
Villa Dubois Guest House Room 2
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...
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
The price is AED 273
AED 584 total
includes taxes & fees
25 Nov - 26 Nov
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
The price is AED 273
AED 584 total
includes taxes & fees
25 Nov - 26 Nov
Villa Dubois Guest House Room 5
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 AED 273
AED 584 total
includes taxes & fees
25 Nov - 26 Nov
Dubois Guest House Room 101
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
The price is AED 273
AED 584 total
includes taxes & fees
23 Nov - 24 Nov
Villa Dubois Guest House Room 4
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, (2)
"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
Room in Town house Rogers Park
Living area
Room in Town house Rogers Park
Room in Town house Rogers Park
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
Garden
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (592)
"Great stay. Will stay again!"
The price is AED 396
AED 573 total
includes taxes & fees
24 Nov - 25 Nov
Sentral Michigan Avenue
Sonder Market Hall
Living area
Sonder Market Hall
3.5 star property
8.6 out of 10, Excellent, (208)
"My stay at Sonder was an absolute delight! The property is very clean and the view and vibe was very cozy and perfect! The manager Jess went above and beyond helping out with questions and took great care of me! I will definitely be coming back! "
The price is AED 206
AED 242 total
includes taxes & fees
22 Dec - 23 Dec
Sonder Market Hall
Sonder South Wabash
Living area
Sonder South Wabash
3.5 star property
9.0 out of 10, Wonderful, (395)
"Nice"
The price is AED 443
AED 520 total
includes taxes & fees
19 Dec - 20 Dec
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.Old Chicago Inn: 10 rooms. 13.5 mi (21.7 km) from the downtown core. Enjoy the free full breakfast 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. Ray’s Bucktown B&B: 11 rooms. 11.7 mi (18.8 km) from the heart of downtown. Enjoy the free cooked breakfast and rooftop terrace. 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. 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.