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Check prices for these dates

Next weekend
12 Sep - 14 Sep
In two weeks
19 Sep - 21 Sep
In one month
3 Oct - 5 Oct
In two months
31 Oct - 2 Nov

B&B in Hillside

Our top choices for Hillside bed & breakfast

Dorothy's
Free WiFi, bed sheets

Dorothy's

3.0 star property
8.2 out of 10, Very Good, (67)
"Very friendly and helpful staff. Rooms and bathrooms are very clean. I enjoyed my stay., it was cozy and comfortable. I would definitely stay at Dorothys again if I am back in the area.. I would also recommend it to friends meeting to stay near Wrigley or downtown."
The price is AED 294
AED 473 total
includes taxes & fees
29 Sep - 30 Sep
Dorothy's
The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (594)
"Was a great stay!"
The price is AED 205
AED 388 total
includes taxes & fees
4 Sep - 5 Sep
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, (371)
"We had an amazing stay at Ray's. They made the entire process from start to finish simple and easy. They went above and beyond for us in many ways and we will definitely be back! "
The price is AED 635
AED 716 total
includes taxes & fees
4 Sep - 5 Sep
Ray's Bucktown B&B
The Publishing House B&B
Staircase

The Publishing House B&B

3.5 star property
9.8 out of 10, Exceptional, (181)
"What a lovely place to stay. This bnb was perect!"
The price is AED 775
AED 875 total
includes taxes & fees
21 Sep - 22 Sep
The Publishing House 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, (480)
"Everything was taken care of! A wonderful stay. "
The price is AED 444
AED 724 total
includes taxes & fees
10 Sep - 11 Sep
House 5863 - Chicago Bed and Breakfast
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (251)
"This was a great alternative to a typical hotel. The staff was extremely helpful and courteous. The room was very nice and the amenities were great. I would definitely stay again!"
Wicker Park Inn
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (470)
"Loved the shared kitchen access! "
The price is AED 604
AED 709 total
includes taxes & fees
4 Sep - 5 Sep
The Sono Chicago
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (116)
"Large uniquely, decorated rooms,very comfortable ,great breakfast, great breakfast space, fun conversations at breakfast"
The price is AED 962
AED 1,068 total
includes taxes & fees
8 Sep - 9 Sep
Harvey House Bed & Breakfast
Villa D' Citta
Lobby sitting area

Villa D' Citta

3.5 star property
9.4 out of 10, Exceptional, (106)
"Would stay again anytime!!"
The price is AED 967
AED 1,135 total
includes taxes & fees
1 Oct - 2 Oct
Villa D' Citta
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (147)
"We were thrilled with the little neighborhood and options for food, drinks and shopping. Super easy to hop on bus to and from Wrigley!"
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Villa Dubois Guest Room 6
Fridge, microwave, oven, stovetop

Villa Dubois Guest Room 6

The price is AED 248
AED 572 total
includes taxes & fees
4 Sep - 5 Sep
Villa Dubois Guest Room 6
Wrigleyville Suites Room 3
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 3

2.0 star property
The price is AED 296
AED 629 total
includes taxes & fees
4 Sep - 5 Sep
Wrigleyville Suites Room 3
Wrigleyville Suites Room 1
Fridge, microwave, oven, stovetop

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 AED 296
AED 629 total
includes taxes & fees
4 Sep - 5 Sep
Wrigleyville Suites Room 1
Dubois Guest House Room 101
TV, fireplace, books

Dubois Guest House Room 101

The price is AED 248
AED 572 total
includes taxes & fees
4 Sep - 5 Sep
Dubois Guest House Room 101
Villa Dubois Guest House Room 5
Fridge, oven, stovetop, coffee/tea maker

Villa Dubois Guest House Room 5

The price is AED 248
AED 572 total
includes taxes & fees
4 Sep - 5 Sep
Villa Dubois Guest House Room 5
Villa Dubois Guest House Room 2
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 2

The price is AED 248
AED 572 total
includes taxes & fees
4 Sep - 5 Sep
Villa Dubois Guest House Room 2
Villa Dubois Guest House Room 4
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 4

The price is AED 248
AED 572 total
includes taxes & fees
4 Sep - 5 Sep
Villa Dubois Guest House Room 4
Dubois Guest House Room 202
Fridge, microwave, oven, stovetop

Dubois Guest House Room 202

2.0 out of 10, (1)
The price is AED 248
AED 572 total
includes taxes & fees
4 Sep - 5 Sep
Dubois Guest House Room 202
Wrigleyville Suites Room 5
Interior

Wrigleyville Suites Room 5

The price is AED 309
AED 645 total
includes taxes & fees
4 Sep - 5 Sep
Wrigleyville Suites Room 5
Wrigleyville Suites Room 2
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 2

2.0 star property
2.0 out of 10, (1)
The price is AED 296
AED 629 total
includes taxes & fees
4 Sep - 5 Sep
Wrigleyville Suites Room 2
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

10/10 Excellent
"Housekeeping was friendly and efficient and staff was very helpful in answering questions. Also, loved how close the area was to all the shopping and tourist activities."
Aalia 4-night trip
Posted 11 hours ago
Hilton Garden Inn Chicago Downtown/Magnificent Mile

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: Dorothy's: 7 rooms. 13.8 mi (22.3 km) from the heart of Hillside.The Villa Toscana: 9 rooms. 13.8 mi (22.3 km) from the downtown core. 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 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.
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.