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Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

Compare 28 B&B in Hillside with updated reviews, rates, and availability.

The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (558)
"Super easy to find parking, quick walk to cubs game and bars after. Safe neighborhood and the greatest pizza place right through the gate. It was awesome!"
The price is AED 400
AED 617 total
includes taxes & fees
5 Jun - 6 Jun
The Villa Toscana
Dorothy's
Free WiFi, bed sheets

Dorothy's

3.0 star property
8.4 out of 10, Very Good, (39)
"I initially came up to Chicago from Indiana and had found this place to stay for my duration. The area was lovely, arrangements were excellent and I loved the cottage feel to the Bed N’ Breakfast next door. If I’m ever in Chicago for another concert or to see more of the place, I’m coming back to Dorothy’s."
The price is AED 397
AED 594 total
includes taxes & fees
2 Jun - 3 Jun
Dorothy's
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (356)
"Breakfast was great, the staff was kind, and it was a pleasant surprise. "
The price is AED 698
AED 788 total
includes taxes & fees
3 Jun - 4 Jun
Ray's Bucktown B&B
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (455)
"Was very warm and welcoming.. room was clean and updated… staff was friendly..! Had a great time…"
The price is AED 666
AED 781 total
includes taxes & fees
4 Jun - 5 Jun
The Sono Chicago
The Publishing House B&B
Staircase

The Publishing House B&B

3.5 star property
9.8 out of 10, Exceptional, (176)
"Incredible service, amazing breakfast and gorgeous rooms."
The price is AED 603
AED 681 total
includes taxes & fees
29 Jun - 30 Jun
The Publishing House B&B
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (244)
"Very cute and dainty place to stay! Lovely staff! Very clean and homey! "
The price is AED 1,094
AED 1,284 total
includes taxes & fees
11 Jun - 12 Jun
Wicker Park Inn
Villa D' Citta
Lobby sitting area

Villa D' Citta

3.5 star property
9.2 out of 10, Wonderful, (100)
"What a wonderful and unique place where everything is so beautifully decorated with the owners personalized touch. The kitchen and amenities are exceptional and the best part was breakfast and visiting with Gina. Will be our only go-to now in Chicago."
The price is AED 1,094
AED 1,284 total
includes taxes & fees
30 Jun - 1 Jul
Villa D' Citta
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (110)
"This was an amazing place to stay, highly recommended for something quiet and relaxing."
The price is AED 962
AED 1,068 total
includes taxes & fees
4 Jun - 5 Jun
Harvey House Bed & Breakfast
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, (135)
"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!
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 473
AED 833 total
includes taxes & fees
1 Jun - 2 Jun
Wrigleyville Suites Room 1
House 5863 - Chicago Bed and Breakfast
Exterior

House 5863 - Chicago Bed and Breakfast

3.5 star property
9.0 out of 10, Wonderful, (473)
"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 460
AED 745 total
includes taxes & fees
11 Jun - 12 Jun
House 5863 - Chicago Bed and Breakfast
Dubois Guest House Room 202
Fridge, microwave, oven, stovetop

Dubois Guest House Room 202

The price is AED 620
AED 1,058 total
includes taxes & fees
8 Jun - 9 Jun
Dubois Guest House Room 202
Dubois Guest House Room 101
TV, fireplace, books

Dubois Guest House Room 101

The price is AED 620
AED 1,058 total
includes taxes & fees
29 Jun - 30 Jun
Dubois Guest House Room 101
Villa Dubois Guest Room 6
Fridge, microwave, oven, stovetop

Villa Dubois Guest Room 6

The price is AED 496
AED 881 total
includes taxes & fees
30 Jun - 1 Jul
Villa Dubois Guest Room 6
Villa Dubois Guest House Room 5
Fridge, oven, stovetop, coffee/tea maker

Villa Dubois Guest House Room 5

The price is AED 496
AED 881 total
includes taxes & fees
30 Jun - 1 Jul
Villa Dubois Guest House Room 5
Dubois Guest House Room 203
Fridge, microwave, oven, stovetop

Dubois Guest House Room 203

The price is AED 744
AED 1,224 total
includes taxes & fees
8 Jun - 9 Jun
Dubois Guest House Room 203
Villa Dubois Guest House Room 2
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 2

The price is AED 620
AED 1,058 total
includes taxes & fees
8 Jun - 9 Jun
Villa Dubois Guest House Room 2
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 473
AED 833 total
includes taxes & fees
1 Jun - 2 Jun
Wrigleyville Suites Room 2
Wrigleyville Suites Room 3
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 3

2.0 star property
The price is AED 473
AED 833 total
includes taxes & fees
1 Jun - 2 Jun
Wrigleyville Suites Room 3
Villa Dubois Guest House Room 1
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 1

The price is AED 744
AED 1,224 total
includes taxes & fees
8 Jun - 9 Jun
Villa Dubois Guest House Room 1
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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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 Sono Chicago: 7 rooms. 13.6 mi (21.9 km) from the heart of downtown. Enjoy the rooftop terrace and fireplace in the lobby. 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.