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Check prices for these dates

Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov
In one month
21 Nov - 23 Nov
In two months
19 Dec - 21 Dec

B&B in Hillside

Private kitchen
The Sono Chicago
The Sono Chicago
3.5 star property
10.0 out of 10, Exceptional, (479)
"Loved the shared kitchen access! "
United States
Jennifer M
The price is AED 551
AED 647 total
includes taxes & fees
27 Oct - 28 Oct
The Sono Chicago
Staircase
The Publishing House B&B
The Publishing House B&B
3.5 star property
9.8 out of 10, Exceptional, (186)
"Wonderful staff, beautiful hotel and great breakfast!"
United States
Veronica
The price is AED 730
AED 824 total
includes taxes & fees
16 Nov - 17 Nov
The Publishing House B&B
Free WiFi, bed sheets
Dorothy's
Dorothy's
3.0 star property
8.4 out of 10, Very Good, (85)
"Clean room beautiful.yards convenient"
United States
Daniel
The price is AED 169
AED 326 total
includes taxes & fees
27 Oct - 28 Oct
Dorothy's
Exterior
The Villa Toscana
The Villa Toscana
2.5 star property
7.8 out of 10, Good, (614)
"Amazing location for the North Halsltead area, but also good for transport in and around the city. Uniquely weird location and place. "
United States
Scott
The price is AED 169
AED 345 total
includes taxes & fees
27 Oct - 28 Oct
The Villa Toscana
Exterior
House 5863 - Chicago Bed and Breakfast
House 5863 - Chicago Bed and Breakfast
3.5 star property
9.0 out of 10, Wonderful, (488)
"Super cute and comfortable place to stay. Erick was very communicative and welcoming. Great snack bar!"
United States
Kirstyn
The price is AED 418
AED 693 total
includes taxes & fees
27 Oct - 28 Oct
House 5863 - Chicago Bed and Breakfast
Property entrance
Wicker Park Inn
Wicker Park Inn
3.5 star property
9.0 out of 10, Wonderful, (256)
"The Wicker Park Inn is clean, beautifully decorated, and the staff is friendly and helpful!"
United States
Elizabeth R
Wicker Park Inn
Lobby sitting area
Villa D' Citta
Villa D' Citta
3.5 star property
9.4 out of 10, Exceptional, (110)
"Great place"
United States
Jeffrey
The price is AED 841
AED 987 total
includes taxes & fees
10 Nov - 11 Nov
Villa D' Citta
Front of property
Ray's Bucktown B&B
Ray's Bucktown B&B
3.5 star property
9.8 out of 10, Exceptional, (380)
"Ray's is such a fun, quirky place to stay - tons of creativity has gone into making it a unique stay. The breakfast is fabulous, on-site parking is convenient, and there is excellent attention to safety and security. I thoroughly enjoyed my stay and look forward to visiting again!"
United States
Tala
The price is AED 599
AED 676 total
includes taxes & fees
27 Oct - 28 Oct
Ray's Bucktown B&B
Property entrance
Harvey House Bed & Breakfast
Harvey House Bed & Breakfast
4.0 star property
9.8 out of 10, Exceptional, (118)
"Large uniquely, decorated rooms,very comfortable ,great breakfast, great breakfast space, fun conversations at breakfast"
United States
Bethany
The price is AED 848
AED 942 total
includes taxes & fees
3 Nov - 4 Nov
Harvey House Bed & Breakfast
5 bedrooms, free WiFi, bed sheets
Five bedroom - 3 bath - Sleeps 12
Five bedroom - 3 bath - Sleeps 12
The price is AED 2,094
AED 3,581 total
includes taxes & fees
11 Nov - 12 Nov
Five bedroom - 3 bath - Sleeps 12
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
"Pleasant comfortable stay"
Guillermo 4-night trip
Posted 6 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.House 5863 - Chicago Bed and Breakfast: 7 rooms. 14.4 mi (23.2 km) from the downtown core. Enjoy the designer toiletries and private yard. The Villa Toscana: 9 rooms. Situated 13.8 mi (22.3 km) from the heart of Hillside. 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. Ray's Bucktown B&B: 11 rooms. Located 11.7 mi (18.8 km) from the core of Hillside. Enjoy the free cooked breakfast and rooftop terrace.
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.