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Check prices for these dates

Next weekend
13 Mar - 15 Mar
In two weeks
20 Mar - 22 Mar
In one month
3 Apr - 5 Apr
In two months
1 May - 3 May

Our top choices for Hillside bed & breakfast

Staircase

The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (197 reviews)
"Very clean room, friendly staff"
United States
STEVEN
The price is SAR 774
SAR 874 total
includes taxes & fees
31 Mar - 1 Apr
The Publishing House B&B
Private kitchen

The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (493 reviews)
"Fantastic place! Very clean, kind and welcoming staff, great breakfast, and great location!"
United States
Catie
The price is SAR 447
SAR 524 total
includes taxes & fees
10 Mar - 11 Mar
The Sono Chicago
Living area

Dorothy's

Dorothy's
3.0 star property
Lakeview
8.4 out of 10, Very Good, (108 reviews)
"cozy and close to cool places"
United States
Winter Fox
The price is SAR 189
SAR 354 total
includes taxes & fees
19 Mar - 20 Mar
Dorothy's
Double Room, Private Bathroom (Venetian) | Terrace/patio

The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
7.8 out of 10, Good, (630 reviews)
"Good location. Nice room. Shared bath. Excellent value. "
United States
Daniel
The price is SAR 149
SAR 325 total
includes taxes & fees
10 Mar - 11 Mar
The Villa Toscana
Courtyard

Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (115 reviews)
"Great place"
United States
Jeffrey
The price is SAR 773
SAR 907 total
includes taxes & fees
9 Mar - 10 Mar
Villa D' Citta
Spa

Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (394 reviews)
"We had the best stay at Rays and will definitely be back! Everything about this place is fantastic, its hard to know where to begin, but the care and love put into their B&B can be felt for real. And had an unbelievably comfy and restful sleep. Woke up feeling refreshed, and had the best made to order breakfast!"
United States
Kristin
The price is SAR 632
SAR 714 total
includes taxes & fees
11 Mar - 12 Mar
Ray's Bucktown B&B
Terrace/patio

Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (260 reviews)
"Fantastic location, spotlessly clean room, and a very comfortable bed. I have stayed here several times and will continue to do so."
United States
Jeffrey
Wicker Park Inn
Courtyard

House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (499 reviews)
"Wonderful room, very good breakfast!"
United States
James
The price is SAR 532
SAR 860 total
includes taxes & fees
9 Mar - 10 Mar
House 5863 - Chicago Bed and Breakfast
Property entrance

Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (122 reviews)
"Great hospitality. The suites have a lot of space and amenities. Beautiful location in the heart of Oak Park "
United States
Elizabeth
The price is SAR 867
SAR 962 total
includes taxes & fees
9 Mar - 10 Mar
Harvey House Bed & Breakfast
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

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

10/10 Excellent
"The location of the hotel is amazing, its really in the center, so its really convenient. The view of the hotel is amazing. "
Elizama 1-night trip
Posted 2 hours ago
LondonHouse Chicago, Curio Collection by Hilton

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 discovering some top attractions, Wrigley Field and Michigan Avenue are worth a stop.
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. 13.9 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. 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. 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.

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