A lush green valley with a winding road, steep mountains, and a misty atmosphere.

Find a Bed and Breakfast in Hillside from CA $145

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Check prices for these dates

Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11
In one month
Oct 23 - Oct 25
In two months
Nov 20 - Nov 22

Our top choices for Hillside bed & breakfast

A well-lit hallway with a wooden dresser, a table with chairs, and a blue patterned rug.

1. Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (135 reviews)
"We had a comfortable stay. Bed was great, host was very accommodating and location was great!"
United States
Monica
The price is CA $414
CA $459 total
includes taxes & fees
Oct 5 - Oct 6
Harvey House Bed & Breakfast
A modern living room with a sofa, a coffee table, and a dining area with a table and chairs.

2. Dorothy's

Dorothy's
2.0 star property
Lakeview
8.6 out of 10, Excellent, (185 reviews)
"Space was so clean and modern. Breakfast was good also. Very nice stay."
United States
Steven
The price is CA $81
CA $145 total
includes taxes & fees
Oct 26 - Oct 27
Dorothy's
A bathroom with a glass-tiled wall, a sink, and a shower area.

3. Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (416 reviews)
"The breakfast is fantastic!! Very unique and fun decor!"
United States
Susan
The price is CA $261
CA $295 total
includes taxes & fees
Sep 29 - Sep 30
Ray's Bucktown B&B
A fire pit surrounded by glass pebbles, with a television displaying a football game in the background.

4. The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
8.0 out of 10, Very good, (676 reviews)
"Was a nice house the room we stayed in was cozy bed was really comfortable and in walking distance to wrigley field would definitely stay here again"
United States
John
The price is CA $107
CA $183 total
includes taxes & fees
Sep 28 - Sep 29
The Villa Toscana
A modern living room with leather sofas, a dining area, and large windows offering a view of greenery.

5. House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (519 reviews)
"good"
United States
jiantao
The price is CA $178
CA $296 total
includes taxes & fees
Oct 4 - Oct 5
House 5863 - Chicago Bed and Breakfast
A wooden staircase with built-in seating and potted plants, leading to a modern interior with large windows and a mezzanine level.

6. The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (217 reviews)
"The best hotel breakfast I have ever had. I will return for the breakfast!"
United States
Kathryn
The price is CA $337
CA $381 total
includes taxes & fees
Oct 25 - Oct 26
The Publishing House B&B
A spacious kitchen with white cabinetry, a central island with bar stools, pendant lighting, and a large window with a view.

7. The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (558 reviews)
"It was a very comfortable hotel. We loved the free street parking, easy access to public transportation, coffee, breakfast, bottled water, bubbly water and snacks. I will stay here again!"
United States
Christie
The price is CA $269
CA $315 total
includes taxes & fees
Sep 27 - Sep 28
The Sono Chicago
A brick building with a sign for The Wicker Park Inn, including a phone number and website.

8. Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (283 reviews)
"Great location. Staff was very helpful.👍"
United States
Michael
The price is CA $418
CA $490 total
includes taxes & fees
Oct 26 - Oct 27
Wicker Park Inn
A grand foyer with a wooden staircase, a chandelier, and a large window.

9. Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (126 reviews)
"What a pleasant stay, staff was welcoming and wanting to make sure our needs were met with our expectations. Meals were abundant and homemade. Rooms w/bath were clean with abundant towels. We will stay again."
United States
Jeffrey
The price is CA $356
CA $418 total
includes taxes & fees
Oct 5 - Oct 6
Villa D' Citta
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a gas stove.

10. Pristine Apartment with Free Street Parking

Pristine Apartment with Free Street Parking
Humboldt Park
The price is CA $475
CA $548 total
includes taxes & fees
Oct 27 - Oct 28
Pristine Apartment with Free Street Parking
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 Chicago

Hilton Chicago

8/10 Good
"Reception and welcome were excellent. Clean, spacious and comfortable room. Lacked a central light switch at door, and we had to run the shower for a long time before hot water came through but was then fine. Bathroom could do with a few more towel rails and would prefer a bar of soap to the liquid soap, but all very clean. Enjoyed o'sheas bar in the evening where service was great and food tasty if a little pricey."
Andrew 1-night trip
Posted less than an hour ago
Hilton Chicago

Find out more about Hillside

Hillside B&B information

Number of reviews
2,514
Accommodation
13 B&B
Lowest Price
CA $145
Highest Price
CA $548

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 Soldier Field 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: The Sono Chicago: 7 rooms. 13.6 mi (21.9 km) from the heart of Hillside. Enjoy the rooftop terrace and fireplace in the lobby. The Villa Toscana: 9 rooms. 13.9 mi (22.3 km) from the downtown core. Dorothy's: 7 rooms. Situated 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 heart of downtown. Enjoy the designer toiletries and private yard. 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 Soldier Field 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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