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

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Our top choices for Hillside bed & breakfast

1. Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (134 reviews)
"This was one of the best B&B properties I’ve ever stayed in. The owner, Beth, was so friendly and accommodating. The room was spacious and so comfortable, and we had a delightful breakfast in the morning that featured bread and pastries from local bakeries. We wished we could stay longer! Highly recommend this charming property!"
United States
Monica
The price is AU$417
includes taxes & fees
10 Sept - 11 Sept
Harvey House Bed & Breakfast

2. The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (548 reviews)
"Close to some great places to eat locally and about an hour walk to river and central business activities......and a very comfy bed!"
United States
Bronwyn
The price is AU$336
includes taxes & fees
9 Sept - 10 Sept
The Sono Chicago

3. The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (213 reviews)
"This was such a perfect place to stay and I'll definitely stay here whenever going to Chicago. It was close enough to downtown to make it easy to access, but far enough away to be out of the hustle and bustle. The staff were all friendly and kind, the room was beautiful, the bed was very comfy, and the whole place had such a fun vibe and great decor. Breakfast was tasty and the menu options felt like something you'd order at your favorite fancy brunch spot, with fruit and pastries to round it...
United States
Julie
The price is AU$433
includes taxes & fees
27 Sept - 28 Sept
The Publishing House B&B

4. Dorothy's

Dorothy's
2.0 star property
Lakeview
8.6 out of 10, Excellent, (175 reviews)
"Great location, just what we needed."
United States
Stephanie
The price is AU$122
includes taxes & fees
9 Sept - 10 Sept
Dorothy's

5. The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
8.0 out of 10, Very good, (669 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 AU$156
includes taxes & fees
9 Sept - 10 Sept
The Villa Toscana

6. Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (414 reviews)
"Superb breakfast and very friendly staff. Great place to stay!"
United States
mary
The price is AU$271
includes taxes & fees
9 Sept - 10 Sept
Ray's Bucktown B&B

7. House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (517 reviews)
"I love the location of this B&B. Right across from a beautiful park, walkable to some fabulous restaurants and shops - and the red line is so close! My room was clean, quiet, cutely decorated. The kitchen was well-stocked with breakfast options. My one recommendation would be - I wish the coffee was higher quality! The host was prompt, friendly, and responsive to my needs. I'll be back for sure!"
United States
Kimberly
The price is AU$291
includes taxes & fees
10 Sept - 11 Sept
House 5863 - Chicago Bed and Breakfast

8. Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (281 reviews)
"Great location. Staff was very helpful.👍"
United States
Michael
The price is AU$502
includes taxes & fees
28 Sept - 29 Sept
Wicker Park Inn

9. Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (124 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 AU$410
includes taxes & fees
7 Oct - 8 Oct
Villa D' Citta

10. Pristine Apartment with Free Street Parking

Pristine Apartment with Free Street Parking
Humboldt Park
The price is AU$703
includes taxes & fees
28 Sept - 29 Sept
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

Find out more about Hillside

Hillside B&B information

Number of reviews
1,191
Accommodation
13 B&B
Lowest Price
AU$122
Highest Price
AU$502

Frequently asked questions

Searching for B&Bs in Hillside?
Whether you're on a romantic trip and want to stay somewhere quiet and intimate, or you're travelling solo and hoping to get some local recommendations, 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 visit.
How do you know if a B&B is a good option for your stay?
With attentive service, opportunities to socialise with other guests and of course a scrumptious breakfast, B&Bs all have a unique environment.
What are the top B&Bs in Hillside?
Here are some well-liked 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 reception. Dorothy's: 7 rooms. 13.8 mi (22.3 km) from the city centre. 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 garden. The Villa Toscana: 9 rooms. 13.9 mi (22.3 km) from the city centre. 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.
When is the best time to stay at a B&B in Hillside?
When you're dreaming of a escape to Hillside, make sure that you take the year-round temperatures into account. The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Hillside are January, November, February and December, with each month seeing an average of 13 cm of snowfall.
What is there to do in Hillside?
Travellers 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 International Airport (ORD), which is located 6.9 mi (11 km) from the city centre. Otherwise, you can search for flights to Chicago Midway Airport (MDW), which is 10.4 mi (16.7 km) away. If you'd like to venture out around the area, you may want a rental car for your journey.

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