Best B&B Hillside in 2026

Q: What are the top B&Bs in Hillside?

Here are some well-liked 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 city centre. The Sono Chicago : 7 rooms. Situated 13.6 mi (21.9 km) from the heart of Hillside. Enjoy the rooftop terrace and fireplace in reception. The Publishing House B&B : 11 rooms. 12.7 mi (20.5 km) from the city centre. Enjoy the free full breakfast and winery. House 5863 - Chicago Bed and Breakfast : 7 rooms. Located 14.4 mi (23.2 km) from the core of Hillside. Enjoy the designer toiletries and private garden.

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Our top choices for Hillside bed & breakfast

The Publishing House B&B

Downtown Chicago

STEVEN

₹23,359 total

includes taxes & fees

10 May - 11 May

The Sono Chicago

Near North Side

Timothy

₹13,062 total

includes taxes & fees

28 Apr - 29 Apr

Dorothy's

Lakeview

Winter Fox

₹11,614 total

includes taxes & fees

27 Apr - 28 Apr

Double Room, Private Bathroom (Venetian) | Terrace/patio

The Villa Toscana

Lakeview

Rico

₹10,694 total

includes taxes & fees

23 Apr - 24 Apr

Ray's Bucktown B&B

Bucktown

Peter

₹17,212 total

includes taxes & fees

26 Apr - 27 Apr

Villa D' Citta

Lincoln Park

Earl

₹25,118 total

includes taxes & fees

23 Apr - 24 Apr

Wicker Park Inn

West Town

Michael

₹23,741 total

includes taxes & fees

27 Apr - 28 Apr

House 5863 - Chicago Bed and Breakfast

Edgewater

James

₹20,209 total

includes taxes & fees

26 Apr - 27 Apr

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Top Hillside Hotel Reviews

Hilton Chicago

10/10 Excellent

"We always book this hotel when staying in Chicago. The overall atmosphere, staff and room cleanliness is what brings us back."

Hotel Riu Plaza Chicago

4/10 Poor

"For the price we paid I expected it to be better than it was. The revolving door doesn’t work and we had to push it with some force to open it every time we went through it. Not one person commented on it. We asked for 2 extra pillows and they called back checking we asked for a blanket. I corrected them with what we asked for and over an hour later they brought one pillow. We tried to go to the rooftop and when it was open the "

Find out more about Hillside

Hillside B&B information

Number of reviews	2,855
Accommodation	9 B&B
Lowest Price	₹10,694
Highest Price	₹25,118

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 Navy Pier 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: 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 city centre. The Sono Chicago: 7 rooms. Situated 13.6 mi (21.9 km) from the heart of Hillside. Enjoy the rooftop terrace and fireplace in reception. The Publishing House B&B: 11 rooms. 12.7 mi (20.5 km) from the city centre. Enjoy the free full breakfast and winery. House 5863 - Chicago Bed and Breakfast: 7 rooms. Located 14.4 mi (23.2 km) from the core of Hillside. Enjoy the designer toiletries and private garden.

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 Navy Pier 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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