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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

Our top choices for Highland Park bed & breakfast

A modern living room with a sofa, a coffee table, and a dining area with a table and chairs.

1. Dorothy's

Dorothy's
2.0 star property
Lakeview
8.6 out of 10, Excellent, (196 reviews)
"I enjoyed my stay"
United States
Kellen
The price is ￥5,104
￥11,539 total
includes taxes & fees
Nov 24 - Nov 25
Dorothy's
A narrow stone pathway leading to a house with a green porch and a large tree overhanging the path.

2. The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
8.2 out of 10, Very good, (688 reviews)
"Nice house set back from the street. Clean room. Nice atmosphere. Would stay again."
United States
John
The price is ￥8,370
￥16,166 total
includes taxes & fees
Nov 10 - Nov 11
The Villa Toscana
A modern living room with leather sofas, a dining area, and large windows offering a view of greenery.

3. House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (525 reviews)
"Honestly great, clean, and did not hear neighbors. Would stay again!"
United States
Malena
The price is ￥18,812
￥31,775 total
includes taxes & fees
Nov 8 - Nov 9
House 5863 - Chicago Bed and Breakfast
A patio with a grill, outdoor seating, and potted plants.

4. Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (423 reviews)
"Thank you again for an amazing stay at Rays!"
United States
Lora
The price is ￥32,663
￥36,874 total
includes taxes & fees
Nov 8 - Nov 9
Ray's Bucktown B&B
A spacious kitchen with white cabinetry, a central island with bar stools, pendant lighting, and a large window with a view.

5. The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
9.8 out of 10, Exceptional, (573 reviews)
"I like that it had a balcony food choice wasn’t my type of style end up ordering food off of site but definitely had all the amenities for you to be ready for the next day. Will be staying again little bit pricey for a short weekend stay but I will definitely be coming back. Very great part of the town hope to own my own own home in this place one day."
United States
Tavarion
The price is ￥19,477
￥22,866 total
includes taxes & fees
Nov 24 - Nov 25
The Sono Chicago
A well-lit hallway with a wooden dresser, a table with chairs, and a blue patterned rug.

6. Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (138 reviews)
"We had a comfortable stay. Bed was great, host was very accommodating and location was great!"
United States
Monica
The price is ￥40,873
￥45,361 total
includes taxes & fees
Nov 10 - Nov 11
Harvey House Bed & Breakfast
A brick building with a sign for The Wicker Park Inn, including a phone number and website.

7. Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (286 reviews)
"Loved the location"
United States
Mary
The price is ￥36,652
￥43,026 total
includes taxes & fees
Nov 29 - Nov 30
Wicker Park Inn
A grand foyer with a wooden staircase, a chandelier, and a large window.

8. Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (129 reviews)
"Very elegant !"
United States
Hernando
The price is ￥32,625
￥38,299 total
includes taxes & fees
Dec 2 - Dec 3
Villa D' Citta
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a gas stove.

9. Pristine Apartment with Free Street Parking

Pristine Apartment with Free Street Parking
Humboldt Park
The price is ￥38,460
￥41,586 total
includes taxes & fees
Nov 30 - Dec 1
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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Learn more about Highland Park

Stroll along tree-lined streets to discover charming boutiques and art galleries in this picturesque lakeside suburb. Catch world-class performances at Ravinia Festival, where you can picnic on the lawn while enjoying live music under the stars.

See all hotels in Highland Park
A pebbly beach with waves at sunset.

Top reviews in Highland Park

A modern living room with a sofa, a coffee table, and a dining area with a table and chairs.
Dorothy's

Dorothy's

Dorothy's
Lakeview

10/10 Excellent

I enjoyed my stay
United States
Kellen
Reviewed November 2, 2026
Dorothy's

Frequently Asked Questions

Searching for B&Bs in Highland Park?

If you're looking for something a little different than your standard hotel, a stay at a bed and breakfast might be the perfect option for your vacation. If your ideal vacation to Highland Park includes spending lots of time outside, Chicago Botanic Garden and Moraine Park are good spots to enjoy the scenery.

How do you know if a B&B is the right choice for your stay?

With attentive service, opportunities to meet guests from other places, and breakfast served on site, B&Bs all have a truly one-of-a-kind environment.

What are the top B&Bs in Highland Park?

Here are some well-liked B&Bs in the surrounding area: The Villa Toscana: 9 rooms. 18.1 mi (29.1 km) from the downtown core. Dorothy's: 7 rooms. Situated 18.1 mi (29.1 km) from the heart of Highland Park. House 5863 - Chicago Bed and Breakfast: 7 rooms. 15 mi (24.2 km) from the heart of downtown. Enjoy the designer toiletries and private yard.

When should I stay at a B&B in Highland Park?

When you're dreaming of a trip to Highland Park, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 69°F, while the coldest months are January and February with an average of 30°F. Average annual precipitation for Highland Park is 47 inches.

What is there to do in Highland Park?

Travelers enjoy Highland Park for its gardens and restaurants. If cultural attractions are high on your list, Ravinia Park and Ravinia Pavilion are spots to check out. You might put Lake Michigan and Chicago Botanic Garden on your list if you want to see more of the area.

How can I get to and around Highland Park?

You can plan your excursions in and around Highland Park ahead of time with these transportation options. Fly into Chicago, IL (PWK-Chicago Executive), which is located 6.8 mi (10.9 km) from the heart of the city. Otherwise, you can search for flights to Chicago O'Hare Intl. Airport (ORD), which is 15.1 mi (24.3 km) away. If you'd like to venture out around the area, consider renting a car to take in more sights.