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Check prices for these dates

Next weekend
Dec 26 - Dec 28
In two weeks
Jan 2 - Jan 4
In one month
Jan 16 - Jan 18
In two months
Feb 13 - Feb 15

Our top choices for Highland Park bed & breakfast

Private kitchen
The Sono Chicago

The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (487)
"The Sono was welcoming, clean and very comfortable. It was easy to find and provided parking! We would absolutely stay here again and would recommend it to friends. "
United States
Ellen
The price is ￥20,352
￥23,892 total
includes taxes & fees
Dec 21 - Dec 22
The Sono Chicago
Living area
Dorothy's

Dorothy's

Dorothy's
3.0 star property
Lakeview
8.4 out of 10, Very Good, (98)
"Can’t beat the price or location. Everything seemed clean and I loved the waffles. "
United States
Ashley
The price is ￥6,096
￥12,598 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Dorothy's
Courtyard
House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (497)
"Nice shared spaces"
United States
Erica
The price is ￥14,128
￥25,793 total
includes taxes & fees
Jan 5 - Jan 6, 2026
House 5863 - Chicago Bed and Breakfast
Double Room, Private Bathroom (Venetian) | Terrace/patio
The Villa Toscana

The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
7.8 out of 10, Good, (627)
"Good location. Nice room. Shared bath. Excellent value. "
United States
Daniel
The price is ￥4,761
￥11,814 total
includes taxes & fees
Dec 21 - Dec 22
The Villa Toscana
Property entrance
Wicker Park Inn

Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (256)
"The Wicker Park Inn is clean, beautifully decorated, and the staff is friendly and helpful!"
United States
Elizabeth R
Wicker Park Inn
Spa
Ray's Bucktown B&B

Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (383)
"Ray's is such a fun, quirky place to stay - tons of creativity has gone into making it a unique stay. The breakfast is fabulous, on-site parking is convenient, and there is excellent attention to safety and security. I thoroughly enjoyed my stay and look forward to visiting again!"
United States
Tala
The price is ￥24,533
￥27,695 total
includes taxes & fees
Dec 21 - Dec 22
Ray's Bucktown B&B
Lobby sitting area
Villa D' Citta

Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (113)
"Great place"
United States
Jeffrey
The price is ￥32,012
￥37,579 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Villa D' Citta
Property entrance
Harvey House Bed & Breakfast

Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (120)
"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 ￥35,923
￥39,867 total
includes taxes & fees
Jan 5 - Jan 6, 2026
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 Highland Park Hotel Reviews

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

10/10 Excellent
"Great hotel with beautiful decorations!"
Teresa 3-night trip
Posted 2 days ago
Thompson Chicago, by Hyatt

Find out more about Highland Park

Highland Park B&B information

Number of reviews
2,359
Accommodation
11 B&B
Lowest Price
￥11,814
Highest Price
￥39,867

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?
Below are some B&Bs in the area: Dorothy's: 7 rooms. 18.1 mi (29.1 km) from the heart of Highland Park.The Villa Toscana: 9 rooms. Situated 18.1 mi (29.1 km) from the heart of Highland Park. House 5863 - Chicago Bed and Breakfast: 7 rooms. Located 15 mi (24.2 km) from the core of Highland Park. 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.