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Check prices for these dates

Next weekend
May 15 - May 17
In two weeks
May 22 - May 24
In one month
Jun 5 - Jun 7
In two months
Jul 3 - Jul 5

Our top choices for Highland Park bed & breakfast

Private kitchen

The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (508 reviews)
"Great place! Easy street parking and within walking distance to shops and restaurants."
United States
Susan
The price is ￥24,073
￥28,259 total
includes taxes & fees
May 11 - May 12
The Sono Chicago
Living area

Dorothy's

Dorothy's
2.0 star property
Lakeview
8.6 out of 10, Excellent, (118 reviews)
"First time at Dorothy's but I've stayed at her sister location so I know the owner/management and what to expect. Great location and the building is kept up very well. My only non happy comment was no dresser in this room. Its ok since this visit was just me. Being able to use a full kitchen and store food in the refrigerator is a major plus"
United States
Robert
The price is ￥7,531
￥14,333 total
includes taxes & fees
May 10 - May 11
Dorothy's
Double Room, Private Bathroom (Venetian) | Terrace/patio

The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
7.8 out of 10, Good, (639 reviews)
"The Villa Toscana is in a great location!"
United States
Sophie
The price is ￥10,988
￥19,150 total
includes taxes & fees
May 12 - May 13
The Villa Toscana
Spa

Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (398 reviews)
"The best breakfast I’ve ever had!!"
United States
Sixto
The price is ￥26,335
￥29,729 total
includes taxes & fees
May 11 - May 12
Ray's Bucktown B&B
Front of property

House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (502 reviews)
"Great place and neighborhood to stay. Walked everywhere, including to the beach. The room had everything I needed. Fresh coffee and breakfast items steps from my room in the morning. Will stay again. "
United States
Cheryl
The price is ￥19,696
￥32,766 total
includes taxes & fees
May 11 - May 12
House 5863 - Chicago Bed and Breakfast
Lobby sitting area

Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (118 reviews)
"Gina and staff were warm and friendly. When our toilet clogged, we got upgraded. When we needed a delayed checkout, they accommodated. We had a fire for a cold night and got delicious eggs and crispy bacon for breakfast. Highly recommend for those lovers of all things Italian. "
United States
Dana
The price is ￥41,167
￥48,325 total
includes taxes & fees
May 12 - May 13
Villa D' Citta
Property entrance

Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (263 reviews)
"Adorable space, comfortable bed, friendly staff"
United States
Marie
The price is ￥34,448
￥40,438 total
includes taxes & fees
May 11 - May 12
Wicker Park Inn
Property entrance

Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (124 reviews)
"The Property was beautiful! When we walked in, the first utterance out of our mouths was "Wow!" Street parking was easy. The room "The Chalet" that we stayed in was spacious with many amenities and was spotless. The bed was very comfortable as well! And being on the third story, we got our stair steps in for our trip! Haha."
United States
Timothy
The price is ￥40,956
￥45,453 total
includes taxes & fees
May 12 - May 13
Harvey House Bed & Breakfast
Fridge, microwave, oven, coffee/tea maker

Pristine Apartment with Free Street Parking

Pristine Apartment with Free Street Parking
Humboldt Park
The price is ￥118,004
￥136,203 total
includes taxes & fees
Jun 2 - Jun 3
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 Highland Park Hotel Reviews

Holiday Inn Chicago North-Evanston by IHG

Holiday Inn Chicago North-Evanston by IHG

10/10 Excellent
"This would be the PERFECT hotel if there was a pool! I love the staff, the location is fantastic, the parking is reasonable and connected to the hotel. I have stayed here twice in the last six weeks and both times were wonderful. The breakfast buffet is FANTASTIC and it's $10 a person. I absolutely recommend this hotel to anyone looking for a soft place to land"
Hannah 1-night trip
Posted 4 hours ago
Holiday Inn Chicago North-Evanston by IHG

Find out more about Highland Park

Highland Park B&B information

Number of reviews
2,272
Accommodation
10 B&B
Lowest Price
￥14,333
Highest Price
￥136,203

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. 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.