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Find a Bed and Breakfast in Highland Park

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Check prices for these dates

Next weekend
Feb 14 - Feb 16
In two weeks
Feb 21 - Feb 23
In one month
Mar 7 - Mar 9
In two months
Apr 4 - Apr 6

Browse Select Highland Park B&B

The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (525)
"Ok"
The price is CA $58
CA $126 total
includes taxes & fees
Feb 5 - Feb 6
The Villa Toscana
Dorothy's
Free WiFi, bed sheets

Dorothy's

3.0 star property
8.2 out of 10, Very good, (20)
"How nice it was and how close it was"
The price is CA $45
CA $104 total
includes taxes & fees
Feb 5 - Feb 6
Dorothy's
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (442)
"Our stay at The Sono was great! We were only staying a night and booked a queen room, and they gave us a free upgrade to a king room since it was unoccupied. The room was fantastic & clean, the breakfast was delicious with lots of variety and the voucher for free street parking made this the best option for our stay. I would definitely stay again."
The price is CA $228
CA $268 total
includes taxes & fees
Feb 16 - Feb 17
The Sono Chicago
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (239)
"The Wicker Park Inn was located close to many transportation options. The breakfast room was bright and sunny with good light breakfast options."
The price is CA $264
CA $310 total
includes taxes & fees
Feb 17 - Feb 18
Wicker Park Inn
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (341)
"This B&B is a gem. Loved it. It’s like staying in someone’s huge, comfortable home with a fabulous hostess. Plenty of parking, creative decor, and the huge made to order breakfast is fabulous. They have snacks, homemade baked goods and all kinds of drinks in the kitchen. They serve breakfast until 11 for late risers. Laundry, sauna, steam room. Will definitely stay again."
The price is CA $251
CA $283 total
includes taxes & fees
Feb 6 - Feb 7
Ray's Bucktown B&B
House 5863 - Chicago Bed and Breakfast
Exterior

House 5863 - Chicago Bed and Breakfast

3.5 star property
9.0 out of 10, Wonderful, (472)
"Erick was very friendly and responsive. The neighborhood around was wonderful. We walked everywhere we went and were able to park on the street with no problems. We would stay again. Thank you!"
House 5863 - Chicago Bed and Breakfast
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (107)
"This is a beautiful little stay that feels like a walk back in time with a wonderful host Beth and delicious options for food and activities! We will be back "
The price is CA $333
CA $370 total
includes taxes & fees
Feb 11 - Feb 12
Harvey House Bed & Breakfast
Villa D' Citta
Lobby sitting area

Villa D' Citta

3.5 star property
9.2 out of 10, Wonderful, (99)
"Unique experience staying within a block of DePaul School of Music. Lovely property with open kitchen and great breakfast/coffee. Nice outdoor area with fire pit. Stayed in Capone suite which was comfortable but noisy as it was downstairs just below the kitchen. Note that private bath is down the hall as this wasn’t explained well when I booked. Would stay again and I do recommend."
The price is CA $297
CA $348 total
includes taxes & fees
Feb 17 - Feb 18
Villa D' Citta
Wrigleyville Suites Room 1
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 1

2.0 star property
2.0 out of 10, (1)
"I would like to say that I was highly disappointed with the customer service, after already having the room booked for over a week I was contacted an hr and a half after check in on the day I was suppose to be there with additional requirements including a $200 fee (Hopefully I get that back) check in was at 3pm I wasnt able to get into my room till 6pm and I had a concert to attend at 8pm this rush caused more stress then it was worth but yes make sure the now $500 room is really worth it...
The price is CA $116
CA $240 total
includes taxes & fees
Feb 6 - Feb 7
Wrigleyville Suites Room 1
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Fridge, microwave, oven, stovetop

Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!

9.8 out of 10, Exceptional, (134)
"Our family of 4 enjoyed our short stay here. Great location that has everything you need a walking distance away. Jon was great to communicate with."
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Wrigleyville Suites Room 3
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 3

2.0 star property
The price is CA $116
CA $240 total
includes taxes & fees
Feb 6 - Feb 7
Wrigleyville Suites Room 3
Room in Town house Rogers Park
Smart TV

Room in Town house Rogers Park

Room in Town house Rogers Park
Presidential Suite
1 bedroom, iron/ironing board, WiFi, bed sheets

Presidential Suite

Presidential Suite
Adorable bed & breakfast in Chicago2222
Pool

Adorable bed & breakfast in Chicago2222

Adorable bed & breakfast in Chicago2222
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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Other property types in Highland Park

Level Chicago – Old Town
Front of property - evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (287)
"Amazing stay ! Love this property every time I’m in Chicago. "
The price is CA $264
CA $343 total
includes taxes & fees
Feb 9 - Feb 10
Level Chicago – Old Town
Wrigleyville Suites
Living area

Wrigleyville Suites

2.0 star property
8.8 out of 10, Excellent, (3)
"All conditions (like the deposit) should be clear in the description. This is not a hotel or a hotel, it's a private place. All this should be clear at the moment of reservation. The property was good enough but the communication with the host was troublesome. And the price is not that low. I will look for a hotel next time. "
The price is CA $105
CA $197 total
includes taxes & fees
Feb 5 - Feb 6
Wrigleyville Suites
Stunning 3 BR in prime Chicago location
Fridge, microwave, oven, stovetop

Stunning 3 BR in prime Chicago location

9.8 out of 10, Exceptional, (87)
"A clean, spacious, affordable option in a perfect location in Lincoln Park. Plan to return in the future."
Stunning 3 BR in prime Chicago location
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.

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, Ravinia Park and Chicago Botanic Garden 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: The Villa Toscana: 9 rooms. 18.1 mi (29.1 km) from the heart of Highland Park.Dorothy’s: 7 rooms. 18.1 mi (29.1 km) from the downtown core.
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.