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Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

Compare 15 B&B in Highland Park with updated reviews, rates, and availability.

The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (558)
"Super easy to find parking, quick walk to cubs game and bars after. Safe neighborhood and the greatest pizza place right through the gate. It was awesome!"
The price is AED 323
AED 526 total
includes taxes & fees
5 Jun - 6 Jun
The Villa Toscana
Dorothy's
Free WiFi, bed sheets

Dorothy's

3.0 star property
8.4 out of 10, Very Good, (39)
"Great location. Super clean and close to transit for easy access to anywhere you need to go. "
The price is AED 320
AED 504 total
includes taxes & fees
4 Jun - 5 Jun
Dorothy's
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (356)
"I loved everything about it!!! The staff, for sure!!! The building and all the fun stuff inside! Breakfast! The neighborhood! I could live there!! "
The price is AED 658
AED 743 total
includes taxes & fees
3 Jun - 4 Jun
Ray's Bucktown B&B
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (456)
"Was very warm and welcoming.. room was clean and updated… staff was friendly..! Had a great time…"
The price is AED 643
AED 755 total
includes taxes & fees
4 Jun - 5 Jun
The Sono Chicago
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (244)
"Gorgeous, clean, lovely breakfast, accommodating staff"
The price is AED 1,094
AED 1,284 total
includes taxes & fees
10 Jun - 11 Jun
Wicker Park Inn
Villa D' Citta
Lobby sitting area

Villa D' Citta

3.5 star property
9.2 out of 10, Wonderful, (100)
"What a wonderful and unique place where everything is so beautifully decorated with the owners personalized touch. The kitchen and amenities are exceptional and the best part was breakfast and visiting with Gina. Will be our only go-to now in Chicago."
The price is AED 1,094
AED 1,284 total
includes taxes & fees
2 Jun - 3 Jun
Villa D' Citta
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (110)
"This was an amazing place to stay, highly recommended for something quiet and relaxing."
The price is AED 962
AED 1,068 total
includes taxes & fees
2 Jun - 3 Jun
Harvey House Bed & Breakfast
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, (135)
"We were thrilled with the little neighborhood and options for food, drinks and shopping. Super easy to hop on bus to and from Wrigley!"
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
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 AED 355
AED 691 total
includes taxes & fees
2 Jun - 3 Jun
Wrigleyville Suites Room 1
House 5863 - Chicago Bed and Breakfast
Exterior

House 5863 - Chicago Bed and Breakfast

3.5 star property
9.0 out of 10, Wonderful, (473)
"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!"
The price is AED 460
AED 745 total
includes taxes & fees
3 Jun - 4 Jun
House 5863 - Chicago Bed and Breakfast
Wrigleyville Suites Room 2
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 2

2.0 star property
2.0 out of 10, (1)
The price is AED 355
AED 691 total
includes taxes & fees
2 Jun - 3 Jun
Wrigleyville Suites Room 2
Wrigleyville Suites Room 3
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 3

2.0 star property
The price is AED 355
AED 691 total
includes taxes & fees
2 Jun - 3 Jun
Wrigleyville Suites Room 3
Five bedroom - 3 bath - Sleeps 12
Free WiFi, bed sheets

Five bedroom - 3 bath - Sleeps 12

The price is AED 3,350
AED 5,210 total
includes taxes & fees
16 Jun - 17 Jun
Five bedroom - 3 bath - Sleeps 12
Wrigleyville Suites Room 6
Interior

Wrigleyville Suites Room 6

Wrigleyville Suites Room 6
Wrigleyville Suites Room 5
Interior

Wrigleyville Suites Room 5

Wrigleyville Suites Room 5
Wrigleyville Suites Room 4
Interior

Wrigleyville Suites Room 4

Wrigleyville Suites Room 4
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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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: 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.