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Check prices for these dates

Next weekend
12 Sep - 14 Sep
In two weeks
19 Sep - 21 Sep
In one month
3 Oct - 5 Oct
In two months
31 Oct - 2 Nov

B&B in Highland Park

Dorothy's
Free WiFi, bed sheets

Dorothy's

3.0 star property
8.2 out of 10, Very Good, (67)
"Very friendly and helpful staff. Rooms and bathrooms are very clean. I enjoyed my stay., it was cozy and comfortable. I would definitely stay at Dorothys again if I am back in the area.. I would also recommend it to friends meeting to stay near Wrigley or downtown."
The price is AED 294
AED 473 total
includes taxes & fees
29 Sep - 30 Sep
Dorothy's
The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (594)
"Was a great stay!"
The price is AED 205
AED 388 total
includes taxes & fees
4 Sep - 5 Sep
The Villa Toscana
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (371)
"We had an amazing stay at Ray's. They made the entire process from start to finish simple and easy. They went above and beyond for us in many ways and we will definitely be back! "
The price is AED 635
AED 716 total
includes taxes & fees
4 Sep - 5 Sep
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, (480)
"Everything was taken care of! A wonderful stay. "
The price is AED 444
AED 724 total
includes taxes & fees
10 Sep - 11 Sep
House 5863 - Chicago Bed and Breakfast
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (251)
"This was a great alternative to a typical hotel. The staff was extremely helpful and courteous. The room was very nice and the amenities were great. I would definitely stay again!"
Wicker Park Inn
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (470)
"Loved the shared kitchen access! "
The price is AED 604
AED 709 total
includes taxes & fees
4 Sep - 5 Sep
The Sono Chicago
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (116)
"Large uniquely, decorated rooms,very comfortable ,great breakfast, great breakfast space, fun conversations at breakfast"
The price is AED 962
AED 1,068 total
includes taxes & fees
8 Sep - 9 Sep
Harvey House Bed & Breakfast
Villa D' Citta
Lobby sitting area

Villa D' Citta

3.5 star property
9.4 out of 10, Exceptional, (106)
"Would stay again anytime!!"
The price is AED 967
AED 1,135 total
includes taxes & fees
1 Oct - 2 Oct
Villa D' Citta
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, (147)
"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 3
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 3

2.0 star property
The price is AED 296
AED 629 total
includes taxes & fees
4 Sep - 5 Sep
Wrigleyville Suites Room 3
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 296
AED 629 total
includes taxes & fees
4 Sep - 5 Sep
Wrigleyville Suites Room 1
Wrigleyville Suites Room 5
Interior

Wrigleyville Suites Room 5

The price is AED 309
AED 645 total
includes taxes & fees
4 Sep - 5 Sep
Wrigleyville Suites Room 5
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 296
AED 629 total
includes taxes & fees
4 Sep - 5 Sep
Wrigleyville Suites Room 2
Wrigleyville Suites Room 4
Interior

Wrigleyville Suites Room 4

The price is AED 309
AED 645 total
includes taxes & fees
4 Sep - 5 Sep
Wrigleyville Suites Room 4
Five bedroom - 3 bath - Sleeps 12
5 bedrooms, free WiFi, bed sheets

Five bedroom - 3 bath - Sleeps 12

The price is AED 2,755
AED 4,425 total
includes taxes & fees
29 Sep - 30 Sep
Five bedroom - 3 bath - Sleeps 12
Wrigleyville Suites Room 6
Interior

Wrigleyville Suites Room 6

Wrigleyville Suites Room 6
Adorable bed & breakfast in Chicago2222
Pool

Adorable bed & breakfast in Chicago2222

2.0 star property
Adorable bed & breakfast in Chicago2222
Presidential Suite
1 bedroom, iron/ironing board, WiFi, bed sheets

Presidential Suite

Presidential Suite
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

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

10/10 Excellent
"Access to airport transportation"
Maria 1-night trip
Posted 7 days ago
Hilton Chicago O'Hare Airport

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. 18.1 mi (29.1 km) from the downtown core. House 5863 - Chicago Bed and Breakfast: 7 rooms. Situated 15 mi (24.2 km) from the heart 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.