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Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

B&B in Highland Park

Dorothy's
1 bedroom, free WiFi, bed sheets

Dorothy's

3.0 star property
8.6 out of 10, Excellent, (52)
"Great little spot with all you need. Clean, cozy and a great breakfast!"
The price is AED 448
AED 655 total
includes taxes & fees
24 Jul - 25 Jul
Dorothy's
The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (584)
"Was a great stay!"
The price is AED 423
AED 644 total
includes taxes & fees
24 Jul - 25 Jul
The Villa Toscana
House 5863 - Chicago Bed and Breakfast
Exterior

House 5863 - Chicago Bed and Breakfast

3.5 star property
9.0 out of 10, Wonderful, (474)
"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 528
AED 830 total
includes taxes & fees
21 Jul - 22 Jul
House 5863 - Chicago Bed and Breakfast
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (367)
"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 738
AED 833 total
includes taxes & fees
23 Jul - 24 Jul
Ray's Bucktown B&B
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (249)
"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, (464)
"Excellent location. Beautiful property, extremely clean."
The price is AED 833
AED 978 total
includes taxes & fees
4 Aug - 5 Aug
The Sono Chicago
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (112)
"Enjoyed my short stay. Wish I could have spent more time here! Quiet, peaceful, safe, and comfortable. I travel frequently for work and this is by far, one of the best experiences I have had. Thank you Beth!"
The price is AED 962
AED 1,102 total
includes taxes & fees
24 Jul - 25 Jul
Harvey House Bed & Breakfast
Villa D' Citta
Lobby sitting area

Villa D' Citta

3.5 star property
9.4 out of 10, Exceptional, (103)
"great B&B and so much more. Friendly and helpful staff, this is my 3rd time here"
The price is AED 1,052
AED 1,235 total
includes taxes & fees
29 Jul - 30 Jul
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, (140)
"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 604
AED 1,019 total
includes taxes & fees
20 Jul - 21 Jul
Wrigleyville Suites Room 1
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 672
AED 1,108 total
includes taxes & fees
20 Jul - 21 Jul
Wrigleyville Suites Room 2
Wrigleyville Suites Room 3
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 3

2.0 star property
The price is AED 604
AED 1,019 total
includes taxes & fees
20 Jul - 21 Jul
Wrigleyville Suites Room 3
Five bedroom - 3 bath - Sleeps 12
5 bedrooms, free WiFi, bed sheets

Five bedroom - 3 bath - Sleeps 12

The price is AED 4,463
AED 6,644 total
includes taxes & fees
12 Aug - 13 Aug
Five bedroom - 3 bath - Sleeps 12
Wrigleyville Suites Room 5
Interior

Wrigleyville Suites Room 5

The price is AED 630
AED 1,055 total
includes taxes & fees
20 Jul - 21 Jul
Wrigleyville Suites Room 5
Wrigleyville Suites Room 6
Interior

Wrigleyville Suites Room 6

The price is AED 630
AED 1,055 total
includes taxes & fees
20 Jul - 21 Jul
Wrigleyville Suites Room 6
Wrigleyville Suites Room 4
Interior

Wrigleyville Suites Room 4

The price is AED 630
AED 1,038 total
includes taxes & fees
20 Jul - 21 Jul
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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Top Highland Park Hotel Reviews

Claridge House

Claridge House

10/10 Excellent
"This hotel is tucked away on a beautiful tree lined street in Old Town, a neighborhood very close to shopping & transportation. I was able to walk with my bags from the redline without any issues. There is a cute little bar on the premises and a nice airy lobby to congregate in. A charming boutique hotel that was clean and refreshed, with a sense of historical value. "
Stefanie 2-night trip
Posted 23 hours ago
Claridge House

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.