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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured B&B in Highland Park

Dorothy's
1 bedroom, free WiFi, bed sheets

Dorothy's

3.0 star property
8.4 out of 10, Very good, (59)
"Great to stay, close walk to many places. Cleaning lady was very helpful and friendly. Rooms a bit small but would definitely stay there again."
The price is AU$205
includes taxes & fees
13 Aug - 14 Aug
Dorothy's
The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (588)
"Was a great stay!"
The price is AU$231
includes taxes & fees
12 Aug - 13 Aug
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, (369)
"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 AU$358
includes taxes & fees
10 Aug - 11 Aug
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, (476)
"Everything was taken care of! A wonderful stay. "
The price is AU$325
includes taxes & fees
11 Aug - 12 Aug
House 5863 - Chicago Bed and Breakfast
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (250)
"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
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (114)
"Large uniquely, decorated rooms,very comfortable ,great breakfast, great breakfast space, fun conversations at breakfast"
The price is AU$461
includes taxes & fees
11 Aug - 12 Aug
Harvey House Bed & Breakfast
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (465)
"Excellent location. Beautiful property, extremely clean."
The price is AU$353
includes taxes & fees
12 Aug - 13 Aug
The Sono Chicago
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, (143)
"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!
Villa D' Citta
Lobby sitting area

Villa D' Citta

3.5 star property
9.4 out of 10, Exceptional, (105)
"Would stay again anytime!!"
The price is AU$475
includes taxes & fees
11 Aug - 12 Aug
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...
Wrigleyville Suites Room 1
Wrigleyville Suites Room 3
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 3

2.0 star property
Wrigleyville Suites Room 3
Wrigleyville Suites Room 2
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 2

2.0 star property
2.0 out of 10, (1)
Wrigleyville Suites Room 2
Five bedroom - 3 bath - Sleeps 12
5 bedrooms, free WiFi, bed sheets

Five bedroom - 3 bath - Sleeps 12

The price is AU$2,297
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 AU$578
includes taxes & fees
10 Aug - 11 Aug
Wrigleyville Suites Room 5
Wrigleyville Suites Room 6
Interior

Wrigleyville Suites Room 6

The price is AU$578
includes taxes & fees
10 Aug - 11 Aug
Wrigleyville Suites Room 6
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 more offbeat than your standard hotel experience, a stay at a bed and breakfast might be the perfect option for your holiday. If your ideal holiday 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 a good option for your stay?
With attentive service, opportunities to meet guests from other places and breakfast served on site, B&Bs all have a unique environment.
What are the top B&Bs in Highland Park?
Here are some well-liked 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 city centre. 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 garden.
When should I book my B&B in Highland Park?
When you're dreaming of a stay in Highland Park, make sure that you take the year-round temperatures into account. The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of -1°C. Average annual precipitation for Highland Park is 1183 mm.
What is there to do in Highland Park?
Travellers enjoy Highland Park for its gardens and restaurants. If cultural attractions are high on your list, Ravinia Park and Ravinia Pavilion are spots to visit. You should 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?
Mapping out your trip in and around Highland Park is easy with these transportation options. Fly into Chicago, IL (PWK-Chicago Executive), which is located 6.8 mi (10.9 km) from the city centre. You can also search for flights into Chicago O'Hare International Airport (ORD), which is 15.1 mi (24.3 km) away. If you'd like to venture out around the area, you may want a rental car for your journey.