Photo by Meghan hernandez

Bed and Breakfast in Highland Park

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
18 Jul - 20 Jul
In two weeks
25 Jul - 27 Jul
In one month
8 Aug - 10 Aug
In two months
5 Sept - 7 Sept

Featured B&B in Highland Park

Dorothy's
Classic design room with a bed, mirror, and lamp, offering a view of a nearby building.

Dorothy's

3.0 star property
8.6 out of 10, Excellent, (49)
"Great little spot with all you need. Clean, cozy and a great breakfast!"
The price is NZ$261
includes taxes & fees
14 July - 15 July
Dorothy's
The Villa Toscana
Stroll through this charming neighborhood to a traditional two-story house with a cozy front porch and balcony.

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (581)
"Was a great stay!"
The price is NZ$267
includes taxes & fees
14 July - 15 July
The Villa Toscana
Ray's Bucktown B&B
Experience the charm of this historic building, featuring a welcoming entrance, lush garden, and large windows offering views of the surrounding area.

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (365)
"Always a treat to stay at Ray’s. Funky kitschy decor from bygone years. By far THE BEST breakfast menu! "
The price is NZ$398
includes taxes & fees
14 July - 15 July
Ray's Bucktown B&B
The Sono Chicago
Enjoy cooking in this well-equipped kitchen with a central island, sink, and oven.

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (463)
"Excellent location. Beautiful property, extremely clean."
The price is NZ$371
includes taxes & fees
14 July - 15 July
The Sono Chicago
House 5863 - Chicago Bed and Breakfast
Stunning corner building with a brick facade and large windows, surrounded by lush greenery.

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 NZ$376
includes taxes & fees
23 July - 24 July
House 5863 - Chicago Bed and Breakfast
Harvey House Bed & Breakfast
Enter a classic space with a traditional feel, featuring a dresser, lamp, and ornate rug.

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (110)
"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 NZ$500
includes taxes & fees
24 July - 25 July
Harvey House Bed & Breakfast
Wicker Park Inn
Welcome to The Wicker Park Inn, a charming urban B&B located at 1329 N. Wicker Park.

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (248)
"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
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Kitchen features a gas range, double sink, and dishwasher.

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

9.8 out of 10, Exceptional, (139)
"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
Step into a grand lobby with a classic staircase, elegant seating area, and beautiful views.

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 NZ$583
includes taxes & fees
14 July - 15 July
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 2
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 2

2.0 star property
2.0 out of 10, (1)
The price is NZ$498
includes taxes & fees
11 July - 12 July
Wrigleyville Suites Room 2
Wrigleyville Suites Room 3
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 3

2.0 star property
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 NZ$3,637
includes taxes & fees
3 Aug - 4 Aug
Five bedroom - 3 bath - Sleeps 12
Wrigleyville Suites Room 6
Enjoy a view of the street from the large window with multiple panes, featuring a plant on the windowsill.

Wrigleyville Suites Room 6

Wrigleyville Suites Room 6
Wrigleyville Suites Room 5
Enjoy a peaceful view of the street from the large window, complete with a potted plant on the windowsill.

Wrigleyville Suites Room 5

The price is NZ$526
includes taxes & fees
11 July - 12 July
Wrigleyville Suites Room 5
Wrigleyville Suites Room 4
Enjoy a view of the street from the large window with multiple panes, featuring a plant on the windowsill.

Wrigleyville Suites Room 4

Wrigleyville Suites Room 4
Presidential Suite
Relax in this serene bedroom with a large bed, ceiling fan, and a dresser with drawers.

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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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: 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 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.