Photo by Meghan hernandez

Bed and Breakfast in Highland Park

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Featured B&B in Highland Park

The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (499)
"Stayed here twice. Both times was problem free and just as I expected. Location is prime. "
The price is NZ$129
includes taxes & fees
25 Nov - 26 Nov
The Villa Toscana
Old Chicago Inn
Fireplace

Old Chicago Inn

2.0 star property
7.4 out of 10, Good, (762)
"Wonderful alternative to usual hotel properties at comparable prices. "
Old Chicago Inn
House 5863 - Chicago Bed and Breakfast
Exterior

House 5863 - Chicago Bed and Breakfast

3.5 star property
9.0 out of 10, Wonderful, (470)
"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$355
includes taxes & fees
26 Nov - 27 Nov
House 5863 - Chicago Bed and Breakfast
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (238)
"This was the second time that I stayed at this property. The rooms are so beautiful and all the people are so friendly. I love the area and easy access to parking, would definitely stay here again and again! :)"
The price is NZ$461
includes taxes & fees
25 Nov - 26 Nov
Wicker Park Inn
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (435)
"We absolutely loved staying here. Everything was clean and comfortable. Breakfast was lovely, and there were beverages and snacks available. Easy check in and out, easy parking, everything was smooth and wonderful. "
The price is NZ$266
includes taxes & fees
25 Nov - 26 Nov
The Sono Chicago
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (331)
"Great place to stay for solo or couples. Breakfast service is incredible. "
The price is NZ$278
includes taxes & fees
2 Dec - 3 Dec
Ray's Bucktown B&B
Villa D' Citta
Lobby sitting area

Villa D' Citta

3.5 star property
9.4 out of 10, Exceptional, (97)
"Unique experience staying within a block of DePaul School of Music. Lovely property with open kitchen and great breakfast/coffee. Nice outdoor area with fire pit. Stayed in Capone suite which was comfortable but noisy as it was downstairs just below the kitchen. Note that private bath is down the hall as this wasn’t explained well when I booked. Would stay again and I do recommend."
The price is NZ$414
includes taxes & fees
2 Dec - 3 Dec
Villa D' Citta
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (105)
"This is a beautiful little stay that feels like a walk back in time with a wonderful host Beth and delicious options for food and activities! We will be back "
The price is NZ$439
includes taxes & fees
25 Nov - 26 Nov
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, (134)
"Our family of 4 enjoyed our short stay here. Great location that has everything you need a walking distance away. Jon was great to communicate with."
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...
Wrigleyville Suites Room 1
Room in Town house Rogers Park
Smart TV

Room in Town house Rogers Park

Room in Town house Rogers Park
Wrigleyville Suites Room 3
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 3

2.0 star property
Wrigleyville Suites Room 3
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

The price is NZ$75
includes taxes & fees
25 Nov - 26 Nov
Adorable bed & breakfast in Chicago2222
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
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.
Don't see what you're looking for?
See all available properties in Highland Park
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Highland Park

Level Chicago – Old Town
Front of property - evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (269)
"Beautiful place with amazing amenities. Perfect stay for adults or families alike! Highly recommend!"
The price is NZ$388
includes taxes & fees
26 Nov - 27 Nov
Level Chicago – Old Town
Walking distance to restaurants, shops and Lake Michigan,
Exterior

Walking distance to restaurants, shops and Lake Michigan,

9.6 out of 10, Exceptional, (173)
"Good location clean"
Walking distance to restaurants, shops and Lake Michigan,
Wrigley/Southport Corridor Garden Oasis +parking!
Exterior

Wrigley/Southport Corridor Garden Oasis +parking!

9.8 out of 10, Exceptional, (66)
"This little apartment is close to my cousin in Wrigleyville and a perfect location to get downtown and to see a Bears game (they are terrible right now). Entry instructions were easy and apartment was very clean."
Wrigley/Southport Corridor Garden Oasis +parking!
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

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, Ravinia Park and Chicago Botanic Garden 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. Old Chicago Inn: 10 rooms. 18.3 mi (29.4 km) from the city centre. Enjoy the free full breakfast and fireplace in reception. House 5863 - Chicago Bed and Breakfast: 7 rooms. 15 mi (24.2 km) from the city centre. 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.