Photo by Meghan hernandez

Bed and Breakfast in Highland Park

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Featured B&B in Highland Park

The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (508)
"Our stay was amazing. Centrally located on the Boystown district. We checked in late at night. We woke up and were freezing. We were a little concerned that we’d be cold the whole stay. We then found a space heater on our room which kept the room extremely room. Staff is very nice and knowledgeable of things to do and aee"
The price is NZ$161
includes taxes & fees
2 Jan - 3 Jan 2025
The Villa Toscana
Dorothy's
Free WiFi, bed sheets

Dorothy's

3.0 star property
8.4 out of 10, Very good, (11)
"UwU"
The price is NZ$148
includes taxes & fees
14 Jan - 15 Jan 2025
Dorothy's
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (337)
"I chose Rays s it was conveniently located near my client. A B&B would never be my choice for a business trip but I feel lucky I found this place. Great accommodations. Felt like a mini vacation. I’m returning when I can. "
The price is NZ$297
includes taxes & fees
1 Jan - 2 Jan 2025
Ray's Bucktown B&B
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (440)
"The Sono Chicago was a dream! Staff & Owner were friendly, accommodating, and gave great advice for dining & entertainment. Our bed was comfortable, bathroom was luxurious, and the balcony was fun for morning coffee. There is a nice rooftop area with seating and fire tables where you can relax/socialize. Parking was convenient and FREE! I def recommend The Sono Chicago!"
The price is NZ$277
includes taxes & fees
1 Jan - 2 Jan 2025
The Sono Chicago
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (107)
"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$454
includes taxes & fees
30 Dec - 31 Dec
Harvey House Bed & 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$380
includes taxes & fees
6 Jan - 7 Jan 2025
Wicker Park Inn
House 5863 - Chicago Bed and Breakfast
Exterior

House 5863 - Chicago Bed and Breakfast

3.5 star property
9.0 out of 10, Wonderful, (472)
"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$395
includes taxes & fees
1 Jan - 2 Jan 2025
House 5863 - Chicago Bed and Breakfast
Villa D' Citta
Lobby sitting area

Villa D' Citta

3.5 star property
9.2 out of 10, Wonderful, (98)
"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$428
includes taxes & fees
6 Jan - 7 Jan 2025
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...
The price is NZ$307
includes taxes & fees
29 Dec - 30 Dec
Wrigleyville Suites Room 1
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!
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
The price is NZ$307
includes taxes & fees
29 Dec - 30 Dec
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)
The price is NZ$307
includes taxes & fees
29 Dec - 30 Dec
Wrigleyville Suites Room 2
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$78
includes taxes & fees
27 Dec - 28 Dec
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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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, (277)
"Great location and stay"
The price is NZ$402
includes taxes & fees
4 Jan - 5 Jan 2025
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, (174)
"We were very pleased with the property. Stayed there over the Thanksgiving holiday & weekend while visiting my older daughter. Nice neighborhood & easy location to get to other parts of the city. Everything was as depicted in the description and communication with management was excellent. Would stay here again."
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, (68)
"Very clean and comfortable place!"
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.

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. Dorothy’s: 7 rooms. 18.1 mi (29.1 km) from the city centre.
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 Chicago Botanic Garden and Lake Michigan 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.