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Compare 14 B&B in Highland Park with updated reviews, rates, and availability.

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (542)
" This was a cute little suprise tucked in behind a row of store fronts in a busy area. It had a little courtyard which would be nice in warmer weather. There was plenty of grab and go food for breakfast. Overall, a pleasant find. However, there is a bright light that shines into room 8 in spite of curtain and a blackout shade might be a nice addition for that room. In addition, the check out maybe should be sent to people the night before as we left very early and had not received it yet....
The price is ¥6,931
¥14,034 total
includes taxes & fees
Apr 14 - Apr 15
The Villa Toscana

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (344)
"What a rad spot...great staff, A M A Z I N G breakfast (can I say Nutella and banana stuffed French toast?!), nice sauna on premise, clean rooms, so much to look at, and I parked in the garage! Will be back...daughters had a blast. "
The price is ¥25,639
¥28,945 total
includes taxes & fees
Apr 13 - Apr 14
Ray's Bucktown B&B

Dorothy's

3.0 star property
8.0 out of 10, Very Good, (27)
"We love Dorothy's! This is such a great, inexpensive option for a stay in a fantastic neighborhood. Would recommend to anyone!"
The price is ¥6,636
¥12,953 total
includes taxes & fees
Apr 15 - Apr 16
Dorothy's

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (450)
"This bed and breakfast was an absolutely breathtaking gem that surpassed every expectation we had, delivering an experience that went well beyond what the photographs could capture. From the moment we arrived, we were struck by the stunning beauty of the place, which seemed to offer everything one could possibly desire in a cozy getaway. The owners were the epitome of hospitality—warm, welcoming, and genuinely sweet—always ready to lend a hand with anything we needed, whether it was local...
The price is ¥19,819
¥23,265 total
includes taxes & fees
Apr 14 - Apr 15
The Sono Chicago

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (242)
"The Wicker Park Inn was located close to many transportation options. The breakfast room was bright and sunny with good light breakfast options."
The price is ¥35,442
¥41,607 total
includes taxes & fees
Apr 14 - Apr 15
Wicker Park Inn

Villa D' Citta

3.5 star property
9.2 out of 10, Wonderful, (99)
"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 ¥30,044
¥35,269 total
includes taxes & fees
Apr 16 - Apr 17
Villa D' Citta

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (110)
"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 ¥34,063
¥37,803 total
includes taxes & fees
Apr 21 - Apr 22
Harvey House Bed & Breakfast

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

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 ¥30,745
¥45,180 total
includes taxes & fees
Apr 29 - Apr 30
House 5863 - Chicago Bed and Breakfast

Room in Town house Rogers Park

Room in Town house Rogers Park

Wrigleyville Suites Room 3

2.0 star property
Wrigleyville Suites Room 3

Wrigleyville Suites Room 2

2.0 star property
2.0 out of 10, (1)
Wrigleyville Suites Room 2

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!

Presidential Suite

Presidential Suite

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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Other property types in Highland Park

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (301)
"Beautiful view, with apartment like feel to the property, safe and secure, walking distance to many resturants, stores and activities."
The price is ¥24,231
¥31,736 total
includes taxes & fees
Apr 21 - Apr 22
Level Chicago – Old Town

Wrigleyville Suites

2.0 star property
9.4 out of 10, Exceptional, (3)
"Very good place at a very good price! Communication is the only need for improvement in my opinion. "
The price is ¥21,234
¥32,300 total
includes taxes & fees
Apr 13 - Apr 14
Wrigleyville Suites

2-bedroom apartment just 2 minutes drive to Wrigley Field

2.0 star property
9.6 out of 10, Exceptional, (8)
"The property is very quiet, clean, well appointed, and is in a great location. It’s only a 3 minute walk to the Brown Line which easily gets you downtown in half an hour and not worry about parking. I did notice the absence of a microwave which would have been an added convenience. Overall, it suited my needs perfectly and will consider it again if I get back to Chicago."
The price is ¥18,433
¥43,663 total
includes taxes & fees
Apr 14 - Apr 15
2-bedroom apartment just 2 minutes drive to Wrigley Field
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 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: 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 downtown core.
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.