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Compare 15 B&B in Highland Park with updated reviews, rates, and availability.

The Villa Toscana
Lounge
The Villa Toscana
2.5 star property
7.8 out of 10, Good, (493)
"Digital check in a little confusing but Brandon was on site and every person there was helpful. It is a big old BnB place. They had breakfast "
The price is SAR 162
SAR 341 total
includes taxes & fees
24 Nov 2024 - 25 Nov 2024
The Villa Toscana
Old Chicago Inn
Property entrance
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, (469)
"Cozy little place. The only adjustment I could make is have better options for breakfast like eggs and bacon and such. No complaints tho because it was still great to sleep in. Super clean"
The price is SAR 502
SAR 801 total
includes taxes & fees
5 Nov 2024 - 6 Nov 2024
House 5863 - Chicago Bed and Breakfast
Wicker Park Inn
Room
Wicker Park Inn
3.5 star property
9.0 out of 10, Wonderful, (237)
"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 SAR 903
SAR 1,060 total
includes taxes & fees
6 Nov 2024 - 7 Nov 2024
Wicker Park Inn
The Sono Chicago
Room
The Sono Chicago
3.5 star property
10.0 out of 10, Exceptional, (433)
"It was very clean and tidy. When we needed new towels they were there. Halfway through our stay everything was deep cleaned. The owners were extremely nice and offered a wide variety for breakfast. Any questions we had were answered quickly and effortlessly. Our room was cozy and the upstairs roof patio had a view that was beyond breathtaking. The place is close to downtown and in a good area to go anywhere in Chicago. "
The price is SAR 541
SAR 635 total
includes taxes & fees
12 Nov 2024 - 13 Nov 2024
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, (328)
"Great stay. Clean and parking was easy. Breakfast was great and pet friendly "
The price is SAR 598
SAR 675 total
includes taxes & fees
6 Nov 2024 - 7 Nov 2024
Ray's Bucktown B&B
Villa D' Citta
Front of property
Villa D' Citta
3.5 star property
9.4 out of 10, Exceptional, (93)
"Edith was amazing! She greeted us each morning with coffee, breakfast, and a smile😊 Except the last morning, a woman that introduced herself as the Asst Manager came in while we were eating and complained about the new coffee maker and was pretty unpleasant, but everything and everyone else was excellent!! "
The price is SAR 773
SAR 908 total
includes taxes & fees
2 Dec 2024 - 3 Dec 2024
Villa D' Citta
Harvey House Bed & Breakfast
Interior
Harvey House Bed & Breakfast
4.0 star property
9.8 out of 10, Exceptional, (103)
"Awesome, comfortable stay good food options would recommend "
The price is SAR 868
SAR 963 total
includes taxes & fees
5 Nov 2024 - 6 Nov 2024
Harvey House Bed & Breakfast
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Dining Room
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
Bedroom with a queen-sized bed, patterned wallpaper, two windows with blinds, and a geometric rug on the floor.
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 SAR 367
SAR 703 total
includes taxes & fees
5 Nov 2024 - 6 Nov 2024
Wrigleyville Suites Room 1
Room in Town house Rogers Park
Living area
Room in Town house Rogers Park
Room in Town house Rogers Park
Wrigleyville Suites Room 3
Cozy bedroom with a grey patterned wallpaper wall, a queen sized bed with grey linens and white towels, two bedside tables with lamps, and a window with natural light.
Wrigleyville Suites Room 3
2.0 star property
The price is SAR 367
SAR 703 total
includes taxes & fees
5 Nov 2024 - 6 Nov 2024
Wrigleyville Suites Room 3
Presidential Suite
Bathroom
Presidential Suite
Presidential Suite
Adorable bed & breakfast in Chicago2222
Point of interest
Adorable bed & breakfast in Chicago2222
The price is SAR 83
SAR 165 total
includes taxes & fees
5 Nov 2024 - 6 Nov 2024
Adorable bed & breakfast in Chicago2222
Wrigleyville Suites Room 2
Bedroom with a metal bunk bed, patterned wallpaper, a wooden chair, and a window with blinds.
Wrigleyville Suites Room 2
2.0 star property
The price is SAR 367
SAR 703 total
includes taxes & fees
5 Nov 2024 - 6 Nov 2024
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.
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Other property types in Highland Park

Level Chicago – Old Town
Outdoor pool
Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (267)
"Service was great, room was neat and very clean. Would stay again!"
The price is SAR 852
SAR 1,064 total
includes taxes & fees
24 Nov 2024 - 25 Nov 2024
Level Chicago – Old Town
Walking distance to restaurants, shops and Lake Michigan,
Large kitchen with open floor plan, hardwood floor throughout.
Walking distance to restaurants, shops and Lake Michigan,
9.6 out of 10, Exceptional, (170)
"We enjoyed our stay in Rogers Park. The property was nice and a welcome retreat at the end of the day. "
Walking distance to restaurants, shops and Lake Michigan,
Ground Floor Studios in Chicago by 747 Lofts
Room
Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
9.8 out of 10, Exceptional, (11)
"Easy to check in, good information for parking in the area. The place was clean and nice."
Ground Floor Studios in Chicago by 747 Lofts
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, Ravinia Park and Chicago Botanic Garden 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.Old Chicago Inn: 10 rooms. 18.3 mi (29.4 km) from the downtown core. Enjoy the free full breakfast and fireplace in the lobby. House 5863 - Chicago Bed and Breakfast: 7 rooms. 15 mi (24.2 km) from the heart of downtown. Enjoy the designer toiletries and private yard.
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.