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, (491)
"This place was great! It was wonderfully located, clean, and ideal for a weekend away. I’m so glad I found it and will definitely keep in mind for future trips! The Halloween decor was fun too!"
The price is NZ$150
includes taxes & fees
17 Nov - 18 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, (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 NZ$358
includes taxes & fees
4 Nov - 5 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, (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 NZ$473
includes taxes & fees
3 Nov - 4 Nov
Wicker Park Inn
The Sono Chicago
Private kitchen
The Sono Chicago
3.5 star property
10.0 out of 10, Exceptional, (432)
"A warm and welcoming beautiful place. The staff was outstanding; from carrying my heavy luggage up three flights to offering great places to eat to accommodating my arrival and departure. Highly recommend. With a spectacular view of the city the rooftop is not to be missed!"
The price is NZ$331
includes taxes & fees
10 Nov - 11 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, (328)
"Great stay. Clean and parking was easy. Breakfast was great and pet friendly "
The price is NZ$301
includes taxes & fees
3 Nov - 4 Nov
Ray's Bucktown B&B
Villa D' Citta
Lobby sitting area
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 NZ$405
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, (103)
"Awesome, comfortable stay good food options would recommend "
The price is NZ$430
includes taxes & fees
4 Nov - 5 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...
The price is NZ$415
includes taxes & fees
3 Nov - 4 Nov
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
The price is NZ$415
includes taxes & fees
3 Nov - 4 Nov
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$74
includes taxes & fees
3 Nov - 4 Nov
Adorable bed & breakfast in Chicago2222
Wrigleyville Suites Room 2
Fridge, microwave, oven, stovetop
Wrigleyville Suites Room 2
2.0 star property
The price is NZ$415
includes taxes & fees
3 Nov - 4 Nov
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
Front of property - evening/night
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 NZ$473
includes taxes & fees
24 Nov - 25 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, (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
Exterior
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 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.