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

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (549)
"Super cute house! Very detailed directions on check in, super easy excellent neighbourhood!"
The price is AED 327
AED 531 total
includes taxes & fees
11 May - 12 May
The Villa Toscana

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (349)
"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 AED 619
AED 699 total
includes taxes & fees
11 May - 12 May
Ray's Bucktown B&B

Dorothy's

3.0 star property
8.0 out of 10, Very Good, (32)
"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 AED 338
AED 525 total
includes taxes & fees
11 May - 12 May
Dorothy's

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (453)
"Was very warm and welcoming.. room was clean and updated… staff was friendly..! Had a great time…"
The price is AED 621
AED 730 total
includes taxes & fees
21 May - 22 May
The Sono Chicago

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (242)
"Great spot for a quick stay!"
The price is AED 1,010
AED 1,185 total
includes taxes & fees
19 May - 20 May
Wicker Park Inn

Villa D' Citta

3.5 star property
9.2 out of 10, Wonderful, (100)
"What a wonderful and unique place where everything is so beautifully decorated with the owners personalized touch. The kitchen and amenities are exceptional and the best part was breakfast and visiting with Gina. Will be our only go-to now in Chicago."
The price is AED 841
AED 987 total
includes taxes & fees
12 May - 13 May
Villa D' Citta

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (110)
"Awesome, comfortable stay good food options would recommend "
The price is AED 962
AED 1,068 total
includes taxes & fees
12 May - 13 May
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...
The price is AED 338
AED 671 total
includes taxes & fees
11 May - 12 May
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 AED 689
AED 1,029 total
includes taxes & fees
11 May - 12 May
House 5863 - Chicago Bed and Breakfast

Wrigleyville Suites Room 3

2.0 star property
The price is AED 338
AED 671 total
includes taxes & fees
11 May - 12 May
Wrigleyville Suites Room 3

Wrigleyville Suites Room 2

2.0 star property
2.0 out of 10, (1)
The price is AED 338
AED 671 total
includes taxes & fees
11 May - 12 May
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, (310)
"It was really nice overall! Would recommend "
The price is AED 772
AED 988 total
includes taxes & fees
12 May - 13 May
Level Chicago – Old Town

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (60)
"This hotel was outstanding in all respects. "
The price is AED 678
AED 776 total
includes taxes & fees
11 May - 12 May
The Gem Museum Suites

Wrigleyville Suites

2.0 star property
8.4 out of 10, Very Good, (6)
The price is AED 476
AED 742 total
includes taxes & fees
11 May - 12 May
Wrigleyville Suites
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.