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Compare 16 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, (507)
"Complimentary breakfast was far beyond "continental", it was handmade from scratch and incredible! That's what really stood out. Otherwise my stay was also great, everything the listing claimed to be."
The price is AED 184
AED 363 total
includes taxes & fees
5 Jan - 6 January 2025
The Villa Toscana
Dorothy's
Room

Dorothy's

3.0 star property
8.4 out of 10, Very Good, (11)
"Love the coziness of the location and th area is nice and safe "
The price is AED 132
AED 284 total
includes taxes & fees
6 Jan - 7 January 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 AED 559
AED 631 total
includes taxes & fees
16 Jan - 17 January 2025
Ray's Bucktown B&B
The Sono Chicago
Room

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 AED 626
AED 735 total
includes taxes & fees
29 Dec - 30 Dec
The Sono Chicago
Harvey House Bed & Breakfast
Interior

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 AED 848
AED 942 total
includes taxes & fees
30 Dec - 31 Dec
Harvey House Bed & Breakfast
Wicker Park Inn
Room

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 AED 672
AED 788 total
includes taxes & fees
5 Jan - 6 January 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 AED 520
AED 820 total
includes taxes & fees
5 Jan - 6 January 2025
House 5863 - Chicago Bed and Breakfast
Villa D' Citta
Front of property

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 AED 756
AED 888 total
includes taxes & fees
6 Jan - 7 January 2025
Villa D' Citta
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 AED 275
AED 587 total
includes taxes & fees
24 Dec - 25 Dec
Wrigleyville Suites Room 1
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!
Room in Town house Rogers Park
Living area

Room in Town house Rogers Park

Room in Town house Rogers Park
Four bedroom apartment

Four bedroom apartment

The price is AED 419
AED 1,134 total
includes taxes & fees
6 Jan - 7 January 2025
Four bedroom apartment
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
2.0 out of 10, (1)
The price is AED 275
AED 587 total
includes taxes & fees
24 Dec - 25 Dec
Wrigleyville Suites Room 2
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 AED 275
AED 587 total
includes taxes & fees
24 Dec - 25 Dec
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 AED 81
AED 162 total
includes taxes & fees
24 Dec - 25 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
Outdoor pool

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (277)
"I loved the amenities available to us - garage parking, washer/dryer in unit, full kitchen and fully furnished. Staff were polite and helpful. Great location"
The price is AED 649
AED 835 total
includes taxes & fees
3 Jan - 4 January 2025
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, (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!
Living area

Wrigley/Southport Corridor Garden Oasis +parking!

9.8 out of 10, Exceptional, (67)
"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 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.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 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?
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.