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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

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, (530)
"4th time staying and enjoy everything as advertised "
The price is AED 202
AED 384 total
includes taxes & fees
24 Feb - 25 Feb
The Villa Toscana
Dorothy's
Room

Dorothy's

3.0 star property
8.2 out of 10, Very Good, (21)
"Was having surgery but was canceled so I didn’t get to stay very long but would definitely stay again"
The price is AED 116
AED 264 total
includes taxes & fees
24 Feb - 25 Feb
Dorothy's
The Sono Chicago
Room

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (444)
"Was very warm and welcoming.. room was clean and updated… staff was friendly..! Had a great time…"
The price is AED 480
AED 564 total
includes taxes & fees
25 Feb - 26 Feb
The Sono Chicago
Wicker Park Inn
Room

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (241)
"Very cute and dainty place to stay! Lovely staff! Very clean and homey! "
The price is AED 672
AED 788 total
includes taxes & fees
24 Feb - 25 Feb
Wicker Park Inn
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (341)
"This B&B is a gem. Loved it. It’s like staying in someone’s huge, comfortable home with a fabulous hostess. Plenty of parking, creative decor, and the huge made to order breakfast is fabulous. They have snacks, homemade baked goods and all kinds of drinks in the kitchen. They serve breakfast until 11 for late risers. Laundry, sauna, steam room. Will definitely stay again."
The price is AED 639
AED 721 total
includes taxes & fees
24 Feb - 25 Feb
Ray's Bucktown B&B
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 766
AED 1,125 total
includes taxes & fees
11 Mar - 12 Mar
House 5863 - Chicago Bed and Breakfast
Harvey House Bed & Breakfast
Interior

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (108)
"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
24 Feb - 25 Feb
Harvey House Bed & Breakfast
Villa D' Citta
Front of property

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 AED 756
AED 888 total
includes taxes & fees
24 Feb - 25 Feb
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 296
AED 620 total
includes taxes & fees
24 Feb - 25 Feb
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!
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 296
AED 620 total
includes taxes & fees
24 Feb - 25 Feb
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 296
AED 620 total
includes taxes & fees
24 Feb - 25 Feb
Wrigleyville Suites Room 3
Room in Town house Rogers Park
Living area

Room in Town house Rogers Park

Room in Town house Rogers Park
Presidential Suite
Bathroom

Presidential Suite

Presidential Suite
Adorable bed & breakfast in Chicago2222
Point of interest

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
Outdoor pool

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (288)
"Amazing stay ! Love this property every time I’m in Chicago. "
The price is AED 529
AED 703 total
includes taxes & fees
27 Feb - 28 Feb
Level Chicago – Old Town
Great 3 bedroom rental unit near Logan Square
Interior

Great 3 bedroom rental unit near Logan Square

9.4 out of 10, Exceptional, (23)
"Safe neighborhood and super responsive host. I would definitely book again."
Great 3 bedroom rental unit near Logan Square
Wrigleyville Suites
Terrace/patio

Wrigleyville Suites

2.0 star property
10.0 out of 10, Exceptional, (2)
The price is AED 295
AED 529 total
includes taxes & fees
24 Feb - 25 Feb
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, 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 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.