Photo by Meghan hernandez

Bed and Breakfast in Highland Park

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Check prices for these dates

Next weekend
21 Mar - 23 Mar
In two weeks
28 Mar - 30 Mar
In one month
11 Apr - 13 Apr
In two months
9 May - 11 May

Featured B&B in Highland Park

The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (534)
"Very accessible "
The price is NZ$140
includes taxes & fees
11 Mar - 12 Mar
The Villa Toscana
Dorothy's
Free WiFi, bed sheets

Dorothy's

3.0 star property
8.4 out of 10, Very good, (24)
"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 NZ$133
includes taxes & fees
11 Mar - 12 Mar
Dorothy's
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (447)
"Nice quiet building in one of the nicest parts of chicago"
The price is NZ$276
includes taxes & fees
11 Mar - 12 Mar
The Sono Chicago
Wicker Park Inn
Premium bedding, desk, laptop workspace, soundproofing

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 NZ$470
includes taxes & fees
11 Mar - 12 Mar
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, (342)
"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 NZ$342
includes taxes & fees
11 Mar - 12 Mar
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 NZ$491
includes taxes & fees
11 Mar - 12 Mar
House 5863 - Chicago Bed and Breakfast
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (109)
"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 NZ$449
includes taxes & fees
17 Mar - 18 Mar
Harvey House Bed & Breakfast
Villa D' Citta
Lobby sitting area

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 NZ$423
includes taxes & fees
18 Mar - 19 Mar
Villa D' Citta
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$284
includes taxes & fees
11 Mar - 12 Mar
Wrigleyville Suites Room 1
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 3
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 3

2.0 star property
The price is NZ$284
includes taxes & fees
11 Mar - 12 Mar
Wrigleyville Suites Room 3
Room in Town house Rogers Park
Smart TV

Room in Town house Rogers Park

Room in Town house Rogers Park
Wrigleyville Suites Room 2
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 2

2.0 star property
2.0 out of 10, (1)
The price is NZ$284
includes taxes & fees
11 Mar - 12 Mar
Wrigleyville Suites Room 2
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

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
Front of property - evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (290)
"Amazing stay ! Love this property every time I’m in Chicago. "
The price is NZ$373
includes taxes & fees
12 Mar - 13 Mar
Level Chicago – Old Town
Wrigleyville Suites
Living area

Wrigleyville Suites

2.0 star property
10.0 out of 10, Exceptional, (2)
The price is NZ$226
includes taxes & fees
11 Mar - 12 Mar
Wrigleyville Suites
Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-parking!
3 bedrooms, WiFi, bed sheets

Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-parking!

9.2 out of 10, Wonderful, (73)
"Loved this location near Wrigley Stadium. "
Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-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 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, Chicago Botanic Garden and Moraine Park 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. Dorothy’s: 7 rooms. 18.1 mi (29.1 km) from the city centre.
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.