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Check prices for these dates

Next weekend
Aug 14 - Aug 16
In two weeks
Aug 21 - Aug 23
In one month
Sep 4 - Sep 6
In two months
Oct 2 - Oct 4

Our top choices for Highland Park bed & breakfast

Living area

1. Dorothy's

Dorothy's
2.0 star property
Lakeview
8.6 out of 10, Excellent, (168 reviews)
"Great location, just what we needed."
United States
Stephanie
The price is ￥10,785
￥18,180 total
includes taxes & fees
Aug 10 - Aug 11
Dorothy's
Presidential Studio Suite, 2 Bedrooms (1st Floor) | Living area | 51-inch flat-screen TV with cable channels, TV, Netflix

2. House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (513 reviews)
"I love the location of this B&B. Right across from a beautiful park, walkable to some fabulous restaurants and shops - and the red line is so close! My room was clean, quiet, cutely decorated. The kitchen was well-stocked with breakfast options. My one recommendation would be - I wish the coffee was higher quality! The host was prompt, friendly, and responsive to my needs. I'll be back for sure!"
United States
Kimberly
The price is ￥19,866
￥33,049 total
includes taxes & fees
Aug 26 - Aug 27
House 5863 - Chicago Bed and Breakfast
Double Room, Private Bathroom (Venetian) | Terrace/patio

3. The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
8.0 out of 10, Very Good, (662 reviews)
"Clean room, self serve breakfast, free street parking permit, cute cats!"
United States
Shu-Ting
The price is ￥13,335
￥21,991 total
includes taxes & fees
Aug 10 - Aug 11
The Villa Toscana
Private kitchen

4. The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (538 reviews)
"Close to some great places to eat locally and about an hour walk to river and central business activities......and a very comfy bed!"
United States
Bronwyn
The price is ￥29,169
￥34,243 total
includes taxes & fees
Aug 9 - Aug 10
The Sono Chicago
Spa

5. Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (412 reviews)
"Superb breakfast and very friendly staff. Great place to stay!"
United States
mary
The price is ￥29,968
￥33,831 total
includes taxes & fees
Aug 9 - Aug 10
Ray's Bucktown B&B
Property entrance

6. Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (132 reviews)
"This was an amazing place to stay, highly recommended for something quiet and relaxing."
United States
Mia
The price is ￥42,729
￥47,421 total
includes taxes & fees
Aug 17 - Aug 18
Harvey House Bed & Breakfast
Lobby sitting area

7. Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (122 reviews)
"Wonderful! Will stay here again."
United States
Elsa
The price is ￥47,200
￥55,409 total
includes taxes & fees
Aug 10 - Aug 11
Villa D' Citta
Property entrance

8. Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (277 reviews)
"clean room, staff was helpful. We enjoyed our stay."
United States
Maggie
The price is ￥48,859
￥57,355 total
includes taxes & fees
Aug 31 - Sep 1
Wicker Park Inn
Coffee/tea maker, fridge, microwave, oven

9. Pristine Apartment with Free Street Parking

Pristine Apartment with Free Street Parking
Humboldt Park
The price is ￥73,990
￥86,311 total
includes taxes & fees
Aug 24 - Aug 25
Pristine Apartment with Free Street Parking
TV

10. Five bedroom - 3 bath - Sleeps 12

Five bedroom - 3 bath - Sleeps 12
Lakeview
The price is ￥133,749
￥251,825 total
includes taxes & fees
Aug 24 - Aug 25
Five bedroom - 3 bath - Sleeps 12
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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Top Highland Park Hotel Reviews

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good
"Staff was amazing, room and bathroom were clean-but linens and bedding were not replaced or made. Breakfast had good options/however the restaurant menu was disappointing. Bedroom and Hall carpet needs replacing. Great location, I would stay here again. Thank you."
Adelaine 2-night trip
Posted 5 hours ago
The Chicago Hotel Collection Ambassador Gold Coast

Find out more about Highland Park

Highland Park B&B information

Number of reviews
2,824
Accommodation
12 B&B
Lowest Price
￥18,180
Highest Price
￥251,825

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?
Here are some well-liked B&Bs in the surrounding area: Dorothy's: 7 rooms. 18.1 mi (29.1 km) from the downtown core. House 5863 - Chicago Bed and Breakfast: 7 rooms. Situated 15 mi (24.2 km) from the heart of Highland Park. Enjoy the designer toiletries and private yard. The Villa Toscana: 9 rooms. 18.1 mi (29.1 km) from the heart of downtown.
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.