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Featured Condo Rentals in Highland Park

Chic Urban Retreat Near Wrigley Field w/Parking

10.0 out of 10, Exceptional, (33)
"The property was amazing, clean and well organized. Parking was a breeze and check in was easy. Would recommend this place to anyone looking to stay in the area."
The price is AU$711
includes taxes & fees
2 Sept - 3 Sept
Chic Urban Retreat Near Wrigley Field w/Parking

Spacious 4BRCondo near Wrigley/Dtwn +FreeParking

9.6 out of 10, Exceptional, (42)
"It was a great place to stay and very spacious!"
The price is AU$1,162
includes taxes & fees
18 Sept - 19 Sept
Spacious 4BRCondo near Wrigley/Dtwn +FreeParking

3BR Modern Condo near Wrigley/Dwtn +Free Parking

9.6 out of 10, Exceptional, (37)
"3 night stay with a family of 5. Was perfect for us! Clean, quiet, and easy to access. Would stay again! "
3BR Modern Condo near Wrigley/Dwtn +Free Parking

Stunning 3 BR in prime Chicago location

9.8 out of 10, Exceptional, (109)
"This property had all the comforts we needed and is in a great location. Would absolutely love to stay there again!"
Stunning 3 BR in prime Chicago location

Lincoln Park/depaul 8 Bed 1 Parking Spot Sleeps 18 by AllSet Turnover

9.4 out of 10, Exceptional, (16)
"We had an absolutely lovely stay here!"
Lincoln Park/depaul 8 Bed 1 Parking Spot Sleeps 18 by AllSet Turnover

Private 2BR/2BA Suites, Desk, Kitchenette, Lake Access, Morse CTA, Loyola Campus

Private 2BR/2BA Suites, Desk, Kitchenette, Lake Access, Morse CTA, Loyola Campus

Entire 2 bedroom with Office & Deck!

8.8 out of 10, Excellent, (13)
"Good stay"
Entire 2 bedroom with Office & Deck!

Wrigley Field All Star Suite 3 Bedrooms 2 Bath

9.4 out of 10, Exceptional, (18)
"Enjoyed a dinner party with friends Place was perfect Management helpful "
The price is AU$1,475
includes taxes & fees
8 Sept - 9 Sept
Wrigley Field All Star Suite 3 Bedrooms 2 Bath

Up to 8 Spacious lovely Chicago-style 3BDR condo. Safe & quiet neighborhood

8.6 out of 10, Excellent, (19)
"This place was clean and host was very nice"
Up to 8 Spacious lovely Chicago-style 3BDR condo. Safe & quiet neighborhood

Parking, Balcony, Near Universities, Ravinia, NAPA & Train to Chicago

9.8 out of 10, Exceptional, (19)
"Everything went well. Will stay again."
Parking, Balcony, Near Universities, Ravinia, NAPA & Train to Chicago

Perfect for Groups! Steps to the Beach and Room for All! Enjoy All Andersonville Has to Offer! by AllSet Turnover

10.0 out of 10, Exceptional, (35)
"Wonderful location and home. Thanks to our hosts!"
Perfect for Groups! Steps to the Beach and Room for All! Enjoy All Andersonville Has to Offer! by AllSet Turnover

Chicago Luxury Penthouse Massive Rooftop Walk to Beach and Restaurants

10.0 out of 10, Exceptional, (2)
"I used to live in Chicago and have a short term rental in Ohio myself. This place is legit. This property is in the best location close to beach restaurants and bars. Perfect for college reunion. Rooftop was awesome place for us to catch up over coffee and plan the day. The kitchen has everything we needed. Speakers throughout was a nice touch. I can’t be more complementary of the hosts responsiveness and helpfulness. We would definitely stay here again."
Chicago Luxury Penthouse Massive Rooftop Walk to Beach and Restaurants

Walking distance to restaurants, shops and Lake Michigan,

9.6 out of 10, Exceptional, (183)
"We had a great time and the property manager was very thoughtful. It was a very cute apartment and great location very close to Loyola."
Walking distance to restaurants, shops and Lake Michigan,

Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms

9.6 out of 10, Exceptional, (24)
"It was great to be able to walk to Cubs games and back right after. It was a cold three days worth of game so very nice to be able to walk across the street and get warm quick. The place was absolutely great! Very spacious and comfy. The property manager was so very easy to work with when we requested an early check in. Thanks and we look forward to our next stay there. Go Cubs Go!!!"
The price is AU$1,693
includes taxes & fees
8 Sept - 9 Sept
Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms

Wrigley Field Grand Slam Suite 4 Bedrooms, 2 Bathrooms

9.0 out of 10, Wonderful, (14)
"We loved the location and the VRBO itself. Clean, stocked with essentials, and easy to communicate with!"
The price is AU$1,708
includes taxes & fees
1 Sept - 2 Sept
Wrigley Field Grand Slam Suite 4 Bedrooms, 2 Bathrooms

Two-Story STUNNER in Iconic Old Town Chicago by AllSet Turnover

9.2 out of 10, Wonderful, (12)
"Our stay was wonderful. We had everything that we needed and more! It was very spacious and clean. "
Two-Story STUNNER in Iconic Old Town Chicago by AllSet Turnover

Bright 2BR Apt w/ Private Entrance & Laundry by AllSet Turnover

2.0 star property
8.8 out of 10, Excellent, (6)
"Stayed 3 nights visiting my son. Good location, large apt., nicely decorated. I wish the tub/shower had a grab bar. The jacuzzi tub has a high profile and is difficult for older adults to step in and out. It was quiet inside--even the nearby train was hard to hear. I did trip several times on the drain cover right outside the entry door. Be careful!"
Bright 2BR Apt w/ Private Entrance & Laundry by AllSet Turnover

NEW LUXURY CONDO WITH PATIO DECK

10.0 out of 10, Exceptional, (176)
"repeat visitor, the place is awesome and Jessica and Shannon are everything a person could ask for in a VRBO host. Thank you!"
NEW LUXURY CONDO WITH PATIO DECK

Wrigley Field Home Run 4 Bedroom, 2 Bathroom

9.6 out of 10, Exceptional, (18)
"Would definitely stay there again "
The price is AU$1,693
includes taxes & fees
8 Sept - 9 Sept
Wrigley Field Home Run 4 Bedroom, 2 Bathroom

The Exclusive- 7 Bed, 6 Bath Retreat

9.6 out of 10, Exceptional, (19)
"Great location for our activities. Responded well to our concerns. The pictures are an accurate representation of the property."
The Exclusive- 7 Bed, 6 Bath Retreat
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

Find out more about Highland Park

Find out more about Highland Park

Highland Park Condo Rentals information

Number of reviews
639
Accommodation
145 Condo Rentals
Lowest Price
AU$711
Highest Price
AU$1,708

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Frequently asked questions

What is there to do in Highland Park near my condo?
Whatever you love doing, Highland Park has loads to keep you on the hop. Marriott Theatre, North Shore Centre for the Performing Arts and Kohl Childrens Museum are on most visitors' agendas. Don't leave without exploring Writers Theatre, Oil Lamp Theatre and Valentino Vineyards either. With Expedia's condo deals in Highland Park, you can discover even more popular attractions like these with the cash you save.