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Check prices for these dates

Next weekend
4 July - 6 July
In two weeks
11 July - 13 July
In one month
25 July - 27 July
In two months
22 Aug - 24 Aug

Featured Condo Rentals in Highland Park

NEW LUXURY CONDO WITH PATIO DECK
Fridge, microwave, oven, stovetop

NEW LUXURY CONDO WITH PATIO DECK

10.0 out of 10, Exceptional, (168)
"This is the perfect place for you to stay when you’re in Chicago. We have stayed here at least four or five times already the place is immaculate. If you need any help someone is there for you ASAP. "
NEW LUXURY CONDO WITH PATIO DECK
Cozy 3BR on Chicago's North Side & Free Parking On-premises!
Fridge, microwave, oven, stovetop

Cozy 3BR on Chicago's North Side & Free Parking On-premises!

10.0 out of 10, Exceptional, (1)
"Rogers Park is a richly diverse and fascinating neighborhood and this place gives great access to what the neighborhood has to offer. It has good transportation to the rest of the north side and downtown. Expect urban funky and fun. "
Cozy 3BR on Chicago's North Side & Free Parking On-premises!
Spacious 4BRCondo near Wrigley/Dtwn +FreeParking
Exterior

Spacious 4BRCondo near Wrigley/Dtwn +FreeParking

9.8 out of 10, Exceptional, (35)
"Fantastic! Great location, parking spot available, very clean! "
Spacious 4BRCondo near Wrigley/Dtwn +FreeParking
Wrigleyville Inn AllStar Unit
Exterior

Wrigleyville Inn AllStar Unit

9.4 out of 10, Exceptional, (18)
"Enjoyed a dinner party with friends Place was perfect Management helpful "
The price is AU$1,442
includes taxes & fees
9 July - 10 July
Wrigleyville Inn AllStar Unit
Classic Lincoln Park 2 bedroom condo- parking included
Outdoor dining

Classic Lincoln Park 2 bedroom condo- parking included

9.8 out of 10, Exceptional, (70)
"We had a great stay at the rental. Stacy was an amazing host. We would definitely stay there again. "
Classic Lincoln Park 2 bedroom condo- parking included
Walking distance to restaurants, shops and Lake Michigan,
Exterior

Walking distance to restaurants, shops and Lake Michigan,

9.8 out of 10, Exceptional, (202)
"Great property and easy process to check in/out. Lots of space and privacy. It was easy to get around and explore the city. "
Walking distance to restaurants, shops and Lake Michigan,
10 min walk to Stevenson Convention Center
Smart TV, books

10 min walk to Stevenson Convention Center

8.4 out of 10, Very good, (6)
"Very good location and clean. "
10 min walk to Stevenson Convention Center
Urban Chicago Escape ~ 1 Mi to Local Beaches!
Fridge, microwave, stovetop, dishwasher

Urban Chicago Escape ~ 1 Mi to Local Beaches!

9.4 out of 10, Exceptional, (17)
"The place was clean and fit our needs. Great location near the lake and close to the train stop."
Urban Chicago Escape ~ 1 Mi to Local Beaches!
Huge Projector and Designated Workspace - Near Wrigley!
2 bedrooms, desk, iron/ironing board, free WiFi

Huge Projector and Designated Workspace - Near Wrigley!

The price is AU$565
includes taxes & fees
14 July - 15 July
Huge Projector and Designated Workspace - Near Wrigley!
Entire 2 bedroom with Office & Deck!
Property grounds

Entire 2 bedroom with Office & Deck!

9.2 out of 10, Wonderful, (11)
"Good stay"
Entire 2 bedroom with Office & Deck!
Spacious 3-bedroom, 2-bath condo, free parking/Oak Park
Fridge, microwave, oven, stovetop

Spacious 3-bedroom, 2-bath condo, free parking/Oak Park

9.0 out of 10, Wonderful, (29)
"It was nice"
Spacious 3-bedroom, 2-bath condo, free parking/Oak Park
Spacious, Clean and Steps from Wrigley Field!
Private kitchen

Spacious, Clean and Steps from Wrigley Field!

9.8 out of 10, Exceptional, (13)
"Place was perfect, clean and comfortable. Location is fantastic!"
Spacious, Clean and Steps from Wrigley Field!
Across From Wrigley Field, Beautiful New 4 Bedroom Featured On Travel Channel!
Exterior

Across From Wrigley Field, Beautiful New 4 Bedroom Featured On Travel Channel!

9.6 out of 10, Exceptional, (22)
"The whole trip was so awesome but the room was so perfect. Being lifelong Cubs fans it was amazing to open the blinds and see wrigley field right there. Thank you so much for letting us have early arrival. It really was needed. We will check on using this property in the future."
The price is AU$1,654
includes taxes & fees
9 July - 10 July
Across From Wrigley Field, Beautiful New 4 Bedroom Featured On Travel Channel!
Free Parking, Balcony, near Universities, NAPA, Ravinia and train to Chicago
Fridge, microwave, oven, stovetop

Free Parking, Balcony, near Universities, NAPA, Ravinia and train to Chicago

10.0 out of 10, Exceptional, (24)
"Awesome stay!"
Free Parking, Balcony, near Universities, NAPA, Ravinia and train to Chicago
Chic Urban Retreat Near Wrigley Field w/Parking
Miscellaneous

Chic Urban Retreat Near Wrigley Field w/Parking

10.0 out of 10, Exceptional, (21)
"The property was nice. It had everything we needed, close to a store, restaurants and the train. "
The price is AU$691
includes taxes & fees
7 July - 8 July
Chic Urban Retreat Near Wrigley Field w/Parking
Just remodeled apartment close to airport and mall
Private kitchen

Just remodeled apartment close to airport and mall

10.0 out of 10, Exceptional, (11)
"The location was great for my purposes, nice apartment, great neighborhood and close to the airport."
The price is AU$370
includes taxes & fees
9 July - 10 July
Just remodeled apartment close to airport and mall
NEW LUXURY PENTHOUSE CONDO
Terrace/patio

NEW LUXURY PENTHOUSE CONDO

10.0 out of 10, Exceptional, (183)
"A perfect place to stay. The rooftop bar has the BEST views of the city, especially around sunset. I would definitely stay here again! "
NEW LUXURY PENTHOUSE CONDO
Stunning 3 BR in prime Chicago location
Fridge, microwave, oven, stovetop

Stunning 3 BR in prime Chicago location

9.8 out of 10, Exceptional, (102)
"Very clean, good location. "
Stunning 3 BR in prime Chicago location
Chicago Chic: Cozy 1BR with Stylish Workspace
Fridge, microwave, oven, stovetop

Chicago Chic: Cozy 1BR with Stylish Workspace

10.0 out of 10, Exceptional, (1)
"We enjoyed our stay here"
Chicago Chic: Cozy 1BR with Stylish Workspace
Walk to Lincoln Park, North Avenue Beach, and Second City! Lovely Old Town Charm! by AllSet Turnover
TV

Walk to Lincoln Park, North Avenue Beach, and Second City! Lovely Old Town Charm! by AllSet Turnover

9.6 out of 10, Exceptional, (22)
"The flat was super spacious and very cute! Walkable to everything that you would need. The location is fantastic as far as access to dining and the lakefront I will definitely be saving this one to visit regularly!"
Walk to Lincoln Park, North Avenue Beach, and Second City! Lovely Old Town Charm! by AllSet Turnover
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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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.