Photo by Meghan hernandez

Search Condo Rentals in Highland Park

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Compare 147 Condo Rentals in Highland Park with updated reviews, rates, and availability.

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

NEW LUXURY CONDO WITH PATIO DECK

10.0 out of 10, Exceptional, (163)
"This is the perfect place for you to stay when youā€™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
Historic Gold Coast Condo - Half Block From Beach & Major Attractions
Interior

Historic Gold Coast Condo - Half Block From Beach & Major Attractions

Historic Gold Coast Condo - Half Block From Beach & Major Attractions
Walking distance to restaurants, shops and Lake Michigan,
Exterior

Walking distance to restaurants, shops and Lake Michigan,

9.6 out of 10, Exceptional, (178)
"We enjoyed our stay in Rogers Park. The property was nice and a welcome retreat at the end of the day. "
Walking distance to restaurants, shops and Lake Michigan,
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!
Stunning 3 BR in prime Chicago location
Fridge, microwave, oven, stovetop

Stunning 3 BR in prime Chicago location

9.8 out of 10, Exceptional, (100)
"We fully enjoyed our stay - location, space, communication were all excellent!"
Stunning 3 BR in prime Chicago location
Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover
TV

Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover

9.4 out of 10, Exceptional, (26)
"The place was super nice, very clean, and quiet. It was perfectly located for our needs. We were visiting my daughter and brand new granddaughter, and hope to make it our new home away from home when we visit."
Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover
Chic Urban Retreat Near Wrigley Field w/Parking
Miscellaneous

Chic Urban Retreat Near Wrigley Field w/Parking

10.0 out of 10, Exceptional, (19)
"Clean, comfortable, professional, smooth and helpful transactions. A wonderful place I look forward to returning to very soon. "
The price is AEDĀ 551
AEDĀ 1,640 total
includes taxes & fees
4 Jun - 5 Jun
Chic Urban Retreat Near Wrigley Field w/Parking
Gorgeous 4 Bedroom with Pool Table steps from Wrigley Field Sleeps 9
Fridge, microwave, oven, stovetop

Gorgeous 4 Bedroom with Pool Table steps from Wrigley Field Sleeps 9

9.8 out of 10, Exceptional, (13)
"Great experience. Would highly recommend"
The price is AEDĀ 1,759
AEDĀ 3,965 total
includes taxes & fees
4 Jun - 5 Jun
Gorgeous 4 Bedroom with Pool Table steps from Wrigley Field Sleeps 9
Spacious, Clean and Steps from Wrigley Field!
Private kitchen

Spacious, Clean and Steps from Wrigley Field!

9.8 out of 10, Exceptional, (11)
"Nice place/ property and location. Having the parking space was a great addition. Close to great restaurants "
Spacious, Clean and Steps from Wrigley Field!
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)
"Property was in a good area, less than 15 min to our destination. Plenty of restaurants and shopping nearby. Mark communication was veey good as well. "
Free Parking, Balcony, near Universities, NAPA, Ravinia and train to Chicago
"Serenity of Evanston" 2 BDR/2Bath Modern-Luxe Suite
Fridge, microwave, oven, stovetop

"Serenity of Evanston" 2 BDR/2Bath Modern-Luxe Suite

10.0 out of 10, Exceptional, (48)
"Great stay!"
"Serenity of Evanston" 2 BDR/2Bath Modern-Luxe Suite
Urban Chicago Vacation Rental Condo Near Beach!
Beach nearby

Urban Chicago Vacation Rental Condo Near Beach!

9.2 out of 10, Wonderful, (19)
"Had a great stay at this property. Property was clean, in good condition and had no issues during the stay. We were in town for college visits and location was great. Easy access to downtown, Loyola and Evanston. Very walkable, convenient for driving to other amenities and felt safe without any issues. Used parking garage just a block away. Easy, no issues and great experience."
Urban Chicago Vacation Rental Condo Near Beach!
NEW LUXURY PENTHOUSE CONDO
Terrace/patio

NEW LUXURY PENTHOUSE CONDO

10.0 out of 10, Exceptional, (181)
"My friends and I have driven down to Chicago every year now for around 4 years and we've stayed at different places each time. This place was the best one we've stayed at yet! Highly stocked and well-organized kitchen as well. Would highly recommend."
NEW LUXURY PENTHOUSE CONDO
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, (28)
"Stayed here for my niece's bah mitzvah. There were 6 of us and it was the perfect size."
Spacious 3-bedroom, 2-bath condo, free parking/Oak Park
Spacious 4BRCondo near Wrigley/Dtwn +FreeParking
Exterior

Spacious 4BRCondo near Wrigley/Dtwn +FreeParking

9.8 out of 10, Exceptional, (34)
"It was a great place to stay and very spacious!"
Spacious 4BRCondo near Wrigley/Dtwn +FreeParking
Chicago Condo: Near Lincoln Park & DePaul!
Fridge, microwave, stovetop, coffee/tea maker

Chicago Condo: Near Lincoln Park & DePaul!

9.6 out of 10, Exceptional, (10)
"You can't beat the location, the street is lovely and quiet and close to public transit, Lincoln Park, shopping, etc. The condo is small but well appointed and clean. (There wasn't soap/shampoos so pack accordingly : )). Overall a lovely place in a great location. "
Chicago Condo: Near Lincoln Park & DePaul!
Chicago 1BR: Stylish Stay with Workspace
Fridge, microwave, oven, stovetop

Chicago 1BR: Stylish Stay with Workspace

Chicago 1BR: Stylish Stay with Workspace
3BR Modern Condo near Wrigley/Dwtn +Free Parking
Miscellaneous

3BR Modern Condo near Wrigley/Dwtn +Free Parking

9.4 out of 10, Exceptional, (30)
"Easy check in and lovely stay- thank you!"
3BR Modern Condo near Wrigley/Dwtn +Free Parking
"Melody of Evanston" 3BD, 2BA UrbanLux Condo
Interior

"Melody of Evanston" 3BD, 2BA UrbanLux Condo

2.0 star property
9.8 out of 10, Exceptional, (9)
"Great location and nice clean property. Will stay here again."
"Melody of Evanston" 3BD, 2BA UrbanLux Condo
Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field
Smart TV, fireplace, printers

Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field

10.0 out of 10, Exceptional, (94)
"Great location and condo will definitely be back !"
Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Frequently asked questions

Why book your condo in Highland Park with Expedia?
Booking a condo in Highland Park is as easy as entering your travel dates and picking a place suited to your needs. After something low cost or luxurious, or a stay that also includes a kitchenette? Use Expediaā€™s search filters to further narrow your search results and find your dream fit.
How can I find cheap condos in Highland Park?
The quickest way to track down cheap condos in Highland Park is with Expediaā€™s convenient filter tool. Tailor your search results by star rating, amenities and budget to secure unbeatable rates in just a few keystrokes.