Photo by Meghan hernandez

Search Condo Rentals in Highland Park

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

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

Stunning 3 BR in prime Chicago location

9.8 out of 10, Exceptional, (91)
"Very clean, good location. "
Stunning 3 BR in prime Chicago location

NEW LUXURY PENTHOUSE CONDO

10.0 out of 10, Exceptional, (173)
"Just wanted to be specific, there is a jetted jacuzzi, not a hot tub. So if you and your party are planning for a little hot tub time, this isn't it, however the jetted jacuzzi AND the jetted shower are to die for! I had a wonderful time with my friends here, and had the most relaxing weekend. Thank you so much for a beautiful and restful stay in the most luxury penthouse!"
NEW LUXURY PENTHOUSE CONDO

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

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

Urban Chicago Vacation Rental Condo Near Beach!

9.0 out of 10, Wonderful, (16)
"This apartment was so cute, quiet and a great stay for my family and I. The host was able to accommodate extra blankets and towels for us during our stay. As well with it being a pet friendly property our dog enjoyed his stay and a little bit of the city life. Dinner is walkable as well as access to the main transit system. This is definitely a good spot for a girls trip or even a single that wanted to different kind of stay in Chicago!"
Urban Chicago Vacation Rental Condo Near Beach!

Spacious 4BRCondo near Wrigley/Dtwn +FreeParking

9.8 out of 10, Exceptional, (29)
"The property was exactly as pictured and described. The neighborhood is quiet and we enjoyed walking it and exploring the area. Ola was very responsive and helpful with any questions we had. The beds were SO COMFORTABLE!!! All in all, a great time was had and we would definitely rent this property again. "
Spacious 4BRCondo near Wrigley/Dtwn +FreeParking

Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover

10.0 out of 10, Exceptional, (23)
"We had a great stay and the accommodations were wonderful. The apartment had everything one would need including games and books. The location is great and plenty of restaurants and stores within walking distance. "
Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover

Classic Lincoln Park 2 bedroom condo- parking included

9.8 out of 10, Exceptional, (64)
"I lived in Chicago for years and this was the first time I brought my son. It was exactly what I was hoping for. Walk up in an old building, restaurant on the bottom floor, transit a quick walk away."
Classic Lincoln Park 2 bedroom condo- parking included

3BR Modern Condo near Wrigley/Dwtn +Free Parking

9.4 out of 10, Exceptional, (29)
"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

North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment

10.0 out of 10, Exceptional, (104)
"We absolutely loved staying at this property. We stayed with three children under the age of 5 and everything we could have thought of for our kids was there. My kids especially loved the sparkles in the tub and some of the toys in the apartment. The host did a great job of recommending places we could go and checking in to make sure we were doing okay. The location is great, within walking distance to the train and great parks. Would recommend this spot to anyone witb families looking to...
North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment

Wrigleyville Inn - Garden Unit

10.0 out of 10, Exceptional, (25)
"The location to Wrigley Field and public transit was great! Cleanest place we’ve ever stayed. The only downside was the very raucous upstairs neighbors who like to karaoke late at night on the weekends."
Wrigleyville Inn - Garden Unit

NEW LUXURY CONDO WITH PATIO DECK

10.0 out of 10, Exceptional, (158)
"It was an amazing weekend with family and friends. The space was perfect for the occasion. Enough space for everyone to be comfortable. The open concept was everything!! I’ll definitely rent again!"
NEW LUXURY CONDO WITH PATIO DECK

Chic Urban Retreat Near Wrigley Field w/Parking

10.0 out of 10, Exceptional, (12)
"This property is conveniently located in a cute neighborhood and had everything we needed for a weekend near Wrigley Field. The parking spot was a great added bonus and check in/out was seamless. We really enjoyed our stay! "
The price is SAR 563
SAR 1,663 total
includes taxes & fees
19 Apr - 20 Apr
Chic Urban Retreat Near Wrigley Field w/Parking

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

10.0 out of 10, Exceptional, (89)
"Easy. Didn’t even need to communicate with owner. Went smoothly."
Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field

Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover

9.6 out of 10, Exceptional, (25)
"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

Chicago Condo: Near Lincoln Park & DePaul!

9.6 out of 10, Exceptional, (8)
"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!

Spacious Wicker Park Hideaway with Parking!

8.8 out of 10, Excellent, (6)
"Very clean with new appliances, cute kitchen and beds were comfy. The location was perfect for visiting our Wicker Park family. Walkable neighborhood. Drove or ubered to the downtown sites. Lots of restaurants and bars nearby. The host was very responsive. Overall great visit. to any questions. "
Spacious Wicker Park Hideaway with Parking!

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

9.8 out of 10, Exceptional, (13)
"My family had a long visit to Chicago and this apartment was perfect! It looks just as it appears in pictures. Very comfortable! We hope to stay here again!"
Parking, Balcony, Near Universities, Ravinia, NAPA & Train to Chicago

Walking distance to restaurants, shops and Lake Michigan,

9.6 out of 10, Exceptional, (175)
"We were very pleased with the property. Stayed there over the Thanksgiving holiday & weekend while visiting my older daughter. Nice neighborhood & easy location to get to other parts of the city. Everything was as depicted in the description and communication with management was excellent. Would stay here again."
Walking distance to restaurants, shops and Lake Michigan,

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

9.0 out of 10, Wonderful, (26)
"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

Walking distance to restaurants, shops and Lake Michigan,

9.8 out of 10, Exceptional, (197)
"Everything was as described. Pretty entry was to “beautiful lady” of a building. The unit we were in was nicely refurbished. Modern but the old building charm maintained. We traveled light so the in suite laundry was great. Brand new fridge the day we got there. Amazing bedding & towels. "
Walking distance to restaurants, shops and Lake Michigan,
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.
Don't see what you're looking for?
See all available properties in Highland Park
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Highland Park

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (302)
"Only thing was no communication on the pool location and the arcade games so I just didn't go and how to work the stove other that it was a beautiful experience. I think you should let people smoke on the balcony. I mean it is a expensive location and marijuana is legal a recreational use think about it. "
The price is SAR 686
SAR 889 total
includes taxes & fees
22 Apr - 23 Apr
Level Chicago – Old Town

Wrigleyville Suites

2.0 star property
9.4 out of 10, Exceptional, (3)
"Very good place at a very good price! Communication is the only need for improvement in my opinion. "
The price is SAR 540
SAR 822 total
includes taxes & fees
17 Apr - 18 Apr
Wrigleyville Suites

Bright Garden Studio

9.0 out of 10, Wonderful, (21)
"clean & nice. "
The price is SAR 296
SAR 873 total
includes taxes & fees
22 Apr - 23 Apr
Bright Garden Studio
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

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 Expedia’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 Expedia’s convenient filter tool. Tailor your search results by star rating, amenities and budget to secure unbeatable rates in just a few keystrokes.