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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Condo Rentals in Highland Park

Spacious 4BRCondo near Wrigley/Dtwn +FreeParking
Fridge, microwave, oven, stovetop

Spacious 4BRCondo near Wrigley/Dtwn +FreeParking

9.8 out of 10, Exceptional, (37)
"Fantastic! Great location, parking spot available, very clean! "
Spacious 4BRCondo near Wrigley/Dtwn +FreeParking
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, (20)
"We met friends for the weekend. This was such a fun, comfortable place to stay. Plus it was a 5 minute walk to the train station, which made sight seeing in Chicago so accessible! We would definitely stay again!"
Urban Chicago Escape ~ 1 Mi to Local Beaches!
Entire 2 bedroom with Office & Deck!
Property grounds

Entire 2 bedroom with Office & Deck!

9.0 out of 10, Wonderful, (12)
"Good stay"
Entire 2 bedroom with Office & Deck!
Walking distance to restaurants, shops and Lake Michigan,
Exterior

Walking distance to restaurants, shops and Lake Michigan,

9.6 out of 10, Exceptional, (183)
"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,
NEW LUXURY CONDO WITH PATIO DECK
Property grounds

NEW LUXURY CONDO WITH PATIO DECK

10.0 out of 10, Exceptional, (173)
"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
Walk to Train: Convenient Skokie Condo!
Interior

Walk to Train: Convenient Skokie Condo!

2.0 star property
10.0 out of 10, Exceptional, (2)
"The condo was spacious and situated in a nice area. Place is located nearby the yellow Skokie CTA line to take you into the city for activities. Host was helpful and quick to respond to any questions we had."
Walk to Train: Convenient Skokie Condo!
Wrigleyville Inn - Unit 1
Terrace/patio

Wrigleyville Inn - Unit 1

10.0 out of 10, Exceptional, (25)
"This home is beautiful, clean, and very well appointed. The location is great and in walking distance to so much. "
Wrigleyville Inn - Unit 1
NEW LUXURY PENTHOUSE CONDO
Terrace/patio

NEW LUXURY PENTHOUSE CONDO

10.0 out of 10, Exceptional, (185)
"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
Just remodeled apartment close to airport and mall
Paper towels

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$392
includes taxes & fees
9 Aug - 10 Aug
Just remodeled apartment close to airport and mall
Stunning 3 BR in prime Chicago location
Fridge, microwave, oven, stovetop

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
Wrigley Field Grand Slam Suite 4 Bedrooms, 2 Bathrooms
Private kitchen

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$1,706
includes taxes & fees
11 Aug - 12 Aug
Wrigley Field Grand Slam Suite 4 Bedrooms, 2 Bathrooms
Lincoln Park/depaul 8 Bed 1 Parking Spot Sleeps 18 by AllSet Turnover
Dining

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

9.6 out of 10, Exceptional, (15)
"We had an absolutely lovely stay here!"
Lincoln Park/depaul 8 Bed 1 Parking Spot Sleeps 18 by AllSet Turnover
Free Parking, Balcony, near Universities, NAPA, Ravinia and train to Chicago
Property grounds

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

10.0 out of 10, Exceptional, (26)
"Awesome stay!"
Free Parking, Balcony, near Universities, NAPA, Ravinia and train to Chicago
Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover
Fridge, microwave, oven, dishwasher

Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover

9.4 out of 10, Exceptional, (28)
"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
Wrigleyville Inn - Unit 3
Fridge, microwave, oven, stovetop

Wrigleyville Inn - Unit 3

10.0 out of 10, Exceptional, (34)
"Great location, great property! Will come here for my next Wrigleyville stay. "
Wrigleyville Inn - Unit 3
Parking, Balcony, Near Universities, Ravinia, NAPA & Train to Chicago
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (18)
"Everything went well. Will stay again."
Parking, Balcony, Near Universities, Ravinia, NAPA & Train to Chicago
Modern Wrigley Oasis with Parking!
Smart TV

Modern Wrigley Oasis with Parking!

9.6 out of 10, Exceptional, (43)
"This was our second stay in this great apartment—big spaces, comfy beds, very clean AND fully stocked on all necessary supplies like dish soap, paper towels, extra towels, and shampoo/body wash. East walk to great restaurants too. "
Modern Wrigley Oasis with Parking!
Chic Urban Retreat Near Wrigley Field w/Parking
Exterior detail

Chic Urban Retreat Near Wrigley Field w/Parking

10.0 out of 10, Exceptional, (25)
"The property was nice. It had everything we needed, close to a store, restaurants and the train. "
The price is AU$702
includes taxes & fees
6 Aug - 7 Aug
Chic Urban Retreat Near Wrigley Field w/Parking
3BR Modern Condo near Wrigley/Dwtn +Free Parking
Fridge, microwave, oven, stovetop

3BR Modern Condo near Wrigley/Dwtn +Free Parking

9.4 out of 10, Exceptional, (33)
"3 night stay with a family of 5. Was perfect for us! Clean, quiet, and easy to access. Would stay again! "
The price is AU$1,280
includes taxes & fees
31 Aug - 1 Sept
3BR Modern Condo near Wrigley/Dwtn +Free Parking
Spacious, Clean and Steps from Wrigley Field!
Private kitchen

Spacious, Clean and Steps from Wrigley Field!

9.8 out of 10, Exceptional, (15)
"Great stay in Wrigleyville. Steps to the park and all the entertainment. Would definitely stay again. "
Spacious, Clean and Steps 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.
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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.