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Condo Rentals in Highland Park

Chic Urban Retreat Near Wrigley Field w/Parking

10.0 out of 10, Exceptional, (37)
"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."
Chic Urban Retreat Near Wrigley Field w/Parking

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

Spacious 3BRCondo near Wrigley/Dtwn +FreeParking

9.6 out of 10, Exceptional, (45)
"It was a great place to stay and very spacious!"
Spacious 3BRCondo near Wrigley/Dtwn +FreeParking

3BR Modern Condo near Wrigley/Dwtn +Free Parking

9.6 out of 10, Exceptional, (39)
"3 night stay with a family of 5. Was perfect for us! Clean, quiet, and easy to access. Would stay again! "
The price is SAR 1,151
SAR 2,396 total
includes taxes & fees
8 Oct - 9 Oct
3BR Modern Condo near Wrigley/Dwtn +Free Parking

Stunning 3 BR in prime Chicago location

9.8 out of 10, Exceptional, (115)
"Great location within walking distance to Wrigley Field and countless restaurants. "
Stunning 3 BR in prime Chicago location

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

10.0 out of 10, Exceptional, (107)
"This was a great house, location, host....made our weekend easy and enjoyable!!"
Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field

Spacious, Clean and Steps from Wrigley Field!

9.8 out of 10, Exceptional, (22)
"Great location, clean and spacious. A little loud with the train close by but added to the Chicago experience! "
Spacious, Clean and Steps from Wrigley Field!

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

NEW LUXURY CONDO WITH PATIO DECK

10.0 out of 10, Exceptional, (181)
"Wonderful place to stay. We would stay there again. "
NEW LUXURY CONDO WITH PATIO DECK

Wrigleyville Inn - Unit 3

10.0 out of 10, Exceptional, (42)
"The property was perfect for our stay. Easy walk to baseball and food options were great."
Wrigleyville Inn - Unit 3

The Exclusive- 7 Bed, 6 Bath Retreat

9.6 out of 10, Exceptional, (19)
"Adam's building was the perfect space for our team offsite in Chicago. Very centrally located with the best coffee in the city downstairs! Would definitely stay here again."
The Exclusive- 7 Bed, 6 Bath Retreat

Wrigleyville Inn - Unit 2

10.0 out of 10, Exceptional, (14)
"Great VRBO! So clean and nice. Will definitely be back!"
Wrigleyville Inn - Unit 2

NEW LUXURY PENTHOUSE CONDO

10.0 out of 10, Exceptional, (190)
"We had a great stay! The house was clean, comfortable, and had everything we needed. Highly recommend!"
NEW LUXURY PENTHOUSE CONDO

Walking distance to restaurants, shops and Lake Michigan,

9.6 out of 10, Exceptional, (184)
"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,

Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover

9.4 out of 10, Exceptional, (29)
"Perfect location. Quiet, beautiful neighborhood. Would definitely stay again. "
Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover

Walking distance to restaurants, shops and Lake Michigan,

9.8 out of 10, Exceptional, (207)
"The place was excellent. In fact everything about our stay was excellent. Ross was a great host. Stay here and you won’t be disappointed!!"
Walking distance to restaurants, shops and Lake Michigan,

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

10.0 out of 10, Exceptional, (32)
"The apartment was very clean and comfortable, it was a great base for a long weekend in the city. Access to transit was very easy, and a nice 20-25 walk to Wrigley Field. We loved Everybody’s Coffee around the corner, great coffee and breakfast!"
Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover

Modern Comfort 2 Bd Condo in Iconic Lincoln Square by AllSet Turnover

9.0 out of 10, Wonderful, (12)
"Location was safe and very convenient. Condo was clean and the kitchen was well enough equipped. Tony's Fish Market was awesome and right behind the condo complex. They are a full grocery store and had hot food and salad bar. The only reason I didn't rate higher was the parking. My assigned spot was great, but someone parked in it one night and the concierge service wanted me to park in a rental spot located offsite and several minute walk away. Not convenient when it's past midnight. Overall a...
Modern Comfort 2 Bd Condo in Iconic Lincoln Square by AllSet Turnover

1910 Charming Historic Flat - Walk to Beach & Loyola!

10.0 out of 10, Exceptional, (2)
"Beautiful house on a quiet one way street that is lined with plenty of shade and trees. Walking distance to a couple restaurants and the train. The house was very clean and had plenty of room for all 8 of us that stayed. "
1910 Charming Historic Flat - Walk to Beach & Loyola!

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

10.0 out of 10, Exceptional, (5)
"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!
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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