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Check prices for these dates

Next weekend
7 Feb - 9 Feb
In two weeks
14 Feb - 16 Feb
In one month
28 Feb - 2 Mar
In two months
28 Mar - 30 Mar

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

Stunning 3 BR in prime Chicago location
Living area

Stunning 3 BR in prime Chicago location

9.8 out of 10, Exceptional, (87)
"A clean, spacious, affordable option in a perfect location in Lincoln Park. Plan to return in the future."
Stunning 3 BR in prime Chicago location
Wrigleyville Inn - Unit 3
1

Wrigleyville Inn - Unit 3

10.0 out of 10, Exceptional, (23)
"Great unit in good neighborhood. "
Wrigleyville Inn - Unit 3
Wrigleyville Inn - Garden Unit
1

Wrigleyville Inn - Garden Unit

10.0 out of 10, Exceptional, (22)
"The garden apartment was perfect for our family gathering. The location is convenient and in a nice neighborhood. The layout provided all of us privacy when we needed it and plenty of room for celebrating! "
Wrigleyville Inn - Garden Unit
Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover
Furniture,Indoors,Living Room,Home Decor,Couch

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

10.0 out of 10, Exceptional, (22)
"We were visiting our nephew, who lives around the block from this rental, so we didn't spend a lot of time in the rental, but it was absolutely sparkling clean, well-appointed, and lovely. We will definitely book it again. "
Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover
NEW LUXURY CONDO WITH PATIO DECK
Room

NEW LUXURY CONDO WITH PATIO DECK

10.0 out of 10, Exceptional, (153)
"My family and I stayed with our dog for a few days to see some old friends before going to visit family for Christmas. The space was exactly how it was described and pictured. The setup was easy, attractive, comfy, and extremely well appointed. It was great to have parking and a comfortable place to visit with everyone. The location is very convenient to markets, restaurants, and shopping. The shower is amazing. Kitchen is top notch. We will definitely stay here again!"
NEW LUXURY CONDO WITH PATIO DECK
Classic Lincoln Park 2 bedroom condo- parking included
Exterior

Classic Lincoln Park 2 bedroom condo- parking included

9.8 out of 10, Exceptional, (62)
"The apartment was as promised, home like with basic pantry supplies. Close to downtown and walkable to Second City."
Classic Lincoln Park 2 bedroom condo- parking included
Hidden East Village Gem
Living Area with 55" UHD Smart TV

Hidden East Village Gem

9.6 out of 10, Exceptional, (33)
"It was great.Only some construction noises that started on building the house next to this building… but that will probably not last long"
Hidden East Village Gem
Walking distance to restaurants, shops and Lake Michigan,
Stunning open floor plan is perfect for entertaining and gatherings.

Walking distance to restaurants, shops and Lake Michigan,

9.8 out of 10, Exceptional, (195)
"Ross, the property manager, is very courteous and helpful. Property clean and well-appointed. Family group with 2 dogs. Took Uber rides into city to see museums and shows. Garage parking was nice. Very quiet neighborhood at night. Overall a nice, well-managed property that we highly recommend."
Walking distance to restaurants, shops and Lake Michigan,
Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover
Home Decor,Furniture,Indoors,Living Room,Table

Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover

9.6 out of 10, Exceptional, (24)
"What a great place! Perfect for a stay close enough to everything! Very comfy beds, and couch (tv remote was literally the only thing I can complain about!)"
Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover
Spacious, Clean and Steps from Wrigley Field!
Dining Room

Spacious, Clean and Steps from Wrigley Field!

9.8 out of 10, Exceptional, (7)
"Great host, very responsive "
Spacious, Clean and Steps from Wrigley Field!
The Inn at Wrigleyville, Beautiful New 4 Bedroom Sleeps 9
Room

The Inn at Wrigleyville, Beautiful New 4 Bedroom Sleeps 9

9.8 out of 10, Exceptional, (20)
"We had a wonderful time meeting friends for the weekend. The proximity to the stadium is the best. "
The price is AED 1,759
AED 3,913 total
includes taxes & fees
3 Feb - 4 Feb
The Inn at Wrigleyville, Beautiful New 4 Bedroom Sleeps 9
"Melody of Evanston" 3BD, 2BA UrbanLux Condo
Living area

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

2.0 star property
10.0 out of 10, Exceptional, (7)
"The property was wonderful! It was clean and located perfectly for getting around the north shore. We enjoyed our visit!! "
"Melody of Evanston" 3BD, 2BA UrbanLux Condo
Elegant Duplex with Chef's Kitchen Near Wrigley Field by AllSet Turnover
Elegantly designed living room with gas fireplace

Elegant Duplex with Chef's Kitchen Near Wrigley Field by AllSet Turnover

9.2 out of 10, Wonderful, (5)
"I’d like to stay again but I can’t find it to rebook "
Elegant Duplex with Chef's Kitchen Near Wrigley Field by AllSet Turnover
Walk to Lincoln Park, North Avenue Beach, and Second City! Lovely Old Town Charm! by AllSet Turnover
Furniture,Couch,Table,Rug,Coffee Table

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

9.6 out of 10, Exceptional, (18)
"My daughter and I had a girls weekend in Chicago and loved the location and neighborhood. The property was updated and clean yet maintained the flavor of city living."
Walk to Lincoln Park, North Avenue Beach, and Second City! Lovely Old Town Charm! by AllSet Turnover
The Bucktown House - Suite #4 - Heart of Wicker/Bucktown, 10 minutes to downtown
Dining

The Bucktown House - Suite #4 - Heart of Wicker/Bucktown, 10 minutes to downtown

9.8 out of 10, Exceptional, (26)
"Great location and nice accommodations. I would recommend but one thing to be aware of are the wooden floors, which is charming, but are squeaky."
The Bucktown House - Suite #4 - Heart of Wicker/Bucktown, 10 minutes to downtown
Chic Urban Retreat Near Wrigley Field w/Parking
Private kitchen

Chic Urban Retreat Near Wrigley Field w/Parking

10.0 out of 10, Exceptional, (8)
"We chose to stay at this propeerty due to its proximity to our son's place. We spent 9 days in Chicago to be with our son and his wife to help them with their new baby. The location was convienient to shopping, restaurants, and other stores. It had everything we needed for a comfortable stay. The hosts were helpful, when we had questions. Overall an excellent experience."
Chic Urban Retreat Near Wrigley Field w/Parking
Huge Lakeview Retreat Sleeping 20 with Parking!

Huge Lakeview Retreat Sleeping 20 with Parking!

8.0 out of 10, Very Good, (1)
"We booked the stay for a professional board retreat, but had major issues with the wifi connection. It never worked at all from one of the 2 included units, and only worked sporadically and with weak signal in the second unit. We had Zoom sessions planned with others joining us that had to be done on telephones since the computers could not get wifi. It was not professional and we were very dissatisfied with this aspect of the stay. Rooms were generally quite nice, but every single bedroom...
Huge Lakeview Retreat Sleeping 20 with Parking!
Featured on the Travel Channel, 4 Bedroom 2 Bath in Wrigley Rooftop Building
Private kitchen

Featured on the Travel Channel, 4 Bedroom 2 Bath in Wrigley Rooftop Building

9.0 out of 10, Wonderful, (12)
"The apartment is literally across the street from the ballpark. Very clean, easy to check in, big space, everything we needed was there, couldn't have asked for more."
The price is AED 1,759
AED 3,913 total
includes taxes & fees
3 Feb - 4 Feb
Featured on the Travel Channel, 4 Bedroom 2 Bath in Wrigley Rooftop Building
Wrigleyville Inn - Unit 1
1

Wrigleyville Inn - Unit 1

10.0 out of 10, Exceptional, (19)
"The owner was very easy to work with, provided timely responses, and the home was very clean. I will look to stay here again in the future when we are looking for Wrigleyville accommodations. "
Wrigleyville Inn - Unit 1
The Exclusive- 7 Bed, 6 Bath Retreat
Top floor kitchen and dining area

The Exclusive- 7 Bed, 6 Bath Retreat

9.6 out of 10, Exceptional, (15)
"This property was perfect for our group. Each bedroom was paired with a bathroom and both kitchens and living room spaces were clean and comfortable. Located across the street for the train, it was easy to get around town"
The Exclusive- 7 Bed, 6 Bath Retreat
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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Other property types in Highland Park

Level Chicago – Old Town
Outdoor pool

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (287)
"Amazing stay ! Love this property every time I’m in Chicago. "
The price is AED 745
AED 956 total
includes taxes & fees
9 Feb - 10 Feb
Level Chicago – Old Town
Wrigleyville Suites
Terrace/patio

Wrigleyville Suites

2.0 star property
8.8 out of 10, Excellent, (3)
"All conditions (like the deposit) should be clear in the description. This is not a hotel or a hotel, it's a private place. All this should be clear at the moment of reservation. The property was good enough but the communication with the host was troublesome. And the price is not that low. I will look for a hotel next time. "
The price is AED 268
AED 498 total
includes taxes & fees
3 Feb - 4 Feb
Wrigleyville Suites
Stunning 3 BR in prime Chicago location
Living area

Stunning 3 BR in prime Chicago location

9.8 out of 10, Exceptional, (87)
"A clean, spacious, affordable option in a perfect location in Lincoln Park. Plan to return in the future."
Stunning 3 BR in prime Chicago location
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

How much do condos in Highland Park cost?
You’ll pay from to per night for condos in Highland Park. No matter your budget, the perfect stay is a click away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your condo in Highland Park with Expedia?
Booking a condo in Highland Park is as simple as working out your travel dates and picking an option that meets your needs. Seeking something budget friendly or upmarket, or a stay that also offers a kitchen? Use Expedia’s search filters to further narrow your search results and find the ideal fit.
How can I find cheap condos in Highland Park?
With Expedia’s helpful filter tool, comparing cheap condos in Highland Park couldn’t be simpler. To view accommodations that are easy on your bank balance, refine your search results by budget, star rating and amenities.