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Check prices for these dates

Next weekend
4 Rab. II - 6 Rab. II
In two weeks
11 Rab. II - 13 Rab. II
In one month
25 Rab. II - 27 Rab. II
In two months
23 Jum. I - 25 Jum. I

Compare 143 Condo Rentals in Highland Park with updated reviews, rates, and availability.

Stunning 3 BR in prime Chicago location
Fridge, microwave, oven, stovetop

Stunning 3 BR in prime Chicago location

9.8 out of 10, Exceptional, (88)
"Accurate description of property. Host was very easy to communicate with. Would recommend!"
Stunning 3 BR in prime Chicago location
NEW LUXURY PENTHOUSE CONDO
Terrace/patio

NEW LUXURY PENTHOUSE CONDO

10.0 out of 10, Exceptional, (170)
"Very clean, property manager was very nice and helpful. Close to everything. Would definitely stay there again. "
NEW LUXURY PENTHOUSE CONDO
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
Pet-Friendly Urban Chicago Vacation Rental Condo
Beach nearby

Pet-Friendly Urban Chicago Vacation Rental Condo

9.2 out of 10, Wonderful, (14)
"Great place to stay. Close to everything. Nice and clean "
Pet-Friendly Urban Chicago Vacation Rental Condo
Spacious 4BRCondo near Wrigley/Dtwn +FreeParking
Exterior

Spacious 4BRCondo near Wrigley/Dtwn +FreeParking

9.8 out of 10, Exceptional, (27)
"Specious and comfy. The balcony was not available, but we just needed the place for a few nights. Clean and nicely done"
Spacious 4BRCondo near Wrigley/Dtwn +FreeParking
Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover
2 bedrooms, iron/ironing board, WiFi, bed sheets

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
Classic Lincoln Park 2 bedroom condo- parking included
Point of interest

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
Miscellaneous

3BR Modern Condo near Wrigley/Dwtn +Free Parking

9.4 out of 10, Exceptional, (26)
"It has been for us the perfect place to visit the city and enjoy an amazing neighborhood. The parking spot makes it even more perfect. Great communication from the property manager on top of that"
3BR Modern Condo near Wrigley/Dwtn +Free Parking
North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment
Exterior

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

10.0 out of 10, Exceptional, (102)
"Really enjoyed our stay. Parking was easy and we could walk to restaurants. Felt very safe and the neighborhood was welcoming. Would stay again."
North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment
Wrigleyville Inn - Garden Unit
Fridge, microwave, oven, stovetop

Wrigleyville Inn - Garden Unit

10.0 out of 10, Exceptional, (24)
"My husband and I drove in to surprise our oldest for her birthday. The space was very clean and comfortable as well as ideally located next door to her home. We would definitely consider staying her again in the future. "
Wrigleyville Inn - Garden Unit
NEW LUXURY CONDO WITH PATIO DECK
Fridge, microwave, oven, stovetop

NEW LUXURY CONDO WITH PATIO DECK

10.0 out of 10, Exceptional, (156)
"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
Chic Urban Retreat Near Wrigley Field w/Parking
Miscellaneous

Chic Urban Retreat Near Wrigley Field w/Parking

10.0 out of 10, Exceptional, (10)
"This was a great home base for our short family getaway to Chicago. Perfect amount of space for family of 4 to crash at the end of each day touristing around Chicago. Very clean. Great communication from hosts. Loved it."
The price is SAR 563
SAR 1,663 total
includes taxes & fees
31 Mar - 1 Apr
Chic Urban Retreat Near Wrigley Field w/Parking
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, (88)
"Property perfectly located near Wrigley Field, superbly clean and appointed."
Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field
Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover
Fridge, microwave, oven, dishwasher

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!
Fridge, microwave, stovetop, coffee/tea maker

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!
Fridge, microwave, oven, stovetop

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
Smart TV

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

9.8 out of 10, Exceptional, (12)
"Everything went well. Will stay again."
Parking, Balcony, Near Universities, Ravinia, NAPA & Train to Chicago
Walking distance to restaurants, shops and Lake Michigan,
Exterior

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
Fridge, microwave, oven, stovetop

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,
Exterior

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.
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Other property types in Highland Park

Level Chicago – Old Town
Front of property - evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (297)
"Spacious, clean rooms! Large windows make for a fabulous view!"
The price is SAR 615
SAR 805 total
includes taxes & fees
31 Mar - 1 Apr
Level Chicago – Old Town
Wrigleyville Suites
Living area

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 529
SAR 809 total
includes taxes & fees
31 Mar - 1 Apr
Wrigleyville Suites
2-bedroom apartment just 2 minutes drive to Wrigley Field
Exterior

2-bedroom apartment just 2 minutes drive to Wrigley Field

2.0 star property
9.6 out of 10, Exceptional, (8)
"The property is very quiet, clean, well appointed, and is in a great location. It’s only a 3 minute walk to the Brown Line which easily gets you downtown in half an hour and not worry about parking. I did notice the absence of a microwave which would have been an added convenience. Overall, it suited my needs perfectly and will consider it again if I get back to Chicago."
The price is SAR 319
SAR 906 total
includes taxes & fees
31 Mar - 1 Apr
2-bedroom apartment just 2 minutes drive to 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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