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Aug 15 - Aug 17
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Oct 3 - Oct 5

Condo Rentals in Highland Park

Spacious 4BRCondo near Wrigley/Dtwn +FreeParking
Enjoy cooking in this well-equipped kitchen with a central island, microwave, oven, refrigerator, sink, and dishwasher.

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
3BR Modern Condo near Wrigley/Dwtn +Free Parking
Enjoy cooking in this well-equipped kitchen with a microwave and oven, adjacent to a cozy living area.

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! "
$701 nightly
The price is $821
Aug 31 - Sep 1
Total includes taxes and fees
3BR Modern Condo near Wrigley/Dwtn +Free Parking
Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field
Relax in this stylish living room with a cozy fireplace, comfortable sofa, and fully equipped kitchen.

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

10.0 out of 10, Exceptional, (103)
"The property is half a block from Wrigley, the owners are easy to communicate with and extremely accommodating. One of the best places I've stayed, would recommend to anyone."
Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field
NEW LUXURY PENTHOUSE CONDO
Relax in a stylish seating area with a wicker sofa, armchair, and coffee table, surrounded by lush greenery and a brick wall.

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
Chic Urban Retreat Near Wrigley Field w/Parking
Situated in a corner, this building offers a unique outdoor seating area with planters.

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. "
$442 nightly
The price is $455
Aug 11 - Aug 12
Total includes taxes and fees
Chic Urban Retreat Near Wrigley Field w/Parking
Entire 2 bedroom with Office & Deck!
Enjoy panoramic views of the surrounding cityscape from this rooftop terrace.

Entire 2 bedroom with Office & Deck!

9.0 out of 10, Wonderful, (12)
"Good stay"
Entire 2 bedroom with Office & Deck!
Spacious, Clean and Steps from Wrigley Field!
Enjoy cooking in this well-equipped kitchen with a central island, microwave, and stove.

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!
Stunning 3 BR in prime Chicago location
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, oven, and dishwasher.

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
NEW LUXURY CONDO WITH PATIO DECK
Relax on the covered patio with a wooden deck, wicker table, and chair.

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
Lincoln Park/depaul 8 Bed 1 Parking Spot Sleeps 18 by AllSet Turnover
Enjoy meals in this stylish dining area with a wooden table and comfortable chairs.

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
Bright 2BR Apt w/ Private Entrance & Laundry by AllSet Turnover
Enjoy cooking in this well-equipped kitchen with an oven, microwave, and refrigerator.

Bright 2BR Apt w/ Private Entrance & Laundry by AllSet Turnover

2.0 star property
9.0 out of 10, Wonderful, (4)
"We rented this apartment for a concert at Wrigley Field during the hottest week of the year (June 26, 2025, iykyk). We loved it and would rent again! The air conditioning worked FANTASTIC, which was needed. There were tons of restaurants in the area. The apartment is about a 20 minute walk to Wrigley Field and about 30 steps from the Brown Line train. $5 to ride trains all day, made exploring Chicago easy. It wasn't hard to find parking nearby during any time of day or day of week (be warned,...
Bright 2BR Apt w/ Private Entrance & Laundry by AllSet Turnover
Walking distance to restaurants, shops and Lake Michigan,
Classic corner building with a central entrance, surrounded by a black iron fence and lush greenery.

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,
Just remodeled apartment close to airport and mall
Enjoy cooking in this well-equipped kitchen with a stainless steel refrigerator and ample counter space.

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."
$233 nightly
The price is $249
Aug 9 - Aug 10
Total includes taxes and fees
Just remodeled apartment close to airport and mall
Wrigley Field Grand Slam Suite 4 Bedrooms, 2 Bathrooms
Enjoy cooking in this well-lit kitchen with stainless steel appliances and a granite countertop.

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!"
$889 nightly
The price is $1,097
Aug 11 - Aug 12
Total includes taxes and fees
Wrigley Field Grand Slam Suite 4 Bedrooms, 2 Bathrooms
Wrigley Field All Star Suite 3 Bedrooms 2 Bath
Stunning hotel facade with an arched window and a touch of greenery.

Wrigley Field All Star Suite 3 Bedrooms 2 Bath

9.4 out of 10, Exceptional, (18)
"Enjoyed a dinner party with friends Place was perfect Management helpful "
$775 nightly
The price is $956
Aug 11 - Aug 12
Total includes taxes and fees
Wrigley Field All Star Suite 3 Bedrooms 2 Bath
Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms
Private kitchen

Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms

9.6 out of 10, Exceptional, (23)
"It was great to be able to walk to Cubs games and back right after. It was a cold three days worth of game so very nice to be able to walk across the street and get warm quick. The place was absolutely great! Very spacious and comfy. The property manager was so very easy to work with when we requested an early check in. Thanks and we look forward to our next stay there. Go Cubs Go!!!"
$889 nightly
The price is $1,097
Aug 11 - Aug 12
Total includes taxes and fees
Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms
Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover
Enjoy cooking in this well-lit kitchen with a central island and stainless steel appliances.

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
Enjoy meals in the kitchen with a central island for dining and stainless steel appliances.

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
Prepare meals in a clean and functional kitchen with a stainless steel stove and ample natural light.

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
1910 Charming Historic Flat - Walk to Beach & Loyola!
Interior

1910 Charming Historic Flat - Walk to Beach & Loyola!

1910 Charming Historic Flat - Walk to Beach & Loyola!
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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Top Highland Park Hotel Reviews

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

10/10 Excellent
"Nice room. The only downside is the noise from the airport. A white noise machine on the bed stand helps to quiet the room"
Michael 1-night trip
Posted 23 hours ago
Hyatt Regency O'Hare Chicago