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Highland Park Holiday Rentals

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Check prices for these dates

In two weeks
12 Sept - 14 Sept
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov
In four months
19 Dec - 21 Dec

Holiday Rentals 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, (345)
"A lot of good food options walkable distance. "
The price is HK$1,741
HK$2,218 total
includes taxes & fees
1 Sept - 2 Sept
Level Chicago – Old Town
The Gem Museum Suites
Private kitchen

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (86)
"Super nice hotel and staff "
The price is HK$1,557
HK$1,783 total
includes taxes & fees
2 Sept - 3 Sept
The Gem Museum Suites
Wrigleyville Suites
Living area

Wrigleyville Suites

2.0 star property
9.2 out of 10, Wonderful, (19)
"Excellent location and very clean! Would stay again!"
The price is HK$866
HK$1,407 total
includes taxes & fees
1 Sept - 2 Sept
Wrigleyville Suites
Charming 2BR in Vibrant Lakeview
2 bedrooms, iron/ironing board, travel cot, WiFi

Charming 2BR in Vibrant Lakeview

9.0 out of 10, Wonderful, (12)
The price is HK$733
HK$1,713 total
includes taxes & fees
1 Sept - 2 Sept
Charming 2BR in Vibrant Lakeview
Clean & Equipped 1BR Apt
1 bedroom, iron/ironing board, WiFi, bed sheets

Clean & Equipped 1BR Apt

8.6 out of 10, Excellent, (16)
"Good experience. Would stay there again "
The price is HK$717
HK$1,578 total
includes taxes & fees
1 Sept - 2 Sept
Clean & Equipped 1BR Apt
Cozy, Fully Set-Up 1BR Space
Fridge, microwave, oven, stovetop

Cozy, Fully Set-Up 1BR Space

9.0 out of 10, Wonderful, (17)
"Great place! 15 min walk to Wrigley "
The price is HK$717
HK$1,578 total
includes taxes & fees
2 Sept - 3 Sept
Cozy, Fully Set-Up 1BR Space
Stylish 1BR in Lakeview Chicago
Fridge, microwave, oven, stovetop

Stylish 1BR in Lakeview Chicago

8.6 out of 10, Excellent, (12)
"This is a great apartment. It was very clean, well equipped kitchen and comfortable bed. Close to restaurants, grocery store, Starbucks and Wrigley Field. We could not find any parking on the street where the apartment is. I do recommend that you get in touch with the property owners couple of days prior to your visit because there is a vetting process prior to getting the keys to the apartment. "
The price is HK$811
HK$1,688 total
includes taxes & fees
2 Sept - 3 Sept
Stylish 1BR in Lakeview Chicago
Cozy studio in Andersonville Chicago
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy studio in Andersonville Chicago

9.2 out of 10, Wonderful, (24)
"It was a great location, internet was a little spotty on streaming services but we were in walking distance to so much it was worth it "
The price is HK$507
HK$1,106 total
includes taxes & fees
2 Sept - 3 Sept
Cozy studio in Andersonville Chicago
Lakeview 2BR Apartment
Fridge, microwave, oven, stovetop

Lakeview 2BR Apartment

9.2 out of 10, Wonderful, (12)
"Great experience overall. Check-in was easy and the unit was very well kept. Very happy that we were so close to so much public transportation. It is a little noisy for those who aren’t used to hearing the L train nearby. Parking is hard to find, but there is paid parking nearby and easy to access public transit. If you plan on parking your car for the full time you’re there."
The price is HK$717
HK$1,695 total
includes taxes & fees
2 Sept - 3 Sept
Lakeview 2BR Apartment
Nice 1BR Spot, Unwind & Relax
TV

Nice 1BR Spot, Unwind & Relax

10.0 out of 10, Exceptional, (15)
"Super clean. Cozy. SAFE. Short drive to nearly every big attraction! Host was very communicative and kind!!"
The price is HK$663
HK$1,514 total
includes taxes & fees
2 Sept - 3 Sept
Nice 1BR Spot, Unwind & Relax
Uptown Studio Gem Sum
TV

Uptown Studio Gem Sum

7.0 out of 10, Good, (4)
"This studio is very clean and is located in a neighborhood with access to anything you would want to do or see. The stairway and halls are not pristine, but studio is good. Neighbors were quiet and seldom seen during my stay. Excellent restaurant right across the street and grocery nearby. Wrigley Field is easy walk. Check in was confusing for me, but it worked out. "
The price is HK$717
HK$1,500 total
includes taxes & fees
1 Sept - 2 Sept
Uptown Studio Gem Sum
Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater
8 bedrooms, desk, iron/ironing board, travel cot

Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater

6.0 out of 10, (2)
"Great space for large groups. Park across the street is a great "feature"."
The price is HK$1,110
HK$6,975 total
includes taxes & fees
30 Sept - 1 Oct
Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater
Relaxing Chicago Studio
Desk, iron/ironing board, WiFi, bed sheets

Relaxing Chicago Studio

10.0 out of 10, Exceptional, (8)
"Had a great stay. Great location. "
The price is HK$624
HK$1,395 total
includes taxes & fees
30 Sept - 1 Oct
Relaxing Chicago Studio
Prime City Stay in a 1BR Apt
1 bedroom, iron/ironing board, travel cot, WiFi

Prime City Stay in a 1BR Apt

9.2 out of 10, Wonderful, (9)
The price is HK$663
HK$1,514 total
includes taxes & fees
7 Sept - 8 Sept
Prime City Stay in a 1BR Apt
Bright & Modern Lakeview Studio
WiFi, bed sheets

Bright & Modern Lakeview Studio

9.0 out of 10, Wonderful, (2)
"Host communicated great and check in and check out was easy"
The price is HK$811
HK$1,610 total
includes taxes & fees
3 Sept - 4 Sept
Bright & Modern Lakeview Studio
Luxurious 3 Bedroom Apartment in Chicago
Microwave, oven, stovetop, dishwasher

Luxurious 3 Bedroom Apartment in Chicago

9.2 out of 10, Wonderful, (23)
"Great property! Would visit again!"
Luxurious 3 Bedroom Apartment in Chicago
Chicago Luxury Penthouse Massive Rooftop Walk to Beach and Restaurants
Terrace/patio

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
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, (39)
"Great place to stay when you’re in town for the Cubbies! "
The price is HK$1,045
HK$2,579 total
includes taxes & fees
2 Sept - 3 Sept
2-bedroom apartment just 2 minutes drive to Wrigley Field
Chicago 1BR: Stylish Stay with Workspace
Fridge, microwave, oven, stovetop

Chicago 1BR: Stylish Stay with Workspace

9.8 out of 10, Exceptional, (6)
The price is HK$312
HK$1,935 total
includes taxes & fees
23 Sept - 24 Sept
Chicago 1BR: Stylish Stay with Workspace
Sleek Style 3BR Haven - Free Parking
3 bedrooms, iron/ironing board, travel cot, WiFi

Sleek Style 3BR Haven - Free Parking

9.6 out of 10, Exceptional, (9)
"Lived our stay here. 3 big bedrooms, clean environment. Close to things we wanted to visit. We will stay here again for sure!"
The price is HK$1,325
HK$2,620 total
includes taxes & fees
16 Sept - 17 Sept
Sleek Style 3BR Haven - Free Parking
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

Find out more about Highland Park

Find out more about Highland Park

Search for holiday rentals in Highland Park on Expedia! You can easily find your home rentals, villas, holiday apartments in Highland Park using one of the methods below:

  • View our selection of featured holiday rentals in Highland Park
  • Use the map to find apartments and other holiday homes in the Highland Park neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Highland Park while they last

Look no further and take a look at our great range of rental properties in Highland Park!

Frequently asked questions

Are there holiday rentals in Highland Park?

Yes, we give you a choice of holiday rentals where you'll be only 14.5 mi (23.4 km) from Six Flags Great America, offering you a more remote option to escape the hustle and bustle. The shops and live music are just a few reasons why travellers like Highland Park. Allow lots of time to check out the gardens and restaurants during your visit.

What are some of the best holiday rentals that Highland Park has to offer?

Amazing 3-bedroom house with WiFi and AC in awesome Chicago: This holiday home rental outside of Highland Park has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals are there in Highland Park?

With 5 Expedia holiday rentals, you're guaranteed to find just the right place for your Highland Park stay.

What can I see and do in Highland Park?

Enjoy the outdoors at Lake Michigan and Chicago Botanic Garden, or simply take in cultural attractions like Ravinia Park and Ravinia Pavilion. Other popular places to visit in the area include Naval Base Great Lakes and Wrigley Field.

What are holiday rentals like in Highland Park?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Highland Park. Holiday rentals offer extras such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.