Jackson Park Highlands, Chicago holiday accommodation: short-term house rentals & properties

Scroll through and select from holiday rentals in Jackson Park Highlands to find one that's perfect for your trip. Holiday rentals offer the amenities that you expect for you and your friends, family or even pets, such as a fireplace and garden. You're sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Jackson Park Highlands

51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi

Sleeps 4 · 1 bedroom · 1 bathroom

Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!

Sleeps 20 · 5 bedrooms · 2+ bathrooms

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Frequently asked questions

How much does it cost to rent a holiday home in Jackson Park Highlands?

Length of stay, property type and season are some things that can affect the price of a holiday home. Simply add your dates of travel to find your ideal fit. From comfy cottages to sprawling villas, all Stayz holiday homes offer terrific value.

How much does it cost to rent a beach house in Jackson Park Highlands?

When you travel and the size and style of the property will determine the cost of your beachside escape. Click on your Jackson Park Highlands travel dates to see all your options on Stayz. Looking for a backyard so the kids can run around, or a pool to keep them busy? Use the filters to pick the features and amenities you want.

What are the top attractions for families in Jackson Park Highlands?

Keep the kids amused at these fun family-friendly attractions in Jackson Park Highlands:

Navy Pier
Chicago Riverwalk
Shedd Aquarium

How old do you have to be to rent a holiday home in Jackson Park Highlands?

You'll have to check with the Jackson Park Highlands holiday home you're looking at on Stayz as the age limit differs. However, generally it's 16, 18 or 21.

How long can I rent a holiday home in Jackson Park Highlands for?

It all depends on the Jackson Park Highlands property. To look over a list of options offering extended stays, just type your dates and guest number into the Stayz search page. Look forward to having the entire property to yourself, along with amenities such as a full kitchen, air conditioning and a backyard where your little ones can play. Keep an eye out for long-term stays that offer discounted weekly or monthly prices.