Chicago holiday homes

We found 3,704 holiday rentals — enter your dates for availability

Take a look at holiday rentals near Chicago O'Hare International Airport (ORD) that provide the perfect home base for your trip. Whether you’re travelling with friends, family or even pets, holiday homes have the amenities that you expect for your stay, such as Wi-Fi and cable TV. Whatever you're looking for, you'll be able to choose a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Chicago, IL (ORD-O'Hare Intl.)

Showing deals for:17 Oct - 24 Oct

Image gallery for Modern Apartment with Private Rooftop Patio & Free Parking in Downtown Chicago

Rooftop Deck with Beautiful City Views
10 out of 10 rating
Exceptional
(7 reviews)

Modern Apartment with Private Rooftop Patio & Free Parking in Downtown Chicago

Chicago, IL

7% off
Price is NZ$9,538
NZ$1,363 per night
includes taxes & fees
Modern Apartment with Private Rooftop Patio & Free Parking in Downtown Chicago

Find spaces that suit your style

  • 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

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