Chicago holiday rentals
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
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 AU$8,650
AU$1,236 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Find the best place to stay - Chicago
Showing deals for: 12 Oct - 15 Oct
Short Drive from Cernan Earth & Space Center! Kitchen, Free Airport Shuttle!
Sleeps 2 · 1 bedroom · 1 bathroom
8.4 out of 10
very good
(6 reviews)
The current price is AU$896
for 3 nights, 1 room
AU$299 per night
includes taxes & fees
Top rated rentals - Chicago
Good location plenty of room
10 out of 10
exceptional
(125 reviews)
Host was terrific. Easy and direct communication. House was as presented. Well equipped, tidy, spacious and comfortable. Location: easy access to shops and city on train.
Little things let it down - missing or broken lights, squeaky doors.
A bit noisy with the L on back fence, but we did know that.
Sarah Jane V.
Stayed Oct 2024
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value