Chicago holiday lettings
We found 3,408 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.
Find spaces that suit your style
House
Condo/Apartment
Find the best place to stay - Chicago
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
Sleeps 5 · 2 bedrooms · 2 bathrooms
8.6 out of 10
excellent
(25 reviews)
Top rated rentals - Chicago
Beautiful home in Warrenville
10 out of 10
exceptional
(110 reviews)
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, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value