Chicago holiday rentals
We found 3,650 holiday rentals — enter your dates for availability
Take a look at holiday rentals close to Chicago Midway Airport (MDW) that can be your home away from home. Whether you're travelling with your children and pets, with friends or just your children, holiday homes have the best amenities for spending time at your holiday home, which might include Wi-Fi and a washer and dryer. What you'll find is a property to rent that has what everyone needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Chicago, IL (MDW-Midway Intl.)
Showing deals for:19 Dec - 26 Dec
Image gallery for 2 Rooftops, 2 Car Garage, 4 Stories|Down-Townhome
8.0 out of 10 rating
Very good
(14 reviews)
2 Rooftops, 2 Car Garage, 4 Stories|Down-Townhome
Chicago, IL
10% off
Price is AU$4,950
for 7 nights, 1 home
AU$707 per night
includes taxes & fees
Find spaces that suit your style
Find the best place to stay - Chicago
The Neighborhood Hotel-Little Italy
Sleeps 4 · 1 bedroom
9.6 out of 10
exceptional
(202 reviews)
Top rated rentals - Chicago
Good location plenty of room
10 out of 10
exceptional
(126 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