Chicago holiday rentals
We found 3,729 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:6 Feb - 13 Feb
Image gallery for Luxury 2BR on Michigan Ave with Private Balcony
9.8 out of 10, Exceptional, (16 reviews)
Exceptional
(16 reviews)
Luxury 2BR on Michigan Ave with Private Balcony
Chicago, IL
7% off
Price is AU$4,730
for 7 nights, 1 apartment
AU$676 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Find the best place to stay - Chicago
Showing deals for: 31 Jan - 3 Feb
Small hidden Gem
Sleeps 4 · 2 bedrooms · 1 bathroom
8.6 out of 10
excellent
(12 reviews)
The current price is AU$643
for 3 nights, 1 apartment
AU$214 per night
includes taxes & fees
Top rated rentals - Chicago
Our Stay
10 out of 10
exceptional
(31 reviews)
We loved our stay. It was comfortable and in a lovely quiet neighbourhood. Great communication. Thank you
Sue P.
Stayed Sept 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