Chicago 27th Street Station holiday lettings
We found 3,657 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals within easy reach of Chicago 27th Street Station that provide the perfect home base for your trip. Whether you're travelling with your children or with friends, holiday homes have the amenities that you expect for your stay, including parking and a TV. No matter what you're looking for, you'll be sure to find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Chicago 27th Street Station
Showing deals for:7 Nov - 14 Nov
Image gallery for River North's Rock N' Roll - In The Heart of the City

9.6 out of 10 rating
Exceptional
(90 reviews)
River North's Rock N' Roll - In The Heart of the City
Chicago, IL
7% off
Price is £2,495
£356 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Find the best place to stay - Chicago 27th Street Station

Kasa Magnificent Mile Chicago
Sleeps 3 · 1 bedroom
9.4 out of 10
exceptional
(460 reviews)
Top rated rentals - Chicago 27th Street Station

Fabulous
10 out of 10
exceptional
(11 reviews)
I wish we came across this property 4 years ago when we dropped off our daughter at the UofC campus. Location is amazing, 7 minutes walk to the campus. The house is spacious and accommodates a large group of people. Very clean and what was really appreciated it was so well stocked - nice shampoos and lotions in all bathrooms, paper towels in the kitchen, a welcome bottle of bubbly wine from the hosts. The check-in and out process was also incredibly easy, and the hosts were very welcoming and responsive for all our requests. We booked it again for the graduation week-end and are really looking forward to coming back.
Natasha M.
Stayed Nov 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, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value