Chicago Heights
4 guests
2 bedrooms
Chicago Loop, Chicago
This pet-friendly apartment in Downtown Chicago puts the city right at your feet, with Millennium Park, The Art Institute, theatres, and shopping just a stroll away. Inside, floor-to-ceiling windows in the main bedroom frame the skyline, while a sleek kitchen with a breakfast bar and a light-filled living space make staying in just as tempting as going out.
Chicago Chill Pad
5 guests
2 bedrooms
Chicago Loop, Chicago
Here awaits The Cooke, where guest security and solace are paramount. Ensconced in the heart of Chicago's distinguished Financial District, this property is a gateway to an array of unforgettable Windy City attractions.
Loop Haven
12 guests
6 bedrooms
Chicago Loop, Chicago
Welcome to The Jordan! Nestled in Chicago's iconic Chicago Loop, this urban oasis provides a tranquil retreat amidst the bustling cityscape.
Chicago Charisma
5 guests
2 bedrooms
Chicago Loop, Chicago
Immerse yourself in the heart of downtown at this retreat tucked away in Chicago's vibrant Financial District. Each experience here invites a journey into iconic city attractions, folds back layers of historic architectural treasures, and strolls along river cruises or the fabled Riverwalk.
Explore the 22 most perfect homes in our collection
You've certainly come to the right place if you are hoping to find one of the finest Holiday Homes with Swimming Pools in Chicago Loop. Our exclusive collection consists solely of homes that have passed our thorough 150-step vetting process with flying colours, so you can book with true peace of mind, knowing that everything from decibel levels in the bedroom to a room's intangible atmosphere has been tested and approved. We don't list a huge number of homes one our site, just the right ones. Each property in our collection comes fully furnished and ready to welcome you, with a fully-equipped kitchen, essential bathroom toiletries, and all linen included. Contact our dedicated team of experts to find the perfect luxury Chicago Loop Home to Rent with a Swimming Pool today, and set up a holiday to remember.
