Chicago Chic
4 guests
2 bedrooms
Chicago Loop, Chicago
This pet-friendly apartment in Downtown Chicago puts the best of the city at your feet. Millennium Park, The Art Institute, theatres, restaurants, and shops are all just a short stroll away.
Rent Chicago Homes with Swimming Pools
We selected the 18 homes worth renting in this location
Home spotlights in Chicago
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.
The Heart of the Loop
16 guests
8 bedrooms
Chicago Loop, Chicago
Welcome to a holiday getaway nestled right in the heart of Chicago’s vibrant Financial District. Just steps from iconic attractions, revel in the rich history of the city through its grand architecture and marvel at the stunning skyline from this retreat.
Charming Chicago Charm
5 guests
2 bedrooms
Chicago Loop, Chicago
Welcome to a gem nestled in the heart of Chicago's Financial District, offering guests a unique blend of historical architecture, city excitement and stunning views over the Chicago Riverwalk. The location is unmatched, mere steps away from Millennium Park and State Street, both alive with incredible cuisine and eclectic shopping experiences.
We selected the top 3% holiday homes in Chicago Homes with Swimming Pools
Explore the 18 most perfect homes in our collection
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Frequently asked questions
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, Cook County, Illinois, United States. 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 Home to Rent with a Swimming Pool today, and set up a holiday to remember.
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