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Chicago Luxury Rental Homes and Villas

Find Luxury Places to Stay Near Chicago

About Chicago Luxury Rental on PickleTrip

PickleTrip™ luxury rentals offer a wide range of amenities, including pickleball courts or nearby facilities, private pools, hot tubs, saunas, game rooms, home theaters, fully equipped kitchens, and spacious living areas. These properties are perfect for those looking for a luxurious and comfortable getaway in Chicago. Whether you are looking for sporty getaway, a romantic retreat, a family vacation, or a gathering with friends, our luxury rentals have everything you need to make your stay unforgettable.

With PickleTrip™, you can choose from a wide range of luxury rental properties, including villas, penthouses, beachfront resorts, and more. Each rental is designed to provide you with the ultimate comfort and luxury, while you enjoy your stay in Chicago. Browse our selection of luxury rentals today and book your dream pickleball vacation with PickleTrip™.

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Frequently Asked Questions About Chicago Luxury Rentals

We have many pet-friendly luxury rentals in the Chicago. The top pet-friendly rentals in Chicago are:

See all pet-friendly rentals in Chicago on PickleTrip

Yes, there are more than 10000 luxury resorts & villas rentals in Chicago that have indoor/outdoor and private swimming pools. Check out our filter option and find your best places to stay near Chicago.
Most of the luxury holiday rentals have an internet facility on PickleTrip. These are some popular places to stay in Chicago that have internet access:

There are more than 10000 luxury rentals with hot tubs available for rent in Chicago.