Central Chicago pickleball Stays, Resort Rentals, & Homes

Frequently Asked Questions About Central Chicago?

What are the top vacation rentals, resorts, and hotels in Central Chicago with Courts?

Experience the ultimate pickleball vacation with PickleTrip™. We offer a variety of premium rental properties, resorts, and hotels with private pickleball courts or nearby facilities in Central Chicago. Whether you're a beginner or a seasoned player, we have the perfect destination for you to stay and play. Book now and discover the best pickleball vacation spots in Central Chicago!

• 52nd Floor MagMile Penthouse - VIEWS, Fireplace, Fitness Center, Pool, WiFi
• Elevate Your Experience: PH#1, A Penthouse Above the Rest in Chicago
• 53rd Floor MagMile Penthouse - VIEWS, Balcony, Pool, WiFi, & Fitness Center
• 51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
• 53/54th Floor MagMile Penthouse - VIEWS, Fireplace, Fitness Center, Balcony
• Magic Factory Loft 2West
• 51/52nd Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Fitness Center
• 52th Floor Penthouse - Fireplace, VIEWS, grocery store in building.
• Magic Factory Loft 2East 4 Bd/3 Ba Families Groups
• Million Dollar Views! Luxury Downtown Skyhouse!

How many pickleball-ready properties have private pools in Central Chicago?

Discover 72 accommodations with private or nearby pickleball courts in Central Chicago. Some of the best destinations to stay and play pickleball are:

• Experience Chic Old Town Living: Spacious Suites, Top Amenities & Iconic Locale
• Linea Luxury Living with Indoor Pool and Rooftop Views in The Loop
• 70 m² Apartment ∙ 2 bedrooms ∙ 6 guests
• Stylish River North Suites: Luxury Living Near Chicago’s Best Shopping&Nightlife

Which vacation rentals, resorts, or hotels in Central Chicago is best for families looking for a pickleball-getaway?

Looking for a fun and active getaway with pickleball courts in ? With PickleTrip™, you'll have access to a wide selection of top-rated properties that offer private pickleball courts or nearby facilities. Make the most of you getaway and ace your A-game while you travel.

• Kasa | Classic 2 BD + Near Grant Park | Chicago
• Group Friendly Spacious 3BR Suite with Optional Parking and Gym Access Sleeps 10 Guest Near McCormick Place and Soldier Field
• 189 m² Hotel ∙ 2 bedrooms ∙ 127 guests

How many PickleTrip vacation rentals or resorts are available in Central Chicago?

PickleTrip™ offers a diverse selection of properties with private pickleball courts or nearby facilities to enhance your pickleball experience on your next trip. With a combination of established great stays and new options in top locations, PickleTrip™ has over 3183 properties listed in Central Chicago in 2025, and the number only continues to grow. By consolidating listings from various providers, PickleTrip™ brings you the best luxury stays for a sporty, professional, and fun travel experience.

Nearby Neighborhood (16)