Far North Side pickleball Stays, Resort Rentals, & Homes

Frequently Asked Questions About Far North Side?

What are the top vacation rentals, resorts, and hotels in Far North Side 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 Far North Side. 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 Far North Side!

• Only Urban Beach House in Chicago
• Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach
• Great Location-Beautiful Friendly Andersonville Neighborhood
• Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!
• The entire FLAT. Stay Like You Own! Central AIR. TWO FULL BATHROOMS. Unique.
• SPACIOUS 3BD - 2BA DUPLEX WITH FAMILY ROOM, KING BED-LAUNDRY ROOM & FIREPLACE
• Best Lincoln Square Location - Spacious 2 bedroom
• Cozy Nest in Chicago's Vibrant Lincoln Square
• STYLISH-LOCAL-COMFY-SAFE 5 night min.
• Family Friendly 2BD/2BA Near Wrigley, Lincoln Square

How many pickleball-ready properties have private pools in Far North Side?

Discover 3 accommodations with private or nearby pickleball courts in Far North Side. Some of the best destinations to stay and play pickleball are:

• Gorgeous Mid Century 3 bed with hot tub near Lincoln Square
• Marriott Chicago O’Hare
• Renaissance Chicago O'Hare Suites Hotel

Which vacation rentals, resorts, or hotels in Far North Side is best for families looking for a pickleball-getaway?

Looking for a fun and active getaway with pickleball courts in Far North Side? 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.

• Classic Edgewater 1BR w/Gym, Deck & Lounge, nr L, by Blueground
• Apartment by the lake
• Rodeway Inn Chicago North Shore - Lincolnwood

How many PickleTrip vacation rentals or resorts are available in Far North Side?

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 626 properties listed in Far North Side 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.

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