2794+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Central Chicago pickleball Stays, Resort Rentals, & Homes

About Central Chicago Vacation Rentals

Discover over 2794 amazing vacation rental options in Central Chicago with pickleball courts or nearby facilities. From resorts to hotels, villas to condos, PickleTrip connects you with a vast selection of pickleball-ready amenities at great prices, providing you with the perfect spot to base your next pickleball vacation. Stay and Play pickleball When You Travel and uncover great stays in Central Chicago.

Find exclusive last-minute deals on vacation rentals, resorts, and hotels with private courts and nearby facilities with PickleTrip™, whether you're traveling solo or with a group. Our platform offers a variety of stay options, from vacation rentals to Airbnb-style properties, all with private pickleball courts or nearby facilities. Compare options from multiple suppliers with a single click to find the perfect stay that fits your budget and style. Places to stay near pickleball courts are an average of 725.64 ft², with prices averaging US $384 per night.

With PickleTrip™, you can easily search for and book your next pickleball vacation rental with courts or nearby facilities. Our platform connects you with the ideal holiday rental to create a lifetime of travel memories. Prices listed are often discounted versus rack rates, so you can secure your perfect place to stay today and get ready to play pickleball in Central Chicago.

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Top Pickleball-Ready Accommodation Types in Central Chicago

Type Count
Holiday Apartments 1747
Vacation Homes 321
Villas 2

Use these Quick Filters to Find a Vacation Rental in Central Chicago

★ Pro Tip: PickleTrip™ is a travel platform, connecting avid pickleball players and enthusiasts with a variety of vacation rentals, resorts, and hotels featuring private pickleball courts or nearby facilities. We curate a vast selection of properties from trusted sources, providing you with unbeatable options and pricing to find the perfect pickleball getaway. Experience unforgettable pickleball matches in Central Chicago with PickleTrip™.

Weather in Central Chicago, IL

View the weather forecast for Central Chicago before booking your Central Chicago Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Central Chicago, IL

PickleTrip offers a large selection of top attractions around Central Chicago . Research things to do on your vacation before you visit Central Chicago.


Navy Pier
McCormick Place
Millennium Park
Soldier Field
Willis Tower
Art Institute of Chicago
Grant Park
John G. Shedd Aquarium
Chicago Theatre
Chicago Riverwalk
Field Museum of Natural History
John Hancock Center
Water Tower Place
House of Blues Chicago
Merchandise Mart
Chicago Children's Museum
Northwestern Memorial Hospital
Cloud Gate
Wintrust Arena
Aon Center

Other Places to Stay in Central Chicago, IL


Chicago 6,826 Properties
Chicago 4,160 Properties
Downtown Chicago 1,527 Properties
The Loop 703 Properties
Near North Side 605 Properties
South Side 369 Properties
South Loop 369 Properties
Near South Side 356 Properties
River North 317 Properties
Prairie District 252 Properties
Streeterville 153 Properties
Rush and Division 88 Properties

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!

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

Discover 64 accommodations with private or nearby pickleball courts in Central Chicago. Some of the best destinations to stay and play pickleball are:

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 Central Chicago? 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.

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 2794 properties listed in Central Chicago in 2026, 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) 
Neighborhood Property Count
Downtown Chicago Vacation Rentals in Chicago, Illinois 1527
The Loop Vacation Rentals in Chicago, Illinois 703
Near North Side Vacation Rentals in Chicago, Illinois 605
Near West Side Vacation Rentals in Chicago, Illinois 370
South Loop Vacation Rentals in Chicago, Illinois 369
Near South Side Vacation Rentals in Chicago, Illinois 356
River North Vacation Rentals in Chicago, Illinois 317
West Town Vacation Rentals in Chicago, Illinois 314
West Loop Vacation Rentals in Chicago, Illinois 219
Streeterville Vacation Rentals in Chicago, Illinois 153
Lincoln Park Vacation Rentals in Chicago, Illinois 152
Bronzeville Vacation Rentals in Chicago, Illinois 91
Old Town Vacation Rentals in Chicago, Illinois 60
River West Vacation Rentals in Chicago, Illinois 51
Gold Coast Vacation Rentals in Chicago, Illinois 37
Printers Row Vacation Rentals in Chicago, Illinois 3802

People Also Ask

There are 2794 Central Chicago, IL Vacation Rentals

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