7839+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Chicago pickleball Stays, Resort Rentals, & Homes

About Chicago Vacation Rentals

Discover over 7839 amazing vacation rental options in 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 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 795.92 ft², with prices averaging $395 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 Chicago.

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Top Pickleball-Ready Accommodation Types in Chicago

Type Count
Holiday Apartments 5119
Vacation Homes 1401
Villas 12
Cottages 4

Use these Quick Filters to Find a Vacation Rental in 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 Chicago with PickleTrip™.

Weather in Chicago, IL

View the weather forecast for Chicago before booking your 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 Chicago, IL

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


Navy Pier
Wrigley Field
McCormick Place
Millennium Park
Union Station
Soldier Field
Willis Tower
Art Institute of Chicago
Naval Base Great Lakes
United Center
Grant Park
John G. Shedd Aquarium
Chicago Museum of Science and Industry
Chicago Theatre
Chicago Riverwalk
Field Museum of Natural History
Six Flags Great America
University of Chicago
Brookfield Zoo
Northwestern University

Other Places to Stay in Chicago, IL


Chicago 7,401 Properties
Central Chicago 1,865 Properties
Downtown Chicago 1,706 Properties
West Side 807 Properties
Near North Side 785 Properties
The Loop 715 Properties
North Side 638 Properties
River North 434 Properties
South Side 382 Properties
Far North Side 375 Properties
South Loop 372 Properties
Near South Side 363 Properties

Frequently Asked Questions About Chicago?

What are the top vacation rentals, resorts, and hotels in 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 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 Chicago!

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

Discover 100 accommodations with private or nearby pickleball courts in Chicago. Some of the best destinations to stay and play pickleball are:

Which vacation rentals, resorts, or hotels in 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.

How many PickleTrip vacation rentals or resorts are available in 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 7839 properties listed in 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) 
Neighborhood Property Count
Downtown Chicago Vacation Rentals in Chicago, Illinois 1706
Near North Side Vacation Rentals in Chicago, Illinois 785
The Loop Vacation Rentals in Chicago, Illinois 715
River North Vacation Rentals in Chicago, Illinois 434
South Loop Vacation Rentals in Chicago, Illinois 372
Near South Side Vacation Rentals in Chicago, Illinois 363
Lakeview Vacation Rentals in Chicago, Illinois 265
West Loop Vacation Rentals in Chicago, Illinois 206
Lincoln Park Vacation Rentals in Chicago, Illinois 158
Hyde Park Vacation Rentals in Chicago, Illinois 95
Logan Square Vacation Rentals in Chicago, Illinois 74
O'Hare Vacation Rentals in Chicago, Illinois 69
Rogers Park Vacation Rentals in Chicago, Illinois 58
Edgewater Vacation Rentals in Chicago, Illinois 58
Gold Coast Vacation Rentals in Chicago, Illinois 54
Wicker Park Vacation Rentals in Chicago, Illinois 50

People Also Ask

There are 7839 Chicago, IL Vacation Rentals

Recently Booked Vacation Rentals in Chicago