266+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. Illinois
  3. Chicago
  4. Cicero

Cicero pickleball Stays, Resort Rentals, & Homes

About Cicero Vacation Rentals

Discover over 266 amazing vacation rental options in Cicero 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 Cicero.

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 739.11 ft², with prices averaging US $292 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 Cicero.

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Top Pickleball-Ready Accommodation Types in Cicero

Type Count
Holiday Apartments 157
Vacation Homes 86

Use these Quick Filters to Find a Vacation Rental in Cicero

★ 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 Cicero with PickleTrip™.

Weather in Cicero, IL

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

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


Morton College
Hawthorne Works Museum
Navy Pier
Wrigley Field
McCormick Place
Millennium Park
Union Station
Soldier Field
Willis Tower
Art Institute of Chicago
United Center
Grant Park
John G. Shedd Aquarium
Chicago Museum of Science and Industry
Chicago Theatre
Chicago Riverwalk
Field Museum of Natural History
University of Chicago
Brookfield Zoo
Northwestern University

Other Places to Stay in Cicero, IL


Hawthorne Works Museum 121 Properties
Morton College 113 Properties

Frequently Asked Questions About Cicero?

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

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

Looking for a fun and active getaway with pickleball courts in Cicero? 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 Cicero?

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 266 properties listed in Cicero 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 (4) 
Neighborhood Property Count
Austin Vacation Rentals in Chicago, Illinois 25
North Lawndale Vacation Rentals in Chicago, Illinois 532
Lawndale Vacation Rentals in Chicago, Illinois 508
Little Village Vacation Rentals in Chicago, Illinois 382

People Also Ask

There are 266 Cicero, IL Vacation Rentals

Recently Booked Vacation Rentals in Cicero