Pilsen pickleball Stays, Resort Rentals, & Homes
Condo
- Chicago
- ·
- Near East Side
- 0.16 mi to center
1 Bedroom
1 Bath
2 Guests
Air Conditioner
Internet
Wellness Facilities
Security/Safety
US $154/Night
7 Nights - US $1,080
Apartment
10.0Exceptional
(4 Reviews)
4 Bedrooms
3 Baths
10 Guests
107.64 ft²
Parking
Balcony/Terrace
View- Air Conditioner
US $354/Night
7 Nights - US $2,475
Bed & Breakfast
9.8Exceptional
(215 Reviews)
1 Bedroom
1 Bath
Breakfast
Kitchen- Air Conditioner
- Internet
US $382/Night
7 Nights - US $2,676
Apartment
- Chicago
- ·
- Downtown Chicago
- 0.41 mi to center
10.0Exceptional
(418 Reviews)
1 Bedroom
1 Bath
4 Guests
Oceanfront- Parking
Pool
Ocean View
US $257/Night
7 Nights - US $1,796
New
Apartment
10.0Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
8 Guests
1851.39 ft²
- Parking
- Air Conditioner
- Internet
Child Friendly
US $287/Night
7 Nights - US $2,007
Apartment
- Chicago
- ·
- Downtown Chicago
- 0.41 mi to center
10.0Exceptional
(234 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $253/Night
7 Nights - US $1,774
Apartment
- Chicago
- ·
- Downtown Chicago
- 0.42 mi to center
10.0Exceptional
(68 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $225/Night
7 Nights - US $1,576
Apartment
- Chicago
- ·
- Downtown Chicago
- 0.42 mi to center
10.0Exceptional
(43 Reviews)
1 Bedroom
1 Bath
2 Guests
735 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $191/Night
7 Nights - US $1,337
Condo
10.0Exceptional
(32 Reviews)
2 Bedrooms
1 Bath
5 Guests
1000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $322/Night
7 Nights - US $2,251
Luxury Places to Stay in Pilsen
Over 3556+ Luxury Places to Stay in or Near Pilsen
New
Apartment
10.0Exceptional
(1 Review)
4 Bedrooms
3 Baths
10 Guests
1076.39 ft²
- Parking
- Pool
- Air Conditioner
- Internet
US $10,000/Night
7 Nights - US $70,000
New
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
6 Bedrooms
4 Baths
12 Guests
1603.82 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $4,976/Night
7 Nights - US $34,831
New
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
5 Bedrooms
3 Baths
12 Guests
1496.18 ft²
EV Charge Station- Parking
- Balcony/Terrace
- Air Conditioner
US $4,545/Night
7 Nights - US $31,814
Apartment
- Chicago
- ·
- River North
- 0.20 mi to center
8 Bedrooms
6 Baths
16 Guests
4800.7 ft²
- Parking
- View
- Air Conditioner
- Internet
US $3,579/Night
7 Nights - US $25,053
Apartment
- Chicago
- ·
- Downtown Chicago
- 0.20 mi to center
10.0Exceptional
(1 Review)
7 Bedrooms
7 Baths
15 Guests
Hot Tub- Parking
- Pool
- Balcony/Terrace
US $3,285/Night
7 Nights - US $22,996
New
Apartment
- Chicago
- ·
- Downtown Chicago
- 0.42 mi to center
4 Bedrooms
4 Baths
10 Guests
5000 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $3,141/Night
7 Nights - US $21,990
Apartment
10.0Exceptional
(1 Review)
9 Bedrooms
9 Baths
16 Guests
4585 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $2,860/Night
7 Nights - US $20,018
Apartment
- Chicago
- ·
- Downtown Chicago
- 0.28 mi to center
8.5Fabulous
(55 Reviews)
16 Bedrooms
14 Baths
38 Guests
1463.89 ft²
Private Pool- Parking
- Pool
- Air Conditioner
US $2,682/Night
7 Nights - US $18,777
Apartment
- Chicago
- ·
- South Loop
- 0.39 mi to center
7.4Very Good
(17 Reviews)
2 Bedrooms
2 Baths
13 Guests
1001.04 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $2,671/Night
7 Nights - US $18,695
Top-Rated Villas with a Pool in Pilsen
Over 906+ Top-Rated Private Villas with a Pool in or Near Pilsen
Apartment
- Chicago
- ·
- Downtown Chicago
- 0.42 mi to center
10.0Exceptional
(14 Reviews)
2 Bedrooms
3 Baths
8 Guests
2600 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $519/Night
7 Nights - US $3,632
Apartment
- Chicago
- ·
- West Loop Gate
- 0.20 mi to center
10.0Exceptional
(11 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $463/Night
7 Nights - US $3,241
Apartment
- Chicago
- ·
- Downtown Chicago
- 0.35 mi to center
10.0Exceptional
(9 Reviews)
2 Bedrooms
2 Baths
5 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $435/Night
7 Nights - US $3,047
Apartment
- Chicago
- ·
- Downtown Chicago
- 0.19 mi to center
10.0Exceptional
(7 Reviews)
4 Bedrooms
3 Baths
9 Guests
3000 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $1,708/Night
7 Nights - US $11,958
Apartment
- Chicago
- ·
- Downtown Chicago
- 0.28 mi to center
10.0Exceptional
(6 Reviews)
3 Bedrooms
2 Baths
6 Guests
700 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $663/Night
7 Nights - US $4,638
Apartment
- Chicago
- ·
- Downtown Chicago
- 0.28 mi to center
10.0Exceptional
(5 Reviews)
3 Bedrooms
2 Baths
6 Guests
1467 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $663/Night
7 Nights - US $4,638
Apartment
- Chicago
- ·
- Downtown Chicago
- 0.35 mi to center
10.0Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
5 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $476/Night
7 Nights - US $3,330
Apartment
- Chicago
- ·
- Downtown Chicago
- 0.92 mi to center
10.0Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $445/Night
7 Nights - US $3,116
Apartment
- Chicago
- ·
- Downtown Chicago
- 0.91 mi to center
10.0Exceptional
(4 Reviews)
3 Bedrooms
3 Baths
8 Guests
2013 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $727/Night
7 Nights - US $5,092
Pet-Friendly Villas in Pilsen
Over 1467+ Pet-Friendly Private Villas in or Near Pilsen
Apartment
10.0Exceptional
(24 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $294/Night
7 Nights - US $2,056
Apartment
- Chicago
- ·
- Lower West Side
- 0.35 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
8 Guests
1603.82 ft²
Spa- Air Conditioner
- Internet
Pet Friendly
US $634/Night
7 Nights - US $4,439
Apartment
- Chicago
- ·
- Near West Side
- 0.34 mi to center
9.6Exceptional
(335 Reviews)
1 Bedroom
1 Bath
3 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $126/Night
7 Nights - US $882
Condo
- Chicago
- ·
- South Loop
- 0.68 mi to center
10.0Exceptional
(14 Reviews)
2 Bedrooms
2 Baths
4 Guests
689 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $359/Night
7 Nights - US $2,515
Apartment
- Chicago
- ·
- Killgubbin
- 0.20 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
8 Guests
1603.82 ft²
- Oceanfront
- Pool
- Ocean View
- View
US $454/Night
7 Nights - US $3,178
Apartment
- Chicago
- ·
- Printers Row
- 0.13 mi to center
10.0Exceptional
(11 Reviews)
2 Bedrooms
2 Baths
7 Guests
1109 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $674/Night
7 Nights - US $4,717
Apartment
- Chicago
- ·
- Bridgeport
- 0.46 mi to center
10.0Exceptional
(11 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $284/Night
7 Nights - US $1,986
Apartment
10.0Exceptional
(4 Reviews)
2 Bedrooms
1 Bath
5 Guests
700 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $474/Night
7 Nights - US $3,319
Apartment
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
6 Guests
700 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $463/Night
7 Nights - US $3,241
Large Private Villas in Pilsen
Over 408+ Large Villas in or Near Pilsen for Groups and Families
Apartment
- Chicago
- ·
- Little Village
- 0.68 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
1 Bath
12 Guests
1000 ft²
- Oceanfront
- Ocean View
- View
- Kitchen
US $211/Night
7 Nights - US $1,477
Apartment
- Chicago
- ·
- River North
- 0.20 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
3 Baths
16 Guests
1205.56 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $1,599/Night
7 Nights - US $11,193
Apartment
3 Bedrooms
1 Bath
10 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $309/Night
7 Nights - US $2,163
Apartment
- Chicago
- ·
- River North
- 0.21 mi to center
9.6Exceptional
(35 Reviews)
2 Bedrooms
2 Baths
10 Guests
800 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $265/Night
7 Nights - US $1,853
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
10 Guests
1119.45 ft²
- EV Charge Station
- Parking
- Spa
- Air Conditioner
US $439/Night
7 Nights - US $3,070
Apartment
- Chicago
- ·
- River North
- 0.21 mi to center
9.6Exceptional
(17 Reviews)
2 Bedrooms
1 Bath
10 Guests
1200 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $205/Night
7 Nights - US $1,438
Apartment
9.6Exceptional
(8 Reviews)
1 Bedroom
1 Bath
10 Guests
1350 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $352/Night
7 Nights - US $2,462
Apartment
- Chicago
- ·
- South Loop
- 0.39 mi to center
9.4Exceptional
(29 Reviews)
2 Bedrooms
2 Baths
13 Guests
1000 ft²
- Kitchen
- Air Conditioner
- Internet
Laundry
US $186/Night
7 Nights - US $1,304
Apartment
- Chicago
- ·
- River North
- 0.21 mi to center
9.2Exceptional
(33 Reviews)
2 Bedrooms
2 Baths
10 Guests
1200 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $280/Night
7 Nights - US $1,957
Wheelchair Accessible Holiday Homes in Pilsen
Over 2074+ Wheelchair Accessible Villas and Holiday Homes in or Near Pilsen
Apartment
10.0Exceptional
(11 Reviews)
2 Bedrooms
1 Bath
4 Guests
550 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $300/Night
7 Nights - US $2,100
Apartment
10.0Exceptional
(2 Reviews)
4 Bedrooms
4 Baths
10 Guests
1345.49 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $434/Night
7 Nights - US $3,038
Hotel
- Chicago
- ·
- Downtown Chicago
- 0.20 mi to center
9.8Exceptional
(1009 Reviews)
1 Bath
- Hot Tub
- Breakfast
- Parking
- Pool
US $743/Night
7 Nights - US $5,202
Apartment
- Chicago
- ·
- River West
- 0.33 mi to center
10.0Exceptional
(10 Reviews)
1 Bedroom
1 Bath
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $143/Night
7 Nights - US $1,003
House
- Chicago
- ·
- Near South Side
- 0.88 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
2 Baths
8 Guests
1797.57 ft²
- View
- Air Conditioner
- Internet
- Pet Friendly
US $441/Night
7 Nights - US $3,089
Apartment
- Chicago
- ·
- West Loop Gate
- 0.19 mi to center
10.0Exceptional
(7 Reviews)
1 Bedroom
1 Bath
2 Guests
350 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $276/Night
7 Nights - US $1,934
Condo
10.0Exceptional
(6 Reviews)
2 Bedrooms
1 Bath
5 Guests
667 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $401/Night
7 Nights - US $2,807
Apartment
- Chicago
- ·
- Near North Side
- 0.47 mi to center
10.0Exceptional
(6 Reviews)
2 Bedrooms
1 Bath
5 Guests
881 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $339/Night
7 Nights - US $2,372
Condo
- Chicago
- ·
- Printers Row
- 0.23 mi to center
10.0Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
5 Guests
667 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $394/Night
7 Nights - US $2,756
Pilsen Villas, Airbnb and Holiday Homes Under $200
Over 1327+ Pilsen Private Villas, Airbnb and Holiday Homes Under $200
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
6 Guests
900 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $186/Night
7 Nights - US $1,299
Apartment
- Chicago
- ·
- South Loop
- 0.22 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
441.32 ft²
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $185/Night
7 Nights - US $1,295
House
- Chicago
- ·
- Bronzeville
- 0.16 mi to center
7.6Very Good
(126 Reviews)
1 Bedroom
1 Bath
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $176/Night
7 Nights - US $1,233
Apartment
- Chicago
- ·
- Prairie District
- 0.03 mi to center
10.0Exceptional
(5 Reviews)
1 Bedroom
1 Bath
4 Guests
550 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $145/Night
7 Nights - US $1,014
Apartment
- Chicago
- ·
- River West
- 0.13 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
3 Guests
1001.04 ft²
- Parking
- Air Conditioner
- Internet
Wheelchair Accessible
US $77/Night
7 Nights - US $539
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
8 Guests
950 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $186/Night
7 Nights - US $1,299
Apartment
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $162/Night
7 Nights - US $1,137
Apartment
- Chicago
- ·
- Heart of Chicago
- 0.16 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $191/Night
7 Nights - US $1,335
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
6 Guests
950 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $161/Night
7 Nights - US $1,126
Instantly Bookable Villa Rentals in Pilsen
Over 2242+ Instantly Bookable Private Villas in or Near Pilsen
Apartment
- Chicago
- ·
- Noble Square
- 0.19 mi to center
10.0Exceptional
(29 Reviews)
1 Bedroom
1 Bath
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $258/Night
7 Nights - US $1,805
Apartment
- Chicago
- ·
- River North
- 0.12 mi to center
9.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $266/Night
7 Nights - US $1,861
Apartment
- Chicago
- ·
- Rush and Division
- 0.25 mi to center
10.0Exceptional
(23 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Laundry
US $268/Night
7 Nights - US $1,879
Condo
- Chicago
- ·
- Pulaski Park
- 0.29 mi to center
10.0Exceptional
(21 Reviews)
1 Bedroom
1 Bath
4 Guests
950 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $285/Night
7 Nights - US $1,992
Apartment
- Chicago
- ·
- Little Village
- 0.82 mi to center
10.0Exceptional
(15 Reviews)
2 Bedrooms
1 Bath
7 Guests
1100 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $283/Night
7 Nights - US $1,982
Apartment
10.0Exceptional
(14 Reviews)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Spa
- Ocean View
- Balcony/Terrace
US $223/Night
7 Nights - US $1,563
House
- Chicago
- ·
- Prairie District
- 0.14 mi to center
10.0Exceptional
(13 Reviews)
2 Bedrooms
2 Baths
5 Guests
1600 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $884/Night
7 Nights - US $6,185
Apartment
- Chicago
- ·
- West Loop Gate
- 0.19 mi to center
10.0Exceptional
(5 Reviews)
1 Bedroom
1 Bath
2 Guests
450 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $359/Night
7 Nights - US $2,513
New
Apartment
10.0Exceptional
(5 Reviews)
1 Bedroom
1 Bath
5 Guests
- Child Friendly
US $300/Night
7 Nights - US $2,102
Book a Last Minute Place to Stay in Pilsen
About Pilsen Vacation Rentals
Discover over 3565 amazing vacation rental options in Pilsen 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 Pilsen.
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 783.76 ft², with prices averaging US $370 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 Pilsen.
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Top Pickleball-Ready Accommodation Types in Pilsen
| Type | Count |
|---|---|
| Holiday Apartments | 2420 |
| Vacation Homes | 314 |
| Villas | 5 |
| Cottages | 1 |
Use these Quick Filters to Find a Vacation Rental in Pilsen
★ 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 Pilsen with PickleTrip™.
Weather in Pilsen, IL
View the weather forecast for Pilsen before booking your Pilsen 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
Frequently Asked Questions About Pilsen?
What are the top vacation rentals, resorts, and hotels in Pilsen 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 Pilsen. 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 Pilsen!
- Cozy 1-bedroom apartment in beautiful Chicago with AC and gym access
- 52nd Floor MagMile Penthouse Views Fireplace Pool
- Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
- 3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
- 51st Floor MagMile Penthouse Views Balcony Pool
- 1F Chicago's Little italy Graystone nearDowntown
- 52nd Floor Penthouse with Skyline Views and Pool
- Brilliant Downtown Chicago 3-Bedroom Condominium
- 50th Floor Mag Mile Views, Balcony, Pool, Gym
- Vibrant 3BR Pilsen Stay Free Parking Near Downtown
How many pickleball-ready properties have private pools in Pilsen?
Discover 55 accommodations with private or nearby pickleball courts in Pilsen. Some of the best destinations to stay and play pickleball are:
- Stylish River North Suites Luxe Comfort Near Chicago’s Best Shopping & Nightlife
- Lux Apts with Lake Views and Top Amenities
- Chic Stay in River North: Luxury Suites, Top Amenities, Near Arts & Nightlife!
- Stylish River North Suites: Luxury Living Near Chicago’s Best Shopping&Nightlife
Which vacation rentals, resorts, or hotels in Pilsen is best for families looking for a pickleball-getaway?
Looking for a fun and active getaway with pickleball courts in Pilsen? 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.
- River North 2BD Condo: Parking, Balcony, Laundry
- Prime Chicago 2BR Skyline - 5 Min to Museum Campus
- Mccormick Place Guest House
How many PickleTrip vacation rentals or resorts are available in Pilsen?
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 3565 properties listed in Pilsen 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 |
|---|---|
| Near West Side Vacation Rentals in Chicago, Illinois | 315 |
| University Village / Little Italy Vacation Rentals in Chicago, Illinois | 86 |
| Lower West Side Vacation Rentals in Chicago, Illinois | 56 |
| Heart of Chicago Vacation Rentals in Chicago, Illinois | 41 |
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