Printers Row 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
10.0Exceptional
(555 Reviews)
1 Bedroom
1 Bath
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $275/Night
7 Nights - US $1,923
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 Printers Row
Over 4198+ Luxury Places to Stay in or Near Printers Row
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
Hotel
- Chicago
- ·
- Rush and Division
- 0.09 mi to center
3 Baths
1515 ft²
- Parking
- Pool
Spa- Balcony/Terrace
US $4,318/Night
7 Nights - US $30,226
New
House
- Chicago
- ·
- Near North Side
- 0.32 mi to center
12 Bedrooms
13 Baths
24 Guests
10631 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $4,015/Night
7 Nights - US $28,103
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
House
- Chicago
- ·
- Gold Coast
- 0.27 mi to center
6 Bedrooms
5 Baths
26 Guests
4294.8 ft²
Private Beach
Breakfast- EV Charge Station
- Parking
US $3,466/Night
7 Nights - US $24,260
House
- Chicago
- ·
- Gold Coast
- 0.29 mi to center
10.0Exceptional
(39 Reviews)
5 Bedrooms
5 Baths
14 Guests
7000 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $3,389/Night
7 Nights - US $23,722
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
Top-Rated Villas with a Pool in Printers Row
Over 1169+ Top-Rated Private Villas with a Pool in or Near Printers Row
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
- ·
- Rush and Division
- 0.24 mi to center
10.0Exceptional
(6 Reviews)
2 Bedrooms
2 Baths
7 Guests
1261 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $423/Night
7 Nights - US $2,960
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
- ·
- Rush and Division
- 0.13 mi to center
10.0Exceptional
(5 Reviews)
3 Bedrooms
2 Baths
10 Guests
2000 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $592/Night
7 Nights - US $4,146
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
Pet-Friendly Villas in Printers Row
Over 1730+ Pet-Friendly Private Villas in or Near Printers Row
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
House
- Chicago
- ·
- Old Town Triangle
- 0.12 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
2 Baths
12 Guests
10763.91 ft²
- Parking
- View
- Air Conditioner
- Internet
US $2,066/Night
7 Nights - US $14,462
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
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
- ·
- 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
- ·
- 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
- Chicago
- ·
- Lower West Side
- 1.59 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
8 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $384/Night
7 Nights - US $2,691
Apartment
- Chicago
- ·
- Near North Side
- 0.13 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $332/Night
7 Nights - US $2,324
Apartment
- Chicago
- ·
- Heart of Chicago
- 0.14 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
3 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $218/Night
7 Nights - US $1,525
Large Private Villas in Printers Row
Over 529+ Large Villas in or Near Printers Row for Groups and Families
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
House
- Chicago
- ·
- River North
- 0.78 mi to center
10.0Exceptional
(3 Reviews)
10 Bedrooms
3 Baths
10 Guests
1205.56 ft²
- Balcony/Terrace
- Air Conditioner
- Internet
- Child Friendly
US $307/Night
7 Nights - US $2,147
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
(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
- 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
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
Apartment
- Chicago
- ·
- Gold Coast
- 0.27 mi to center
9.2Exceptional
(10 Reviews)
2 Bedrooms
2 Baths
14 Guests
800 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $433/Night
7 Nights - US $3,032
Wheelchair Accessible Holiday Homes in Printers Row
Over 2612+ Wheelchair Accessible Villas and Holiday Homes in or Near Printers Row
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
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
- ·
- 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
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
Printers Row Villas, Airbnb and Holiday Homes Under $200
Over 1515+ Printers Row 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
- 0.35 mi to center
7.0Very Good
(79 Reviews)
1 Bedroom
1 Bath
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $125/Night
7 Nights - US $875
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
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
5 Guests
947.22 ft²
- View
- Air Conditioner
- Internet
- Child Friendly
US $90/Night
7 Nights - US $630
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 Printers Row
Over 2661+ Instantly Bookable Private Villas in or Near Printers Row
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
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
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
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 Printers Row
About Printers Row Vacation Rentals
Discover over 4207 amazing vacation rental options in Printers Row 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 Printers Row.
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 801.24 ft², with prices averaging US $406 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 Printers Row.
Show more
Show less
Top Pickleball-Ready Accommodation Types in Printers Row
| Type | Count |
|---|---|
| Holiday Apartments | 2750 |
| Vacation Homes | 461 |
| Villas | 6 |
Use these Quick Filters to Find a Vacation Rental in Printers Row
★ 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 Printers Row with PickleTrip™.
Weather in Printers Row, IL
View the weather forecast for Printers Row before booking your Printers Row 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
Other Places to Stay in Printers Row, IL
Frequently Asked Questions About Printers Row?
What are the top vacation rentals, resorts, and hotels in Printers Row 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 Printers Row. 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 Printers Row!
- Cozy 1-bedroom apartment in beautiful Chicago with AC and gym access
- The Sono Chicago
- 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
- 4BR Old Town Chicago Loft | Walk to Wells St
- 52nd Floor Penthouse with Skyline Views and Pool
- Luxury House in the heart of Old Town with Parking
How many pickleball-ready properties have private pools in Printers Row?
Discover 81 accommodations with private or nearby pickleball courts in Printers Row. 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
- Stay One Chicago
- Chic Stay in River North: Luxury Suites, Top Amenities, Near Arts & Nightlife!
Which vacation rentals, resorts, or hotels in Printers Row is best for families looking for a pickleball-getaway?
Looking for a fun and active getaway with pickleball courts in Printers Row? 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
- ENVITAE Hotel | 2 Bedroom Luxury Apartments
How many PickleTrip vacation rentals or resorts are available in Printers Row?
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 4207 properties listed in Printers Row 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 |
|---|---|
| Downtown Chicago Vacation Rentals in Chicago, Illinois | 1397 |
| The Loop Vacation Rentals in Chicago, Illinois | 642 |
| South Loop Vacation Rentals in Chicago, Illinois | 290 |
| Near South Side Vacation Rentals in Chicago, Illinois | 271 |
Map
