Second City, IL pickleball Stays, Resort Rentals, & Homes

     

1 Court Nearby

Cottage

Private Cozy Cottage House in Lincoln Park w/Porch

• Chicago
• ·
• Sheffield Neighbors
• 0.27 mi to center

10.0

Exceptional

(1 Review)

1 Bedroom 1 Bath 4 Guests

• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner
• 
  Internet

US $111/Night 7 Nights - US $774

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Apartment

Cozy Modern 1BR Apt, 10-min Walk to Wrigley Field - Stratford 1E 3E rep

• Chicago
• ·
• Lake View East
• 0.30 mi to center

10.0

Exceptional

(14 Reviews)

1 Bedroom 1 Bath 2 Guests 699.65 ft²

• 
  Internet
• 
  Child Friendly
• 
  Security/Safety

US $256/Night 7 Nights - US $1,792

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      Highly Rated

Bed & Breakfast

The Sono Chicago

• Chicago
• ·
• Old Town
• 0.21 mi to center

10.0

Exceptional

(566 Reviews)

1 Bedroom 1 Bath

• 
  Parking
• 
  Balcony/Terrace
• 
  Air Conditioner
• 
  Internet

US $195/Night 7 Nights - US $1,364

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1 Court Nearby

Condo

Cozy 1-bedroom apartment in beautiful Chicago with AC and gym access

• Chicago
• ·
• Near East Side
• 0.16 mi to center

1 Bedroom 1 Bath 2 Guests

• 
  Air Conditioner
• 
  Internet
• 
  Child Friendly
• 
  Wellness Facilities

US $150/Night 7 Nights - US $1,049

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Apartment

Bootlegger House Sleeps 10-20 Free TV & Parking

• Chicago
• ·
• Lake View East
• 0.18 mi to center

10.0

Exceptional

(4 Reviews)

6 Bedrooms 2 Baths 20 Guests 3498.27 ft²

• 
  Private Beach
• 
  EV Charge Station
• 
  Parking
• 
  Ocean View

US $482/Night 7 Nights - US $3,371

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House

Wrigleyville Inn

• Chicago
• ·
• Lakeview
• 0.05 mi to center

10.0

Exceptional

(30 Reviews)

1 Bedroom 1 Bath

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

US $531/Night 7 Nights - US $3,717

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      Price Dropped

Apartment

Gold Coast Group Retreat + Breathtaking Views

• Chicago
• ·
• Near North Side
• 0.13 mi to center

10.0

Exceptional

(1 Review)

4 Bedrooms 4 Baths 10 Guests

• 
  Parking
• 
  Pool
• 
  Balcony/Terrace
• 
  Kitchen

US $1,007/Night 7 Nights - US $7,052

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Apartment

Modern 3BR Apt in Boystown, 12-min walk to Wrigley - Stratford 1S

• Chicago
• ·
• Lake View East
• 0.31 mi to center

10.0

Exceptional

(4 Reviews)

3 Bedrooms 1 Bath 6 Guests 1001.04 ft²

• 
  Air Conditioner
• 
  Internet
• 
  Child Friendly
• 
  Security/Safety

US $517/Night 7 Nights - US $3,619

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      Highly Rated

Bed & Breakfast

Ray's Bucktown B&B

• Chicago
• ·
• Bucktown
• 0.21 mi to center

9.8

Exceptional

(420 Reviews)

1 Bedroom 1 Bath

• 
  Breakfast
• 
  Parking
• 
  Spa
• 
  Balcony/Terrace

US $245/Night 7 Nights - US $1,715

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New

Apartment

Beautifully Set Up 2BR Space

• Chicago
• ·
• Wrigleyville
• 0.09 mi to center

10.0

Exceptional

(1 Review)

2 Bedrooms 1 Bath 6 Guests

• 
  Kitchen
• 
  Air Conditioner
• 
  Internet
• 
  Pet Friendly

US $231/Night 7 Nights - US $1,620

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House

Stunning 5BR Home in Heart of Chicago with 2 Rooftops

• Chicago
• ·
• Wicker Park
• 0.38 mi to center

10.0

Exceptional

(3 Reviews)

5 Bedrooms 3 Baths 16 Guests 4004.17 ft²

• 
  Hot Tub
• 
  Parking
• 
  Balcony/Terrace
• 
  View

US $2,234/Night 7 Nights - US $15,637

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      Highly Rated

House

Great location! Spacious 6BD Home + Garage!

• Chicago
• ·
• Bucktown
• 0.84 mi to center

9.2

Exceptional

(55 Reviews)

5 Bedrooms 3 Baths 12 Guests 3000 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

US $606/Night 7 Nights - US $4,239

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House

The Village Inn by Dakota Gal Digs

• Chicago
• ·
• Sheffield Neighbors
• 0.18 mi to center

10.0

Exceptional

(3 Reviews)

3 Bedrooms 2 Baths 8 Guests 1001.04 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  Air Conditioner
• 
  Internet

US $832/Night 7 Nights - US $5,827

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      Price Dropped

Apartment

1BR Well-Equipped Apartment

• Chicago
• ·
• Lakeview
• 0.93 mi to center

8.4

Excellent

(11 Reviews)

1 Bedroom 1 Bath 2 Guests

• 
  Kitchen
• 
  Air Conditioner
• 
  Internet
• 
  Pet Friendly

US $192/Night 7 Nights - US $1,343

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New

Apartment

High-Floor 2BRs with City & Lake Views

• Chicago
• ·
• The Loop
• 0.60 mi to center

4 Bedrooms 4 Baths 10 Guests 2638 ft²

• 
  Hot Tub
• 
  Parking
• 
  Pool
• 
  Balcony/Terrace

US $1,501/Night 7 Nights - US $10,507

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      Price Dropped

Apartment

River West 3BR Penthouse Duo: Skyline Comfort

• Chicago
• ·
• River West
• 0.21 mi to center

6 Bedrooms 5 Baths 14 Guests

• 
  Hot Tub
• 
  Parking
• 
  Pool
• 
  Balcony/Terrace

US $1,267/Night 7 Nights - US $8,866

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New

House

Stunning Gold Coast Home 12BD 6BA & Rooftop Patio

• Chicago
• ·
• Gold Coast
• 0.19 mi to center

12 Bedrooms 7 Baths 23 Guests 4000 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

US $1,128/Night 7 Nights - US $7,898

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New

House

NEW! Skyline Views River West Townhouse; 2 Parking Incl

• Chicago
• ·
• River West
• 0.20 mi to center

4 Bedrooms 3 Baths 12 Guests 2251 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

US $810/Night 7 Nights - US $5,671

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New

Apartment

2-bedroom apartment in fantastic Chicago with cool AC

• Chicago
• ·
• Sheffield Neighbors
• 0.13 mi to center

2 Bedrooms 1 Bath 6 Guests

• 
  Kitchen
• 
  Air Conditioner
• 
  Internet
• 
  Pet Friendly

US $796/Night 7 Nights - US $5,572

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New

Apartment

Prime West Loop 2BR Duo + Enjoy Unique Gatherings

• Chicago
• ·
• West Loop
• 0.37 mi to center

4 Bedrooms 4 Baths 10 Guests

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

US $763/Night 7 Nights - US $5,338

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      Price Dropped

Apartment

South Loop Rooftop With In and Out Parking 4

• Chicago
• ·
• The Loop
• 0.46 mi to center

4 Bedrooms 4 Baths 10 Guests 2000 ft²

• 
  Breakfast
• 
  Parking
• 
  Kitchen
• 
  Air Conditioner

US $658/Night 7 Nights - US $4,605

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New

Apartment

South Loop Rooftop With In and Out Parking 6

• Chicago
• ·
• The Loop
• 0.46 mi to center

4 Bedrooms 4 Baths 9 Guests 2000 ft²

• 
  Breakfast
• 
  Parking
• 
  Kitchen
• 
  Air Conditioner

US $544/Night 7 Nights - US $3,805

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New

Apartment

Boho City Escape | Parking + Balcony

• Chicago
• ·
• West Town
• 0.66 mi to center

2 Bedrooms 2 Baths 6 Guests 830 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

US $476/Night 7 Nights - US $3,335

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New

Apartment

Luxury River North Loft | Walk to Mag Mile, Riverwalk & Top Restaurants

• Chicago
• ·
• Downtown Chicago
• 0.44 mi to center

2 Bedrooms 2 Baths 5 Guests

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

US $467/Night 7 Nights - US $3,272

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