Kathy Osterman Beach Pet Friendly Vacation Rentals

      Highly Rated

Apartment

W3 - Spacious 2BR Apt + Free On-site Parking

• Chicago
• ·
• Uptown
• 0.40 mi to center

10.0

Exceptional

(70 Reviews)

2 Bedrooms 2 Baths 4 Guests 1500 ft²

• 
  Parking
• 
  Kitchen
• 
  Air Conditioner
• 
  Internet

US $450/Night 7 Nights - US $3,147

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Apartment

Wrigleyville Art Deco Suite Garage

• Chicago
• ·
• Wrigleyville
• 0.22 mi to center

10.0

Exceptional

(5 Reviews)

4 Bedrooms 2 Baths 10 Guests 1205.56 ft²

• 
  Parking
• 
  Air Conditioner
• 
  Internet
• 
  Pet Friendly

US $480/Night 7 Nights - US $3,361

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      Price Dropped

Bed & Breakfast

The Villa Toscana

• Chicago
• ·
• Boystown
• 0.11 mi to center

8.0

Excellent

(667 Reviews)

1 Bedroom 1 Bath

• 
  Parking
• 
  Internet
• 
  Pet Friendly
• 
  Security/Safety

US $141/Night 7 Nights - US $985

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New

Condo

Family Friendly 2BD/2BA Near Wrigley, Lincoln Square

• Chicago
• ·
• Uptown
• 0.79 mi to center

10.0

Exceptional

(64 Reviews)

2 Bedrooms 2 Baths 4 Guests 1000 ft²

• 
  Oceanfront
• 
  Breakfast
• 
  Parking
• 
  Ocean View

US $440/Night 7 Nights - US $3,077

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Apartment

The Dakin Estate 4BR Art Deco Speakeasy Duplex

• Chicago
• ·
• Wrigleyville
• 0.23 mi to center

10.0

Exceptional

(1 Review)

4 Bedrooms 2 Baths 12 Guests 23680.6 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  Air Conditioner
• 
  Internet

US $1,018/Night 7 Nights - US $7,129

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      Highly Rated

Hotel

The Guesthouse Hotel

• Chicago
• ·
• Ravenswood
• 0.75 mi to center

9.8

Exceptional

(408 Reviews)

1 Bath

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

US $433/Night 7 Nights - US $3,028

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      Highly Rated

Apartment

The Holiday Lake House - 2br 2bth - 50 steps from the beach!

• Chicago
• ·
• Rogers Park
• 0.64 mi to center

10.0

Exceptional

(64 Reviews)

2 Bedrooms 2 Baths 6 Guests 1100 ft²

• 
  Hot Tub
• 
  Parking
• 
  Ocean View
• 
  Balcony/Terrace

US $421/Night 7 Nights - US $2,950

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New

Apartment

The Velvet Manor Luxe 3BR Jacuzzi Garage

• Chicago
• ·
• Uptown
• 0.89 mi to center

10.0

Exceptional

(1 Review)

3 Bedrooms 1 Bath 8 Guests 1496.18 ft²

• 
  Parking
• 
  Air Conditioner
• 
  Internet
• 
  Pet Friendly

US $781/Night 7 Nights - US $5,467

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House

Wrigleyville Inn

• Chicago
• ·
• Lakeview
• 0.05 mi to center

10.0

Exceptional

(28 Reviews)

1 Bedroom 1 Bath

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

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

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      Highly Rated

Apartment

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

• Chicago
• ·
• Uptown
• 0.25 mi to center

10.0

Exceptional

(58 Reviews)

1 Bedroom 1 Bath 2 Guests 441 ft²

• 
  Oceanfront
• 
  Ocean View
• 
  Balcony/Terrace
• 
  View

US $266/Night 7 Nights - US $1,862

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Apartment

Wrigleyville Art Deco Retreat Garage

• Chicago
• ·
• Wrigleyville
• 0.22 mi to center

10.0

Exceptional

(1 Review)

3 Bedrooms 1 Bath 8 Guests 1097.92 ft²

• 
  Parking
• 
  Air Conditioner
• 
  Internet
• 
  Pet Friendly

US $488/Night 7 Nights - US $3,414

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Apartment

Vintage City Chic: The Artist's Haven. 5 Blocks from Lake Michigan!

• Chicago
• ·
• Rogers Park
• 0.36 mi to center

10.0

Exceptional

(24 Reviews)

2 Bedrooms 1 Bath 6 Guests 1200 ft²

• 
  Parking
• 
  Kitchen
• 
  Air Conditioner
• 
  Internet

US $352/Night 7 Nights - US $2,466

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House

Spacious Chicago Group Home! Walk to Train & Eats

• Chicago
• ·
• Ravenswood
• 0.64 mi to center

10.0

Exceptional

(1 Review)

3 Bedrooms 2 Baths 6 Guests 2002.09 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  Internet
• 
  Pet Friendly

US $326/Night 7 Nights - US $2,282

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      Price Dropped

Apartment

This 2 bedroom 2 bathroom elegantly furnished home is ready for all your needs. Featuring a primary bedroom suite, TV room, dining room, and additional sitting areas.

• Chicago
• ·
• Rogers Park
• 0.16 mi to center

10.0

Exceptional

(16 Reviews)

2 Bedrooms 2 Baths 4 Guests 1750 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

US $418/Night 7 Nights - US $2,924

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Apartment

Wrigleyville Oasis Modern Comfort Steps from Wrigley Field

• Chicago
• ·
• Lakeview
• 0.24 mi to center

10.0

Exceptional

(6 Reviews)

1 Bedroom 1 Bath 6 Guests 900 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

US $414/Night 7 Nights - US $2,898

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New

Apartment

Spacious King 1BD Top Floor Walkable Edgewater

• Chicago
• ·
• Edgewater
• 0.69 mi to center

10.0

Exceptional

(6 Reviews)

1 Bedroom 1 Bath 2 Guests 1250 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

US $302/Night 7 Nights - US $2,116

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Apartment

Wrigleyville Retreat 1BR Sleeps 6 Full Kitchen

• Chicago
• ·
• Wrigleyville
• 0.27 mi to center

10.0

Exceptional

(4 Reviews)

1 Bedroom 1 Bath 6 Guests 900 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

US $348/Night 7 Nights - US $2,437

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Apartment

Beautiful Bollywood 3 Bed Gem near Loyola University/Rogers Park/Lake Michigan

• Chicago
• ·
• West Ridge
• 0.11 mi to center

10.0

Exceptional

(1 Review)

2 Bedrooms 1 Bath 6 Guests

• 
  Kitchen
• 
  Air Conditioner
• 
  Internet
• 
  Pet Friendly

US $302/Night 7 Nights - US $2,112

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Apartment

2BR/1BA Apt w/Modern Amenities Rogers Park + Free Parking

• Chicago
• ·
• Rogers Park
• 0.14 mi to center

10.0

Exceptional

(1 Review)

2 Bedrooms 1 Bath 4 Guests

• 
  Parking
• 
  Kitchen
• 
  Air Conditioner
• 
  Internet

US $245/Night 7 Nights - US $1,712

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Apartment

Chicago Lakefront Vacation Rental · Fire Pit Patio · Loyola Beach

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

10.0

Exceptional

(1 Review)

1 Bedroom 1 Bath 5 Guests

• 
  Ocean View
• 
  Balcony/Terrace
• 
  View
• 
  Kitchen

US $239/Night 7 Nights - US $1,671

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      Price Dropped

Apartment

Elite 2BR Art Deco sanctuary. High style.

• Chicago
• ·
• Wrigleyville
• 0.22 mi to center

9.8

Exceptional

(10 Reviews)

2 Bedrooms 1 Bath 6 Guests 1000 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

US $610/Night 7 Nights - US $4,273

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Apartment

King Bed & In-Unit Laundry!

• Chicago
• ·
• West Ridge
• 0.57 mi to center

9.8

Exceptional

(10 Reviews)

1 Bedroom 1 Bath 5 Guests

• 
  Oceanfront
• 
  Parking
• 
  Ocean View
• 
  Balcony/Terrace

US $187/Night 7 Nights - US $1,311

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      Highly Rated

Apartment

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

• Chicago
• ·
• North Center
• 0.70 mi to center

9.6

Exceptional

(96 Reviews)

2 Bedrooms 1 Bath 6 Guests 700 ft²

• 
  Parking
• 
  Ocean View
• 
  View
• 
  Kitchen

US $287/Night 7 Nights - US $2,006

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Condo

MODERN COMPLETELY REMODELED Bright, Spacious Flat STEPS from Wrigley Field &Bars

• Chicago
• ·
• Lakeview
• 0.24 mi to center

9.6

Exceptional

(25 Reviews)

2 Bedrooms 2 Baths 4 Guests 1070 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

US $235/Night 7 Nights - US $1,643

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