Skydeck Ledge, IL Pet Friendly Vacation Rentals

      Highly Rated

Condo

NEW LUXURY CONDO WITH PATIO DECK

• Chicago
• ·
• Ukrainian Village
• 0.13 mi to center

10.0

Exceptional

(222 Reviews)

1 Bedroom 1 Bath 5 Guests

• 
  Hot Tub
• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen

US $281/Night 7 Nights - US $1,969

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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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      Highly Rated

Apartment

The Neighborhood Hotel-Little Italy

• Chicago
• ·
• Near West Side
• 0.34 mi to center

9.6

Exceptional

(368 Reviews)

1 Bedroom 1 Bath 3 Guests

• 
  Kitchen
• 
  Air Conditioner
• 
  Internet
• 
  Pet Friendly

US $126/Night 7 Nights - US $882

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      Highly Rated

House

Luxury House in the heart of Old Town with Parking

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

10.0

Exceptional

(71 Reviews)

5 Bedrooms 7 Baths 12 Guests 6200 ft²

• 
  Parking
• 
  Spa
• 
  Balcony/Terrace
• 
  Kitchen

US $1,961/Night 7 Nights - US $13,725

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      Price Dropped

House

Stylish 3BR Gem in Prime Location

• Chicago
• ·
• Near South Side
• 0.88 mi to center

10.0

Exceptional

(2 Reviews)

1 Bedroom 2 Baths 8 Guests 1797.57 ft²

• 
  View
• 
  Air Conditioner
• 
  Internet
• 
  Pet Friendly

US $385/Night 7 Nights - US $2,692

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      Highly Rated

Apartment

Kasa Magnificent Mile Chicago

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

9.4

Exceptional

(959 Reviews)

1 Bedroom 1 Bath 2 Guests

• 
  Parking
• 
  Ocean View
• 
  View
• 
  Kitchen

US $303/Night 7 Nights - US $2,120

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      Price Dropped

Condo

Ukrainian Village 3BR/3BA Private Patio, Parking

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

10.0

Exceptional

(41 Reviews)

3 Bedrooms 3 Baths 7 Guests 2400 ft²

• 
  Hot Tub
• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen

US $426/Night 7 Nights - US $2,980

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Apartment

Spacious Modern Pilsen Retreat Sleeps 8 Near Downtown Chicago

• Chicago
• ·
• Lower West Side
• 0.35 mi to center

10.0

Exceptional

(1 Review)

3 Bedrooms 2 Baths 8 Guests 1603.82 ft²

• 
  Air Conditioner
• 
  Internet
• 
  Pet Friendly
• 
  Sports/Activities

US $634/Night 7 Nights - US $4,439

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      Highly Rated

Apartment

Kasa South Loop Chicago

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

9.4

Exceptional

(553 Reviews)

1 Bedroom 1 Bath 2 Guests

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

US $186/Night 7 Nights - US $1,302

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Apartment

Luxury Loft Collection 901 - Terrace - River North

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

10.0

Exceptional

(36 Reviews)

3 Bedrooms 3 Baths 10 Guests 2300 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

US $595/Night 7 Nights - US $4,163

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House

3-Story Townhome Free Parking Private Patio Washer-Dryer

• Chicago
• ·
• Mid-North District
• 0.23 mi to center

10.0

Exceptional

(1 Review)

2 Bedrooms 2 Baths 8 Guests 1399.31 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  View
• 
  Air Conditioner

US $631/Night 7 Nights - US $4,415

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      Price Dropped

Apartment

Spacious 4BR Central Apartment w/Skyline Views

• Chicago
• ·
• River North
• 0.79 mi to center

10.0

Exceptional

(33 Reviews)

4 Bedrooms 3 Baths 10 Guests 1250 ft²

• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner
• 
  Internet

US $266/Night 7 Nights - US $1,860

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Apartment

3BR Luxury Modern Apartment

• Chicago
• ·
• Killgubbin
• 0.20 mi to center

10.0

Exceptional

(1 Review)

3 Bedrooms 3 Baths 8 Guests 1603.82 ft²

• 
  Oceanfront
• 
  Pool
• 
  Ocean View
• 
  View

US $442/Night 7 Nights - US $3,092

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Condo

MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba

• Chicago
• ·
• South Loop
• 0.49 mi to center

10.0

Exceptional

(31 Reviews)

2 Bedrooms 2 Baths 6 Guests 958 ft²

• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner
• 
  Internet

US $333/Night 7 Nights - US $2,333

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Apartment

Luxury Loft Collection 02 - Terrace - River North

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

10.0

Exceptional

(29 Reviews)

3 Bedrooms 3 Baths 12 Guests 2200 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

US $547/Night 7 Nights - US $3,831

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      Price Dropped

House

Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces

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

10.0

Exceptional

(24 Reviews)

6 Bedrooms 4 Baths 26 Guests

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

US $1,023/Night 7 Nights - US $7,161

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Apartment

Luxury Designer Loft 302 | River North

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

10.0

Exceptional

(23 Reviews)

3 Bedrooms 2 Baths 8 Guests 1000 ft²

• 
  Parking
• 
  Ocean View
• 
  View
• 
  Kitchen

US $429/Night 7 Nights - US $3,006

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House

Luxury SOHO Styled Two-Level Townhouse - Old Town

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

10.0

Exceptional

(22 Reviews)

3 Bedrooms 3 Baths 14 Guests 2400 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

US $543/Night 7 Nights - US $3,800

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House

THE COMPOUND Large Exquisite House Private Yard 'Best Location' Well Appointed

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

10.0

Exceptional

(18 Reviews)

6 Bedrooms 6 Baths 32 Guests 4000 ft²

• 
  Hot Tub
• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen

US $1,078/Night 7 Nights - US $7,548

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Condo

Cozy Downtown MICH AVE #7 | gym+rooftop

• Chicago
• ·
• South Loop
• 0.68 mi to center

10.0

Exceptional

(15 Reviews)

2 Bedrooms 2 Baths 4 Guests 689 ft²

• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner
• 
  Internet

US $311/Night 7 Nights - US $2,180

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New

Condo

Dtown Penthouse 3bd VIEWS+Parking +Gym

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

10.0

Exceptional

(13 Reviews)

3 Bedrooms 2 Baths 8 Guests 1292 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

US $760/Night 7 Nights - US $5,318

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Apartment

NEW 4BD/4BTH - 2 UNITS - Wicker Park

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

10.0

Exceptional

(12 Reviews)

1 Bedroom 4 Baths 8 Guests

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

US $563/Night 7 Nights - US $3,941

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Condo

Designer Loft in Fulton Market with Parking

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

10.0

Exceptional

(12 Reviews)

3 Bedrooms 2 Baths 8 Guests

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

US $530/Night 7 Nights - US $3,711

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      Price Dropped

Apartment

Downtown 3bd Penthouse| Lake Mich VIEWS +gym

• Chicago
• ·
• Printers Row
• 0.21 mi to center

10.0

Exceptional

(12 Reviews)

3 Bedrooms 2 Baths 6 Guests 915 ft²

• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner
• 
  Internet

US $454/Night 7 Nights - US $3,181

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