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Vacation Rentals in Chicago

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50 rentals in Chicago.
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Sonder at 943 Crosby | Two-Bedroom Apartment, holiday rental in Chicago
Sonder at 943 Crosby | Two-Bedroom Apartment, holiday rental in Chicago
Sonder at 943 Crosby | Two-Bedroom Apartment, holiday rental in Chicago

Sonder at 943 Crosby | Two-Bedroom Apartment

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Retro Apartment in Andersonville, holiday rental in Chicago
Retro Apartment in Andersonville, holiday rental in Chicago
Retro Apartment in Andersonville, holiday rental in Chicago

Retro Apartment in Andersonville

Condo/Apartment in Andersonville, Edgewater, West Edgewater, Far North Side
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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LOGAN SQUARE: Chic, Comfy 1st Floor 2 BDRM APT! Parking Incld!

Holiday Rental House in North Side, Logan Square
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Logan Square 2 BR/1 BA-modern, near METRA, holiday rental in Chicago
Logan Square 2 BR/1 BA-modern, near METRA, holiday rental in Chicago
Logan Square 2 BR/1 BA-modern, near METRA, holiday rental in Chicago

Logan Square 2 BR/1 BA-modern, near METRA

Condo/Apartment in North Side, Logan Square
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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3BR Spacious Home Away From Home, holiday rental in Chicago
3BR Spacious Home Away From Home, holiday rental in Chicago
3BR Spacious Home Away From Home, holiday rental in Chicago

3BR Spacious Home Away From Home

Condo/Apartment
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Chic, Cozy home, by Blue Line Train Stop + Free parking, holiday rental in Chicago
Chic, Cozy home, by Blue Line Train Stop + Free parking, holiday rental in Chicago
Chic, Cozy home, by Blue Line Train Stop + Free parking, holiday rental in Chicago

Chic, Cozy home, by Blue Line Train Stop + Free parking

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful 2BR 2 BATH 10 Minutes from the United Center!, holiday rental in Chicago
Beautiful 2BR 2 BATH 10 Minutes from the United Center!, holiday rental in Chicago
Beautiful 2BR 2 BATH 10 Minutes from the United Center!, holiday rental in Chicago

Beautiful 2BR 2 BATH 10 Minutes from the United Center!

Condo/Apartment
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Bright & Clean Apt in Front of Lovely Park!, holiday rental in Chicago
Bright & Clean Apt in Front of Lovely Park!, holiday rental in Chicago
Bright & Clean Apt in Front of Lovely Park!, holiday rental in Chicago

Bright & Clean Apt in Front of Lovely Park!

Condo/Apartment
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Trendy|Comfortable|1BR|Lincoln Square, holiday rental in Chicago
Trendy|Comfortable|1BR|Lincoln Square, holiday rental in Chicago
Trendy|Comfortable|1BR|Lincoln Square, holiday rental in Chicago

Trendy|Comfortable|1BR|Lincoln Square

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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⭐|Stylish|Comfy|Lincoln Sq.| 2BR |✨|Near Wrigley|⭐, holiday rental in Chicago
⭐|Stylish|Comfy|Lincoln Sq.| 2BR |✨|Near Wrigley|⭐, holiday rental in Chicago
⭐|Stylish|Comfy|Lincoln Sq.| 2BR |✨|Near Wrigley|⭐, holiday rental in Chicago

⭐|Stylish|Comfy|Lincoln Sq.| 2BR |✨|Near Wrigley|⭐

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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2BR/1BA Garden Apt in Irving Park, Superfast Wifi!, holiday rental in Chicago
2BR/1BA Garden Apt in Irving Park, Superfast Wifi!, holiday rental in Chicago
2BR/1BA Garden Apt in Irving Park, Superfast Wifi!, holiday rental in Chicago

2BR/1BA Garden Apt in Irving Park, Superfast Wifi!

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Modern Amenities in Vintage Logan Square 2 Bedroom, holiday rental in Chicago
Modern Amenities in Vintage Logan Square 2 Bedroom, holiday rental in Chicago
Modern Amenities in Vintage Logan Square 2 Bedroom, holiday rental in Chicago

Modern Amenities in Vintage Logan Square 2 Bedroom

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Newly Renovated 3 bed 2 Bath, Conveniently Located, holiday rental in Chicago
Newly Renovated 3 bed 2 Bath, Conveniently Located, holiday rental in Chicago
Newly Renovated 3 bed 2 Bath, Conveniently Located, holiday rental in Chicago

Newly Renovated 3 bed 2 Bath, Conveniently Located

Condo/Apartment
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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✨Rustic Studio Apartment Heart of Lincoln Square✨, holiday rental in Chicago
✨Rustic Studio Apartment Heart of Lincoln Square✨, holiday rental in Chicago
✨Rustic Studio Apartment Heart of Lincoln Square✨, holiday rental in Chicago

✨Rustic Studio Apartment Heart of Lincoln Square✨

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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⭐️Cozy|Intimate|1BR In Lincoln Square⭐️, holiday rental in Chicago
⭐️Cozy|Intimate|1BR In Lincoln Square⭐️, holiday rental in Chicago
⭐️Cozy|Intimate|1BR In Lincoln Square⭐️, holiday rental in Chicago

⭐️Cozy|Intimate|1BR In Lincoln Square⭐️

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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2-bed 2-bath(full) condo 10 min walk from transit, holiday rental in Chicago
2-bed 2-bath(full) condo 10 min walk from transit, holiday rental in Chicago
2-bed 2-bath(full) condo 10 min walk from transit, holiday rental in Chicago

2-bed 2-bath(full) condo 10 min walk from transit

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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North-Side of Chicago near Wrigley + 90/94 + CTA Addison Blue Line Station, holiday rental in Chicago
North-Side of Chicago near Wrigley + 90/94 + CTA Addison Blue Line Station, holiday rental in Chicago
North-Side of Chicago near Wrigley + 90/94 + CTA Addison Blue Line Station, holiday rental in Chicago

North-Side of Chicago near Wrigley + 90/94 + CTA Addison Blue Line Station

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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New! Modern 2BR, 65-inch TV & Lux King Bed, holiday rental in Chicago
New! Modern 2BR, 65-inch TV & Lux King Bed, holiday rental in Chicago
New! Modern 2BR, 65-inch TV & Lux King Bed, holiday rental in Chicago

New! Modern 2BR, 65-inch TV & Lux King Bed

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Warm|Cozy|Lovely|1BR|Lincoln Sq.|, holiday rental in Chicago
Warm|Cozy|Lovely|1BR|Lincoln Sq.|, holiday rental in Chicago
Warm|Cozy|Lovely|1BR|Lincoln Sq.|, holiday rental in Chicago

Warm|Cozy|Lovely|1BR|Lincoln Sq.|

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Lincoln Square Newly Remolded Unit w/ Central HVAC, holiday rental in Chicago
Lincoln Square Newly Remolded Unit w/ Central HVAC, holiday rental in Chicago
Lincoln Square Newly Remolded Unit w/ Central HVAC, holiday rental in Chicago

Lincoln Square Newly Remolded Unit w/ Central HVAC

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Charming|Comfortable|1BR|Lincoln Square, holiday rental in Chicago
Charming|Comfortable|1BR|Lincoln Square, holiday rental in Chicago
Charming|Comfortable|1BR|Lincoln Square, holiday rental in Chicago

Charming|Comfortable|1BR|Lincoln Square

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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COZY & Modern 3 Bedroom Stay in Logan Square, holiday rental in Chicago
COZY & Modern 3 Bedroom Stay in Logan Square, holiday rental in Chicago
COZY & Modern 3 Bedroom Stay in Logan Square, holiday rental in Chicago

COZY & Modern 3 Bedroom Stay in Logan Square

Condo/Apartment
4 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Deluxe Edgewater 1BR w/ patio, W/D, 2 blocks to lakefront, by Blueground, holiday rental in Chicago
Deluxe Edgewater 1BR w/ patio, W/D, 2 blocks to lakefront, by Blueground, holiday rental in Chicago
Deluxe Edgewater 1BR w/ patio, W/D, 2 blocks to lakefront, by Blueground, holiday rental in Chicago

Deluxe Edgewater 1BR w/ patio, W/D, 2 blocks to lakefront, by Blueground

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Sleek Edgewater 1BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, holiday rental in Chicago
Sleek Edgewater 1BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, holiday rental in Chicago
Sleek Edgewater 1BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, holiday rental in Chicago

Sleek Edgewater 1BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Cute, Cozy, Elegant Budlong Woods, holiday rental in Chicago
Cute, Cozy, Elegant Budlong Woods, holiday rental in Chicago
Cute, Cozy, Elegant Budlong Woods, holiday rental in Chicago

Cute, Cozy, Elegant Budlong Woods

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Hip Edgewater Studio w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, holiday rental in Chicago
Hip Edgewater Studio w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, holiday rental in Chicago
Hip Edgewater Studio w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, holiday rental in Chicago

Hip Edgewater Studio w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Sunny Edgewater 2BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, holiday rental in Chicago
Sunny Edgewater 2BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, holiday rental in Chicago
Sunny Edgewater 2BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, holiday rental in Chicago

Sunny Edgewater 2BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Amazing Edgewater 2BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, holiday rental in Chicago
Amazing Edgewater 2BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, holiday rental in Chicago
Amazing Edgewater 2BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, holiday rental in Chicago

Amazing Edgewater 2BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Spacious Penthouse Suite 10 Mins From DTW Chicago, holiday rental in Chicago
Spacious Penthouse Suite 10 Mins From DTW Chicago, holiday rental in Chicago
Spacious Penthouse Suite 10 Mins From DTW Chicago, holiday rental in Chicago

Spacious Penthouse Suite 10 Mins From DTW Chicago

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Dreamy Edgewater 3BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, holiday rental in Chicago
Dreamy Edgewater 3BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, holiday rental in Chicago
Dreamy Edgewater 3BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, holiday rental in Chicago

Dreamy Edgewater 3BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Comfy Garden Suite in Andersonville, holiday rental in Chicago
Comfy Garden Suite in Andersonville, holiday rental in Chicago
Comfy Garden Suite in Andersonville, holiday rental in Chicago

Comfy Garden Suite in Andersonville

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Modern Edgewater 1BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, holiday rental in Chicago
Modern Edgewater 1BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, holiday rental in Chicago
Modern Edgewater 1BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, holiday rental in Chicago

Modern Edgewater 1BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Private 1 BR 1 BA Guest Suite, holiday rental in Chicago
Private 1 BR 1 BA Guest Suite, holiday rental in Chicago
Private 1 BR 1 BA Guest Suite, holiday rental in Chicago

Private 1 BR 1 BA Guest Suite

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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2 bdrm close to dwntwn/Midway w/ free parking!!, holiday rental in Chicago
2 bdrm close to dwntwn/Midway w/ free parking!!, holiday rental in Chicago
2 bdrm close to dwntwn/Midway w/ free parking!!, holiday rental in Chicago

2 bdrm close to dwntwn/Midway w/ free parking!!

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
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Cute new Garden unit located between Andersonville and Lincoln Square , Chicago., holiday rental in Chicago
Cute new Garden unit located between Andersonville and Lincoln Square , Chicago., holiday rental in Chicago
Cute new Garden unit located between Andersonville and Lincoln Square , Chicago., holiday rental in Chicago

Cute new Garden unit located between Andersonville and Lincoln Square , Chicago.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Ideal Edgewater 1BR w/ patio, W/D, 2 blocks to lakefront, by Blueground, holiday rental in Chicago
Ideal Edgewater 1BR w/ patio, W/D, 2 blocks to lakefront, by Blueground, holiday rental in Chicago
Ideal Edgewater 1BR w/ patio, W/D, 2 blocks to lakefront, by Blueground, holiday rental in Chicago

Ideal Edgewater 1BR w/ patio, W/D, 2 blocks to lakefront, by Blueground

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Luxe Edgewater Studio w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, holiday rental in Chicago
Luxe Edgewater Studio w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, holiday rental in Chicago
Luxe Edgewater Studio w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, holiday rental in Chicago

Luxe Edgewater Studio w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Ideal Edgewater 1BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, holiday rental in Chicago
Ideal Edgewater 1BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, holiday rental in Chicago
Ideal Edgewater 1BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, holiday rental in Chicago

Ideal Edgewater 1BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Happy Haven, holiday rental in Chicago
Happy Haven, holiday rental in Chicago
Happy Haven, holiday rental in Chicago

Happy Haven

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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3/1 HOME APT | NORTHSIDE | CUBS, holiday rental in Chicago
3/1 HOME APT | NORTHSIDE | CUBS, holiday rental in Chicago
3/1 HOME APT | NORTHSIDE | CUBS, holiday rental in Chicago

3/1 HOME APT | NORTHSIDE | CUBS

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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Greystone, 3500 sq ft, Rooftop Access, Sleeps 16, holiday rental in Chicago
Greystone, 3500 sq ft, Rooftop Access, Sleeps 16, holiday rental in Chicago
Greystone, 3500 sq ft, Rooftop Access, Sleeps 16, holiday rental in Chicago

Greystone, 3500 sq ft, Rooftop Access, Sleeps 16

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
More info
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Cozy & Spacious 2 Bedroom/ 1 Bath By UIC, holiday rental in Chicago
Cozy & Spacious 2 Bedroom/ 1 Bath By UIC, holiday rental in Chicago
Cozy & Spacious 2 Bedroom/ 1 Bath By UIC, holiday rental in Chicago

Cozy & Spacious 2 Bedroom/ 1 Bath By UIC

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Sunny, second floor 3-bedroom with free parking, holiday rental in Chicago
Sunny, second floor 3-bedroom with free parking, holiday rental in Chicago
Sunny, second floor 3-bedroom with free parking, holiday rental in Chicago

Sunny, second floor 3-bedroom with free parking

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Great 3 bedroom rental unit near Logan Square, holiday rental in Chicago
Great 3 bedroom rental unit near Logan Square, holiday rental in Chicago
Great 3 bedroom rental unit near Logan Square, holiday rental in Chicago

Great 3 bedroom rental unit near Logan Square

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Vantage appartement 9' ceiling, just renovated, holiday rental in Chicago
Vantage appartement 9' ceiling, just renovated, holiday rental in Chicago
Vantage appartement 9' ceiling, just renovated, holiday rental in Chicago

Vantage appartement 9' ceiling, just renovated

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Cutest 2BR in Logan with Free Parking and Garden, holiday rental in Chicago
Cutest 2BR in Logan with Free Parking and Garden, holiday rental in Chicago
Cutest 2BR in Logan with Free Parking and Garden, holiday rental in Chicago

Cutest 2BR in Logan with Free Parking and Garden

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Clean & Cozy entire 3 bedroom unit 7 miles from downtown, holiday rental in Chicago
Clean & Cozy entire 3 bedroom unit 7 miles from downtown, holiday rental in Chicago
Clean & Cozy entire 3 bedroom unit 7 miles from downtown, holiday rental in Chicago

Clean & Cozy entire 3 bedroom unit 7 miles from downtown

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Beautiful, sunny and spacious 3BD/ 1BA-minutes from Downtown, holiday rental in Chicago
Beautiful, sunny and spacious 3BD/ 1BA-minutes from Downtown, holiday rental in Chicago
Beautiful, sunny and spacious 3BD/ 1BA-minutes from Downtown, holiday rental in Chicago

Beautiful, sunny and spacious 3BD/ 1BA-minutes from Downtown

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Great Chicago getaway, holiday rental in Chicago
Great Chicago getaway, holiday rental in Chicago
Great Chicago getaway, holiday rental in Chicago

Great Chicago getaway

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Lincoln Square Oasis - Bright, Clean and in Great Location, holiday rental in Chicago
Lincoln Square Oasis - Bright, Clean and in Great Location, holiday rental in Chicago
Lincoln Square Oasis - Bright, Clean and in Great Location, holiday rental in Chicago

Lincoln Square Oasis - Bright, Clean and in Great Location

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
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