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Chicago Vacation Rentals

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49 rentals in Chicago.
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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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Historic Andersonville Coach House, vacation rental in Chicago
Historic Andersonville Coach House, vacation rental in Chicago
Historic Andersonville Coach House, vacation rental in Chicago

Historic Andersonville Coach House

Holiday Rental House in Edgewater, Far North Side
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Retro Apartment in Andersonville, vacation rental in Chicago
Retro Apartment in Andersonville, vacation rental in Chicago
Retro Apartment in Andersonville, vacation 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 2 BR/1 BA-modern, near METRA, vacation rental in Chicago
Logan Square 2 BR/1 BA-modern, near METRA, vacation rental in Chicago
Logan Square 2 BR/1 BA-modern, near METRA, vacation 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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Cozy, Comfortable and Convenient apartment. Close to everything!, vacation rental in Chicago
Cozy, Comfortable and Convenient apartment. Close to everything!, vacation rental in Chicago
Cozy, Comfortable and Convenient apartment. Close to everything!, vacation rental in Chicago

Cozy, Comfortable and Convenient apartment. Close to everything!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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3BR Spacious Home Away From Home, vacation rental in Chicago
3BR Spacious Home Away From Home, vacation rental in Chicago
3BR Spacious Home Away From Home, vacation rental in Chicago

3BR Spacious Home Away From Home

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Chicago Modern Condo- Perfect for family time or a good time in Chicago., vacation rental in Chicago
Chicago Modern Condo- Perfect for family time or a good time in Chicago., vacation rental in Chicago
Chicago Modern Condo- Perfect for family time or a good time in Chicago., vacation rental in Chicago

Chicago Modern Condo- Perfect for family time or a good time in Chicago.

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Chic, Cozy home, by Blue Line Train Stop + Free parking, vacation rental in Chicago
Chic, Cozy home, by Blue Line Train Stop + Free parking, vacation rental in Chicago
Chic, Cozy home, by Blue Line Train Stop + Free parking, vacation 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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Spacious 3-bedroom, 2-bath condo, free parking/Oak Park, vacation rental in Chicago
Spacious 3-bedroom, 2-bath condo, free parking/Oak Park, vacation rental in Chicago
Spacious 3-bedroom, 2-bath condo, free parking/Oak Park, vacation rental in Chicago

Spacious 3-bedroom, 2-bath condo, free parking/Oak Park

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Trendy|Comfortable|1BR|Lincoln Square, vacation rental in Chicago
Trendy|Comfortable|1BR|Lincoln Square, vacation rental in Chicago
Trendy|Comfortable|1BR|Lincoln Square, vacation rental in Chicago

Trendy|Comfortable|1BR|Lincoln Square

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Quiet, family getaway. Puppers welcome!, vacation rental in Chicago
Quiet, family getaway. Puppers welcome!, vacation rental in Chicago
Quiet, family getaway. Puppers welcome!, vacation rental in Chicago

Quiet, family getaway. Puppers welcome!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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⭐|Stylish|Comfy|Lincoln Sq.| 2BR |✨|Near Wrigley|⭐, vacation rental in Chicago
⭐|Stylish|Comfy|Lincoln Sq.| 2BR |✨|Near Wrigley|⭐, vacation rental in Chicago
⭐|Stylish|Comfy|Lincoln Sq.| 2BR |✨|Near Wrigley|⭐, vacation 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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✨Rustic Studio Apartment Heart of Lincoln Square✨, vacation rental in Chicago
✨Rustic Studio Apartment Heart of Lincoln Square✨, vacation rental in Chicago
✨Rustic Studio Apartment Heart of Lincoln Square✨, vacation 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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Bright & Clean Apt in Front of Lovely Park!, vacation rental in Chicago
Bright & Clean Apt in Front of Lovely Park!, vacation rental in Chicago
Bright & Clean Apt in Front of Lovely Park!, vacation rental in Chicago

Bright & Clean Apt in Front of Lovely Park!

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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North-Side of Chicago near Wrigley + 90/94 + CTA Addison Blue Line Station, vacation rental in Chicago
North-Side of Chicago near Wrigley + 90/94 + CTA Addison Blue Line Station, vacation rental in Chicago
North-Side of Chicago near Wrigley + 90/94 + CTA Addison Blue Line Station, vacation 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
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New! Modern 2BR, 65-inch TV & Lux King Bed, vacation rental in Chicago
New! Modern 2BR, 65-inch TV & Lux King Bed, vacation rental in Chicago
New! Modern 2BR, 65-inch TV & Lux King Bed, vacation rental in Chicago

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

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

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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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NEW! Lovely Oak Park Apt, Easy Access to Downtown!, vacation rental in Chicago
NEW! Lovely Oak Park Apt, Easy Access to Downtown!, vacation rental in Chicago
NEW! Lovely Oak Park Apt, Easy Access to Downtown!, vacation rental in Chicago

NEW! Lovely Oak Park Apt, Easy Access to Downtown!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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2BR/1BA Garden Apt in Irving Park, Superfast Wifi!, vacation rental in Chicago
2BR/1BA Garden Apt in Irving Park, Superfast Wifi!, vacation rental in Chicago
2BR/1BA Garden Apt in Irving Park, Superfast Wifi!, vacation 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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Lincoln Square Newly Remolded Unit w/ Central HVAC, vacation rental in Chicago
Lincoln Square Newly Remolded Unit w/ Central HVAC, vacation rental in Chicago
Lincoln Square Newly Remolded Unit w/ Central HVAC, vacation rental in Chicago

Lincoln Square Newly Remolded Unit w/ Central HVAC

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Spacious 3 BR - Beautiful Natural Light - West CHI, vacation rental in Chicago
Spacious 3 BR - Beautiful Natural Light - West CHI, vacation rental in Chicago
Spacious 3 BR - Beautiful Natural Light - West CHI, vacation rental in Chicago

Spacious 3 BR - Beautiful Natural Light - West CHI

Condo/Apartment
4 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming|Comfortable|1BR|Lincoln Square, vacation rental in Chicago
Charming|Comfortable|1BR|Lincoln Square, vacation rental in Chicago
Charming|Comfortable|1BR|Lincoln Square, vacation rental in Chicago

Charming|Comfortable|1BR|Lincoln Square

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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COZY & Modern 3 Bedroom Stay in Logan Square, vacation rental in Chicago
COZY & Modern 3 Bedroom Stay in Logan Square, vacation rental in Chicago
COZY & Modern 3 Bedroom Stay in Logan Square, vacation rental in Chicago

COZY & Modern 3 Bedroom Stay in Logan Square

Condo/Apartment
4 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful 2BR 2 BATH 10 Minutes from the United Center!, vacation rental in Chicago
Beautiful 2BR 2 BATH 10 Minutes from the United Center!, vacation rental in Chicago
Beautiful 2BR 2 BATH 10 Minutes from the United Center!, vacation 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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Deluxe Edgewater 1BR w/ patio, W/D, 2 blocks to lakefront, by Blueground, vacation rental in Chicago
Deluxe Edgewater 1BR w/ patio, W/D, 2 blocks to lakefront, by Blueground, vacation rental in Chicago
Deluxe Edgewater 1BR w/ patio, W/D, 2 blocks to lakefront, by Blueground, vacation 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
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Sleek Edgewater 1BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, vacation rental in Chicago
Sleek Edgewater 1BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, vacation rental in Chicago
Sleek Edgewater 1BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, vacation 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
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Cute, Cozy, Elegant Budlong Woods, vacation rental in Chicago
Cute, Cozy, Elegant Budlong Woods, vacation rental in Chicago
Cute, Cozy, Elegant Budlong Woods, vacation rental in Chicago

Cute, Cozy, Elegant Budlong Woods

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Cute and Cozy 2 Bedroom, vacation rental in Chicago
Cute and Cozy 2 Bedroom, vacation rental in Chicago
Cute and Cozy 2 Bedroom, vacation rental in Chicago

Cute and Cozy 2 Bedroom

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Hip Edgewater Studio w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, vacation rental in Chicago
Hip Edgewater Studio w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, vacation rental in Chicago
Hip Edgewater Studio w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, vacation 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
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Sunny Edgewater 2BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, vacation rental in Chicago
Sunny Edgewater 2BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, vacation rental in Chicago
Sunny Edgewater 2BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, vacation 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
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Amazing Edgewater 2BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, vacation rental in Chicago
Amazing Edgewater 2BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, vacation rental in Chicago
Amazing Edgewater 2BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, vacation 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
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Newly Renovated 3 bed 2 Bath, Conveniently Located, vacation rental in Chicago
Newly Renovated 3 bed 2 Bath, Conveniently Located, vacation rental in Chicago
Newly Renovated 3 bed 2 Bath, Conveniently Located, vacation 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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Spacious Penthouse Suite 10 Mins From DTW Chicago, vacation rental in Chicago
Spacious Penthouse Suite 10 Mins From DTW Chicago, vacation rental in Chicago
Spacious Penthouse Suite 10 Mins From DTW Chicago, vacation rental in Chicago

Spacious Penthouse Suite 10 Mins From DTW Chicago

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Dreamy Edgewater 3BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, vacation rental in Chicago
Dreamy Edgewater 3BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, vacation rental in Chicago
Dreamy Edgewater 3BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, vacation 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
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Comfy Garden Suite in Andersonville, vacation rental in Chicago
Comfy Garden Suite in Andersonville, vacation rental in Chicago
Comfy Garden Suite in Andersonville, vacation rental in Chicago

Comfy Garden Suite in Andersonville

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Modern Edgewater 1BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, vacation rental in Chicago
Modern Edgewater 1BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, vacation rental in Chicago
Modern Edgewater 1BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, vacation 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
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Private 1 BR 1 BA Guest Suite, vacation rental in Chicago
Private 1 BR 1 BA Guest Suite, vacation rental in Chicago
Private 1 BR 1 BA Guest Suite, vacation rental in Chicago

Private 1 BR 1 BA Guest Suite

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

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

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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⭐️Cozy|Intimate|1BR In Lincoln Square⭐️, vacation rental in Chicago
⭐️Cozy|Intimate|1BR In Lincoln Square⭐️, vacation rental in Chicago
⭐️Cozy|Intimate|1BR In Lincoln Square⭐️, vacation rental in Chicago

⭐️Cozy|Intimate|1BR In Lincoln Square⭐️

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cute new Garden unit located between Andersonville and Lincoln Square , Chicago., vacation rental in Chicago
Cute new Garden unit located between Andersonville and Lincoln Square , Chicago., vacation rental in Chicago
Cute new Garden unit located between Andersonville and Lincoln Square , Chicago., vacation rental in Chicago

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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Ideal Edgewater 1BR w/ patio, W/D, 2 blocks to lakefront, by Blueground, vacation rental in Chicago
Ideal Edgewater 1BR w/ patio, W/D, 2 blocks to lakefront, by Blueground, vacation rental in Chicago
Ideal Edgewater 1BR w/ patio, W/D, 2 blocks to lakefront, by Blueground, vacation 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
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Luxe Edgewater Studio w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, vacation rental in Chicago
Luxe Edgewater Studio w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, vacation rental in Chicago
Luxe Edgewater Studio w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, vacation 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
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Modern Amenities in Vintage Logan Square 2 Bedroom, vacation rental in Chicago
Modern Amenities in Vintage Logan Square 2 Bedroom, vacation rental in Chicago
Modern Amenities in Vintage Logan Square 2 Bedroom, vacation 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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Ideal Edgewater 1BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, vacation rental in Chicago
Ideal Edgewater 1BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, vacation rental in Chicago
Ideal Edgewater 1BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground, vacation 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
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3/1 HOME APT | NORTHSIDE | CUBS, vacation rental in Chicago
3/1 HOME APT | NORTHSIDE | CUBS, vacation rental in Chicago
3/1 HOME APT | NORTHSIDE | CUBS, vacation rental in Chicago

3/1 HOME APT | NORTHSIDE | CUBS

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

Greystone, 3500 sq ft, Rooftop Access, Sleeps 16

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

Cozy & Spacious 2 Bedroom/ 1 Bath By UIC

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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2-bed 2-bath(full) condo 10 min walk from transit, vacation rental in Chicago
2-bed 2-bath(full) condo 10 min walk from transit, vacation rental in Chicago
2-bed 2-bath(full) condo 10 min walk from transit, vacation rental in Chicago

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

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Great 3 bedroom rental unit near Logan Square, vacation rental in Chicago
Great 3 bedroom rental unit near Logan Square, vacation rental in Chicago
Great 3 bedroom rental unit near Logan Square, vacation rental in Chicago

Great 3 bedroom rental unit near Logan Square

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Luxury Condominium in Chicago, vacation rental in Chicago
Luxury Condominium in Chicago, vacation rental in Chicago
Luxury Condominium in Chicago, vacation rental in Chicago

Luxury Condominium in Chicago

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 1
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