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Chicago Vacation Rentals

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Bedrooms

Bathrooms

Amenities

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5 km
49 rentals in Chicago.
The following properties within 32 kms of Chicago match all your filters:
Brand new private 2 bedroom unit, vacation rental in Chicago
Brand new private 2 bedroom unit, vacation rental in Chicago
Brand new private 2 bedroom unit, vacation rental in Chicago

Brand new private 2 bedroom unit

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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N Ridgeway · Logan Square Cozy Apartment - Games+Arcade - Patio, vacation rental in Chicago
N Ridgeway · Logan Square Cozy Apartment - Games+Arcade - Patio, vacation rental in Chicago
N Ridgeway · Logan Square Cozy Apartment - Games+Arcade - Patio, vacation rental in Chicago

N Ridgeway · Logan Square Cozy Apartment - Games+Arcade - Patio

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Family-friendly, stylish Chicago Apartment in Logan Square, vacation rental in Chicago
Family-friendly, stylish Chicago Apartment in Logan Square, vacation rental in Chicago
Family-friendly, stylish Chicago Apartment in Logan Square, vacation rental in Chicago

Family-friendly, stylish Chicago Apartment in Logan Square

Condo/Apartment in North Side, Logan Square
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Home away from home. Perfect for remote workers., vacation rental in Chicago
Home away from home. Perfect for remote workers., vacation rental in Chicago
Home away from home. Perfect for remote workers., vacation rental in Chicago

Home away from home. Perfect for remote workers.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cozy 2 Bedroom on a Quite Street, vacation rental in Chicago
Cozy 2 Bedroom on a Quite Street, vacation rental in Chicago
Cozy 2 Bedroom on a Quite Street, vacation rental in Chicago

Cozy 2 Bedroom on a Quite Street

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

Clean & Cozy entire 3 bedroom unit 7 miles from downtown

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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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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Charming Chicago Retreat with Modern Comforts - Spa Bath, vacation rental in Chicago
Charming Chicago Retreat with Modern Comforts - Spa Bath, vacation rental in Chicago
Charming Chicago Retreat with Modern Comforts - Spa Bath, vacation rental in Chicago

Charming Chicago Retreat with Modern Comforts - Spa Bath

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Amazing, sunny and spacious 3BD/ 1BA-minutes from Downtown, vacation rental in Chicago
Amazing, sunny and spacious 3BD/ 1BA-minutes from Downtown, vacation rental in Chicago
Amazing, sunny and spacious 3BD/ 1BA-minutes from Downtown, vacation rental in Chicago

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

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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CPS3 Logan Square Corner 3BR Apt Walkable to Highlights, vacation rental in Chicago
CPS3 Logan Square Corner 3BR Apt Walkable to Highlights, vacation rental in Chicago
CPS3 Logan Square Corner 3BR Apt Walkable to Highlights, vacation rental in Chicago

CPS3 Logan Square Corner 3BR Apt Walkable to Highlights

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spacious Chicago Brick stone, vacation rental in Chicago
Spacious Chicago Brick stone, vacation rental in Chicago
Spacious Chicago Brick stone, vacation rental in Chicago

Spacious Chicago Brick stone

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
More info
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Payment Protection
La Villita - Gateway to Chicago (2 bedroom apartment 10 mins from downtown), vacation rental in Chicago
La Villita - Gateway to Chicago (2 bedroom apartment 10 mins from downtown), vacation rental in Chicago
La Villita - Gateway to Chicago (2 bedroom apartment 10 mins from downtown), vacation rental in Chicago

La Villita - Gateway to Chicago (2 bedroom apartment 10 mins from downtown)

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Payment Protection
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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In the Heart of Little Mexico! Shared Stylish Apartment in Chicago, vacation rental in Chicago
In the Heart of Little Mexico! Shared Stylish Apartment in Chicago, vacation rental in Chicago
In the Heart of Little Mexico! Shared Stylish Apartment in Chicago, vacation rental in Chicago

In the Heart of Little Mexico! Shared Stylish Apartment in Chicago

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Airy Avondale Getaway with King Bed, vacation rental in Chicago
Airy Avondale Getaway with King Bed, vacation rental in Chicago
Airy Avondale Getaway with King Bed, vacation rental in Chicago

Airy Avondale Getaway with King Bed

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Bright, Modern 2 BR in Logan Square w/ Parking, vacation rental in Chicago
Bright, Modern 2 BR in Logan Square w/ Parking, vacation rental in Chicago
Bright, Modern 2 BR in Logan Square w/ Parking, vacation rental in Chicago

Bright, Modern 2 BR in Logan Square w/ Parking

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
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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
More info
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Cozy Private Bedroom and bathroom with full kitchen, vacation rental in Chicago
Cozy Private Bedroom and bathroom with full kitchen, vacation rental in Chicago
Cozy Private Bedroom and bathroom with full kitchen, vacation rental in Chicago

Cozy Private Bedroom and bathroom with full kitchen

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Retro 2 bedroom bungalow in Chicago's Avondale neighborhood, vacation rental in Chicago
Retro 2 bedroom bungalow in Chicago's Avondale neighborhood, vacation rental in Chicago
Retro 2 bedroom bungalow in Chicago's Avondale neighborhood, vacation rental in Chicago

Retro 2 bedroom bungalow in Chicago's Avondale neighborhood

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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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
More info
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Bedroom 2 Comfy Pvt - Shared BA - Living Room - Washer Dryer - Pet & Family Fr., vacation rental in Chicago
Bedroom 2 Comfy Pvt - Shared BA - Living Room - Washer Dryer - Pet & Family Fr., vacation rental in Chicago
Bedroom 2 Comfy Pvt - Shared BA - Living Room - Washer Dryer - Pet & Family Fr., vacation rental in Chicago

Bedroom 2 Comfy Pvt - Shared BA - Living Room - Washer Dryer - Pet & Family Fr.

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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Lovely & Cozy 1-bedroom Suite 8 mins from UIC, vacation rental in Chicago
Lovely & Cozy 1-bedroom Suite 8 mins from UIC, vacation rental in Chicago
Lovely & Cozy 1-bedroom Suite 8 mins from UIC, vacation rental in Chicago

Lovely & Cozy 1-bedroom Suite 8 mins from UIC

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Pvt Rm Bdrm 4 Comfy Pvt Rm - Shared Bath/Liv, vacation rental in Chicago
Pvt Rm Bdrm 4 Comfy Pvt Rm - Shared Bath/Liv, vacation rental in Chicago
Pvt Rm Bdrm 4 Comfy Pvt Rm - Shared Bath/Liv, vacation rental in Chicago

Pvt Rm Bdrm 4 Comfy Pvt Rm - Shared Bath/Liv

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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Bdrm 1 Comfy Pvt Rm - Shared Bath/Liv, vacation rental in Chicago
Bdrm 1 Comfy Pvt Rm - Shared Bath/Liv, vacation rental in Chicago
Bdrm 1 Comfy Pvt Rm - Shared Bath/Liv, vacation rental in Chicago

Bdrm 1 Comfy Pvt Rm - Shared Bath/Liv

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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Pvt Rm Bdrm 3 Comfy Pvt Rm - Shared Bath/Liv, vacation rental in Chicago
Pvt Rm Bdrm 3 Comfy Pvt Rm - Shared Bath/Liv, vacation rental in Chicago
Pvt Rm Bdrm 3 Comfy Pvt Rm - Shared Bath/Liv, vacation rental in Chicago

Pvt Rm Bdrm 3 Comfy Pvt Rm - Shared Bath/Liv

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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Sunny 2nd Floor Apartment in Humboldt Park, vacation rental in Chicago
Sunny 2nd Floor Apartment in Humboldt Park, vacation rental in Chicago
Sunny 2nd Floor Apartment in Humboldt Park, vacation rental in Chicago

Sunny 2nd Floor Apartment in Humboldt Park

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Quiet Chicago Townhome - 7 Mi to Downtown!, vacation rental in Chicago
Quiet Chicago Townhome - 7 Mi to Downtown!, vacation rental in Chicago
Quiet Chicago Townhome - 7 Mi to Downtown!, vacation rental in Chicago

Quiet Chicago Townhome - 7 Mi to Downtown!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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LOGAN SQUARE: Chic, Comfy 1st Floor 2 BDRM APT! Parking Incld!, vacation rental in Chicago
LOGAN SQUARE: Chic, Comfy 1st Floor 2 BDRM APT! Parking Incld!, vacation rental in Chicago
LOGAN SQUARE: Chic, Comfy 1st Floor 2 BDRM APT! Parking Incld!, vacation rental in Chicago

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
More info
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Great Chicago getaway, vacation rental in Chicago
Great Chicago getaway, vacation rental in Chicago
Great Chicago getaway, vacation rental in Chicago

Great Chicago getaway

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Vintage/Modern Hideaway in Logan Square, vacation rental in Chicago
Vintage/Modern Hideaway in Logan Square, vacation rental in Chicago
Vintage/Modern Hideaway in Logan Square, vacation rental in Chicago

Vintage/Modern Hideaway in Logan Square

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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FREE PARKING! Desirable Logan Square Location with Modern Touches and Beautiful, vacation rental in Chicago
FREE PARKING! Desirable Logan Square Location with Modern Touches and Beautiful, vacation rental in Chicago
FREE PARKING! Desirable Logan Square Location with Modern Touches and Beautiful, vacation rental in Chicago

FREE PARKING! Desirable Logan Square Location with Modern Touches and Beautiful

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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3710 W Diversey · Lovely Logan Square 2 Bedroom, vacation rental in Chicago
3710 W Diversey · Lovely Logan Square 2 Bedroom, vacation rental in Chicago
3710 W Diversey · Lovely Logan Square 2 Bedroom, vacation rental in Chicago

3710 W Diversey · Lovely Logan Square 2 Bedroom

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Minutes from Downtown Gorgeous ,spacious 2BD/ 1BA w/ Parking, vacation rental in Chicago
Minutes from Downtown Gorgeous ,spacious 2BD/ 1BA w/ Parking, vacation rental in Chicago
Minutes from Downtown Gorgeous ,spacious 2BD/ 1BA w/ Parking, vacation rental in Chicago

Minutes from Downtown Gorgeous ,spacious 2BD/ 1BA w/ Parking

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Stylish 1,400SQFT Top-Floor| 18 min drive to S. Loop|Parking, W/D, Backyard, vacation rental in Chicago
Stylish 1,400SQFT Top-Floor| 18 min drive to S. Loop|Parking, W/D, Backyard, vacation rental in Chicago
Stylish 1,400SQFT Top-Floor| 18 min drive to S. Loop|Parking, W/D, Backyard, vacation rental in Chicago

Stylish 1,400SQFT Top-Floor| 18 min drive to S. Loop|Parking, W/D, Backyard

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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home sweet home chicago - garage parking & downtown in 20m, vacation rental in Chicago
home sweet home chicago - garage parking & downtown in 20m, vacation rental in Chicago
home sweet home chicago - garage parking & downtown in 20m, vacation rental in Chicago

home sweet home chicago - garage parking & downtown in 20m

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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1,400 SqFt Stylish Top Floor.15min Dr to S. Loop or Med District., vacation rental in Chicago
1,400 SqFt Stylish Top Floor.15min Dr to S. Loop or Med District., vacation rental in Chicago
1,400 SqFt Stylish Top Floor.15min Dr to S. Loop or Med District., vacation rental in Chicago

1,400 SqFt Stylish Top Floor.15min Dr to S. Loop or Med District.

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Modern 3-Bed Stay w/ Firepit, 15 Minutes to Downtown, vacation rental in Chicago
Modern 3-Bed Stay w/ Firepit, 15 Minutes to Downtown, vacation rental in Chicago
Modern 3-Bed Stay w/ Firepit, 15 Minutes to Downtown, vacation rental in Chicago

Modern 3-Bed Stay w/ Firepit, 15 Minutes to Downtown

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Chic Chicago Getaway w/ Deck, 7 Mi to Downtown!, vacation rental in Chicago
Chic Chicago Getaway w/ Deck, 7 Mi to Downtown!, vacation rental in Chicago
Chic Chicago Getaway w/ Deck, 7 Mi to Downtown!, vacation rental in Chicago

Chic Chicago Getaway w/ Deck, 7 Mi to Downtown!

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 7
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
More info
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North-Side of Chicago near Wrigley, vacation rental in Chicago
North-Side of Chicago near Wrigley, vacation rental in Chicago
North-Side of Chicago near Wrigley, vacation rental in Chicago

North-Side of Chicago near Wrigley

Condo/Apartment in Irving Park, Northwest Side
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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BoHo House - Hip hangout spot near local bars+eats, vacation rental in Chicago
BoHo House - Hip hangout spot near local bars+eats, vacation rental in Chicago
BoHo House - Hip hangout spot near local bars+eats, vacation rental in Chicago

BoHo House - Hip hangout spot near local bars+eats

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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LA3 3BR Comfy Apt in Logan Square, vacation rental in Chicago
LA3 3BR Comfy Apt in Logan Square, vacation rental in Chicago
LA3 3BR Comfy Apt in Logan Square, vacation rental in Chicago

LA3 3BR Comfy Apt in Logan Square

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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LA2 Relaxing 3BR Logan Square with King Beds & Washer, vacation rental in Chicago
LA2 Relaxing 3BR Logan Square with King Beds & Washer, vacation rental in Chicago
LA2 Relaxing 3BR Logan Square with King Beds & Washer, vacation rental in Chicago

LA2 Relaxing 3BR Logan Square with King Beds & Washer

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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LA1 3-BR Gem with Parking and In-Unit Laundry, vacation rental in Chicago
LA1 3-BR Gem with Parking and In-Unit Laundry, vacation rental in Chicago
LA1 3-BR Gem with Parking and In-Unit Laundry, vacation rental in Chicago

LA1 3-BR Gem with Parking and In-Unit Laundry

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Beautiful 5BR Reunion Home near O'Hare and Downtown Chicago, vacation rental in Chicago
Beautiful 5BR Reunion Home near O'Hare and Downtown Chicago, vacation rental in Chicago
Beautiful 5BR Reunion Home near O'Hare and Downtown Chicago, vacation rental in Chicago

Beautiful 5BR Reunion Home near O'Hare and Downtown Chicago

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Logan Square Cozy 4BR/2BA, Free Parking, W/D, vacation rental in Chicago
Logan Square Cozy 4BR/2BA, Free Parking, W/D, vacation rental in Chicago
Logan Square Cozy 4BR/2BA, Free Parking, W/D, vacation rental in Chicago

Logan Square Cozy 4BR/2BA, Free Parking, W/D

Condo/Apartment
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Historic Hermosa - 20 min to Downtown - 3000 sqft, vacation rental in Chicago
Historic Hermosa - 20 min to Downtown - 3000 sqft, vacation rental in Chicago
Historic Hermosa - 20 min to Downtown - 3000 sqft, vacation rental in Chicago

Historic Hermosa - 20 min to Downtown - 3000 sqft

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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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
More info
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Spacious Apartment in Hermosa Park, vacation rental in Chicago
Spacious Apartment in Hermosa Park, vacation rental in Chicago
Spacious Apartment in Hermosa Park, vacation rental in Chicago

Spacious Apartment in Hermosa Park

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Showing results 1-49 of 49
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