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Oak Park Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Neighborhood

Distance from

5 mi
119 rentals in Oak Park.
Stylish Luxe King bed w/Free Parkng near DT Oak Pk, vacation rental in Oak Park
Stylish Luxe King bed w/Free Parkng near DT Oak Pk, vacation rental in Oak Park
Stylish Luxe King bed w/Free Parkng near DT Oak Pk, vacation rental in Oak Park

Stylish Luxe King bed w/Free Parkng near DT Oak Pk

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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1BR Apartment - Walk to Shops - Downtown OAK PARK, vacation rental in Oak Park
1BR Apartment - Walk to Shops - Downtown OAK PARK, vacation rental in Oak Park
1BR Apartment - Walk to Shops - Downtown OAK PARK, vacation rental in Oak Park

1BR Apartment - Walk to Shops - Downtown OAK PARK

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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A quiet stay while you are away, vacation rental in Oak Park
A quiet stay while you are away, vacation rental in Oak Park
A quiet stay while you are away, vacation rental in Oak Park

A quiet stay while you are away

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Peaceful 2 Bed w FirePit Free Parking 15 mins to Downtown Chicago, vacation rental in Oak Park
Peaceful 2 Bed w FirePit Free Parking 15 mins to Downtown Chicago, vacation rental in Oak Park
Peaceful 2 Bed w FirePit Free Parking 15 mins to Downtown Chicago, vacation rental in Oak Park

Peaceful 2 Bed w FirePit Free Parking 15 mins to Downtown Chicago

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

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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Charming Chicago Retreat with Modern Comforts - Spa Bath, vacation rental in Oak Park
Charming Chicago Retreat with Modern Comforts - Spa Bath, vacation rental in Oak Park
Charming Chicago Retreat with Modern Comforts - Spa Bath, vacation rental in Oak Park

Charming Chicago Retreat with Modern Comforts - Spa Bath

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Top floor of Historic Oak Park Home / 2 Car Grge, vacation rental in Oak Park
Top floor of Historic Oak Park Home / 2 Car Grge, vacation rental in Oak Park
Top floor of Historic Oak Park Home / 2 Car Grge, vacation rental in Oak Park

Top floor of Historic Oak Park Home / 2 Car Grge

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Luxe Ranch & Spa House Retreat! Pets Welcome, vacation rental in Oak Park
Luxe Ranch & Spa House Retreat! Pets Welcome, vacation rental in Oak Park
Luxe Ranch & Spa House Retreat! Pets Welcome, vacation rental in Oak Park

Luxe Ranch & Spa House Retreat! Pets Welcome

Rental Home
3 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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2BR 2 BATH MINUTES FROM DOWNTOWN, vacation rental in Oak Park
2BR 2 BATH MINUTES FROM DOWNTOWN, vacation rental in Oak Park
2BR 2 BATH MINUTES FROM DOWNTOWN, vacation rental in Oak Park

2BR 2 BATH MINUTES FROM DOWNTOWN

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Chicago-Style, Vintage, Tv NFL PASS, vacation rental in Oak Park
Charming Chicago-Style, Vintage, Tv NFL PASS, vacation rental in Oak Park
Charming Chicago-Style, Vintage, Tv NFL PASS, vacation rental in Oak Park

Charming Chicago-Style, Vintage, Tv NFL PASS

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Spacious brand new condo - 15 mins from downtown Chicago! Sleeps 4, vacation rental in Oak Park
Spacious brand new condo - 15 mins from downtown Chicago! Sleeps 4, vacation rental in Oak Park
Spacious brand new condo - 15 mins from downtown Chicago! Sleeps 4, vacation rental in Oak Park

Spacious brand new condo - 15 mins from downtown Chicago! Sleeps 4

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy, Comfortable and Convenient apartment. Close to everything!, vacation rental in Oak Park
Cozy, Comfortable and Convenient apartment. Close to everything!, vacation rental in Oak Park
Cozy, Comfortable and Convenient apartment. Close to everything!, vacation rental in Oak Park

Cozy, Comfortable and Convenient apartment. Close to everything!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Retro 2 bedroom bungalow in Chicago's Avondale neighborhood, vacation rental in Oak Park
Retro 2 bedroom bungalow in Chicago's Avondale neighborhood, vacation rental in Oak Park
Retro 2 bedroom bungalow in Chicago's Avondale neighborhood, vacation rental in Oak Park

Retro 2 bedroom bungalow in Chicago's Avondale neighborhood

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Rockin' 2BR Apartment in the Heart of Oak Park, vacation rental in Oak Park
Rockin' 2BR Apartment in the Heart of Oak Park, vacation rental in Oak Park
Rockin' 2BR Apartment in the Heart of Oak Park, vacation rental in Oak Park

Rockin' 2BR Apartment in the Heart of Oak Park

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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BEAUTIFUL COZY APARTMENT, vacation rental in Oak Park
BEAUTIFUL COZY APARTMENT, vacation rental in Oak Park
BEAUTIFUL COZY APARTMENT, vacation rental in Oak Park

BEAUTIFUL COZY APARTMENT

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Comfortable home in historic Oak Park- open For Thanksgiving and Christmas!!!, vacation rental in Oak Park
Comfortable home in historic Oak Park- open For Thanksgiving and Christmas!!!, vacation rental in Oak Park
Comfortable home in historic Oak Park- open For Thanksgiving and Christmas!!!, vacation rental in Oak Park

Comfortable home in historic Oak Park- open For Thanksgiving and Christmas!!!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Historic Oak Park Apartment ~ 8 Mi to Downtown, vacation rental in Oak Park
Historic Oak Park Apartment ~ 8 Mi to Downtown, vacation rental in Oak Park
Historic Oak Park Apartment ~ 8 Mi to Downtown, vacation rental in Oak Park

Historic Oak Park Apartment ~ 8 Mi to Downtown

Condo/Apartment
4 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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FREE PARKING! Desirable Logan Square Location with Modern Touches and Beautiful, vacation rental in Oak Park
FREE PARKING! Desirable Logan Square Location with Modern Touches and Beautiful, vacation rental in Oak Park
FREE PARKING! Desirable Logan Square Location with Modern Touches and Beautiful, vacation rental in Oak Park

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

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Spacious, lovely 2bed 1bath with free parking, vacation rental in Oak Park
Spacious, lovely 2bed 1bath with free parking, vacation rental in Oak Park
Spacious, lovely 2bed 1bath with free parking, vacation rental in Oak Park

Spacious, lovely 2bed 1bath with free parking

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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8 MILES FROM DOWNTOWN CHICAGO!!!, vacation rental in Oak Park
8 MILES FROM DOWNTOWN CHICAGO!!!, vacation rental in Oak Park
8 MILES FROM DOWNTOWN CHICAGO!!!, vacation rental in Oak Park

8 MILES FROM DOWNTOWN CHICAGO!!!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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INSTA-WORTHY Loft+Condo, FREE Parking, Near Downtown Chicago, vacation rental in Oak Park
INSTA-WORTHY Loft+Condo, FREE Parking, Near Downtown Chicago, vacation rental in Oak Park
INSTA-WORTHY Loft+Condo, FREE Parking, Near Downtown Chicago, vacation rental in Oak Park

INSTA-WORTHY Loft+Condo, FREE Parking, Near Downtown Chicago

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 11
Match: Sleeps
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Top floor of Historic Oak Park Villa / 2 Car Grge, vacation rental in Oak Park
Top floor of Historic Oak Park Villa / 2 Car Grge, vacation rental in Oak Park
Top floor of Historic Oak Park Villa / 2 Car Grge, vacation rental in Oak Park

Top floor of Historic Oak Park Villa / 2 Car Grge

Condo/Apartment
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Picture Perfect 3Bed Steps from Train and FLW, vacation rental in Oak Park
Picture Perfect 3Bed Steps from Train and FLW, vacation rental in Oak Park
Picture Perfect 3Bed Steps from Train and FLW, vacation rental in Oak Park

Picture Perfect 3Bed Steps from Train and FLW

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spacious brand new condo - 15 min from downtown Chicago! Sleeps 6, vacation rental in Oak Park
Spacious brand new condo - 15 min from downtown Chicago! Sleeps 6, vacation rental in Oak Park
Spacious brand new condo - 15 min from downtown Chicago! Sleeps 6, vacation rental in Oak Park

Spacious brand new condo - 15 min from downtown Chicago! Sleeps 6

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming  3 beds 2 baths close  15 min Chicago walk to trains hold 6 pp parking, vacation rental in Oak Park
Charming  3 beds 2 baths close  15 min Chicago walk to trains hold 6 pp parking, vacation rental in Oak Park
Charming  3 beds 2 baths close  15 min Chicago walk to trains hold 6 pp parking, vacation rental in Oak Park

Charming 3 beds 2 baths close 15 min Chicago walk to trains hold 6 pp parking

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Classic Oak Park Home, 11 Mi to Downtown Chicago!, vacation rental in Oak Park
Classic Oak Park Home, 11 Mi to Downtown Chicago!, vacation rental in Oak Park
Classic Oak Park Home, 11 Mi to Downtown Chicago!, vacation rental in Oak Park

Classic Oak Park Home, 11 Mi to Downtown Chicago!

Rental Home
6 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Chic 3bed 2bath Home with free parking close to United Center, vacation rental in Oak Park
Chic 3bed 2bath Home with free parking close to United Center, vacation rental in Oak Park
Chic 3bed 2bath Home with free parking close to United Center, vacation rental in Oak Park

Chic 3bed 2bath Home with free parking close to United Center

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Modern Victorian Vibes ❤️ | Character & Charm, vacation rental in Oak Park
Modern Victorian Vibes ❤️ | Character & Charm, vacation rental in Oak Park
Modern Victorian Vibes ❤️ | Character & Charm, vacation rental in Oak Park

Modern Victorian Vibes ❤️ | Character & Charm

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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NEW in 2022! The CHICAGO GAME ROOM, vacation rental in Oak Park
NEW in 2022! The CHICAGO GAME ROOM, vacation rental in Oak Park
NEW in 2022! The CHICAGO GAME ROOM, vacation rental in Oak Park

NEW in 2022! The CHICAGO GAME ROOM

Condo/Apartment
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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H&H 1896 - Free Parking, Fully Stocked, & Spacious - 15 mins to downtown, vacation rental in Oak Park
H&H 1896 - Free Parking, Fully Stocked, & Spacious - 15 mins to downtown, vacation rental in Oak Park
H&H 1896 - Free Parking, Fully Stocked, & Spacious - 15 mins to downtown, vacation rental in Oak Park

H&H 1896 - Free Parking, Fully Stocked, & Spacious - 15 mins to downtown

Rental Home
6 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Chicago Home-  4 bd 3 ba- 1  spot in the  garage.  30 mins to downtown., vacation rental in Oak Park
Chicago Home-  4 bd 3 ba- 1  spot in the  garage.  30 mins to downtown., vacation rental in Oak Park
Chicago Home-  4 bd 3 ba- 1  spot in the  garage.  30 mins to downtown., vacation rental in Oak Park

Chicago Home- 4 bd 3 ba- 1 spot in the garage. 30 mins to downtown.

Rental Home
5 bedrooms
4 bathrooms
Sleeps 2
Match: Sleeps
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Oak Park 3000 sq ft, sleep 16, vacation rental in Oak Park
Oak Park 3000 sq ft, sleep 16, vacation rental in Oak Park
Oak Park 3000 sq ft, sleep 16, vacation rental in Oak Park

Oak Park 3000 sq ft, sleep 16

Rental Home
6 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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N Ridgeway · Logan Square Cozy Apartment - Games+Arcade - Patio, vacation rental in Oak Park
N Ridgeway · Logan Square Cozy Apartment - Games+Arcade - Patio, vacation rental in Oak Park
N Ridgeway · Logan Square Cozy Apartment - Games+Arcade - Patio, vacation rental in Oak Park

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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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JaRes’ Place newly renovated centrally located in the heart of Chicago/Galewood, vacation rental in Oak Park
JaRes’ Place newly renovated centrally located in the heart of Chicago/Galewood, vacation rental in Oak Park
JaRes’ Place newly renovated centrally located in the heart of Chicago/Galewood, vacation rental in Oak Park

JaRes’ Place newly renovated centrally located in the heart of Chicago/Galewood

Condo/Apartment
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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2nd floor walk up 3 bedroom 1 bath with parking, vacation rental in Oak Park
2nd floor walk up 3 bedroom 1 bath with parking, vacation rental in Oak Park
2nd floor walk up 3 bedroom 1 bath with parking, vacation rental in Oak Park

2nd floor walk up 3 bedroom 1 bath with parking

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Modern Vibes 1br/1ba Oak Park, vacation rental in Oak Park
Modern Vibes 1br/1ba Oak Park, vacation rental in Oak Park
Modern Vibes 1br/1ba Oak Park, vacation rental in Oak Park

Modern Vibes 1br/1ba Oak Park

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Mins to DT & Frank Lloyd Wright, vacation rental in Oak Park
Mins to DT & Frank Lloyd Wright, vacation rental in Oak Park
Mins to DT & Frank Lloyd Wright, vacation rental in Oak Park

Mins to DT & Frank Lloyd Wright

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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The Oak Park Loft, Including Garage, vacation rental in Oak Park
The Oak Park Loft, Including Garage, vacation rental in Oak Park
The Oak Park Loft, Including Garage, vacation rental in Oak Park

The Oak Park Loft, Including Garage

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Quiet Chicago Townhome: Walk to Subway Stations, vacation rental in Oak Park
Quiet Chicago Townhome: Walk to Subway Stations, vacation rental in Oak Park
Quiet Chicago Townhome: Walk to Subway Stations, vacation rental in Oak Park

Quiet Chicago Townhome: Walk to Subway Stations

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming Oak Park 4BD/3.5BA and 2 Private Parking by AllSet Turnover, vacation rental in Oak Park
Charming Oak Park 4BD/3.5BA and 2 Private Parking by AllSet Turnover, vacation rental in Oak Park
Charming Oak Park 4BD/3.5BA and 2 Private Parking by AllSet Turnover, vacation rental in Oak Park

Charming Oak Park 4BD/3.5BA and 2 Private Parking by AllSet Turnover

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Award-winning, charming, 1-bedroom apartment with AC, WiFi in Pleasant Oak Park, vacation rental in Oak Park
Award-winning, charming, 1-bedroom apartment with AC, WiFi in Pleasant Oak Park, vacation rental in Oak Park
Award-winning, charming, 1-bedroom apartment with AC, WiFi in Pleasant Oak Park, vacation rental in Oak Park

Award-winning, charming, 1-bedroom apartment with AC, WiFi in Pleasant Oak Park

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Logan Square :The place to be in Chicago.Spacious & sunny 2-Br apt.Free parking, vacation rental in Oak Park
Logan Square :The place to be in Chicago.Spacious & sunny 2-Br apt.Free parking, vacation rental in Oak Park
Logan Square :The place to be in Chicago.Spacious & sunny 2-Br apt.Free parking, vacation rental in Oak Park

Logan Square :The place to be in Chicago.Spacious & sunny 2-Br apt.Free parking

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Space&style New rehab, first flr + bsmt of duplex, driveway prkng, walk to train, vacation rental in Oak Park
Space&style New rehab, first flr + bsmt of duplex, driveway prkng, walk to train, vacation rental in Oak Park
Space&style New rehab, first flr + bsmt of duplex, driveway prkng, walk to train, vacation rental in Oak Park

Space&style New rehab, first flr + bsmt of duplex, driveway prkng, walk to train

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Fantastic 4 BR 2BR, Minutes from Downtown Chicago!, vacation rental in Oak Park
Fantastic 4 BR 2BR, Minutes from Downtown Chicago!, vacation rental in Oak Park
Fantastic 4 BR 2BR, Minutes from Downtown Chicago!, vacation rental in Oak Park

Fantastic 4 BR 2BR, Minutes from Downtown Chicago!

Condo/Apartment
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cozy 3 Bdrm. Apt.  sleeps 5 guests in the historic neighborhood of Oak Park IL, vacation rental in Oak Park
Cozy 3 Bdrm. Apt.  sleeps 5 guests in the historic neighborhood of Oak Park IL, vacation rental in Oak Park
Cozy 3 Bdrm. Apt.  sleeps 5 guests in the historic neighborhood of Oak Park IL, vacation rental in Oak Park

Cozy 3 Bdrm. Apt. sleeps 5 guests in the historic neighborhood of Oak Park IL

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Updated Chicago Bungalow on a Beautiful and Calm Neighborhood Greenway Boulevard, vacation rental in Oak Park
Updated Chicago Bungalow on a Beautiful and Calm Neighborhood Greenway Boulevard, vacation rental in Oak Park
Updated Chicago Bungalow on a Beautiful and Calm Neighborhood Greenway Boulevard, vacation rental in Oak Park

Updated Chicago Bungalow on a Beautiful and Calm Neighborhood Greenway Boulevard

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Oak Park, IL, entire house, short walk to train., vacation rental in Oak Park
Oak Park, IL, entire house, short walk to train., vacation rental in Oak Park
Oak Park, IL, entire house, short walk to train., vacation rental in Oak Park

Oak Park, IL, entire house, short walk to train.

Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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❤️ Lowest Rates! Fun & Stylish 3BR in Logan Square, vacation rental in Oak Park
❤️ Lowest Rates! Fun & Stylish 3BR in Logan Square, vacation rental in Oak Park
❤️ Lowest Rates! Fun & Stylish 3BR in Logan Square, vacation rental in Oak Park

❤️ Lowest Rates! Fun & Stylish 3BR in Logan Square

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Comfy Avondale Flat - Sleeps 4, vacation rental in Oak Park
Comfy Avondale Flat - Sleeps 4, vacation rental in Oak Park
Comfy Avondale Flat - Sleeps 4, vacation rental in Oak Park

Comfy Avondale Flat - Sleeps 4

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Modern Deluxe Studio Suite in Oak Park!, vacation rental in Oak Park
Modern Deluxe Studio Suite in Oak Park!, vacation rental in Oak Park
Modern Deluxe Studio Suite in Oak Park!, vacation rental in Oak Park

Modern Deluxe Studio Suite in Oak Park!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Showing results 1-50 of 119
Frequently Asked Questions about Oak Park