We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Oak Park Holiday Rentals

List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0+ rooms, 2+ guests
Distance from
1 mi
Price per night
£0
£1,000+
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
Neighbourhood
Show more
50 rentals in Oak Park.
Sort by:
Tripadvisor Sort
Heart of Oak Park, train ride to downtown Chicago.  WIFI & Cable Included!, holiday rental in Oak Park

Heart of Oak Park, train ride to downtown Chicago. WIFI & Cable Included!

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Oak Park Bungalow, holiday rental in Oak Park

Oak Park Bungalow

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Well-located Town Home for 6 People with Car Port And Private Entrance., holiday rental in Oak Park

Well-located Town Home for 6 People with Car Port And Private Entrance.

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Comfortable home in historic Oak Park- open For Thanksgiving and Christmas!!!, holiday rental in Oak Park

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

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Beautiful 2-bedroom apt. on a quiet tree-lined rstreet close to downtown Chicago, holiday rental in Oak Park

Beautiful 2-bedroom apt. on a quiet tree-lined rstreet close to downtown Chicago

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Sunny Jumbo Studio in the Heart of Oak Park, holiday rental in Oak Park

Sunny Jumbo Studio in the Heart of Oak Park

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Oak Park Beauty Sleeps 1 to 8 Guests, holiday rental in Oak Park

Oak Park Beauty Sleeps 1 to 8 Guests

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Modern Victorian With Old World Charm, holiday rental in Oak Park

Modern Victorian With Old World Charm

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Condo, holiday rental in Oak Park

Condo

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Dorothy's Place, holiday rental in Oak Park

Dorothy's Place

South Austin, West Side, Austin
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Save time - get the best Oak Park rentals sent straight to your email!
Contemporart Celebrity themed private parking runs to downtown, holiday rental in Oak Park

Contemporart Celebrity themed private parking runs to downtown

South Austin, West Side, Austin
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
LUXE* TOWN HOUSE DUPLEX MIN FROM DOWNTOWN CHICAGO, holiday rental in Oak Park

LUXE* TOWN HOUSE DUPLEX MIN FROM DOWNTOWN CHICAGO

Garfield Park, West Garfield Park, West Side
4 bedrooms
2 bathrooms
Sleeps 20
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Beautiful Chicago Mansion ~ 20 Minutes Downtown/O'Hare On Blue Line, holiday rental in Oak Park

Beautiful Chicago Mansion ~ 20 Minutes Downtown/O'Hare On Blue Line

Irving Park, Northwest Side
7 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Fully Furnished and rehabbed townhouse with off-street parking and yard, holiday rental in Oak Park

Fully Furnished and rehabbed townhouse with off-street parking and yard

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Charming apartment, fantastic location! Spacious 4 bedroom, a rare find!, holiday rental in Oak Park

Charming apartment, fantastic location! Spacious 4 bedroom, a rare find!

4 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Stunning New 6 Bedroom Home w/ Parking in Chicago (Superhosts), holiday rental in Oak Park

Stunning New 6 Bedroom Home w/ Parking in Chicago (Superhosts)

Albany Park, Mayfair, Far North Side
6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Peaceful Country Home near O’hare airport, holiday rental in Oak Park

Peaceful Country Home near O’hare airport

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Pup Friendly Apartment with Fenced Backyard, holiday rental in Oak Park

Pup Friendly Apartment with Fenced Backyard

Kilbourn Park, Northwest Side
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Make It Your Own - 15 Minutes to Chicago, holiday rental in Oak Park

Make It Your Own - 15 Minutes to Chicago

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Comfy Quarters, holiday rental in Oak Park

Comfy Quarters

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Real 15 Min to City & McCormick Place. See Ad for Details. Quiet Safe Area. View, holiday rental in Oak Park

Real 15 Min to City & McCormick Place. See Ad for Details. Quiet Safe Area. View

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Oak Park's Historic Getaway w/FHS, holiday rental in Oak Park

Oak Park's Historic Getaway w/FHS

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Private Floor - 8 miles from ORD + Shopping/Food, holiday rental in Oak Park

Private Floor - 8 miles from ORD + Shopping/Food

Belmont Cragin, Northwest Side, Belmont Central
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Spacious homely feeling apartment in Jefferson Park, holiday rental in Oak Park

Spacious homely feeling apartment in Jefferson Park

Albany Park, Far North Side
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
$99 +Chicago / Airport / Lake -in just  20 minutes!!, holiday rental in Oak Park

$99 +Chicago / Airport / Lake -in just 20 minutes!!

Jefferson Park, Far North Side
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Large Beautiful Aparment a REAL 20 <inutes to Everything, holiday rental in Oak Park

Large Beautiful Aparment a REAL 20 <inutes to Everything

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Beautiful Fully Furnished Apartment, 20 minutes from Downtown Chicago., holiday rental in Oak Park

Beautiful Fully Furnished Apartment, 20 minutes from Downtown Chicago.

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Eclectic Vibe - Oak Park/Forest Park, Pets OK, holiday rental in Oak Park

Eclectic Vibe - Oak Park/Forest Park, Pets OK

0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
ITALIAN garden apartment ! GREAT location ! Kids friendly!!, holiday rental in Oak Park

ITALIAN garden apartment ! GREAT location ! Kids friendly!!

Old Irving Park, Northwest Side
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Luxurious Condo in Top Rated Neighborhood near O'hare with Complete Privacy, holiday rental in Oak Park

Luxurious Condo in Top Rated Neighborhood near O'hare with Complete Privacy

Far North Side
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Governors Manor in Great Location with 6 Bedrooms, holiday rental in Oak Park

Governors Manor in Great Location with 6 Bedrooms

North Side, Logan Square
5 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
More info
Check-in
Check-out

Modish 1-BR Apt in the Heart of Lincoln Square

Lincoln Square, Ravenswood, Far North Side
0 bedrooms
0 bathrooms
Sleeps 0
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Nice apartment two bedrooms

Theater District, Downtown / The Loop, Central
0 bedrooms
0 bathrooms
Sleeps 0
Match: Sleeps
More info
Check-in
Check-out

Möblierte 1-Zimmer-Apartment in N State St &amp; W Illinois St Chicago

Near North Side, Central
0 bedrooms
0 bathrooms
Sleeps 0
Match: Sleeps
More info
Check-in
Check-out

Furnished 1-Bedroom Apartment at N State St & W Illinois St Chicago

Near North Side, Central
0 bedrooms
0 bathrooms
Sleeps 0
Match: Sleeps
More info
Check-in
Check-out

Eingerichtete Studio-Apartment in W Grand Ave &amp; N State St Chicago

Near North Side, Central
0 bedrooms
0 bathrooms
Sleeps 0
Match: Sleeps
More info
Check-in
Check-out

Möblierte 1-Zimmer-Apartment in N State St &amp; W Illinois St Chicago

Near North Side, Central
0 bedrooms
0 bathrooms
Sleeps 0
Match: Sleeps
More info
Check-in
Check-out

Möblierte 1-Zimmer-Apartment in N State St &amp; W Illinois St Chicago

Near North Side, Central
0 bedrooms
0 bathrooms
Sleeps 0
Match: Sleeps
More info
Check-in
Check-out

Möblierte 1-Zimmer-Apartment in N State St &amp; W Illinois St Chicago

Near North Side, Central
0 bedrooms
0 bathrooms
Sleeps 0
Match: Sleeps
More info
Check-in
Check-out

Möblierte 3-Zimmer Stadthaus in N Wells St &amp; W Scott St Chicago

Near North Side, Old Town, Central
0 bedrooms
0 bathrooms
Sleeps 0
Match: Sleeps
More info
Check-in
Check-out

Επιπλωμένο Διαμέρισμα με 1 υπνοδωμάτιο στο Ν State St &amp; W Illinois St Σικάγο

Near North Side, Central
0 bedrooms
0 bathrooms
Sleeps 0
Match: Sleeps
More info
Check-in
Check-out

Eingerichtete Studio-Apartment in W Grand Ave &amp; N State St Chicago

Near North Side, Central
0 bedrooms
0 bathrooms
Sleeps 0
Match: Sleeps
More info
Check-in
Check-out

Furnished 1-Bedroom Apartment at N State St & W Illinois St Chicago

Near North Side, Central
0 bedrooms
0 bathrooms
Sleeps 0
Match: Sleeps
More info
Check-in
Check-out

Möblierte 1-Zimmer-Apartment in N State St &amp; W Illinois St Chicago

Near North Side, Central
0 bedrooms
0 bathrooms
Sleeps 0
Match: Sleeps
More info
Check-in
Check-out

Furnished Studio Apartment at W Grand Ave & N State St Chicago

Near North Side, Central
0 bedrooms
0 bathrooms
Sleeps 0
Match: Sleeps
More info
Check-in
Check-out

Ferienwohnung Chicago

Downtown / The Loop, Central
0 bedrooms
0 bathrooms
Sleeps 0
Match: Sleeps
More info
Check-in
Check-out

Near Downtown and McCormick Place

Chinatown, South Side, Armour Square
0 bedrooms
0 bathrooms
Sleeps 0
Match: Sleeps
More info
Check-in
Check-out

West Loop 2 bed 2 Bath Blackhawks Bulls!

West Side, Near West Side, West Loop
0 bedrooms
0 bathrooms
Sleeps 0
Match: Sleeps
More info
Check-in
Check-out

Luxury Penthouse South Loop

South Loop, Near South Side, Central
0 bedrooms
0 bathrooms
Sleeps 0
Match: Sleeps
More info
Check-in
Check-out

cozy one bedroom apt / mccormick place/bronzevill

Chinatown, South Side, Armour Square
0 bedrooms
0 bathrooms
Sleeps 0
Match: Sleeps
More info
Check-in
Check-out
PreviousNext
1