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Oak Park
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Cottages, Villas, Apartments in Oak Park
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Illinois (IL)
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Internet or Wifi (96)
Air Conditioning (89)
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Other outdoor space (35)
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Kid friendly (91)
Pet friendly (29)
Elder access (7)
Smoking allowed (7)
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Condominium/Apartment (70)
Holiday Rental House (27)
Cabin Holiday Rental (0)
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Staffed Property (2)
Waterfront (1)
Housekeeping Included (1)
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North Side (3)
Logan Square (3)
Distance from
5 mi
Frank Lloyd Wright Home and Studio
Frank Lloyd Wright's Unity Temple
Ernest Hemingway Birthplace Museum
Oak Park Public Library
Wright Plus Architectural Housewalk
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97 rentals
in Oak Park.
A Comfortable Stay While You are Away
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 8
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Charming 1BR/1BA Hideaway in Oak Park, IL
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 3
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Stylish Luxe King bed w/Free Parkng near DT Oak Pk
14 reviews
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
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Chic Suite/Mins to L Train /Laundry/Free Parking
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 5
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1BR Apartment - Walk to Shops - Downtown OAK PARK
8 reviews
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 3
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Cozy Apt with Fireplace in Frank Lloyd Historic District
2 reviews
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
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A quiet stay while you are away
4 reviews
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Brand new private 2 bedroom unit
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 5
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FLW Historic District Oak Park ! 4 BDRM FREE PKG
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 7
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Relaxing Oak Park Home
6 reviews
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 6
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Comfy Avondale Flat - Sleeps 4
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 5
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Elegant King Bed/FirePit/Suite
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 5
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Sunny Coach House in Historic Oak Park
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 3
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N Ridgeway · Logan Square Cozy Apartment - Games+Arcade - Patio
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 5
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Lovely, Spacious 2 bed, 1 bath
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
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Sunny Jumbo Studio in the Heart of Oak Park
3 reviews
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Family-friendly, stylish Chicago Apartment in Logan Square
Condo/Apartment in North Side, Logan Square
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3 bedrooms
1 bathroom
Sleeps 7
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Oak Park 3 Bed Beauty/Close2Chicago/Sleeps 1-8 Guests
48 reviews
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
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Home away from home. Perfect for remote workers.
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 6
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Cozy 2 Bedroom on a Quite Street
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 6
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Clean & Cozy entire 3 bedroom unit 7 miles from downtown
Condo/Apartment
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3 bedrooms
1 bathroom
Sleeps 7
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Logan Square 2 BR/1 BA-modern, near METRA
9 reviews
Condo/Apartment in North Side, Logan Square
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2 bedrooms
1 bathroom
Sleeps 4
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Charming Chicago Retreat with Modern Comforts - Spa Bath
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Top floor of Historic Oak Park Home / 2 Car Grge
3 reviews
Condo/Apartment
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3 bedrooms
1 bathroom
Sleeps 6
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Cozy modern unit w/ easy access to downtown Chi
7 reviews
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 5
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CPS3 Logan Square Corner 3BR Apt Walkable to Highlights
Condo/Apartment
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3 bedrooms
2 bathrooms
Sleeps 6
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Large, sunny 3 bedroom apartment two blocks from down town Oak Park.
20 reviews
Condo/Apartment
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3 bedrooms
1 bathroom
Sleeps 8
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Beautiful Chicago 2BD 1BA, minutes from Downtown!
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
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Downtown Oak Park Steps to Theater, Dining, Shopping, Train, 20 min -> Chicago
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 5
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Modern Vibes 1br/1ba Oak Park
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Private 1 BR 1 BA Guest Suite
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
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Chic, spacious 3bed, 2 bath home
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 7
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1 bed 1 bath cozy apartment 42-1
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Spacious brand new condo - 15 mins from downtown Chicago! Sleeps 4
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
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Cozy1 BDRM apartment Located In The Heart Of Downtown Oak Park by Glow & Explore
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
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KING LOVELY SPACE
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 3
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Cozy, Comfortable and Convenient apartment. Close to everything!
5 reviews
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
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Chic Retreat in Historic House PARK FREE
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Lovely One Bedroom Near The Beautiful Oak Park Chicago
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Quiet, family getaway. Puppers welcome!
1 review
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Rockin' 2BR Apartment in the Heart of Oak Park
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
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Chicago Modern Condo- Perfect for family time or a good time in Chicago.
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 6
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Bedroom 2 Comfy Pvt - Shared BA - Living Room - Washer Dryer - Pet & Family Fr.
Condo/Apartment
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1 bedroom
2 bathrooms
Sleeps 2
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Heart of Oak Park, train ride to downtown Chicago. WIFI & Cable Included!
9 reviews
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 5
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Oak Park Bungalow
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 6
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Pvt Rm Bdrm 4 Comfy Pvt Rm - Shared Bath/Liv
Condo/Apartment
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1 bedroom
2 bathrooms
Sleeps 2
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BEAUTIFUL COZY APARTMENT
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 3
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Bdrm 1 Comfy Pvt Rm - Shared Bath/Liv
Condo/Apartment
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1 bedroom
2 bathrooms
Sleeps 2
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Comfortable home in historic Oak Park- open For Thanksgiving and Christmas!!!
10 reviews
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
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Quiet Chicago Townhome - 7 Mi to Downtown!
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 6
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Showing results 1-50 of 97
Frequently Asked Questions about Oak Park
Do any holiday rentals in Oak Park have a pool?
Yes, here are some popular holiday rentals in Oak Park that have a pool:
A Comfortable Stay While You are Away
Charming 1BR/1BA Hideaway in Oak Park, IL
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
See all holiday rentals with a pool in Oak Park on Tripadvisor
Do any holiday rentals in Oak Park have internet access?
Yes, here are some popular holiday rentals in Oak Park that have internet access:
A Comfortable Stay While You are Away
Charming 1BR/1BA Hideaway in Oak Park, IL
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
See all holiday rentals in Oak Park on Tripadvisor
What are the best pet friendly rentals in Oak Park?
The best pet friendly rentals in Oak Park are:
A Comfortable Stay While You are Away
1BR Apartment - Walk to Shops - Downtown OAK PARK
Cozy Apt with Fireplace in Frank Lloyd Historic District
See all pet friendly holiday rentals in Oak Park on Tripadvisor
What are some great rentals in Oak Park that are kid friendly?
Some of the most popular kid friendly rentals in Oak Park are:
A Comfortable Stay While You are Away
Charming 1BR/1BA Hideaway in Oak Park, IL
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
See all kid friendly holiday rentals in Oak Park on Tripadvisor