
Apartment holiday rentals in Oak Park
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Quick stats about apartment rentals in Oak Park

Total holiday rentals
Explore 150 holiday rentals in Oak Park

Nightly prices starting at
Oak Park holiday rentals start at $17 NZD per night before taxes and fees

Verified guest reviews
Over 11,820 verified reviews to help you choose

Family-friendly holiday rentals
80 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
90 properties have a dedicated workspace

Wi-Fi availability
150 of Oak Park holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Oak Park rentals

4.8 Average rating
Oak Park stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated apartment rentals in Oak Park
Guests agree: These apartments are highly rated for location, cleanliness and more.

Sunny Jumbo Studio
Bright and sunny Oak Park jumbo garden studio, steps from cute downtown, train to Chicago, and amazing local tourist destinations- like the Hemingway Home and the Wright Studio. This welcoming studio was completely rehabbed and updated. We put a lot of care into designing a relaxing apartment with all the amenities. The main room features a king-sized bed, office nook, and fully stocked entertainment area, with games, books, and a TV. The spacious kitchen and luxurious bathroom are brand new!

Sunny 1 bedroom apartment 1 block from restaurants
This sunny second floor apartment perched in an 1890’s farmhouse offers traditional charm with many contemporary touches. It showcases a variety of original art. Located on a quiet street but just steps away from restaurants, bars and shops, off-street parking is included. Two nearby trains provide easy access to downtown Chicago and O’Hare Airport. An enclosed porch directly off the kitchen overlooks a beautiful prairie garden. You can relax on the backyard patio with gas grill and fire pit.

Cheerful Remodel Prime Location
Relax in this newly remodeled and beautifully decorated apartment while recharging from a long day of sightseeing in the big city! We are a block from the Green Line train to downtown! With a 5 minute walk to Whole Foods, Trader Joes, and downtown Oak Park, you can't get a better location than this! Pets are welcome on a case-by-case basis, please mention your pet in your inquiry so we can learn more about them prior to approval and be sure to register them when you select number of guests.

The Belvidere
Charm abounds in this perfectly situated 2nd floor unit, steps to downtown Forest Park and Oak Park, where you will find shops, restaurants, grocery, cafes, parks, and more right at your fingertips! Walk to Metra, Green, or Blue Line El stop to take train into Chicago. Playground & Splashpad directly across the street! Full rehabbed kitchen & bath, enclosed back porch, fenced in backyard & parking included. Guests have described feeling immediately at home as they step into this sunlit space.

A Quiet Stay While You Are Away Oak Park
Welcome to our cozy and comfortable home located in a quiet neighborhood. Our space is perfect for couples, solo travelers, small families, and long-term stays. This is a beautiful, modernist home located in the Frank Lloyd Wright District Neighborhood, a designated historic district known for its collection of homes designed by the famous architect Frank Lloyd Wright. This district features a collection of some of his iconic designs and is a destination for architecture enthusiasts.

Home in Forest Park downstairs.
Enjoy a private ground floor apartment which is centrally-located with easy access , to the city. You will have a functional kitchen, laundry facility outside your back door and fast internet. Forest Park is located about 20 minutes from downtown Chicago and about 30 minutes from O’Hara international airport. You are within walking distance of many boutiques, restaurants, parks and also public transportation. Please make a note that there will be a $30 per guest fee if more than four.

SuperHost and Super Location Central OP
4.98 Star Superhost rating for this ideal Centrally-located, light, bright, spacious 2 bedroom 1 bath 2nd floor unit in a beautifully updated vintage building! Central air and forced air heat, hardwood floors throughout. Wonderful floor plan to enjoy your stay while you are "in", Near public transportation when you want to "be on the go"! Designated work space, high speed WIFI and 1 parking space on premises. Deck off the kitchen for outdoor space. Keyless access. 1 King/ 1 Queen bed

Top floor of Historic Oak Park Home /2 Car Garage
Secluded but never isolated; 3 blocks from the L-line, next door to Hemingway's birthplace, surrounded by dozens of Frank Lloyd Wright homes, 30 min from the Loop, MDW and ORD, makes this location an ideal platform for the cultural explorer. Experience an ambiance that supports the work-from-home Urban Professional, combining it with a multibedroom layout designed to accommodate family and friends. Gig-speed internet supports sophisticated professional and gaming applications.

Studio Apartment in Oak Park
Nestled in Oak Park's historic district, this charming studio apartment is within walking distance of cafes, shops, restaurants, a movie theater, and the CTA/Metra for city and suburban excursions. Featuring a comfortable queen-sized bed, a newly updated full bathroom, and a kitchenette, it sits mere steps from Ernest Hemingway's childhood home and a few blocks from Frank Lloyd Wright's residence and studio. Enjoy the serenity of this historic home and its hidden garden oasis.

Chicago-Style, Vintage, Cable & NFL PASS 42-1
→ Introducing our newly renovated and furnished apartment unit nestled in the charming Oak Park Art District. Richly characteristic brick building, Chicago style, situated in a safe and quiet neighborhood. ★ Property Features: • One block away: Oak Park Art District • Vintage Chicago style brick building • Safe, quiet neighborhood • Newly renovated and furnished • Smart TV with Cable • Free Laundry Room • Free Parking for short stays, long stays limit spots please confirm.

A Little Slice of Heaven in Oak Park, IL
A private space with a fun vintage vibe. Located several blocks from the El and the Eisenhower, it’s really easy to access the city. It also includes free off-street parking which is a must. The space is located in my basement and has a private entrance. I do live in the house above so you will hear some noises including my dog - but we do try to be quiet. The space includes a bedroom, spacious living area and an updated bathroom. Please contact me with any questions

Cheerful Oak Park Apartment
Welcome to our lovely space, located above a unique piano restoration shop. Spacious and relaxing, with plenty to enjoy staying in, and 5-minutes walking distance to cafes, grocery, bars, restaurants, and more. The apartment is down the street from a Botanic Garden, and there is a nice arts district nearby. Easily accessible to downtown Oak Park and Chicago with nearby public transportation and expressway (downtown Chicago is about 25-35 min. drive, 35-45 min. by train).
Popular amenities for Oak Park apartment rentals
Weekly apartment rentals

Modern NEW Deluxe Studio in Oak Park

The Lantern: Ultimate 2 Bed Forest Park Escape!

Chic & Cozy OakPark 1br apt near Chicago w/parking

Urban oasis in Oak Park

Historic Hotspot: Downtown Oak Park w/parking spot

Gorgeous Penthouse with Parking in Heart of Forest Park

2nd floor walk up above House. 3 bed 1 bath

Serene 1-Bedroom Suite in Oak Park (Free Parking!)
Private apartment rentals

Bright & Spacious Boho Oasis: A Warm Retreat

Beautiful & Cozy 2bd/1b Near O’Hare & Metra (MD-W)

Clean and Comfy Updated Apt in Convenient Location

Small But Mighty 700 Sqft Cottage Apt (1BR/1BA)

Sunny Retreat in Forest Park

Large sunny 3BR apt. in downtown Oak Park

Prairie Style Apartment

Luxurious Lifestyle
Apartment rentals with a hot tub

Top Floor Views + Central Comfort

Super Paradise+65 Amenities*Downtown 15 Min

The Aerial Oasis (Indoor Pool • Fitness Center)

Skyline Oasis: City & Lake Views

Luxury 3BD Penthouse – Private Patio+Skyline Views

Level One Bedroom Suite | Fulton Market

Belmont Pleasures - hot tub / arcade gaming room

420 friendly apt with 2 queens,1 full,1 twin bed
When is the best time to visit Oak Park?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $185 NZD | $180 NZD | $200 NZD | $191 NZD | $226 NZD | $233 NZD | $241 NZD | $244 NZD | $210 NZD | $222 NZD | $200 NZD | $205 NZD |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°C |
Destinations to explore
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- Rentals with a fireplace Oak Park
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- Fitness-friendly rentals Oak Park
- Family-friendly rentals Oak Park
- Rentals with a washing machine and dryer Oak Park
- Pet-friendly rentals Oak Park
- Rentals with a patio Oak Park
- Rentals with a fire pit Oak Park
- Apartment rentals Cook County
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- Apartment rentals United States
- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Grant Park
- Navy Pier
- Chicago River Walk
- Soldier Field
- 875 North Michigan Avenue
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- The Field Museum
- Guaranteed Rate Field
- Union Park
- Lincoln Park Zoo
- Wilmot Mountain Ski Resort
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- Washington Park Zoo
- Museum of Science and Industry
- Oak Street Beach
- Illinois Beach State Park
- Indiana Dunes State Park





