
Vacation rentals in Oak Park
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Top-rated vacation rentals in Oak Park
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Walk to Oak Park from a Bright Madison Street Loft
Crowned "The best in neighborhood dining" according to a 2008 Chicago Tribune readers poll, the variety of Forest Park restaurants offer something for everyone. The unit is a charming two bedroom, two bath loft a stone’s throw from historic Oak Park and just three blocks from the CTA Blue Line making downtown Chicago a 20 minute train ride away. The condo includes additional amenities such as: - Elevator in building •Secure front and back entrances. •One assigned parking spot in the back of the building. •Full kitchen with stainless steel appliances (stove, dishwasher, refrigerator), cookware, and dinnerware. •Granite countertops. •Two full bathrooms. The master bathroom includes a Jacuzzi tub. •Two full bedrooms. Both have queen sized beds. •Smart TV with cable access and access to Netflix. •Central Air conditioning •Working fireplace •Balcony with a view of downtown Chicago's skyline •Washer and dryer in unit. Just to the east lies historic Oak Park, which offers an array of attractions such as: •Brookfield Zoo •Chicago Architecture Foundation •Ernest Hemmingway Museum and Birthplace •Frank Lloyd Wright Home and Studio •Frank Llyod Wright’s Unity Temple •Oak Park Conservatory After soaking up some attractions in Oak Park, Chicago is only a short twenty minute train ride away, and it offers such noteworthy experiences as: •Shedd Aquarium •Architecture River Cruise •Skydeck Chicago •Navy Pier •The Field Museum •John Hancock Observatory •Adler Planetarium •Art Institute of Chicago •The Museum of Science and Industry The loft and both doors to our building have key-less entry pads. We will email you your personal entry code along with check in instructions a couple days before your arrival. Each guest is given their own personal code. Codes are programmed the day of check in and deleted shortly after check out. We are as available as you need. Centrally positioned in the Madison Street shopping and dining district, the loft is conveniently surrounded by local eateries and pubs within minutes of downtown Chicago and the United Center, and just blocks from the CTA blue line. We are located half a mile from the L - Blue Line. We are the Forest Park Stop on the blue line. The blue line will take you into the city. It is about an 8 to 10 minute walk from the loft. An Uber/Lyft ride into the city ranges from $15 to $25 and takes around 15 to 20 minutes. We are one mile from the Metra train line (Union Pacific - West). The Metra dead ends into Union Station. There are a number of Metra lines that take you to surrounding suburbs. We are also one mile from the Green Line - Oak Park Stop. The Green Line is another line on the L. The third bed is a queen sleeper sofa. There is a strict no smoking policy in our building. You can not smoke on the balcony - it will result in a $500 fine. The neighborhood is vibrant in the summer and sound can travel into the unit.

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.

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.

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).

Private 2 BR Oak Park Garden Apt
This spacious 2 BR garden apartment is fully furnished, private Kitchen and Bathroom ! In a safe, quiet neighborhood, stay cool and comfortable while you rest. 1 block from the Austin Blue line and the 290/ Eisenhower express way. Approx 20 minutes to Downtown Chicago or Midway Airport and 30 mins to O'hare Airport. Oak Park is a wonderfully diverse community and holds the largest collection of Frank Lloyd Wright homes. It is also the childhood home of Ernest Hemingway.

Mid-Century Charm. Near Chicago. Low Cleaning Fee!
Step back in time a bit with our charming 2nd floor walk-up in a quiet, safe suburb. Parking included on-site. Vintage, welcoming vibe. We're a 20-30 minute drive to downtown Chicago (depending on traffic). The unit is on the 2nd Floor and is separate from the rest of the house (we live on the 1st floor). 1 Dedicated Guest Parking spot (included). Additional Free Parking is available. Great wifi. 3-season back porch. Record Player (Real Vinyl!)

Peaceful Oak Park Condo Next to Green Line Metro
Very private, quiet space amidst the activity of Downtown Oak Park. The layout of the space is ideal, as bedrooms are at one end, and the living space is at the other. Private outdoor deck. Oak Park is a beautiful neighborhood full of great places to eat, drink, and shop. Metro and Green line is steps away which means access to anywhere in the city of Chicago. Private parking too!

Bright & Spacious Victorian-FREE PKG walk to train
This historic Queen Anne home built in 1889 is in the heart of Oak Park. Walk to all tourist attractions, public transportation that takes you directly to downtown Chicago, great restaurants, boutiques and grocery stores. It’s the perfect base for exploring Oak Park and Chicago. We kindly ask that you read our full listing description and our house rules prior to booking.

Lovely Central Oak Park TH w/parking & on Green el
Great central Oak Park location, close to everything including dining, Green Line, Metra, and OPRF High School. Enjoy farm fresh produce, eggs, and cheese or pick up some famous Farmers Market Donuts from the Oak Park Farmers Market just steps out your front door every Saturday May-October. Free (driveway) parking for one car. Backyard & deck space off the kitchen.
Popular amenities for Oak Park vacation rentals
Other great vacation rentals in Oak Park

A Pleasant Stay in Oak Park

Prairie Style Apartment

Spacious Oak Park 4bd/3.5ba and Parking

Home in Forest Park Upstairs.

Historic Hotspot: Downtown Oak Park w/parking spot

Oak Park - Wine House!

1 bedroom garden apartment in Forest Park

2 BR • CTA Blue Line to Chicago • Free Parking
When is the best time to visit Oak Park?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ327 | ﺩ.ﺇ323 | ﺩ.ﺇ375 | ﺩ.ﺇ386 | ﺩ.ﺇ474 | ﺩ.ﺇ488 | ﺩ.ﺇ518 | ﺩ.ﺇ514 | ﺩ.ﺇ441 | ﺩ.ﺇ437 | ﺩ.ﺇ404 | ﺩ.ﺇ378 |
| 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 |
Frequently Asked Questions
Where should I stay in Oak Park?
Make yourself at home in Oak Park by choosing from our most frequently booked neighborhoods. We have over 650 vacation rentals in Rehm Park, and over 2,430 vacation rentals in Oak Park.
Are there pet-friendly vacation rentals in Oak Park?
Four-legged friends are welcome in Oak Park. Choose from more than 90 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Oak Park?
Yes! Work meets play with ease at over 190 vacation rentals in Oak Park featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there family-friendly apartment rentals in Oak Park?
Oak Park has more than 80 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in condo rentals in Oak Park?
Experience the best of Oak Park with our condo rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do condo rentals in Oak Park have wifi?
Absolutely! We offer over 20 condo rentals with wifi in Oak Park. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Oak Park have a bbq area?
Absolutely! We offer over 10 apartment rentals with a bbq area in Oak Park. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Oak Park have a gym?
Absolutely! We offer over 10 apartment rentals with a gym in Oak Park. Enjoy a tailored experience with all the comforts you desire.
Quick stats about vacation rentals in Oak Park

Total vacation rentals
Explore 340 vacation rentals in Oak Park

Nightly prices starting at
Oak Park vacation rentals start at ﺩ.ﺇ37 per night before taxes and fees

Verified guest reviews
Over 21,370 verified reviews to help you choose

Family-friendly vacation rentals
170 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 90 rentals that welcome pets

Rentals with dedicated workspaces
190 properties have a dedicated workspace

Wi-Fi availability
340 of Oak Park vacation rentals include wi-fi access

Popular amenities for guests
Guests love Monthly stays, Gym, and BBQ grill across Oak Park rentals

4.7 Average rating
Oak Park stays receive an average rating of 4.7 out of 5 from guests
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- Rentals with a fireplace Oak Park
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- Rentals with a washer and dryer Oak Park
- Rentals with a fire pit Oak Park
- Rentals with a patio Oak Park
- Pet-friendly rentals Oak Park
- Condo rentals Oak Park
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- Rentals with outdoor seating Oak Park
- House rentals Oak Park
- Family-friendly rentals Oak Park
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- Chicago River Walk
- Soldier Field
- 875 North Michigan Avenue
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- The Field Museum
- Wicker Park
- Wilmot Mountain Ski Resort
- Lincoln Park Zoo
- Garfield Park Conservatory
- Oak Street Beach
- Frank Lloyd Wright Home and Studio
- Brookfield Zoo
- Illinois Beach State Park
- Willis Tower
- Washington Park Zoo




