Holiday houses in Oak Park

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.

1 bedroom garden apartment in Forest Park

Unique private garden apartment in our single family residence. Great location approximately 8 miles directly west of downtown Chicago. Close to shopping, dining, entertainment and public transportation to the city. One bedroom & best for 2 people but could sleep 3 ($50 fee) for short stays. It's important to note that this is a garden/ground/lower level apartment. The ceilings are relatively low at 6.5'. This would not be the best space for tall people. Free parking in front of the house.

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!

Cozy, 1 Bedroom Apt. w/ Kitchen & Parking for 4

Enjoy our historic district three-flat w/ free parking in upscale, safe Oak Park just 3 blocks to the train, easy access to Chicago. Enjoy some tranquil time in our little eco suburban farm. Check out the gardens and visit our 6 friendly chickens. This non-smoking unit with full kitchen is perfect for tourists, families, or business travelers. We require no check-out chores. Easy highway and airport access. No parties. Booking age, 25 or at least one 5 ⭐️ review. Visit profile for more units.

Retro Modern Bungalow | free parking | fire pit

Experience the city in style at Retro Modern Bungalow, the perfect pad for up to 4 friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a fully fenced, pup-friendly backyard. Enjoy central HVAC, speedy WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage or catch the train a few blocks away.

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.

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).

The Chicago Game Room (Oak Park, IL)

There is no other rental like this in the Chicago area! Located in the first suburb west of Chicago, this 4-bedroom, two-level private apartment is brand new and ready for your group to enjoy. It features an amazing game room/living room with cathedral ceilings, skylights, gas fireplace, bar seating, pool table, shuffleboard/bowling table, dart board, four bedrooms + sleeper sofa, full kitchen, spa-like bathrooms, in-unit washer/dryer, and private deck. GUESTS = 8 MAX

Oak Park Victorian by FLW Studio

Discover historic charm in our updated 4-bedroom Victorian home in the iconic Frank Lloyd Wright district. Comfortably sleeps 8. Features a fully equipped kitchen, dedicated workspace, and modern amenities. Perfectly located for exploring local gems on foot or a quick 15-min drive to downtown Chicago. Enjoy private parking and easy access to public transit. Ideal for families and groups seeking a stylish, central retreat.

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.