Vacation rentals in Oak Park

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.

Historic Hotspot: Downtown Oak Park w/parking spot

Short and long-term stays are welcome. Oak Park is known for its historic homes, treelined streets, and downtown area filled with shops and eateries - you’ll appreciate the location. The area is walkable and has easy access to all transportation lines. One off-street parking spot included. The spacious apartment is great for families, small groups, business stays and events. We can provide things such as a changing pad, high-chair, etc. Long-term stays will have access to washer and dryer.

Architect-Designed 2BR Oak Park Flat

Enjoy this beautifully appointed two-bedroom, one-bath apartment, located a short stroll from historic Oak Park cultural attractions with easy access to Chicago’s Green Line. Our unique accommodations feature a galley-style kitchen with full amenities, an inviting living and dining area filled with natural light, and a shared roof deck. The full renovation reflects the mission of South Blvd Properties and award-winning Elements Architectural Group to create restful spaces for life together.

3BR/1BA With Private Garage, Near Train & Shops

Welcome to our beautiful, modern, and spacious apartment in Oak Park's Gunderson Historic District! Walk to the park, train station, shops, and restaurants in this highly walkable neighborhood. The apartment features 3 bedrooms with 3 queen beds, 1 large bathroom, a sofa, and an inflatable mattress upon request. Enjoy fast Wi-Fi, a fully stocked kitchen, an in-unit washer/dryer, and a private garage parking space. Perfect for work or vacation, just 15–20 minutes from downtown Chicago!

Space & Style Duplex Near Downtown w/Parking

2024 Gut rehab! Spacious w/A+ location! 1 of 2 apts in a two flat. King bed! W/D! This unit = Main floor + finished bsmnt. 3 bdrms + 2.5 baths. Steps to FLW Home. 20 min to downtown Chicago. Walk to dining + train. Open living/dining/kitchen/sunroom. Powder room. Primary w/king + ensuite. 2nd bedroom w/queen + 3rd bedroom w/2 double beds, walk-in closet. 2nd full bath + work/gameroom. Coffee bar, pantry. Private entry/deck. Driveway parking. Upstairs apt not included in this listing.

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

Guest Favorite Stay in Oak Park| In Unit Laundry

2nd-floor unit with elevator access. Older building with radiant heat managed by the building. Includes an all-in-one electric washer and dryer. Welcome to your stylish Oak Park retreat! This newly remodeled 2BR/2BA apartment blends modern comfort with historic charm. Enjoy a bright space with a full kitchen, cozy living area, and designer touches. Walk to shops, cafes, and parks, or use nearby transit for easy access to Chicago. Perfect for families, friends, or business stays.

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.

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.

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!