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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. We include one off-street parking spot. The apartment is great for families and small groups and even set up well for business stays and events. We can provide things such as a changing pad, high-chair, etc. Long-term stays may access laundry.

Rockin' 2Bed steps to shops/food/train

This musically-inspired vintage 2 BR is perfectly placed in Oak Park and we know you'll have a rockin' vacation here. Steps to shops, cafes, train, and FL Wright home. With a cassette wall, reading nook, and many other cute touches. The apartment is a vintage brownstone with charming details, like original woodwork. Street parking available. Easy access to Chicago.The place is an older Chicago brownstone, with a lived-in feel. NO PARTIES!! Upstairs neighbors can be heard walking and moving

Oak Park cozy carriage house-lovely, walkable area

Our comfortable, stylish retreat has everything you need to relax and recharge. Whether you are visiting to explore all that beautiful Oak Park and downtown Chicago offer or desire a peaceful space to work. -> Quiet, walkable street near popular cafes, restaurants, taverns, parks, historic homes -> Steps from the "L" Blue Line Oak Park station -> Stocked w/ snacks + gourmet coffee/tea set-up (grinder, AeroPress, and Keurig) -> Onsite off-street parking -> A/C + heat -> garden sitting area

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.

A Pleasant Stay in Oak Park

Welcome to our bright and peaceful townhouse in Oak Park, IL! Just steps from the vibrant Oak Park Arts District, you'll be close to the area’s best shops and restaurants. Recently renovated from top to bottom, the home features high-quality materials and a clean, modern style that beautifully honors its vintage charm. Located in a residential neighborhood step to the train, downtown Oak Park and 15 minutes to Chicago. We offer a calm and stylish space where guests can relax and unwind.

Stylish & Spacious 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.

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.

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.

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.

Sunny Coach House in Historic Oak Park

This bright, cozy coach house is your ideal base in Oak Park. It was originally the coachman's quarters behind a 1909 Prairie-style house, now converted into guest lodging with all the modern amenities above a detached garage. The coach house is at the end of a long driveway (free parking included!) on a quiet street, in the heart of the Frank Lloyd Wright district, a short walk from trains to downtown Chicago.

Modern+Spacious W/King Bed, Walk to Town-Park Free

This historic Queen Anne home built in 1889 is in the heart of Oak Park. Centrally located and within walking distance to all tourist attractions, public transportation, 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. 4 guests maximum-no visitors allowed