Family-friendly holiday rentals in Oak Park

Walk to Oak Park from Our Sunny Turn of the Century Apt

Soak up the vintage charm of this apartment dating back to 1908. This newly remodeled space is an elegant retreat, featuring 10-foot ceilings, local art treasures, and plush linens. A relaxing outdoor lounge area awaits after a busy day exploring. Pets are welcome on a case by case basis (contact host). The space is a charming two bedroom, one bathroom first-floor unit in a two unit historic home built in 1908. The apartment combines historic details with modern conveniences such as central heat and air, a dishwasher and washing machine and dryer access. The Monroe House is a stone’s throw from historic Oak Park and just three blocks from the CTA Blue Line making downtown Chicago a 25 minute train ride away. The condo includes additional amenities such as: •Smart TV for watching any account may you have (Netflix, Hulu etc...) •Central Air conditioning •Front and back porches for your enjoyment •Washer and dryer on site Just to the east lies historic Oak Park, and 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 taking in the local attractions, Chicago is only a 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 You will have access to the entire unit and the basement so you can use the washing machine and dryer. We also have a back patio with a chiminea, patio table that seats 6, and a grill/smoker. You are welcome to use the backyard at anytime during your stay. We live in the top unit and are as available as you need. That being said, we very much respect your privacy and will not be checking in with you in person unless you request it. It is located in the Madison district, with acclaimed restaurants, pubs, and unique boutiques. Downtown Chicago is a 25-minute train ride away. The local brewery across the street offers delicious beers and creative meals for the whole family. We have a parking pad located behind our building. You can fit two cars on your side of the parking pad if they are parked in tandem. Some street parking is also available. We are located .4 miles from the CTA Blue Line train - Forest Park Stop. It is about a 6 - 10 minute walk from the flat. You can also take an Uber/Lyft into the city. It is about a 15 - 25 minute ride and it costs between $15 and $25. We are located about one mile from the Metra Station (Union Pacific West) and CTA Green Line - Oak Park Stop. Third bed is a queen sleeper sofa. We provide sheets and blankets for the sleeper sofa. You can smoke in the backyard. An ashtray is provided.

Studio Mins Walk to DT OAK PARK

You will find yourself having a comfortable stay at this centrally located studio just a 5 minute walk from Frank Lloyd Wright Home & Studio, surrounded by beautiful homes yet right next to a variety of shops, cafes and restaurants with Petersen's Ice Cream being right next door, Broken Tart cafe, and Giordano's Pizza right across the street, enjoy the beautiful architecture on a scenic 10 minute walk from this studio to Downtown Oak Park for an even bigger selection of dining and entertainment.

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

Circle Back Modern Apartment

Sit on your leafy private patio and enjoy your coffee before heading out to the city- or wind down at the end of the day with a cold beer. Steps to coffee shops, neighborhood pubs, and the Blue Line train this beautifully updated and decorated apartment is the perfect landing pad for your Chicago adventure. FREE off-street parking, free in-unit laundry, a cute coffee station- basically every amenity we could think of! This will be the place you want to stay every time you visit Chicago.

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.

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.

Clean, Central Studio/ Urban Farm, Parking, for 4

Escape to an enchanting garden studio nestled in Oak Park's famous historic district. Discover our private urban farm with full gardens and 6 cheerful hens. Stroll to charming stores, cafes, and restaurants, or hop the nearby "L" for effortless Chicago adventures. Free parking, easy airport access. This serene, non-smoking studio with a kitchenette requires no check-out chores. No parties, 4 guests max. Booking age, 25 or at least one 5 ⭐️ review. Visit profile for more units.

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.

Chic Retreat in Historic Victorian House-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 Perfect for long-term stays. 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.