Apartment holiday rentals in Oak Park

4.91 out of 5 average rating, 152 reviews

Large Renovated 1st FL Suite Forest Park/Oak Park

Thoroughly cleaned & sanitized before each stay* Newly renovated private 1st-floor apartment in the heart of Forest Park. Just steps from Madison St. where you will find coffee shops, restaurants & shopping. You are also close to downtown Oak Park with just a quick walk. We are conveniently located just 15-20 minutes to downtown Chicago & O'hare, with easy transportation via buses trains & expressways. This spacious place is perfect for couples, business travelers, solo guests, & families.

4.9 out of 5 average rating, 167 reviews

Stunning 2bd 1bath w/free parking, W/D & fireplace

Whether you're here to visit family or friends, to attend a conference in the city or a quick getaway, your family will love renting our entire flat. It has all the comforts of home located on a beautiful block in the historic Frank Lloyd Wright District in Oak Park. Here, you will be close to The Frank Lloyd Wright Home/Studio, downtown Oak Park, amazing restaurants and attractions, the Green and Blue line trains that will take you to downtown Chicago, and major highways and shopping centers.

Top guest favourite

4.99 out of 5 average rating, 161 reviews

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

4.85 out of 5 average rating, 109 reviews

Bright & Gorgeous- 5* Location- Queen Beds - Pkg

Leave your worries behind at this peaceful, secure retreat with plenty of space to relax. 2nd-floor duplex to 3rd floor. Just a 15-minute drive to/from downtown. Easily walk to everything: - Groceries, sushi, coffee shop, brewery - Nightlife, live music, and great food - Playgrounds, parks, public pool, & tennis courts Enjoy all the comforts of home in a charming, urban-suburban mix. - Only 1.5 blocks to the Oak Park Av. CTA "L" Blue Line stop & I-290 Housebroken dogs welcome.

4.85 out of 5 average rating, 296 reviews

Cozy and Character-Rich Chicago Style, Tv 42-2

→ Introducing our newly renovated and furnished apartment unit nestled in the charming Oak Park Art District. Experience vintage Chicago style living in this richly characteristic brick building, situated in a safe and quiet neighborhood. ★ Property Features: • One block away from the Oak Park Art District • Vintage Chicago style brick building • Safe, quiet neighborhood • Newly renovated and furnished • Smart TV with Cable and option to use other apps • Free Laundry Room • Free Parking

4.92 out of 5 average rating, 151 reviews

Walking Distance to Everything.

The Green Line CTA "L" train is only 3 blocks away and departs every 10 minutes. Metra shares a station and departs once an hour. Freight trains also pass by. You will hear these trains train throughout the night. Most people are not disturbed by this sound. If you are a light sleeper I recommend earplugs for sleeping. Taxi from the Airport, around $80. Neighborhood parking is limited. If you have a vehicle please read parking instructions. Free for the first 3 nights then $7 a night.

Superhost

4.83 out of 5 average rating, 133 reviews

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.

4.94 out of 5 average rating, 177 reviews

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.

4.83 out of 5 average rating, 289 reviews

Home in Forest Park downstairs.

Enjoy a private ground floor apartment which is centrally-located with easy access , to the city. You will have a functional kitchen, laundry facility outside your back door and fast internet. Forest Park is located about 20 minutes from downtown Chicago and about 30 minutes from O’Hara international airport. You are within walking distance of many boutiques, restaurants, parks and also public transportation. Please make a note that there will be a $30 per guest fee if more than four.

4.89 out of 5 average rating, 163 reviews

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

Top guest favourite

4.97 out of 5 average rating, 112 reviews

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).