
Vacation rentals in Oak Park
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Quick stats about vacation rentals in Oak Park

Total vacation rentals
Explore 300 vacation rentals in Oak Park

Nightly prices starting at
Oak Park vacation rentals start at ﺩ.ﺇ 37 per night before taxes and fees

Verified guest reviews
Over 22,070 verified reviews to help you choose

Family-friendly vacation rentals
150 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 80 rentals that welcome pets

Rentals with dedicated workspaces
160 properties have a dedicated workspace

Wi-Fi availability
290 of Oak Park vacation rentals include wi-fi access

Popular amenities for guests
Guests love Monthly stays, Gym, and BBQ grill across Oak Park rentals

4.7 Average rating
Oak Park stays receive an average rating of 4.7 out of 5 from guests
Top-rated vacation rentals in Oak Park
Guests agree: these stays are highly rated for location, cleanliness, and more.

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.

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.. Keyless access. 1 King/ 1 Queen bed.Owner lives on the 1st floor

Curated & Spacious Duplex Near Downtown w/Parking
A warm, curated home with two floors of living space. Perfect for families with kids, groups of friends and multi-generational living. The main floor + finished basement total 3 bdrms + 2.5 baths. Primary suite is on the main floor. Two secondary bedrooms are on the lower w/ a full bath. 20 min to downtown Chicago. Walk to dining + train+ FLW Home. Open living/dining/kitchen/sunroom. Remote work space. Coffee bar. Private entry/deck. Driveway parking. Central AC. Upstairs apartment is separate.

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.

Gallery Loft of Oak Park #1 Top Host in IL
Gallery Loft of Oak Park <a href="https://news.airbnb.com/the-number-one-new-host-in-each-us-state/">2021 #1 Top Host in Illinois</a> is a Chicagoland gem near the birthplace of Ernest Hemingway, Frank Lloyd Wright Home/Studio. 2nd story flat furnished in vintage mcm style, featuring local artists. Walking distance to live music (Fitzgerald's, Friendly Music Community), and restaurants. Firepit access, easy street parking and kitchen well stocked. Private porch. Perfect long/short term stays.

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.

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.

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.

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.

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!

Picture Perfect 3Bed Steps from Train and FLW
Welcome to your beautiful 3 bedroom home-away-from-home! From the Insta-worthy forest room to the cozy fireplace reading nook to the modern ice crusher in the kitchen, we've put so much thought into this home that we're sure you won't ever want to leave. Welcoming and newly updated, this unit is close to restaurants, shopping, the best of Frank Lloyd Wright, and the train to the city.

Stylish Coachhouse in lovely Oak Park!
Enjoy the privacy and artistry of your very own coachhouse. The interior is a personalized mix of artistic, industrial and farmhouse. Cool colors, personalized details and local art included. You have your own washer, dryer, complete kitchen, and private patio space. Walk the lovely neighborhood, to the L train, or even to a local brewery.
Popular amenities for Oak Park vacation rentals
Other great vacation rentals in Oak Park

Oak Park - Wine House!

Coach House•Theater•Parking•6 minute Walk to FLW

Guest Favorite Stay in Oak Park| In Unit Laundry

A Pleasant Stay in Oak Park

Architect-Designed 2BR Oak Park Flat

2nd Floor Apartment in the Heart of Oak Park

Large 2 BR Apt in FLW Historic Dist. in Oak Park!

3BR/1BA With Private Garage, Near Train & Shops
When is the best time to visit Oak Park?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 353 | ﺩ.ﺇ 375 | ﺩ.ﺇ 419 | ﺩ.ﺇ 430 | ﺩ.ﺇ 529 | ﺩ.ﺇ 555 | ﺩ.ﺇ 518 | ﺩ.ﺇ 514 | ﺩ.ﺇ 441 | ﺩ.ﺇ 437 | ﺩ.ﺇ 404 | ﺩ.ﺇ 378 |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°C |
Frequently Asked Questions
What are the best places to stay in Oak Park?
Stays near downtown Oak Park are often recommended for easy access to dining, shopping, and transit. Neighborhoods close to parks or historic districts have a quieter ambiance and blend community with convenience.
What are the best things to do in Oak Park with kids?
Families often explore interactive exhibits at the Children’s Museum, play in Scoville Park, or visit local libraries for storytime. Many parks have playgrounds, and seasonal events provide hands-on activities for children.
What are some of the best things to do in Oak Park?
Discover Oak Park’s historic architecture, visit local museums, and attend community theater or art shows. Independent shops, farmers markets, and neighborhood parks add variety to daily adventures.
How is the weather in Oak Park?
Oak Park has cold winters around 19–33°F (-7–0°C), while summers bring warmer afternoons near 68–85°F (20–29°C). Spring and autumn have milder temperatures and occasional rain, so packing layers is helpful.
When is the best time to visit Oak Park?
Late spring through early fall is often recommended, with warmer temperatures and outdoor festivals. Winter has lower temperatures, so pack accordingly if you plan to visit during colder months.
What are the best places to visit in Oak Park?
Explore the Frank Lloyd Wright Home and Studio, the Ernest Hemingway Birthplace Museum, and Scoville Park for a glimpse of local history. Art galleries and cultural centers around downtown highlight Oak Park’s creative roots.
What are some hiking trails in Oak Park?
Oak Park has tree-lined walking paths in local parks, such as Austin Gardens and Lindberg Park. Trail enthusiasts often explore nature preserves around the area or venture into nearby forested spaces for varied experiences.
What are some family activities we can do in Oak Park?
Families can explore parks with playgrounds, join events at the local library, or visit interactive museum spaces. Community centers and seasonal festivals provide hands-on fun for all ages.
What are some of the best day trip ideas from Oak Park?
Nearby areas have cultural museums, nature preserves, and lakeshore parks that are often recommended for day trips. Chicago's downtown, with its theaters and riverfront walks, is a frequently suggested destination for visitors.
Are there any pet friendly accommodations available in Oak Park?
Several Oak Park vacation rentals welcome pets, especially houses and ground-floor apartments near green spaces. Local parks such as Lindberg Park make outings with your dog convenient.
What are some local tips for visiting Oak Park?
Consider exploring Oak Park by foot or bicycle to appreciate historic architecture and murals. Locals suggest sampling small businesses, packing layers for unpredictable weather, and checking out neighborhood events to connect with the community.
What is Oak Park known for?
Oak Park is known for its historic architecture, including several Frank Lloyd Wright-designed homes, its literary heritage linked to Ernest Hemingway, and vibrant community arts. The area has diverse eateries and independent shops.
What are the best hidden gems to explore in Oak Park?
Oak Park has lesser-known murals and community gardens that locals often highlight. Small galleries, independent bookshops, and historic alleys near the arts district offer quiet places to explore.
What are the best foods to try in Oak Park?
Oak Park has a mix of locally rooted cuisines, with pizza, classic Chicago-style hot dogs, and diverse vegetarian dishes frequently suggested. Independent bakeries, global eateries, and seasonal farmers market fare round out the food scene.
What should I bring for a trip to Oak Park?
Pack versatile layers, as temperatures range from around 19°F (-7°C) in winter to 85°F (29°C) in summer. Comfortable shoes are helpful for walking through historic districts and parks, and a reusable water bottle suits busy days out.
What is the nightlife in Oak Park like?
Oak Park has neighborhood bars, music venues, café lounges, and spots with occasional live performances. The scene is relaxed, with locals gathering for casual dining, craft drinks, and community events.
What are the most popular events or festivals in Oak Park?
Oak Park hosts seasonal festivals, including an arts-focused event often recommended in summer and community celebrations around Labor Day weekend. Local farmers markets and neighborhood block parties are also frequently suggested.
Are there family friendly vacation rentals in Oak Park?
Oak Park has a variety of family-friendly vacation rentals, including apartments and houses near parks and schools. Many hosts include amenities such as play spaces, high chairs, and board games.
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