Vacation Rentals By Owner In Oak Park, IL

$190.04

Relaxing Oak Park Home

Oak Park, Illinois, United States

This charming Oak Park Bungalow offers a quiet relaxing environment to unwind after a busy day of site seeing in Chicago or enjoying the historic beauty of Oak Park. brThe home has been updated but still maintains its historic charm. The location puts you 4 blocks from the train to downtown Chicago. By auto you can be in the loop in 15 minutes. Oak Park offers a safe walking community. Get to live entertainment, restaurants, or historic tours in a short walk. brbrThe home is converted into two units: the main home and an one bedroom garden apartment with a rear entrance. The home/rental space is two story with two bedrooms on the top floor and one on the main floor next to the full kitchen. .brbrAll bedrooms sleep 2 people. Total guest capacity is 6. Location, Location, Location; easy entrance to the highway, walk to the train, or just enjoy a quiet night after a day and evening of enjoying Chicago.brbrEarly Checkin: Early check in is an option only if there is no guest checking out the same day. You must call a week or more in advance. The cost for early check in is $30 per hour earlier then the normal check in time (4:30pm). This cost must be paid in advance and is not refundable if you do not arrive early. brbrIncluded in the rental:brTowel ServicebrFull grocery one block awaybrQuiet, safe, and securebrBefore accepting please understand the following:brNo parties or events of any size. Village rule require that only the registered guest are allowed in or around the property. No exceptions!brNo pets brDid I mention Location, location, location!

3

Bed

1

Bath

6

Sleeps

$650.46

/ Nightly

Private Vacation Home

Historic F. Lloyd Wright District Spanish Colonial

Oak Park, Illinois, United States

Step inside for mid-century charm! Step outside to the Frank Lloyd Wright district of Oak Park - a time capsule of prairie-style architecture. You’ll be steps away from among the most historic homes in America - and you’ll be steps away from our bustling downtown - with shops, restaurants, theater, and easy rides to downtown Chicago. When you’re done seeing the sites and enjoying the area, step inside to a quiet recluse filled with ornate features and comfortable styling. Live in history!

Bed

Bath

Sleeps

$1001.7

/ Nightly

Private Vacation Home

Elegantly decorated spacious 4 bedroom, 5 bathroom home in historic Oak Park

Oak Park, Illinois, United States

This home is meticulously decorated with amazing opulent lighting, stain glass pocket doors, and a great floor plan. The home offers two Primary bedrooms including en suite bathrooms. One of the bedrooms is situated on the first floor for extra privacy. The en-suite bathroom on the first floor offers a walk-in shower with grab bars for easier use for elderly guests or guests with additional needs. The other bedrooms are on the second floor. All bedrooms are super spacious, include closet space, and large windows with views of the gardens and yards. Don’t forget to take advantage of the classic and elegant wallpapered dinning room, offering 8 + chairs, a large dinning table, beautiful China, and a masterpiece of a chandelier. If you need to finish some work, sit in the charming office surrounded by windows, stain glass lighting, and enter through the French double doors. This home also offers 4 fireplaces, a reading area, and a large hot tub for some extra relaxation. The beautiful updated attic offers a gym with a view. The basement offers high ceilings, an entertainment area, and a pool table. Lastly, eat al fresco on the deck patio, gazebo, or hang by the Adirondack chairs. You’ll have access to the grill and large kitchen area. A crib, pack and play, and high chair are available upon request. Entry to the home is contactless with a personal access code. Street parking is ample. We do offer a parking spot in the rear by the garage for a compact car. brbrRECENTLY RENOVATED: Kitchen has been recently remodeled; offering new Bosch appliances, blinds, cabinets, and quartz countertops. Bathroom in the first floor has recently been wallpapered and remodeled. And the backyard space has been updated with a Gazebo and firepit. brbr

Bed

Bath

Sleeps

$183.98

/ Nightly

Apartment

Comfortable home in historic Oak Park- open For Thanksgiving and Christmas!!!

Oak Park, Illinois, United States

The first floor flat is a large bright 2 bedroom apartment with a new bathroom. The kitchen features Stainless Steel Fagor appliances, granite counter tops and maple flooring. We have hardwood floors in the Living Room & Dining Room. Two carpeted bedrooms with a queen in one and Full in the second. LvRm with couch & love seat and Futon in game room creates even more space. The apartment is fully furnished including all kitchen items with a piano for your use, ATT U-verse TV, internet and phone. brbrExtra space is provided inside with a Playroom in the full basement with a TV , Foosball table and a laundry room. brbrOutside makes the house so much more than staying in a hotel. A shared, fenced yard can be used for evening grilling or relaxing around the fire-pit. Both the Front & Back porches are covered with the front easily accommodating seating for 6. Plus you’ll have access to one garage parking space! brbrIt is available for a minimum of four days.

Bed

Bath

Sleeps

$243.27

/ Nightly

Apartment

8 MILES FROM DOWNTOWN CHICAGO!!!

Oak Park, Illinois, United States

Free Parking! Gorgeous sunporch with beautiful and spacious backyard. This modern unit is updated with SS appliances and washer and dryer. Two living room spaces are great for entertaining, central air and heat; located on a quiet cul-de-sac! Downtown Oak Park is a 5 min drive or leisure walk. Enjoy nearby historic sites and tours…book now!!

2

Bed

1

Bath

4

Sleeps

$243.27

/ Nightly

Apartment

Beautifully renovated 2 bedroom apartment in Frank Lloyd Wright District

Oak Park, Illinois, United States

Enjoy your stay in this completely renovated 2 bedroom basement apartment in the heart of historic Oak Park, IL. Just 2 blocks from Frank Lloyd Wright’s Home & Studio, Ernest Hemingway’s birthplace museum, and downtown Oak Park’s dining, shops, and cafés. The Green Line El is a 5 minute walk, providing a quick 20-minute ride to downtown Chicago. The apartment offers modern finishes, Wi-Fi, a smart TV, and free street parking right out front for a comfortable and convenient stay.brbrThe space:brStep into this modern, thoughtfully curated basement retreat designed for comfort and convenience. This fully renovated space offers a stylish and welcoming stay, perfect for both business and leisure travelers.brbrThe unit features two comfortable bedrooms, a spacious, modern kitchen, and a beautifully updated full bathroom. Guests can enjoy a smart TV, high-speed Wi-Fi, and a large fully equipped kitchen with everything needed for cooking and dining at home.brbrThe location is unbeatable—just two blocks from the Frank Lloyd Wright Home and Studio, Ernest Hemingway’s Birthplace, and Downtown Oak Park, where you’ll find a variety of shops, cafes, and restaurants. The Green Line el is a short walk away, making it easy to reach Downtown Chicago in about 20 minutes.brbrThis home offers the perfect balance of convenience and comfort, allowing you to explore the area with ease while returning to a quiet, relaxing spacebrbrPlease note: This is a basement unit with private access. As with many classic homes in the area, some sound may travel between floors (such as occasional creaky floors or plumbing noise). The hosts live upstairs, are mindful of noise, and kindly ask guests to be respectful as well. Quiet hours expected 10:00pm-8:00am. Strictly no parties or gatherings. No guests aside from the max 4 people booking the home. No pets allowed.brbrGuest access:brGuests have full use of the private basement unit. Access is through the front door only and down a short flight of stairs. The backdoor is for emergency use only and backyard use is not allowed. Free street parking available in front of home.brbrOther things to notebrNo smoking is allowed anywhere on the property. A $750 smoking fee will apply if detected in the unit.brbrPlease note: This is a basement unit with private access. As with many classic homes in the area, some sound may travel between floors (such as occasional creaky floors or plumbing noise). The hosts live upstairs, are mindful of noise, and kindly ask guests to be respectful as well. Quiet hours expected 10:00pm-8:00am.brbrStrictly no parties or gatherings. No guests aside from the max 4 people booking the home. No pets allowed.

2

Bed

1

Bath

4

Sleeps

$206.39

/ Nightly

Apartment

Cozy and bright 2 bedroom apartment in Oak Park!

Oak Park, Illinois, United States

This 2-bedroom 3rd floor walk up apartment is perfect for your escape to Oak Park. Inside, guests find a beautiful space featuring one queen bed and one full bed, ideal for a comfortable stay. The apartment stays cozy with heating and cool with AC, making it a phenomenal retreat year-round. A well-equipped bathroom includes a hair dryer for convenience. Whether you’re relaxing after a day of exploring or preparing for your next adventure, this marvelous apartment offers everything you need. Experience the magic of Oak Park and the Chicagoland area at our apartment. Owners live onsite if you need anything!

Bed

Bath

Sleeps

$202.63

/ Nightly

Apartment

Chic Retreat, 2 Queen Beds, FREE PARKING, Walk to Train

Oak Park, Illinois, United States

You will be in the heart of downtown Oak Park, within walking distance to public transportation that takes you directly to downtown Chicago, restaurants, shops, grocery stores and everything Oak Park has to offer.brbr You will be delighted as you walk in this top floor (3rd floor) apartment, (not recommended for people with mobility issues or are not physically able to climb 3 set of stairs). You’ll notice high ceilings, wooden beams, exposed brick, comfortable furniture and a clean, clean crisp feel.brbrOur kitchen is fully equipped to prepare your favorite meal and it has all new appliances. brbrOur bathroom has a claw foot bathtub with shower. brbrRadiant heat and window air conditioning brbr FREE PARKING for one vehicle in our private parking lot in back of our property, please park only in your assigned space brbr Claw foot tub is for showering onlybrbr Laundry facilitybrbr 2 OCCUPANTS ONLY - NO VISITORS ALLOWEDbr NOT SUITABLE FOR CHILDRENbrThis apartment is on the 3rd floor. Not recommended for people with mobility issues or are not physically capable to climb 3 sets of stairs.brbrWe kindly ask that you read our full listing description and our house rules prior to booking.

Bed

Bath

Sleeps

$217.51

/ Nightly

Apartment

Heart of Oak Park, train ride to downtown Chicago. WIFI & Cable Included!

Oak Park, Illinois, United States

Enjoy your stay in Oak Park at this prairie architecture themed apartment. It is located in the lower level of a new construction home. As you enter, you will be blown away by the soaring 9-10' ceilings and open & airy layout. Spacious master bedroom with queen bed, dressers and walk-in closet. Second bedroom contains two twin beds. brbrLiving room features a futon style couch for extra sleeping capacity. Five people can be accommodated in the apartment. The heart of the apartment is the vast living room/dining room area. Enjoy meals at the dining room table, which seats eight. Relax in the living room with a flat screen TV with a basic cable package. brbrVery large eat-in kitchen is fully stocked for all your cooking needs. Stainless steel appliances include a dishwasher, microwave & garbage disposal. Washer & dryer are provided & private parking is available on site. Fresh linens & towels are provided to all guests.brbrThere is both a front and back entrance to the apartment. There is 100% separation between the apartment and the home to which it is connected. Guests enjoy the privacy provided by the accommodations. Complimentary WIFI is provided. brbrThe apartment is located within a mile of the biggest Oak Park tourist attractions. The Frank Lloyd Wright Home & Studio is four blocks away. Downtown Oak Park is about a half mile away. A 20 minute train ride from downtown Oak Park takes you to everything that downtown Chicago has to offer. Alternatively, you can get to downtown with a quick nine mile drive down the expressway. brbrNo pets, no smoking/vaping and absolutely no parties.

Bed

Bath

Sleeps

$412.73

/ Nightly

Apartment

Top floor of Historic Oak Park Home /2 Car Garage

Oak Park, Illinois, United States

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.brbrExperience an ambiance that supports the work-from-home Urban Professional, combining it with a multibedroom layout designed to accommodate family and friends.brbrGig-speed internet supports sophisticated professional and gaming applications.brbrThis elegant living room, eat in kitchen, three bedroom and on full bathroom home is located in one of Oak Parks Historic Buildings originally erected by the Kettlestrings family the founders of Oak Park as we know it. brbrSolid hardwood floors ample closets equipped with 1 king, 1 queen, and 2 twin beds.brbrShared washer and dryer in the basement.

Bed

Bath

Sleeps

$206.06

/ Nightly

Private Vacation Home

Attractive Coach House Apartment for rent in Oak Park.

Oak Park, Illinois, United States

Discover the beauty of Oak Park from this 4-bedroom house. This adorable home offers three bathrooms, making it easy for guests to get ready at their own pace. Enjoy a comfortable stay with heating and AC to keep the temperature just right. Whether you’re relaxing indoors or exploring nearby, this perfect spot provides a welcoming space to recharge. It’s easy to see why you’ll have an enjoyable time at our place.

Bed

Bath

Sleeps

$377.93

/ Nightly

Apartment

The Oak Park Loft, Including Garage

Oak Park, Illinois, United States

A newly renovated space with an exquisite bathroom tailored for sophisticated guests. This Oak Park Loft combines the modern with the historic. It puts you in the center of all that matters in Chicago. In 30 minutes you can be at the Loop, Midway or O'Hare. Ethnic dining is at your fingertips with dozens of restaurants and coffeeshops just around the corner. A hop on the L takes you anywhere in the city. brbrTake a walk and you find yourself tracing Frank Lloyd Wright and Ernest Hemingway. Garage Included.brThis time we wanted to design something elegant and fun. This Kettlestrings' Home, built in the 1880s had a wonderful attic, that had been untouched for a 130-years. We brought in Errol Kirsch, a renown urban architect. The village of Oak Park made sure we combined the old with the new meeting all historic requirements. The result is an elegant space with an exquisite bathroom for the sophisticated guest.

Bed

Bath

Sleeps

$406.08

/ Nightly

Apartment

Modern Oak Park Getaway 3BR 2BA with Yard, 20 mins to Chicago Loop, near Train

Oak Park, Illinois, United States

WELCOME!brbrEnjoy comfort and luxury in this spacious 3-bedroom home in Oak Park’s historic district. Family-friendly and steps from the world-famous Frank Lloyd Wright Home and Studio, Hemingway Birthplace Museum, downtown Oak Park, Trader Joe's, Whole Foods, Target, and public transit to Chicago. Newly renovated, spotless, and stylish.brNo parties, events, gatherings, weapons, dangerous items or disruptive behavior allowed.brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 queen bedbr- Bedroom 2: 1 queen bedbr- Bedroom 3: 1 queen bedbr- Additional Sleeping: 1 portable crib, 1 twin folding bed/cotbrbrLOCATION HIGHLIGHTSbr- Steps from Frank Lloyd Wright Studio, Hemingway Birthplace Museum, and downtown Oak Park.br- Short walk to local restaurants, Lake Theater, playground, parks, public transit, and grocery stores including Trader Joe’s & Whole Foods.br- 20 minutes ride to downtown Chicago.br- 25 minutes ride to O'Hare Airport.brbrINDOOR SPACEbr-- Spacious & Modern: Fully renovated, all-new appliances and stylish furnishings.br-- Entertainment: 75 smart TV.br-- Free Fast Wifibr- Cozy Comfort: Queen-size, high-quality mattresses and blackout curtains.br-- Smart Lock Self-Check-In/Out.br-- Coffee Bar: Well-stocked and ready for your morning brew.br-- Bathrooms: Well-stocked shampoo, conditioner, bodywash, toilet paper, hairdryers and more.br-- Quiet & Peaceful: Smoke-free & family-friendly.br-- Dedicated Office Areabr-- Convenient Parking: Plenty of street parking right in front of the listing upon arrival.brbrGUEST ACCESSbrAccess Code for Smart Lock via VRBO message before check-in.brbrPARKINGbrStreet parking is super EASY! – Plenty of spots available for multiple vehicles.brStreet Parking: Available directly in front of the house, 7 days a week, upon arrival.brOvernight Parking: $15 per vehicle per night.brIf you need overnight parking, please notify the host in advance and provide your vehicle’s license plate and the state it was issued in for village registration, due to the following overnight parking restrictions:br• Overnight street parking is prohibited from 2:30 AM to 6:00 AM unless you have a parking permit or pass.brWe can assist with obtaining a digital overnight parking pass for $15 per night per vehicle.brbrLATE CHECK IN NOTE:brPlease plan to arrive during the designated check-in hours 3:00-10:00PM. Check-ins after 10:00PM are not permitted unless approved in advance by the host. Please reach out to the host if you plan to arrive after 10PM. We will try our best to accommodate.brbrID VERIFICATIONbrID verification is essential to make online bookings safe and avoid fraud. Occasionally guests may be asked to verify their identities by hosts. Only government issued IDs are acceptable.brbrSECURITY:brWe prioritize your privacy and safety. Rest assured, there are No security cameras or recording devices inside the listing unit. However, exterior security cameras are in place around the building solely to monitor the building, including the front and rear entrances of the building, garage, stairway, and laundry area, where there is no expectation of privacy.

3

Bed

2

Bath

7

Sleeps

$369.31

/ Nightly

Private Vacation Home

First floor unit of a delightful retreat in the Frank Lloyd Wright district.

Oak Park, Illinois, United States

Enjoy spacious rooms, high ceilings, or step onto the balcony deck while enjoying your morning coffee. A perfect blend of modern comforts and captivating architecturebrbrCentral Oak Park: 3 blocksbrTrain Station: 4 blocksbrDowntown Chicago: 20m drivebrWhole Foods: 6 blocksbrTrader Joe’s: 2 blocksbrAustin Gardens: 2 blocksbrbrBook today! We can't wait to host you!

2

Bed

1

Bath

6

Sleeps

$353.15

/ Nightly

Apartment

Oak Park Gem Next to Green Line In Unit Laundry

Oak Park, Illinois, United States

Combined electric washer/dryer in unit.brbrWelcome to your stylish home in Oak Park! This beautifully designed 2 bed, 2 bath apartment offers the perfect blend of comfort and convenience. Enjoy a fully equipped kitchen, spacious living area, and modern finishes throughout. In-unit laundry makes extended stays easy, while building amenities include a fully equipped gym and an accessible rooftop with great views. Ideal for anyone seeking a comfortable stay just 15 minutes from Chicago.brbrThe space:brbrLocated in the heart of **Oak Park**, this modern 2-bedroom, 2-bath apartment offers a comfortable and thoughtfully designed living space ideal for both short and extended stays. The open-concept layout features a bright living area, contemporary furnishings, and a fully equipped kitchen with sleek finishes and ample storage. Both bedrooms are spacious, with comfortable beds and generous closet space, while the two full bathrooms provide added privacy and convenience.brbrThe unit includes in-unit laundry for effortless day-to-day living. Guests also enjoy access to premium building amenities, including a fully equipped fitness center and a beautifully maintained rooftop deck perfect for relaxing or taking in the surrounding views. Combining style, functionality, and a prime location near shopping, dining, and public transportation, this property offers a seamless and elevated stay experience.brbrGuest access:brbrYou’ll have access the the entire unit during your stay.brbrOther things to note:brbrWe do not have designated parking but free street parking is available in the neighborhood. That said, please take care to read any signs indicating no parking or tow zones to avoid any issues. Parking availability can fluctuate depending on the time of day, and if you arrive later in the evening, there’s a chance that spots might be harder to find.brbrIn case you run into this situation, we suggest using the SpotHero app or ParkWhiz to easily locate an affordable and convenience parking spot nearby.brbr**HOUSE RULES**brbrWe want you to have a comfortable and enjoyable stay! To help keep the space safe, clean, and pleasant for everyone, please review and follow the house rules below. Failure to comply may result in cancellation or additional charges.brbrShoes off, please. Kindly remove shoes upon entering the unit.brbrNo smoking anywhere inside the unit or on the property. Smoking will result in immediate cancellation and a $200 damage fee.brbrNo drugs, including marijuana.brbrNo illegal activities anywhere on the property.brbrNo parties or events.brbrNo outside visitors.brbrNo overnight guests without prior approval from the host.brbrFood storage: Please store all food in designated areas and do not leave food out to help prevent pests.brbrKitchen use: Feel free to use the kitchen, but please clean up after yourself. Wash dishes, wipe counters, stove, and microwave. No dirty dishes left in the sink overnight.brbrDamages: If anything is broken or damaged, please let us know right away so we can arrange repair or replacement.brbrCheckout cleaning:brPlease wash dishes, return moved furniture to its original place, and take out the trash before checkout.brThe standard cleaning fee covers normal turnover cleaning. If the unit is left excessively dirty (dirty dishes, trash left throughout the unit, etc.), an additional cleaning fee of up to $100 may apply.brbrTowels & linens: Provided for your entire stay. If you need extras, please let us know in advance. A $50 fee applies to cover the cleaner’s trip. Paid laundry facilities are available in the building.brbrLost keys: A $300 fee applies for lock and key replacement. Please note that lost keys cannot be replaced immediately, and you may temporarily lose access to the unit and building amenities.brbrQuiet hours: Please observe quiet hours from 10:00 PM – 8:00 AM.brbrLate checkout: Checkout time is 11:00 AM. Late checkout without prior approval will incur a $50 fee, which covers the cleaner’s waiting time.brbrThank you for your understanding and cooperation -we truly appreciate it and look forward to hosting you!

Bed

Bath

Sleeps

$228.96

/ Nightly

Apartment

Spacious, lovely 2bed 1bath with free parking

Oak Park, Illinois, United States

Bring the whole family to enjoy this great place with lots of comforts and space. brbrBeautifully decorated with reclaimed barn wood throughout the home and a completely remodeled kitchen with cute bistro table to enjoy your coffee. brbrWonder around this beautiful, quiet Frank Lloyd Wright neighborhood to see beautiful Victorian homes and architect or take a brisk walk to downtown Oak Park before taking in the sites in Downtown Chicago. brbrWhether you stay for a while or a few days, welcome home!

Bed

Bath

Sleeps

$402.97

/ Nightly

Apartment

Cozy Chic 4BD 2BA Oak Park Penthouse

Oak Park, Illinois, United States

You will enjoy easy access to everything from this centrally located place near downtown Oak Park, right on Division St. This 4-bedroom 2-bathroom condo can accommodate up to 8 guests. This beautiful contemporary newly rehabbed beauty has an in-unit furnace and thermostat. Equipped with free parking, a big bonus for travellers looking to go to downtown Chicago for business or vacation. Less than a mile away from the CTA/Metra station. (PLEASE NOTE: THIS CONDO IS ON THE FOURTH FLOOR WITH NO ELEVATOR)

Bed

Bath

Sleeps

Select Dates for Price

Apartment

Walking Distance to everything...

Oak Park, Illinois, United States

The Green Line CTA L train (Metro) is only 3 blocks away and departs every 10 minutes. Metra shares a station and departs once an hour. Neighborhood street parking is limited. This place is best for people planning on using the train and uber. 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.brbr There is also a Hospital and Fire House nearby. Fire trucks and ambulances will be passing at night. Parking is very limited in front of this apartment especially at night. Each room has a queen size bed. Separate Living room / dining room and a fully Supplied kitchen. Due to close proximity of the train you will hear different sounds thought the night. Please keep this in mind. If you are a light sleeper you may need earplugs.

3

Bed

1

Bath

4

Sleeps

Select Dates for Price

Apartment

2nd floor walk up 3 bedroom 1 bath with parking

Oak Park, Illinois, United States

Book now at this at this peaceful and centrally-located place. Second floor walk up above main house. This house features a king size bed, wifi, a fully loaded kitchen with coffee and one parking space.

3

Bed

1

Bath

4

Sleeps

$204.43

/ Nightly

Apartment

BEAUTIFUL COZY APARTMENT

Oak Park, Illinois, United States

ACROSS THE STREET FROM THE BEST WINERY EVER, WALKING DISTANCE TO SHOPPING, FOOD, MOVIES. BEAUTIFIL ROOF TOP WITH THE VEIW OF THE CITY. RELAXTION, CLOSE TO DOWNTOWN CHICAGO. QUIET BUILDING TO RELAX AND ENOY OR EVEN WORK FROM.

2

Bed

1

Bath

3

Sleeps

Vacation Rentals By Owner In Oak Park, IL

$190.04

$650.46

$1001.7

$183.98

$243.27

$243.27

$206.39

$202.63

$217.51

$412.73

$206.06

$377.93

$406.08

$369.31

$353.15

$228.96

$402.97

$204.43

Most popular vacation rentals in Oak Park

$248.04

$380.72

$377.93

$350.00

$340.61

$328.99

$317.11

$206.06

$196.32

$202.63

Most Popular Cities in Illinois