
Holiday rentals in Oak Park
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Top-rated holiday rentals in Oak Park
Guests agree: these stays are highly rated for location, cleanliness and more.

1920s fully updated unique open artist loft space
True artist living loft space!!! One of a kind space in a safe area of the western suburbs close to the city and easy commute to shops stores. very close to trains buses and expressways. Private parking lot. No unit above or below. Quiet and private spacious updated wide open loft. Hardwood floors throughout forced heat and ac slated steel designer bathroom.. Double oven dishwasher electric cooktop sub zero fridge microwave and toaster oven. Ceiling fans two beds. Can sleep 6 for added cost

Clean, 1 Bedroom Apt. w/ Kitchen & Parking for 4
Enjoy our historic district three-flat w/ free parking in upscale, safe Oak Park just 3 blocks to the train, easy access to Chicago. Enjoy some tranquil time in our little eco suburban farm. Check out the gardens and visit our 6 friendly chickens. This non-smoking unit with full kitchen is perfect for tourists, families, or business travelers. We require no check-out chores. Easy highway and airport access. No parties. Booking age, 25 or at least one 5 ⭐️ review. Visit profile for more units.

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

Vintage Chicago-Style 1 bed, Cable & NFL PASS 40-1
→ 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

Retro Modern Bungalow | free parking | fire pit
Experience the city in style at Retro Modern Bungalow, the perfect pad for up to 4 friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a fully fenced, pup-friendly backyard. Enjoy central HVAC, speedy WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage or catch the train a few blocks away.

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 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 for outdoor space. Keyless access. 1 King/ 1 Queen bed

Cozy guest studio, great for couples!
This unique place has a style all its own. Enjoy this beautiful, cozy guest studio with modern touches and well furnished living area, small kitchenette with mini fridge and microwave to reheat a quick bite before heading to the city, full bathroom with rainfall shower and handheld sprayer to help you relax after a long day. Flat screen TV with Xfinity streaming device so you can connect your accounts and enjoy your favorite shows and movies for a quiet stay in.

Home in Forest Park Upstairs.
In this cozy apartment you will have a functional kitchen, in unit laundry, fast WiFi connection and access to a back yard.. The property is located 30 minutes from O'Hara International Airport, 20 minutes from Downtown Chicago via I-290, and 40 minutes away from Midway Airport. Forest Park is a very safe, vibrant and diverse suburb of Chicago. You will be within walking distance of many different restaurants, boutiques, bars, parks, and public transit.

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

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.

2-bedroom Apartment in the heart of Oak Park
You and your family will be at the center of Oak Park and a walking distance from architecturally significant homes and the L Train to downtown Chicago. Frank Lloyd Wright's home and studio are a two-minute walk as are shops, dining and entertainment. The apartment features two bedrooms, a large living/dining area and a basement with a foosball and a movie projector.
Popular amenities for Oak Park holiday rentals
Other great holiday rentals in Oak Park

Single bedroom with Asian decor in family home

Lakefront Room, basement, Safest Neighborhood

Egyptian Room - Free Parking, 1 block to CTA

Antique Filled Home

OakPark Gem. Family-Friendly Getaway near Downtown

Grove Flat

Chi-Town Hideout #3

Spacious Home Base for Families and Groups
When is the best time to visit Oak Park?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 76 | € 75 | € 87 | € 90 | € 110 | € 114 | € 120 | € 120 | € 103 | € 99 | € 96 | € 95 |
| 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
Where should I stay in Oak Park?
Make yourself at home in Oak Park by choosing from our most frequently booked neighborhoods. We have over 650 vacation rentals in Rehm Park, and over 2,430 vacation rentals in Oak Park.
Are there pet-friendly vacation rentals in Oak Park?
Four-legged friends are welcome in Oak Park. Choose from more than 80 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Oak Park?
Yes! Work meets play with ease at over 170 vacation rentals in Oak Park featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do apartment rentals in Oak Park have wifi?
Absolutely! We offer over 140 apartment rentals with wifi in Oak Park. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in apartment rentals in Oak Park?
Experience the best of Oak Park with our apartment rentals, starting at about $10 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Oak Park have a gym?
Absolutely! We offer over 10 apartment rentals with a gym in Oak Park. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Oak Park have a bbq area?
Absolutely! We offer over 10 apartment rentals with a bbq area in Oak Park. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly apartment rentals in Oak Park?
Oak Park has more than 70 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Quick stats about holiday rentals in Oak Park

Total holiday rentals
Explore 320 holiday rentals in Oak Park

Nightly prices starting at
Oak Park holiday rentals start at € 9 per night before taxes and fees

Verified guest reviews
Over 20,840 verified reviews to help you choose

Family-friendly holiday rentals
150 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 80 rentals that welcome pets

Rentals with dedicated workspaces
170 properties have a dedicated workspace

Wifi availability
320 of Oak Park holiday rentals include wifi 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
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- Family-friendly rentals Oak Park
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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- 875 North Michigan Avenue
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- The Field Museum
- Oak Street Beach
- Wicker Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- The Beverly Country Club
- Museum of Science and Industry
- Brookfield Zoo
- Wilmot Mountain Ski Resort
- Willis Tower
- Illinois Beach State Park
- Washington Park Zoo
- The 606




