
Apartment vacation rentals in Oak Park
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Top-rated apartment rentals in Oak Park
Guests agree: these apartments are highly rated for location, cleanliness, and more.

1 bedroom garden apartment in Forest Park
Unique private garden apartment in our single family residence. Great location approximately 8 miles directly west of downtown Chicago. Close to shopping, dining, entertainment and public transportation to the city. One bedroom & best for 2 people but could sleep 3 ($50 fee) for short stays. It's important to note that this is a garden/ground/lower level apartment. The ceilings are relatively low at 6.5'. This would not be the best space for tall people. Free parking in front of the house.

City-Accessible Basement Retreat
Discover a perfect mix of small-town charm and city life in this cozy basement unit. Situated just a 7-minute walk from the train station, downtown Chicago is easily accessible for work/leisure. The neighborhood is a treasure trove of local restaurants, bars, and stores, ensuring you're never far from what you need. A convenient gas station/store is right behind your home for quick needs. Ideal for a simple, connected lifestyle with the city’s pulse at your doorstep. Your urban retreat awaits!

Lovely, spacious 2bd, 1bath home w/free parking
Bring the whole family to enjoy this great place with lots of comforts and space. Beautifully decorated with reclaimed barn wood throughout the home and a completely remodeled kitchen with cute bistro table to enjoy your coffee. Wonder 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. Whether you stay for a while or a few days, welcome home!

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

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

Private apartment with retro vibe
December discount dates! Cozy 1 BR apartment with retro touches in Berwyn a block from Oak Park. 2nd floor private apartment. Wifi, cable, premium channels. Full kitchen. Queen bed plus brand new twin sofa bed, + 1 more twin available. EASY free street parking right by unit. Quick drive to City. Convenient to both airports, United Center and walk to Fitzgerald’s Club. Near Blue Line, restaurants, great bakery. NO smoking, candles or glitter! Pets MUST be pre-approved and never left

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

Cosmopolitan Nest in Oak Park North Side
Whether visiting Oak Park's historic district or exploring the Windy City for the renowned museums and its nightlife, we welcome you into our home. You are guaranteed a peaceful stay in your own apartment with private entrance on the first floor in our single family home. We are a professional family who maintain a quiet residence. CTA public transportation just steps away.
Popular amenities for Oak Park apartment rentals
Weekly apartment rentals

Springfield Serenity

Moonbeam Abode

2 Bed Apartment | Convenient Access to Downtown

Luxurious Lifestyle

Historic Hotspot: Downtown Oak Park w/parking spot

Best Deal in Chicago | Great Food & Free Parking

Treetop Vista • Spacious Luxe Near DT Chi+Parking

Studio Apartment in Oak Park
Private apartment rentals

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

Spacious Oasis Berwyn with Free Parking

Modern NEW Deluxe Studio in Oak Park

Cute, Clean, Cozy Apartment in Pilsen

Urban oasis in Oak Park

Mid-Century Charm. Near Chicago. Low Cleaning Fee!

Top floor of Historic Oak Park Home /2 Car Garage

Avondale Cozy 1 Bedroom Attic Apartment 4th FL
Apartment rentals with a hot tub

Top Floor Views + Central Comfort

Spacious Beautiful Condo

Skyline Oasis: City & Lake Views

Level One Bedroom Suite | Fulton Market

Sentral 1 Bedroom Apt in South Loop Chicago

Winter Escape 1 BR in Wicker Parl|1 FREE G Parking

Belmont Pleasures - hot tub / arcade gaming room

2Bed 2Bath 15min to Wrigley with Parking& Balcony
When is the best time to visit Oak Park?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$21,146 GYD | G$25,124 GYD | G$24,496 GYD | G$23,449 GYD | G$27,636 GYD | G$28,474 GYD | G$29,521 GYD | G$29,940 GYD | G$25,752 GYD | G$25,124 GYD | G$25,124 GYD | G$26,799 GYD |
| 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 |
Quick stats about apartment rentals in Oak Park

Total vacation rentals
Explore 140 vacation rentals in Oak Park

Nightly prices starting at
Oak Park vacation rentals start at G$2,094 GYD per night before taxes and fees

Verified guest reviews
Over 10,660 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
90 properties have a dedicated workspace

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

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool 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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- 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




