Holiday rentals with a patio in Oak Park

Find and book unique rentals with patio on Airbnb

Top-rated rentals with patio in Oak Park

Guests agree: these rentals with a patio are highly rated for location, cleanliness and more.

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Guest favourite

Flat in Forest Park

4.99 out of 5 average rating, 89 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.

24–31 Jan

$161 SGD per night

Guest favourite

Flat in Oak Park

4.91 out of 5 average rating, 104 reviews

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!

24 Sep – 1 Oct

$170 SGD per night

Guest favourite

Flat in Berwyn

4.87 out of 5 average rating, 137 reviews

The Green Bungalow: Charming 1-BR apt. with patio

Situated in a residential neighborhood just outside the city limits, this lovely 2nd floor apartment is blocks from the Blue Line train and highway. Our newly renovated vintage unit has a full kitchen, hardwood floors, plenty of natural light, a backyard patio and its own private entrance. Our bungalow is walking distance to cafes, restaurants, shopping, music and nightlife. Enjoy the charm of the suburbs while having easy access to all the attractions Chicago's downtown has to offer.

11–18 Jul

$146 SGD per night

Guest favourite

Flat in Oak Park

5.0 out of 5 average rating, 65 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).

6–13 Sep

$194 SGD per night

Guest favourite

Townhouse in Oak Park

4.91 out of 5 average rating, 78 reviews

Downtown Oak Park - Luxury 3 bed 3.5 bath Townhome

Entire townhome located in charming downtown Oak Park. Luxury accommodations. Free Parking. Dog friendly. Highly-walkable area. Attached two-car garage. Chicago's El and Metra train stops a short 2-block walk. Both trains bring you to the heart of downtown with the El extending into many Chicago neighborhoods. Shopping, restaurants, Target, Trader Joe's and Frank Lloyd Wright homes within walking distance. TVs logged into Hulu, Disney +, ESPN, Netflix and HBO Max.

2–9 Sep

$390 SGD per night

Superhost

Apartment in Oak Park

4.78 out of 5 average rating, 49 reviews

Lovely condo in the heart of Downtown Oak Park!

The whole group will enjoy easy access to everything from this centrally located place. 2 bedrooms, 2 baths, lots of living space. Open concept kitchen, living, dining, and extra space for work/play space. In-unit laundry. Great outdoor deck, free parking all in the heart of downtown Oak Park with restaurants, theater, street fests, parks, green line/metra for easy access to Chicago. Quiet unit with its own entrance and no shared walls. You will love it here!

7–14 Dec

$223 SGD per night

Guest favourite

Home in Oak Park

4.97 out of 5 average rating, 71 reviews

Clean, Comfy Duplex with Kitchen & Free Parking

This historic district home with full kitchen, free parking & train access makes this clean 1st-floor 1-bedroom duplex perfect for tourists, families, or business travelers. Minimum age to book 25. Not only are we minutes from Chicago & situated in a safe, upscale neighborhood, we require no check-out chores. Enjoy historic Oak Park with easy highway access & 3 blocks to the train. Near both airports. No parties. For additional units, visit my hosting profile

25 Aug – 1 Sep

$226 SGD per night

Superhost

Flat in Berwyn

5.0 out of 5 average rating, 4 reviews

The Cosmopolitan Unit

Feel like you traveled all around the world by visiting our Cosmopolitan Unit. Each bedroom is inspired by different city from all around the globe. 3 bedroom apartment with fully equipped kitchen. Fast wi-fi and TV in each bedroom. For those who enjoy working out while on vacation, we even have a Peloton bike. This second floor apartment is located within 15-20 min drive from downtown Chicago. Public transportation and restaurants within walking distance.

4–11 Nov

$182 SGD per night

Guest favourite

Flat in Forest Park

4.96 out of 5 average rating, 28 reviews

Clean and Comfy Updated Apt in Convenient Location

Comfortable, clean and stylish living with spacious living room and dining area. Super cute eat-in kitchen and bathroom have been totally renovated. 2 bedrooms with comfortable mattresses: one queen and one full. Outside spaces are charming w fire pit and bbq grill. Laundry and 1 parking spot included. Short walk to downtown Forest Park for dining and shopping. Easy access to 290, blue line and airport. Small town feel with big city access.

24 Sep – 1 Oct

$212 SGD per night

Guest favourite

Flat in Chicago

4.97 out of 5 average rating, 31 reviews

Serene Escape with King Sleep Number Bed, No Fees!

Welcome to our meticulously designed oasis! Relax in luxury on a king-sized Sleep Number bed, refresh in the marbled bathroom with a rain shower, and indulge your culinary passions in the farmhouse-inspired chef's kitchen. Bright, airy, and inviting, our space offers a serene escape. Conveniently located near Belmont CTA Blue Line Station and bus stops, it's the perfect base for your Chicago adventure. Book now for sophistication and comfort!

23–30 Aug

$193 SGD per night

Guest favourite

Flat in Cicero

4.98 out of 5 average rating, 201 reviews

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy

Quiet city side street. Walking distance to dozens of restaurants and stores. Walking distance to Public Transportation including Metra train, CTA Pink line, Direct CTA Bus to Midway Airport. You will be a short 20-minute drive to Downtown Chicago, 15 minutes to United Center or Soldier Field. Perfect for the quick getaway, the night before your flight, or even the long work assignment. Relax on the Patio with a fire pit and grill.

11–18 Dec

$170 SGD per night

Guest favourite

Guest suite in Wheaton

4.85 out of 5 average rating, 100 reviews

Cozy Wheaton Home

Cozy lower level apartment close to DT Wheaton & Glen Ellyn, restaurants, coffee shops, and shopping. Only 40 minutes outside of the DT Chicago! Train station is walking distance. You'll have the entire lower level of our home to yourself! You'll be able to enjoy your own private entrance, living space, and parking . There is everything you need, coffee, tea, mini fridge, microwave, and a comfy couch with a Firestick TV!

13–20 Feb

$153 SGD per night