Holiday rentals in Oak Park

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Top-rated holiday rentals in Oak Park

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Guest favourite

Guest suite in Oak Park

4.89 out of 5 average rating, 399 reviews

Entire upstairs in Arts and Crafts Oak Park home

You have the use of the entire upstairs (with a separate, lockable private entrance) and bicycles. With two bedrooms, bathroom and a common area with a futon, table, fridge, microwave, coffee maker and kettle, it is flexible for individuals, couples, families or small groups. Free overnight parking. We're a quick walk to the CTA Blue line, coffee shops and restaurants, parks, musical venues, the Oak Park Arts District, and a quick drive to downtown. Our home is cozy, in a friendly neighborhood.

22–29 Dec

$163 SGD per night

Guest favourite

Home in Berwyn

4.92 out of 5 average rating, 237 reviews

Private apartment with retro vibe

Gunderson Getaway is a cosy one BR apartment with some retro style touches in Berwyn a block from Oak Park. 2nd floor private apartment. Wifi, cable, premium channels. Full kitchen. Queen bed plus sofa & extra single bed 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, groceries, great bakery. NO smoking, candles or glitter! Pets MUST be pre-approved and never left alone.

5–12 Sep

$142 SGD per night

Superhost

Flat in Oak Park

4.84 out of 5 average rating, 489 reviews

Sunny Jumbo Studio NO cleaning fee!

Bright and sunny Oak Park jumbo garden studio, steps from cute downtown, train to Chicago, and amazing local tourist destinations- like the Hemingway Home and the Wright Studio. This welcoming studio was completely rehabbed and updated. We put a lot of care into designing a relaxing apartment with all the amenities. The main room features a king-sized bed, office nook, and fully stocked entertainment area, with games, books, and a TV. The spacious kitchen and luxurious bathroom are brand new!

20–27 Jan

$187 SGD per night

Guest favourite

Flat in Oak Park

4.91 out of 5 average rating, 101 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!

20–27 Sep

$196 SGD per night

Guest favourite

Loft in Oak Park

4.98 out of 5 average rating, 342 reviews

Contemporary Oak Park Loft

This affordable loft is ideal for getaways, exploring Chicago, staycations, or work-from-home office space. The loft is a clean, private, second-story apartment with a 5-star rating. The high-speed Wi-Fi and large office area with a roomy, contemporary desk for laptop and ample plugs for all the electronics needed. The kitchenette provides the needed coffee, micro, and mini-fridge with some simple breakfast treats to get you going in the morning. Parking is available on the parking pad.

7–14 Jul

$130 SGD per night

Guest favourite

Flat in Oak Park

4.89 out of 5 average rating, 287 reviews

Cozy Vintage Chicago-Style, 1 bed with Cable

→ 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

5–12 Nov

$157 SGD per night

Guest favourite

Flat in Forest Park

4.99 out of 5 average rating, 184 reviews

Walk to Oak Park from this Newly Remodeled Gem

This is an open, bright and comfortable home that has been fully renovated, but still has the historic charm of an older house (early 1900s). With a completely updated kitchen you have everything you need to fix a good meal or you can choose to eat out at one of the many restaurants and bars/brew pubs within close proximity. The apartment has an office nook with a desk and chair for getting your work done, or you can kick back and relax in the living and dining spaces.

27 Oct – 3 Nov

$172 SGD per night

Guest favourite

Apartment in Oak Park

4.88 out of 5 average rating, 163 reviews

Attractive Flat - Historic Oak Park

Attractive One Bedroom Flat for Rent in Historic Downtown Oak Park. Truly - one of the Best Locations in all of Chicago. Two Blocks from the Epicenter of this lovely city. Easy Access to Public Transportation to Downtown Chicago or the Greater Metro Area. The Elevated train -and- the Metra Train (15 Minutes by Train to Downtown) are each a quick walk. See “ property description “ For Important information for all perspective Guests:

28 Mar – 4 Apr

$185 SGD per night

Guest favourite

Flat in Forest Park

5.0 out of 5 average rating, 216 reviews

Like a Treehouse!

If you're coming to Illinois for any medical procedure that's no longer available in your home state, reach out to us about discounts. You'll feel like you're in a tree house in our 850 sq ft coach house, above our workshop/garage, behind our home in historic Forest Park (with "The Mayberriest Downtown!"- Chicago Magazine), right next to Oak Park. Just 8 miles west of Downtown Chicago, convenient to I-290 and the Blue Line train.

8–15 Sep

$162 SGD per night

Superhost

Guest suite in Oak Park

4.84 out of 5 average rating, 154 reviews

Private garden suite in quiet safe Oak Park

Keep it simple and peaceful while staying in Oak Park. Enjoy this classic garden unit located in an idealistic tree covered neighborhood. Located a 10 min from the Frank Lloyd Wright Home and Studio and Ernest Hemingway home and museum. Green line CTA is a 10 min walk away as well with easy access to Chicago. Enjoy historic Oak Park, thriving Chicago, and a good sleep. Or come to work from home, Netflix, and relax.

10–17 Dec

$197 SGD per night

Guest favourite

Flat in Forest Park

4.82 out of 5 average rating, 107 reviews

Home away from home downstairs

Enjoy a stylish experience at this centrally-located, easy access , ground floor apartment. You will have a fully equipped kitchen, laundry facility outside your back door and super fast internet. Forest Park is located about 20 minutes from downtown Chicago and about 30 minutes from O’Hara international airport. You are within walking distance of many boutiques, restaurants, parks and also public transportation.

8–15 Nov

$153 SGD per night

Guest favourite

Flat in Oak Park

4.87 out of 5 average rating, 127 reviews

A Little Slice of Heaven in Oak Park, IL

A private space with a fun vintage vibe. Located several blocks from the El and the Eisenhower, it’s really easy to access the city. It also includes free off-street parking which is a must. The space is located in my basement and has a private entrance. The space includes a bedroom, living area and a bathroom. Space is great if you are in town to work or for fun! Please contact me with any questions.

18–25 Mar

$134 SGD per night