Oak Park vacation rentals

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Top-rated vacation rentals in Oak Park

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Guest favorite

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.

Dec 22 – 29

$104 per night

Guest favorite

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.

Sep 5 – 12

$91 per night

Superhost

Apartment in Oak Park

4.84 out of 5 average rating, 488 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!

Jan 20 – 27

$121 per night

Guest favorite

Apartment 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!

Sep 20 – 27

$124 per night

Guest favorite

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.

Jul 7 – 14

$83 per night

Guest favorite

Apartment 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

Nov 5 – 12

$100 per night

Guest favorite

Apartment 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.

Oct 27 – Nov 3

$109 per night

Guest favorite

Condo 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:

Mar 18 – 25

$118 per night

Guest favorite

Apartment 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.

Jul 23 – 30

$115 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.

Dec 10 – 17

$126 per night

Guest favorite

Apartment 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.

Mar 18 – 25

$85 per night

Guest favorite

Apartment in Oak Park

4.86 out of 5 average rating, 245 reviews

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.

Sep 19 – 26

$66 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Oak Park vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Oak Park's top sights

Frank Lloyd Wright Home and Studio184 locals recommend

Downtown Oak Park9 locals recommend

Trader Joe's52 locals recommend

Jewel-Osco13 locals recommend

Classic Cinemas Lake Theatre72 locals recommend

West Suburban Medical Center6 locals recommend

Other great vacation rentals in Oak Park

Superhost

Condo in Oak Park

4.79 out of 5 average rating, 308 reviews

Peaceful Oak Park Condo Next to Green Line Metro

Sep 25 – Oct 2

$145 per night

Guest favorite

Apartment in Forest Park

4.82 out of 5 average rating, 107 reviews

Home away from home downstairs

Nov 28 – Dec 5

$102 per night

Guest favorite

Apartment in Oak Park

4.93 out of 5 average rating, 136 reviews

Walking Distance to Everything.

Aug 17 – 24

$167 per night

Guest favorite

Apartment in Oak Park

4.94 out of 5 average rating, 156 reviews

A quiet stay while you are away

Jan 22 – 29

$105 per night

Guest favorite

Apartment in Forest Park

4.83 out of 5 average rating, 162 reviews

Cozy & Convenient Oak Park incl parking / transit

Jun 29 – Jul 6

$94 per night

Guest favorite

Apartment in Berwyn

4.87 out of 5 average rating, 136 reviews

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

Jul 11 – 18

$93 per night

Guest favorite

Apartment in Forest Park

4.9 out of 5 average rating, 123 reviews

Large Renovated 1st FL Suite Forest Park/Oak Park

Dec 22 – 29

$162 per night

Guest favorite

Apartment in Forest Park

4.95 out of 5 average rating, 132 reviews

Large, modern 2 bedroom in heart of Forest Park

Sep 22 – 29

$145 per night

Show all

Other great vacation rentals in Oak Park

Guest favorite

Apartment in Oak Park

5.0 out of 5 average rating, 65 reviews

Cheerful Oak Park Apartment

Sep 6 – 13

$123 per night

Guest favorite

Apartment in Forest Park

4.99 out of 5 average rating, 87 reviews

Sunny 1 bedroom apartment 1 block from restaurants

Nov 14 – 21

$103 per night

Guest favorite

Apartment in Oak Park

4.98 out of 5 average rating, 84 reviews

Lovely 2-bedroom rental in the heart of Oak Park

Mar 29 – Apr 5

$99 per night

Guest favorite

Apartment in Forest Park

4.83 out of 5 average rating, 12 reviews

City-Accessible Basement Retreat

Nov 20 – 27

$77 per night

Guest favorite

Apartment in Oak Park

4.97 out of 5 average rating, 30 reviews

2BR/2BA Oak Park Gem - Ideal Comfort

Sep 7 – 14

$151 per night

Guest favorite

Apartment in Oak Park

4.97 out of 5 average rating, 29 reviews

2QB Downtown Oak Park, free parking, CTA & Metra

Sep 4 – 11

$143 per night

Guest favorite

Guesthouse in Oak Park

4.9 out of 5 average rating, 63 reviews

Sunny Coach House in Historic Oak Park

Sep 28 – Oct 5

$133 per night

Guest favorite

Apartment in Forest Park

4.96 out of 5 average rating, 78 reviews

1 bedroom garden apartment in Forest Park

Sep 30 – Oct 7

$106 per night

Show all

Quick stats about vacation rentals in Oak Park

Total rentals	320 properties
Wifi availability	320 properties include access to wifi
Rentals with dedicated workspaces	170 properties have a dedicated workspace
Pet-friendly rentals	70 properties allow pets
Family-friendly rentals	140 properties are a good fit for families
Total number of reviews	16K reviews

Frequently Asked Questions

Are there pet-friendly vacation rentals in Oak Park?
Four-legged friends are welcome in Oak Park. Choose from more than 70 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.
Are there family-friendly vacation rentals in Oak Park?
Oak Park has more than 140 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Oak Park have air conditioning?
Absolutely! We offer over 120 house rentals with air conditioning 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 guesthouse rentals in Oak Park have wireless internet?
Absolutely! We offer over 10 guesthouse rentals with wireless internet in Oak Park. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Oak Park have a gym?
Absolutely! We offer over 20 apartment rentals with a gym in Oak Park. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Oak Park have a bbq area?
Absolutely! We offer over 20 house rentals with a bbq area in Oak Park. Enjoy a tailored experience with all the comforts you desire.

Oak Park vacation rentals

Top-rated vacation rentals in Oak Park

Vacation rentals for every style

Houses

Apartments

Hotels

Popular amenities for Oak Park vacation rentals

Stay near Oak Park's top sights

Other great vacation rentals in Oak Park

Condo in Oak Park

Apartment in Forest Park

Apartment in Oak Park

Apartment in Oak Park

Apartment in Forest Park

Apartment in Berwyn

Apartment in Forest Park

Apartment in Forest Park

Other great vacation rentals in Oak Park

Apartment in Oak Park

Apartment in Forest Park

Apartment in Oak Park

Apartment in Forest Park

Apartment in Oak Park

Apartment in Oak Park

Guesthouse in Oak Park

Apartment in Forest Park

Quick stats about vacation rentals in Oak Park

Total rentals

Wifi availability

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Are there pet-friendly vacation rentals in Oak Park?

Are there vacation rentals with a dedicated workspace in Oak Park?

Are there family-friendly vacation rentals in Oak Park?

Do house rentals in Oak Park have air conditioning?

How much does it cost to stay in apartment rentals in Oak Park?

Do guesthouse rentals in Oak Park have wireless internet?

Do apartment rentals in Oak Park have a gym?

Do house rentals in Oak Park have a bbq area?

Destinations to explore