Oak Park vacation rentals

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Top-rated vacation rentals in Oak Park

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite

Guest suite in Oak Park

4.89 out of 5 average rating, 394 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 4 – 11

$102 per night
Superhost

Apartment in Oak Park

4.79 out of 5 average rating, 164 reviews

Cozy modern unit w/ easy access to downtown Chi

Enjoy a newly remodeled two bedroom basement unit in the historic Oak Park suburb of Chicago. This unit is within walking distance to local cafes, amazing restaurants, ice cream shops, and a grocery store to meet your needs. Explore the nearby Frank Lloyd Wright district and the birthplace of Ernest Hemingway. Walk 2 blocks to the train leading to all neighborhoods of Chicago, or simply enjoy a relaxing stay in the cozy apartment. Easy access to nearby airports. Pets welcome with additional fee.

Jun 19 – 26

$95 per night
Guest favorite

Home in Berwyn

4.92 out of 5 average rating, 232 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 3 – 10

$98 per night

Popular amenities for Oak Park vacation rentals

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
Classic Cinemas Lake Theatre72 locals recommend
West Suburban Medical Center6 locals recommend
Jewel-Osco13 locals recommend

Other great vacation rentals in Oak Park

Guest favorite

Apartment in Forest Park

4.83 out of 5 average rating, 161 reviews

Cozy & Convenient Oak Park incl parking / transit

Jun 14 – 21

$89 per night
Guest favorite

Apartment in Oak Park

4.95 out of 5 average rating, 154 reviews

A quiet stay while you are away

Jan 13 – 20

$107 per night
Guest favorite

Apartment in Berwyn

4.86 out of 5 average rating, 132 reviews

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

Jun 3 – 10

$84 per night
Guest favorite

Apartment in Oak Park

4.88 out of 5 average rating, 103 reviews

Stunning 2bd 1bath w/free parking, W/D & fireplace

Jul 14 – 21

$136 per night
Guest favorite

Apartment in Oak Park

4.91 out of 5 average rating, 167 reviews

Large sunny 3BR apt. in downtown Oak Park

Sep 25 – Oct 2

$189 per night
Superhost

Guest suite in Oak Park

4.82 out of 5 average rating, 149 reviews

Private 2 BR Oak Park Garden Apt

Jul 14 – 21

$116 per night
Superhost

Apartment in Oak Park

4.87 out of 5 average rating, 146 reviews

Small But Mighty 700 Sqft Cottage Apt (1BR/1BA)

Apr 19 – 26

$85 per night
Guest favorite

Apartment in Berwyn

4.92 out of 5 average rating, 144 reviews

Friendly Rock ’n’ Roll Retreat

Feb 13 – 20

$99 per night
Guest favorite

Apartment in Forest Park

4.96 out of 5 average rating, 226 reviews

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

Aug 23 – 30

$106 per night
Guest favorite

Apartment in Forest Park

4.95 out of 5 average rating, 129 reviews

Large, modern 2 bedroom in heart of Forest Park

Nov 4 – 11

$143 per night
Guest favorite

Apartment in Berwyn

4.99 out of 5 average rating, 248 reviews

Berwyn Betty Apartment

Feb 17 – 24

$139 per night
Guest favorite

Apartment in Cicero

4.98 out of 5 average rating, 190 reviews

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

Oct 19 – 26

$107 per night

Other great vacation rentals in Oak Park

Guest favorite

Apartment in Forest Park

4.99 out of 5 average rating, 85 reviews

Sunny 1 bedroom apartment 1 block from restaurants

Feb 19 – 26

$103 per night
Guest favorite

Apartment in Oak Park

5.0 out of 5 average rating, 63 reviews

Cheerful Oak Park Apartment

Sep 12 – 19

$119 per night
Guest favorite

Guesthouse in Oak Park

4.94 out of 5 average rating, 70 reviews

O'Malley Oasis!

Jun 24 – Jul 1

$141 per night
Guest favorite

Apartment in Oak Park

4.96 out of 5 average rating, 27 reviews

2BR/2BA Oak Park Gem - Ideal Comfort

Jun 18 – 25

$142 per night
Guest favorite

Apartment in Forest Park

4.96 out of 5 average rating, 76 reviews

1 bedroom garden apartment in Forest Park

Jan 10 – 17

$95 per night
Guest favorite

Apartment in Forest Park

4.93 out of 5 average rating, 75 reviews

Home away from home upstairs.

Oct 28 – Nov 4

$104 per night
Guest favorite

Apartment in Forest Park

4.93 out of 5 average rating, 42 reviews

Enjoy the Chicago | Modern 2 Bedroom Apartment

Apr 17 – 24

$100 per night
Guest favorite

Guesthouse in Oak Park

4.9 out of 5 average rating, 62 reviews

Sunny Coach House in Historic Oak Park

Jul 6 – 13

$143 per night
Superhost

Apartment in Oak Park

5.0 out of 5 average rating, 4 reviews

Cozy Hideaway Mins From Downtown Chicago/Suburbs

Apr 24 – May 1

$153 per night
Guest favorite

Apartment in Oak Park

4.91 out of 5 average rating, 11 reviews

Gorgeous/Quiet/Apt/Free Parking/FirePit/Close 2 DT

May 5 – 12

$126 per night
Guest favorite

Apartment in Oak Park

5.0 out of 5 average rating, 17 reviews

The Artist's Loft - Oak Park

Dec 10 – 17

$150 per night
Guest favorite

Home in Oak Park

4.97 out of 5 average rating, 63 reviews

Clean, Comfy Duplex with Kitchen & Free Parking

Apr 29 – May 4

$139 per night

Quick stats about vacation rentals in Oak Park

Total rentals

320 properties

Wifi availability

310 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 guesthouse rentals in Oak Park have air conditioning?

    Absolutely! We offer over 10 guesthouse 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 condo rentals in Oak Park?

    Experience the best of Oak Park with our condo rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Oak Park have wireless internet?

    Absolutely! We offer over 130 house 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 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.

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Oak Park