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 9 – 16

R2,225 ZAR per night

Guest favorite

Apartment in Oak Park

4.88 out of 5 average rating, 104 reviews

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

Whether you're here to visit family or friends, to attend a conference in the city or a quick getaway, your family will love renting our entire flat. It has all the comforts of home located on a beautiful block in the historic Frank Lloyd Wright District in Oak Park. Here, you will be close to The Frank Lloyd Wright Home/Studio, downtown Oak Park, amazing restaurants and attractions, the Green and Blue line trains that will take you to downtown Chicago, and major highways and shopping centers.

Oct 4 – 11

R2,483 ZAR per night

Guest favorite

Apartment in Oak Park

4.85 out of 5 average rating, 527 reviews

Long stays welcome@warm&cute vintage 2BR

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

Sep 27 – Oct 4

R2,008 ZAR 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 10 – 17

R1,831 ZAR per night

Superhost

Apartment in Oak Park

4.89 out of 5 average rating, 331 reviews

Charming Chicago-Style, Vintage, Tv NFL PASS

→ 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

Jan 17 – 24

R1,623 ZAR per night

Guest favorite

Apartment in Oak Park

4.93 out of 5 average rating, 136 reviews

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.

Dec 15 – 22

R3,321 ZAR per night

Guest favorite

Apartment in Forest Park

4.99 out of 5 average rating, 185 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

R2,382 ZAR 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 14 – 21

R2,600 ZAR 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.

Sep 4 – 11

R2,285 ZAR 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.

Mar 19 – 26

R2,767 ZAR per night

Guest favorite

Apartment in Forest Park

4.84 out of 5 average rating, 109 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.

Nov 7 – 14

R2,303 ZAR 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.

Feb 21 – 28

R1,867 ZAR 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 21 – 28

R3,212 ZAR per night

Guest favorite

Home in Berwyn

4.92 out of 5 average rating, 237 reviews

Private apartment with retro vibe

Sep 5 – 12

R1,732 ZAR 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 6 – 13

R2,039 ZAR per night

Guest favorite

Apartment in Forest Park

4.95 out of 5 average rating, 233 reviews

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

Oct 5 – 12

R2,528 ZAR 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

R2,025 ZAR per night

Guest favorite

Apartment in Cicero

4.98 out of 5 average rating, 200 reviews

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

Jan 19 – 26

R2,348 ZAR per night

Guest favorite

Home in Forest Park

4.9 out of 5 average rating, 221 reviews

Charming dog friendly 2-Bath Bungalow Near Chicago

Jun 25 – Jul 2

R2,961 ZAR per night

Guest favorite

Apartment in Forest Park

4.93 out of 5 average rating, 581 reviews

Peaceful oasis in Forest Park

Aug 12 – 19

R3,337 ZAR per night

Show all

Other great vacation rentals in Oak Park

Guest favorite

Apartment in Forest Park

4.99 out of 5 average rating, 88 reviews

Sunny 1 bedroom apartment 1 block from restaurants

Jan 27 – Feb 3

R2,273 ZAR per night

Guest favorite

Apartment in Oak Park

5.0 out of 5 average rating, 65 reviews

Cheerful Oak Park Apartment

Sep 26 – Oct 3

R2,699 ZAR per night

Guest favorite

Apartment in Oak Park

4.97 out of 5 average rating, 30 reviews

2BR/2BA Oak Park Gem - Ideal Comfort

Jan 1 – 8

R3,347 ZAR per night

Guest favorite

Apartment in Forest Park

4.86 out of 5 average rating, 14 reviews

City-Accessible Basement Retreat

Aug 15 – 22

R1,696 ZAR 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

R3,158 ZAR per night

Guest favorite

Apartment in Forest Park

4.96 out of 5 average rating, 78 reviews

1 bedroom garden apartment in Forest Park

Mar 10 – 17

R2,101 ZAR per night

Guest favorite

Apartment in Oak Park

5.0 out of 5 average rating, 19 reviews

The Artist's Loft - Oak Park

Mar 17 – 24

R3,182 ZAR per night

Guest favorite

Apartment in Oak Park

5.0 out of 5 average rating, 7 reviews

Spacious Kng Bed Free pkng perfect 4 long stays

Feb 16 – 23

R2,808 ZAR 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

Apartments

Houses

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

Home in Berwyn

Apartment in Forest Park

Apartment in Forest Park

Apartment in Berwyn

Apartment in Cicero

Home in Forest Park

Apartment in Forest Park

Other great vacation rentals in Oak Park

Apartment in Forest Park

Apartment 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

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