Oak Park vacation rentals

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Top-rated vacation rentals in Oak Park

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Guest favorite

Loft in Forest Park

4.96 out of 5 average rating, 463 reviews

Walk to Oak Park from a Bright Madison Street Loft

Crowned "The best in neighborhood dining" according to a 2008 Chicago Tribune readers poll, the variety of Forest Park restaurants offer something for everyone. The unit is a charming two bedroom, two bath loft a stone’s throw from historic Oak Park and just three blocks from the CTA Blue Line making downtown Chicago a 20 minute train ride away. The condo includes additional amenities such as: - Elevator in building •Secure front and back entrances. •One assigned parking spot in the back of the building. •Full kitchen with stainless steel appliances (stove, dishwasher, refrigerator), cookware, and dinnerware. •Granite countertops. •Two full bathrooms. The master bathroom includes a Jacuzzi tub. •Two full bedrooms. Both have queen sized beds. •Smart TV with cable access and access to Netflix. •Central Air conditioning •Working fireplace •Balcony with a view of downtown Chicago's skyline •Washer and dryer in unit. Just to the east lies historic Oak Park, which offers an array of attractions such as: •Brookfield Zoo •Chicago Architecture Foundation •Ernest Hemmingway Museum and Birthplace •Frank Lloyd Wright Home and Studio •Frank Llyod Wright’s Unity Temple •Oak Park Conservatory After soaking up some attractions in Oak Park, Chicago is only a short twenty minute train ride away, and it offers such noteworthy experiences as: •Shedd Aquarium •Architecture River Cruise •Skydeck Chicago •Navy Pier •The Field Museum •John Hancock Observatory •Adler Planetarium •Art Institute of Chicago •The Museum of Science and Industry The loft and both doors to our building have key-less entry pads. We will email you your personal entry code along with check in instructions a couple days before your arrival. Each guest is given their own personal code. Codes are programmed the day of check in and deleted shortly after check out. We are as available as you need. Centrally positioned in the Madison Street shopping and dining district, the loft is conveniently surrounded by local eateries and pubs within minutes of downtown Chicago and the United Center, and just blocks from the CTA blue line. We are located half a mile from the L - Blue Line. We are the Forest Park Stop on the blue line. The blue line will take you into the city. It is about an 8 to 10 minute walk from the loft. An Uber/Lyft ride into the city ranges from $15 to $25 and takes around 15 to 20 minutes. We are one mile from the Metra train line (Union Pacific - West). The Metra dead ends into Union Station. There are a number of Metra lines that take you to surrounding suburbs. We are also one mile from the Green Line - Oak Park Stop. The Green Line is another line on the L. The third bed is a queen sleeper sofa. There is a strict no smoking policy in our building. You can not smoke on the balcony - it will result in a $500 fine. The neighborhood is vibrant in the summer and sound can travel into the unit.

Dec 9 – 16

G$26,676 GYD per night

Guest favorite

Guest suite in Oak Park

4.89 out of 5 average rating, 402 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 7 – 14

G$24,164 GYD 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

G$19,541 GYD per night

Superhost

Apartment in Oak Park

4.84 out of 5 average rating, 493 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!

Nov 5 – 12

G$25,703 GYD per night

Guest favorite

Apartment in Oak Park

4.91 out of 5 average rating, 103 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!

Oct 11 – 18

G$29,941 GYD per night

Guest favorite

Loft in Oak Park

4.98 out of 5 average rating, 345 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.

G$19,479 GYD 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:

Sep 16 – 23

G$28,275 GYD per night

Guest favorite

Apartment in Forest Park

5.0 out of 5 average rating, 217 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.

Oct 14 – 21

G$23,409 GYD per night

Superhost

Guest suite in Oak Park

4.85 out of 5 average rating, 155 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.

Jan 27 – Feb 3

G$30,070 GYD per night

Guest favorite

Apartment in Forest Park

4.85 out of 5 average rating, 110 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.

Jan 3 – 10

G$23,493 GYD per night

Guest favorite

Apartment in Oak Park

4.88 out of 5 average rating, 128 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 25 – Mar 4

G$20,358 GYD per night

Guest favorite

Apartment in Oak Park

4.86 out of 5 average rating, 247 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.

Oct 3 – 10

G$15,871 GYD 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

Guest favorite

Apartment in Forest Park

4.83 out of 5 average rating, 162 reviews

Cozy & Convenient Oak Park w Parking / Transit

Jun 7 – 14

G$21,819 GYD per night

Superhost

Condo in Oak Park

4.79 out of 5 average rating, 308 reviews

Peaceful Oak Park Condo Next to Green Line Metro

Oct 5 – 12

G$33,877 GYD per night

Guest favorite

Apartment in Oak Park

4.93 out of 5 average rating, 136 reviews

Walking Distance to Everything.

Oct 3 – 10

G$40,540 GYD per night

Guest favorite

Guest suite in Chicago

4.98 out of 5 average rating, 111 reviews

Gorgeous Studio 15 Minutes From Ohare!

Sep 13 – 20

G$18,567 GYD per night

Guest favorite

Apartment in Forest Park

4.95 out of 5 average rating, 133 reviews

Large, modern 2 bedroom in heart of Forest Park

Oct 1 – 8

G$34,319 GYD per night

Guest favorite

Apartment in Cicero

4.98 out of 5 average rating, 201 reviews

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

Mar 21 – 28

G$25,652 GYD per night

Guest favorite

Apartment in Berwyn

4.92 out of 5 average rating, 148 reviews

Friendly Rock ’n’ Roll Retreat

Jan 3 – 10

G$22,089 GYD per night

Guest favorite

Guesthouse in Oak Park

4.99 out of 5 average rating, 72 reviews

Stylish Coachhouse in lovely Oak Park!

Apr 20 – 27

G$27,550 GYD per night

Show all

Other great vacation rentals in Oak Park

Guest favorite

Apartment in Oak Park

5.0 out of 5 average rating, 7 reviews

Spacious Kng Bed Free pkng perfect 4 long stays

Jan 31 – Feb 7

G$27,389 GYD per night

Guest favorite

Apartment in Oak Park

4.97 out of 5 average rating, 30 reviews

2BR/2BA Oak Park Gem - Ideal Comfort

Dec 3 – 10

G$36,405 GYD per night

Guest favorite

Guesthouse in Oak Park

4.91 out of 5 average rating, 66 reviews

Sunny Coach House in Historic Oak Park

Mar 12 – 19

G$31,582 GYD per night

Guest favorite

Apartment in Forest Park

4.87 out of 5 average rating, 15 reviews

City-Accessible Basement Retreat

Dec 20 – 27

G$18,453 GYD per night

Guest favorite

Apartment in Oak Park

4.95 out of 5 average rating, 41 reviews

First floor of Historic Oak Park Villa / 2Car Grge

Feb 7 – 14

G$31,201 GYD per night

Guest favorite

Apartment in Oak Park

5.0 out of 5 average rating, 19 reviews

The Artist's Loft - Oak Park

Mar 13 – 20

G$33,694 GYD per night

Guest favorite

Apartment in Forest Park

4.96 out of 5 average rating, 79 reviews

1 bedroom garden apartment in Forest Park

Feb 26 – Mar 5

G$22,854 GYD per night

Guest favorite

Home in Berwyn

5.0 out of 5 average rating, 75 reviews

Retro Modern Bungalow | free parking | pets ok

Nov 12 – 19

G$27,783 GYD 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 condo rentals in Oak Park?
Experience the best of Oak Park with our condo rentals, starting at about $50 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 120 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 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

Apartment in Forest Park

Condo in Oak Park

Apartment in Oak Park

Guest suite in Chicago

Apartment in Forest Park

Apartment in Cicero

Apartment in Berwyn

Guesthouse in Oak Park

Other great vacation rentals in Oak Park

Apartment in Oak Park

Apartment in Oak Park

Guesthouse in Oak Park

Apartment in Forest Park

Apartment in Oak Park

Apartment in Oak Park

Apartment in Forest Park

Home in Berwyn

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 condo rentals in Oak Park?

Do house 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