Oak Park Vacation Rentals from $75: Search Short-Term Rentals

Q: Are there vacation rentals in Oak Park?

Yes, we have vacation rentals in Oak Park close to Oak Park Conservatory, or you can choose a secluded option if you're looking for extra privacy while you relax. Tourists like the array of shops and top-notch restaurants in Oak Park. While you're here, grab a bite or have a drink at the cafes.

Q: What are some of the best vacation rentals that Oak Park has to offer?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line : This vacation home rental outside of Oak Park is located in the city center and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

Q: How many vacation rentals are there in Oak Park?

With 28 Expedia vacation rentals, you're sure to find just the right place for your Oak Park stay.

Q: What’s there to see and do in Oak Park?

Cultural attractions include Ernest Hemingway Museum and House and Madison Street Theatre, whereas Oak Park Conservatory and Mills Park are a couple of picturesque spots to enjoy the outdoors. Other popular places to visit in the area include Wrigley Field and Soldier Field.

Q: What’s a vacation rental in Oak Park like?

Vacation rentals are private properties you can stay in for several days or longer in Oak Park. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll feel right at home. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from public hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for a small group gathering.

Check prices for these dates

In two weeks

In two months

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In four months

Our top choices for Oak Park vacation rentals

A modern living room with a grey sofa, white and patterned cushions, a round coffee table, and a ceiling fan.

1. Chic Suite/Mins to L Train /Laundry/Free Parking

Oak Park

Makenna

$181 nightly

Nov 17 - Nov 18

Total with taxes and fees

2. Stylish Luxe King bed w/Free Parkng near DT Oak Pk

Oak Park

Robin D.

$194 nightly

Nov 17 - Nov 18

Total with taxes and fees

A modern living room with a grey sofa, two armchairs, a coffee table, and a dining area with a wooden table and chairs.

3. Luxury Retreat w/ King Bed, 3-in-1 Pool Table, 15 Min to Chicago, Free Parking

Oak Park

"We had a very good stay overall and would definitely consider staying here again. The price was excellent for the location, and it was only about a 15–20 minute walk to the train, making it easy to get into the city. The neighborhood felt safe and had several great restaurants nearby.The unit is in an older apartment building, but it’s clear the hosts are putting effort into updating it, and we appreciated the improvements they’ve already made. The host was also very responsive and easy to...

K G.

$216 nightly

Nov 28 - Nov 29

Total with taxes and fees

A spacious living room with a grand piano, a comfortable sofa, and a dining area with a chandelier.

4. Historic Oak Park Home

Oak Park

Janette

$311 nightly

Nov 16 - Nov 17

Total with taxes and fees

A single-story house with a covered porch, a front door, and a small garden area.

5. Private Coach House in FLW District w/ Theater, Arcade & Kid-Friendly Yard

Oak Park

Willow M.

$326 nightly

Dec 1 - Dec 2

Total with taxes and fees

A garage with a white door, brick pillars, and a car parked inside.

6. Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage Parking

Oak Park

$318 nightly

Nov 13 - Nov 14

Total with taxes and fees

A modern living room with a large flat-screen TV, a brown sofa, a wooden coffee table, and a potted orchid.

7. Oak Park 3BR/2BA Walk to Frank Lloyd Wright & Hemingway Home, 15 Min to Chicago

Oak Park

Brian T.

$412 nightly

Nov 15 - Nov 16

Total with taxes and fees

8. First floor of Historic Oak Park Villa, Grge:2Cars

Oak Park

Steve P.

$337 nightly

Nov 16 - Nov 17

Total with taxes and fees

A white two-story house with a porch, steps, and a small table with chairs.

9. Oak Park Victorian by FLW Studio

Oak Park

Margaret L.

$520 nightly

Dec 7 - Dec 8

Total with taxes and fees

A modern living room with a flat-screen TV, grey sofas, a coffee table, and a dining area with a table and chairs.

10. Comfy Premier Luxe Retreat with Free Parking

Oak Park

$220 nightly

Nov 16 - Nov 17

Total with taxes and fees

Two people playing croquet on a well-maintained lawn with a small white structure in the background.

11. At Home in Oak Park

Oak Park

Melissa

A modern dining area with a white table, chairs, and a chandelier. There is a painting on the wall and a plant on the sideboard.

12. Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

Belmont Cragin

Jacob

$294 nightly

Nov 15 - Nov 16

Total with taxes and fees

A dining area with a table set for two, a black leather sofa, and a ceiling fan.

13. Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

Berwyn

Cynthia M.

$165 nightly

Nov 16 - Nov 17

Total with taxes and fees

A modern living room with a blue sofa, a patterned rug, and a television.

14. Great Area Logan Square Apt Games Pets - Sleeps 5

Avondale

Deborah J.

$176 nightly

Nov 16 - Nov 17

Total with taxes and fees

Step into a bright, airy space where comfort and style flow seamlessly from the cozy living area into a chic dining room. Whether you're curled up on the sectional with a blanket and coffee or gathering around the modern wood table for a meal with fr

15. Theater • Game Room • Gym • Firepit • 4BR Home

Belmont Cragin

Jason

$475 nightly

Nov 16 - Nov 17

Total with taxes and fees

A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

16. Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Maywood

Carl T.

$270 nightly

Nov 16 - Nov 17

Total with taxes and fees

A marble countertop with a cheese platter, grapes, nuts, and a bottle of wine.

17. Game Room • Fire-pit • Playground • Gym • Billiard

Belmont Cragin

Rhiannon

$415 nightly

Nov 17 - Nov 18

Total with taxes and fees

A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

18. Classic Forest Park Foursquare < 1 Mi to Blue Line

Forest Park

$444 nightly

Nov 16 - Nov 17

Total with taxes and fees

A desk with a computer monitor, keyboard, mouse, a lamp, a mug, a plant, and a clock.

19. Private Workspace • Sleeps 4 • Modern and Stylish

Irving Park

Karin S.

$274 nightly

Nov 21 - Nov 22

Total with taxes and fees

A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

20. Sleeps 18 • 8BR • Game Room • Gym • Theater

Portage Park

Anonymous traveler

$731 nightly

Nov 17 - Nov 18

Total with taxes and fees

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Top Oak Park Hotel Reviews

River Hotel

10/10 Excellent

"."

Congress Plaza Hotel

8/10 Good

"This is an older hotel with a lot of rooms, so I am never sure what to expect -- but this was a good stay. We stored our bags at the beginning and end of our stay with no problems. Our room was in the north tower and it had been refurbished. Beds were comfortable enough, and it was clean even if some parts of the room (i.e. doors and windows) show their age. You can't beat the location for sightseeing and it's close to multiple L stations. For a Bears home game weekend, the room was the most reasonably priced I could find downtown. It will never be the nicest hotel in downtown Chicago, but it quite often offers the best value."

Find out more about Oak Park

Everything you need to know about Oak Park vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oak Park vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oak Park vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oak Park vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oak Park. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Oak Park in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $75 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Oak Park rentals

At Expedia, we put the best Oak Park vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Oak Park rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oak Park vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oak Park. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Frequently asked questions

Are there vacation rentals in Oak Park?

Yes, we have vacation rentals in Oak Park close to Oak Park Conservatory, or you can choose a secluded option if you're looking for extra privacy while you relax. Tourists like the array of shops and top-notch restaurants in Oak Park. While you're here, grab a bite or have a drink at the cafes.

What are some of the best vacation rentals that Oak Park has to offer?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This vacation home rental outside of Oak Park is located in the city center and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Oak Park?

With 28 Expedia vacation rentals, you're sure to find just the right place for your Oak Park stay.

What’s there to see and do in Oak Park?

Cultural attractions include Ernest Hemingway Museum and House and Madison Street Theatre, whereas Oak Park Conservatory and Mills Park are a couple of picturesque spots to enjoy the outdoors. Other popular places to visit in the area include Wrigley Field and Soldier Field.

What’s a vacation rental in Oak Park like?

Vacation rentals are private properties you can stay in for several days or longer in Oak Park. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll feel right at home. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from public hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for a small group gathering.

Oak Park Vacation Rentals

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Check prices for these dates

Our top choices for Oak Park vacation rentals

1. Chic Suite/Mins to L Train /Laundry/Free Parking

2. Stylish Luxe King bed w/Free Parkng near DT Oak Pk

3. Luxury Retreat w/ King Bed, 3-in-1 Pool Table, 15 Min to Chicago, Free Parking

4. Historic Oak Park Home

5. Private Coach House in FLW District w/ Theater, Arcade & Kid-Friendly Yard

6. Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage Parking

7. Oak Park 3BR/2BA Walk to Frank Lloyd Wright & Hemingway Home, 15 Min to Chicago

8. First floor of Historic Oak Park Villa, Grge:2Cars

9. Oak Park Victorian by FLW Studio

10. Comfy Premier Luxe Retreat with Free Parking

11. At Home in Oak Park

12. Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

13. Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

14. Great Area Logan Square Apt Games Pets - Sleeps 5

15. Theater • Game Room • Gym • Firepit • 4BR Home

16. Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

17. Game Room • Fire-pit • Playground • Gym • Billiard

18. Classic Forest Park Foursquare < 1 Mi to Blue Line

19. Private Workspace • Sleeps 4 • Modern and Stylish

20. Sleeps 18 • 8BR • Game Room • Gym • Theater

Find vacation rentals that suit your style

Top Oak Park Hotel Reviews

River Hotel

Find out more about Oak Park

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