Oak Park Vacation Rentals from AED 226: 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.

A historic house with a porch, a tower, and a sign indicating it is the birthplace of Ernest Hemingway.

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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

AED 778 total

includes taxes & fees

18 Nov - 19 Nov

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

Oak Park

Robin D.

AED 816 total

includes taxes & fees

17 Nov - 18 Nov

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.

AED 959 total

includes taxes & fees

30 Nov - 1 Dec

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

AED 1,309 total

includes taxes & fees

16 Nov - 17 Nov

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.

AED 1,576 total

includes taxes & fees

14 Dec - 15 Dec

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

AED 1,337 total

includes taxes & fees

14 Dec - 15 Dec

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.

AED 1,733 total

includes taxes & fees

15 Nov - 16 Nov

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

Oak Park

Steve P.

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.

AED 2,186 total

includes taxes & fees

7 Dec - 8 Dec

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

AED 933 total

includes taxes & fees

14 Dec - 15 Dec

A two-story house with a brick exterior, a sloped roof, and a front porch.

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

AED 1,335 total

includes taxes & fees

15 Nov - 16 Nov

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.

AED 648 total

includes taxes & fees

17 Nov - 18 Nov

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.

AED 709 total

includes taxes & fees

16 Nov - 17 Nov

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

AED 2,118 total

includes taxes & fees

16 Nov - 17 Nov

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.

AED 1,059 total

includes taxes & fees

16 Nov - 17 Nov

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

AED 1,800 total

includes taxes & fees

17 Nov - 18 Nov

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

AED 1,744 total

includes taxes & fees

16 Nov - 17 Nov

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.

AED 1,187 total

includes taxes & fees

21 Nov - 22 Nov

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

AED 3,269 total

includes taxes & fees

17 Nov - 18 Nov

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Find vacation rentals that suit your style

Top Oak Park Hotel Reviews

A well-lit hallway with a wooden dresser, a table with chairs, and a blue patterned rug.

Harvey House Bed & Breakfast

Oak Park

10/10 Excellent

Even though it was our first time there, we were greeted and treated like old friends. It is obvious that the staff strives to make your stay the most comfortable experience possible. It is the little details that caught my eye, for instance, there is a copy of the Jimmy Stewart movie Harvey in each room (the name is The Harvey House). A honors bar on the landing. A complete array of personal items such as bath salts and body soaps in your room. Bath robes that are actually comfortable. If...

Rochelle

A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."

Carleton of Oak Park

Oak Park

10/10 Excellent

Lorel

Historic Oak Park Home

Oak Park

10/10 Excellent

judith

A modern dining area with tables and chairs, a reception desk, and a large screen wall.

Holiday Inn Express and Suites Chicago West Oak Park by IHG

Oak Park

10/10 Excellent

Garry

A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

10/10 Excellent

Jennifer

A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.

L7 CHICAGO by LOTTE HOTELS

Downtown Chicago

10/10 Excellent

Erin

An outdoor rooftop lounge with seating, planters, and a view of surrounding high-rise buildings.

Hampton Inn Chicago West Loop Fulton Market Area

Downtown Chicago

10/10 Excellent

We will definitely be staying here again! Great location, clean room, and great service. They even have a great complimentary breakfast which is a must have in a city like Chicago. The staff was great also. We had to switch trains for an earlier one due to weather and got into Chicago in the AM. Check in is 4pm and with two small children we were worried about what to do for hours but the staff helped us out and luckily had a room available.

Alexander

A hotel lobby with a bar area, a chandelier, and a reception desk.

Residence Inn Chicago Downtown/Loop

Downtown Chicago

10/10 Excellent

Sergio

A hotel with a modern glass facade, signage for SpringHill Suites, and a well-lit entrance.

Springhill Suites by Marriott Chicago Downtown/ River North

Downtown Chicago

10/10 Excellent

Recently stayed at the Springhill Suites/River North. Could not have picked a better location for the first time in Chicago. Tons of local dining options. Close to landmarks. Easily walked to the Magnificient Mile(Michigan Ave) Walked to the subway to go to Wrigley Field and the United Center. Hotel was excellent. Clean, the staff was excellent in all areas. Free breakfast was fresh and good. Highly recommend overall.

Michael

A modern hotel with a colorful awning and a glass facade.

Aloft by Marriott Chicago Downtown River North

Downtown Chicago

10/10 Excellent

stephen

An outdoor seating area with a fire pit, wooden benches, and tables, surrounded by large windows and string lights.

The Emily Hotel

Downtown Chicago

10/10 Excellent

Marvene

A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

10/10 Excellent

blerina

The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.

Hotel Riu Plaza Chicago

Downtown Chicago

10/10 Excellent

We chose this hotel last minute and we were nervous because there were a couple recent negative reviews. There were 4 of us in our family and couldn't find anything negative to say about the hotel. The only disappointing fact was that the rooftop bar was not open but that wasn't a big deal. Everything was very clean. I actually wiped the floor in our room with a wet, white wash cloth, it was clean! There was no hair in the bathroom from a previous guest. There was no hair in the bed from a...

Donna

A corridor with ornate black metal railings and a patterned carpet.

Staypineapple, An Iconic Hotel, The Loop

Downtown Chicago

10/10 Excellent

Natalya

A modern dining area with round tables and chairs, large windows, and a view of a cityscape.

Sofitel Chicago Magnificent Mile

Downtown Chicago

10/10 Excellent

Denine

A rooftop terrace with outdoor seating, a pergola, and a view of surrounding high-rise buildings.

Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

Downtown Chicago

10/10 Excellent

Lyn

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

Change your mind

Treat yourself

Be picky

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

Harvey House Bed & Breakfast

10/10 Excellent

Frequently Asked Questions

Are there vacation rentals in Oak Park?

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

How many vacation rentals are there in Oak Park?

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

What’s a vacation rental in Oak Park like?