Oak Park Vacation Rentals

Compare 59 available properties from 18 providers
Oak Park
Save up to 45%

Best Vacation Home Deals in Oak Park

-21%
e.g. 10/20 - 10/27
Apartment ∙ 4 guests ∙ 2 bedrooms
Oak Park, Oak Park Township, Illinois, United States
from $159 $201
VRBO
4.3
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-45%
e.g. 1/26 - 2/2
House ∙ 5 guests ∙ 2 bedrooms
Oak Park, Oak Park Township, Illinois, United States
from $122 $221
VRBO
4.9
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-17%
e.g. 1/19 - 1/26
House ∙ 8 guests ∙ 3 bedrooms
Oak Park, Oak Park Township, Illinois, United States
from $137 $166
VRBO
4.8
View deal

Discover a vacation home fitting your preferences among the 59 fantastic vacation rentals from several vacation rental websites in Oak Park. HomeToGo immediately shows the best offers by comparing all of the available vacation homes in Oak Park from 18 different providers.

Recommended Vacation Rentals in Oak Park

Rent a vacation accommodation in Oak Park: from $27 per night

House ∙ 6 guests ∙ 3 bedrooms
Oak Park, Oak Park Township, Illinois, United States
from $159
VRBO
4.8
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Apartment ∙ 4 guests ∙ 1 bedroom
Oak Park, Oak Park Township, Illinois, United States
from $115
VRBO
4.6
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Apartment ∙ 4 guests ∙ 2 bedrooms
Oak Park, Oak Park Township, Illinois, United States
from $159
VRBO
4.3
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Apartment ∙ 8 guests ∙ 3 bedrooms
Oak Park, Oak Park Township, Illinois, United States
from $140
VRBO
5.0
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Apartment ∙ 6 guests ∙ 2 bedrooms
Forest Park, Proviso Township, Illinois, United States
from $98
VRBO
4.9
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Apartment ∙ 5 guests ∙ 2 bedrooms
Montclare, Chicago, Illinois, United States
from $147
HomeAway.com.sg
4.0
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Apartment ∙ 5 guests ∙ 3 bedrooms
South Austin, Chicago, Illinois, United States
from $124
VRBO
5.0
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Apartment ∙ 6 guests ∙ 2 bedrooms
Chicago, Cook County, Illinois, United States
from $100
Wimdu
5.0
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Vacation Houses With Pools

Pool
House ∙ 5 guests ∙ 2 bedrooms
Oak Park, Oak Park Township, Illinois, United States
from $122
VRBO
4.9
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Pool
House ∙ 8 guests ∙ 3 bedrooms
Oak Park, Oak Park Township, Illinois, United States
from $137
VRBO
4.8
View deal
Pool
Apartment ∙ 7 guests ∙ 2 bedrooms
Elmwood Park, Leyden Township, Illinois, United States
from $193
VRBO
4.9
View deal
Pool
House ∙ 11 guests ∙ 4 bedrooms
Elmwood Park, Leyden Township, Illinois, United States
from $268
VRBO
4.9
View deal
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Popular Rental Amenities in Oak Park

  • Internet (35)
  • Kitchen (32)
  • TV (32)
  • No smoking (32)
  • AC (31)
  • Parking (30)
  • Microwave (21)
  • Washer (19)
  • No pets (16)
  • Grill (16)
  • Dishwasher (15)
  • Yard (12)
Properties can be chosen based on the amenities they offer. Above, you will find the number of rentals that offer a specific feature in Oak Park. HomeToGo's data shows that "internet" and "TVs" are the most commonly provided features in Oak Park. Plan your vacation in advance if you plan to go fishing or you like to end your days curled up by the fire. There are just 3 listed rentals providing "fishing" and 6 rentals providing "fireplaces."

The Weather in Oak Park

34°
19°
36°
21°
48°
32°
59°
41°
73°
54°
81°
63°
84°
68°
84°
68°
77°
61°
64°
48°
50°
36°
39°
27°
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Check out our climate diagram to find the perfect month for your vacation. July is the warmest month in Oak Park with average maximum temperatures of 84°. However, temperatures can go lower than 19° in Oak Park in January. December is the wettest month.

20 of the 59 listed properties in Oak Park are apartment rentals. They account for nearly half of the property types in this destination (48.78%). Additionally, these vacation accommodations have a median size of 1,810 ft² as well as an average price of $162 per night. Moreover, this type of residence is the perfect choice for medium-sized groups and families, as the majority of apartment rentals can accommodate 5 guests. If you would prefer something else, you can look for many other offers, such as house rentals, which are another typical type of property in Oak Park. While apartment rentals in Oak Park have an average size of 1,810 ft², house rentals have an average size of 1,520 ft².
Show all 59 properties
Art & Culture

Turn-of-the-century architecture

Oak Park was home to the premiere architects of America's Prairie School, including Louis Sullivan, George W, Maher, and most famously Frank Lloyd Wright. Of course, this makes the street scenes of Oak Park an inspiring setting of living history.

A 15-minute walk from downtown will lead you to Frank Lloyd Wright's lodgings and office. The museum provides an intimate portrayal of the Mission Movement creator – he designed his home with clean edges, expansive spaces, and open layouts. Daily tours will walk you through the life of the famed architect.

You can also tour the Maher-designed Pleasant Home on the south side of town. It is the only building of his open to the public. His Prairie style was a precursor to Wright's simplistic methods – creating that basic frame of straight lines and smooth curves with minute details. The site regularly hosts live music from touring and local musicians, lectures, and various film screenings.

Family Activities

Oak Park spurs the imagination

Because Oak Park offers a small-town feel, family-friendly activities are plentiful. From communing with nature to fostering your child's imagination, Oak Park always has something up its sleeve on those days when your kids are bored and you're out of ideas!

Established in 1929, the Oak Park Conservatory boasts 3 different greenhouses; one dedicated to the desert, tropical and Mediterranean landscapes. Some of their plants are over 80 years old. Age-appropriate workshops and field trips are scheduled regularly, along with wine nights for the parents

About a 10-minute drive from the downtown area, you will find a treasure for kids: Wonder Works. This hands-on children's museum fosters learning through art, performance, design, and building. With interactive imaginary play areas and an organic garden, children will thrive in this haven for playful learning.

Oak Park is a diverse town. While it may seem that Chicago overshadows the perks of this municipality, "the OP" holds it own!

We compare more than 300 providers, including:

Booking.com Vacation Rentals in Oak Park VRBO Vacation Rentals in Oak Park HomeAway Vacation Rentals in Oak Park TripAdvisor Vacation Rentals in Oak Park VacationRentals.com Vacation Rentals in Oak Park HouseTrip Vacation Rentals in Oak Park FlipKey Vacation Rentals in Oak Park Wimdu Vacation Rentals in Oak Park 9flats.com Vacation Rentals in Oak Park VaycayHero Vacation Rentals in Oak Park PerfectPlaces.com Vacation Rentals in Oak Park Homestay.com Vacation Rentals in Oak Park only-apartments Vacation Rentals in Oak Park Interhome Vacation Rentals in Oak Park Bedycasa Vacation Rentals in Oak Park Novasol Vacation Rentals in Oak Park HomeEscape Vacation Rentals in Oak Park

Vacation Destinations Near Oak Park