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Oak Park Vacation Rentals

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  2. United States of America
  3. Illinois
  4. Oak Park

Our Favorite Vacation Rentals in Oak Park

  • Bangtel's The Playhouse
    Bangtel's The Playhouse
     
    Booking.comFrom $900
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  • Condo
    Condo
     
    HolidayLettingsFrom $556
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  • Gorgeous Garden Unit Hideaway
    Gorgeous Garden Unit Hideaway
     
    Booking.comFrom $195
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  • Contemporart Celebrity themed private parking runs to downtown
    Contemporart Celebrity themed private parking runs to downtown
     
    HolidayLettingsFrom $211
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  • Comfy room, Safe area & FREE PARKING!
    Comfy room, Safe area & FREE PARKING!
    Good
    Booking.comFrom $105
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  • Make It Your Own - 15 Minutes to Chicago
    Make It Your Own - 15 Minutes to Chicago
     
    HolidayLettingsFrom $186
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  • Charming Apartments Near Downtown Chicago
    Charming Apartments Near Downtown Chicago
    Nice
    Booking.comFrom $150
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  • Dorothy's Place
    Dorothy's Place
     
    HolidayLettingsFrom $215
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See all 185 deals in Oak Park

Oak Park Vacation Rentals with a Pool

  • Garden oasis on 4 private lots humboldt park
    Garden oasis on 4 private lots humboldt park
    Excellent
    AirbnbFrom $185
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See all deals in Oak Park with a pool

Oak Park Vacation Rentals with Wi-Fi

  • Little Gem Double Rm Home Base for Chicago Trips!
    Little Gem Double Rm Home Base for Chicago Trips!
    Excellent
    AirbnbFrom $73
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  • Vintage Entire Apartment Retreat
    Vintage Entire Apartment Retreat
    Excellent
    AirbnbFrom $184
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  • 1 bedroom 1 bathroom apartment #40-1
    1 bedroom 1 bathroom apartment #40-1
    Excellent
    AirbnbFrom $118
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  • Flexible Apt. for 8 by Oak Park-CHI
    Flexible Apt. for 8 by Oak Park-CHI
    Excellent
    AirbnbFrom $211
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See all deals in Oak Park with WiFis

Oak Park Pet-Friendly Vacation Rentals

  • Host Dinner at a Radiant Home with a Spacious Roof Patio
    Host Dinner at a Radiant Home with a Spacious Roof Patio
    Excellent
    AirbnbFrom $468
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  • Urban Farm Fun 2!
    Urban Farm Fun 2!
    Good
    AirbnbFrom $146
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  • Delve into Humboldt Pk & Logan Sq area in Luxury
    Delve into Humboldt Pk & Logan Sq area in Luxury
    Excellent
    AirbnbFrom $333
    View Deal
See all deals in Oak Park that allow pets

Oak Park Travel Guide

Oak Park, Illinois is a small, residential village just next to the West Side of Chicago. It’s best known as a quiet place to stay with easy access to all the Windy City has to offer. The town has a population of 50,000 residents, and is bursting with history.

Things to Do in Oak Park

If you’re visiting Oak Park, you’ll be able to visit all the best of Chicago, but don’t miss out on some of the town’s great sites, either! The Brookfield Zoo is home to nearly 5,000 animals and is open every day. The Cernan Earth and Space is great for the budding astronaut in you, and the Ernest Hemingway Birthplace is the perfect site for any good bookworm. Don’t miss out on the Frank Lloyd Wright Home and Studio tour. Garfield Conservatory is another popular site with thousands of plants and flower types.

Best Time to Visit Oak Park

The best time to visit Oak Park, Illinois is from April to September to enjoy the best of the warm weather.

Price and Availability in Oak Park

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The most expensive month to stay in a vacation rental in Oak Park is in December, while the cheapest month is in April. The most popular time to book a vacation rental in Oak Park is in the high season in July. Oak Park has its low season in January, when less people are visiting and the vacation home occupancy rate drops.
The cheapest day to stay at a vacation rental in Oak Park tends to be Tuesday, while the most expensive day tends to be Saturday. Vacation homes in Oak Park tend to be busiest on Fridays, while it tends to be much quieter on Tuesdays.

The Weather in Oak Park

95º 52º
7.6
95º 61º
1.94
96º 60º
4
95º 42º
2.32
88º 28º
6.26
53º 18º
2.15
54º 17º
2.51
60º -10º
0.91
66º -1º
4.39
60º 22º
1.27
80º 21º
1.43
96º 45º
4.19
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Rainy days
This climate histogram shows you the weather patterns in Oak Park. The hottest month in Oak Park is August, when temperatures peak at 96 ˚F. The coolest month is January, when temperatures drop to -10 ˚F. The wettest month in Oak Park is June with 7.6 inches of rain, while the driest month is January with 0.91 inches of rain.

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