Oak Park Vacation Rentals

Our Favorite Vacation Rentals in Oak Park

  • Celebrity
    NiceHome/Apartment
    Booking.com
    From
    $114
  • Condo
     2br Home/Apartment
    HolidayLettings
    From
    $556
  • Beautiful Room in Chicago
    NiceFamily Stay
    Booking.com
    From
    $70
  • Make It Your Own - 15 Minutes to Chicago
     Home/Apartment
    HolidayLettings
    From
    $168
  • 3128 w lexington
     Home/Apartment
    Booking.com
    From
    $399
  • Dorothy's Place
     3br Home/Apartment
    HolidayLettings
    From
    $200
  • Huy Lyndale 2R NEW Logan Square WiFi Watch Cubs!
     Home/Apartment
    Booking.com
    From
    $165
  • Comfy Quarters
     Home/Apartment
    HolidayLettings
    From
    $243

Check prices for these upcoming dates

Oak Park Vacation Rentals with Wi-Fi

  • Little Gem Double Rm Home Base for Chicago Trips!
    ExcellentHome/Apartment
    Airbnb
    From
    $62
  • Peaceful Oak Park Condo Next to Green Line Metro
    Excellent3br Home/Apartment
    Airbnb
    From
    $240
  • Getaway to Historic Oak Park, Large 3BR Flat
    Excellent3br Home/Apartment
    Airbnb
    From
    $190
  • Cozzy Corner 1
    Excellent2br Home/Apartment
    Airbnb
    From
    $114

Oak Park Pet-Friendly Vacation Rentals

  • 2 BR apartment near O'Hare
     2br Home/Apartment
    HolidayLettings
    From
    $139
  • Resort Like Building 3 bedrooms 2 Bath indoor swiming pool, tennis court, shoppi
     3br Home/Apartment
    HolidayLettings
    From
    $773
  • Brand New Garden Level Room in Chicago
     Home/Apartment
    HolidayLettings
    From
    $60
  • Oak Park Full Kitchen, Entire house to yourself
     4br Home/Apartment
    Airbnb
    From
    $214

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

Most expensive
Most availability
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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 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 Weather in Oak Park

Rainy days
95 º42
2
88 º28
6
53 º18
2
54 º17
3
60 º-10
1
66 º-1
4
60 º22
1
80 º21
1
96 º45
4
95 º52
8
95 º61
2
96 º60
4
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Rainy days

This climate histogram shows you the weather patterns in Oak Park. The hottest month in Oak Park is May, when temperatures peak at 96 ˚F. The coolest month is December, when temperatures drop to -10 ˚F. The wettest month in Oak Park is July with 7.6 inches of rain, while the driest month is December with 0.91 inches of rain.

What Expert Travelers Think

  • — I use and I recommend AllTheRooms because it is a complete platform. It helps to save a lot of time, it gives all the main information about price, location, and features. In a few steps, I can easily find the best place to stay according to my criteria.

    My Anasa
    My AnasaMy Anasa
  • — Whenever I am making travel plans I always use comparison sites to find the best accommodation for us at the best price. Whether it be for hotel stays or private rentals AllTheRooms makes this so much easier and quicker as it brings all my searches into one place, with a great offering of options

    Sarah Pool
    Sarah PoolTammymum
  • — The great thing about AllTheRooms is their ability to cover all bases. If you are travelling solo, with a partner, friends or even a larger family. There is something there for everyone and that is a hugely powerful tool that I believe it boasts moreso than competitors.

    Max Hobbs
    Max HobbsLTL Mandarin School

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