Oak Park Vacation Rentals

Our Favorite Vacation Rentals in Oak Park

  • Cozy Bedroom with City access via public transit
     Family Stay
    Booking.com
    From
    $54
  • Oak Park Beauty Sleeps 1 to 8 Guests
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $223
  • 9Twenty-Eight
     Country House
    Booking.com
    From
    $220
  • Contemporart Celebrity themed private parking runs to downtown
     2br Home/Apartment
    HolidayLettings
    From
    $211
  • Hip and Trendy Condo in Logan Square, Near Wrigley HL3
     Home/Apartment
    Booking.com
    From
    $162
  • Oak Park Bungalow
    Good3br Home/Apartment
    HolidayLettings
    From
    $261
  • Perfect place to enjoy the city or just relax
     Home/Apartment
    Booking.com
    From
    $95
  • Make It Your Own - 15 Minutes to Chicago
     Home/Apartment
    HolidayLettings
    From
    $186

Check prices for these upcoming dates

Oak Park Vacation Rentals with Wi-Fi

  • Coachhouse in central OP 4 blk to L
    ExcellentHome/Apartment
    Airbnb
    From
    $122
  • Little Gem Double Rm Home Base for Chicago Trips!
    ExcellentHome/Apartment
    Airbnb
    From
    $63
  • Cozy Oak Park Hideaway
    Excellent2br Home/Apartment
    Airbnb
    From
    $107
  • Upscale Oak Park Flat, 3 BR + Deck, 13 min to CHI
    Excellent3br Home/Apartment
    Airbnb
    From
    $264

Oak Park Pet-Friendly Vacation Rentals

  • Luxe Chicago Townhome w/ Balcony - 20 Mins to DT!
     2br Home/Apartment
    HolidayLettings
    From
    $235
  • 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
    $37
  • Beautiful Room in Chicago
     Home/Apartment
    HolidayLettings
    From
    $37

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
51°
2
65° -2°
2
80° 27°
6
83° 42°
8
91° 51°
3
97° 62°
4
91° 60°
4
91° 57°
8
88° 26°
5
58°
1
62° 13°
1
55° -22°
1
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Rainy days

This climate histogram shows you the weather patterns in Oak Park. The warmest months in Oak Park are June and July, when temperatures reach 97 ˚F. The coolest month is December, when temperatures drop to -22 ˚F. The wettest month in Oak Park is August with 7.6 inches of rain, while the driest month is December with 1.1 inches of rain.

What Expert Travelers Think

  • — My favorite thing about AllTheRooms is that it combines both rentals and hotels available so you can see an entire view of what is available in a certain area. I was able to see listings on AllTheRooms that I never even saw on other travel sites!

    Daniella Flores
    Daniella FloresILIKETODABBLE
  • — I love that AllTheRooms has everything in one place when I need to find accommodations that fit my family. Plus it provides all the details I need to help me make the best choice. I often recommend AllTheRooms to friends and family visiting NYC and they agree that it’s a great. Such a time saver!

    Monica
    MonicaNYCTechMommy
  • — Like the buttons on the calendar which say today, tomorrow - that will make it easy for booking on the road. Website looks great - clean and easy to understand.

    Samantha Wragg
    Samantha WraggCoco Travels

Vacation Rentals in Oak Park

Find the perfect accommodation for your trip at AllTheRooms.com. We aggregate Airbnb, Priceline, Bed and Breakfast and more. AllTheRooms has 239 vacation rentals, hotels and other great places to stay during your time in Oak Park, with everything from budget hostels and homestays to extravagant Airbnbs and hotels. A vacation in Oak Park can be budget-friendly - our lowest price accommodation is available at $15 a night. An average vacation rental in Oak Park costs on average $103 per night.

Those needing to get some work done during their trip to Oak Park can pick from 180 places to stay that provide WiFi. 22 places to stay include a breakfast. Fitness fanatics can get a workout in during their stay by choosing from 8 accommodations that have gyms. If you are driving to Oak Park, you'll want to pick from 163 places to stay that provide parking.

Those traveling with a dog, cat or some other animal can stay in any of 20 accommodations that are designated as pet-friendly.

187 accommodations in Oak Park have been reviewed; 73% are rated excellent or good. You can instantly book any of 79 places to stay right now.

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