$28 Cheap Flights to Oak Park, IL

View $28 flight on Tue, Oct 14, 2025Opens in a new window

Popular airlines to Oak Park

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How much is the cheapest flight to Oak Park?

Prices were available within the past 7 days and start at $28 for one-way flights and $76 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Tue, Oct 7 - Wed, Oct 29
ATL
Atlanta
MDW
Chicago
$76 Roundtrip, found 3 days ago
$76
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Oct 7 from Atlanta to Chicago, returning Wed, Oct 29, priced at $76 found 3 days ago
Spirit Airlines
Sat, Oct 4 - Wed, Oct 8
LGA
New York
ORD
Chicago
$76 Roundtrip, found 1 hour ago
$76
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sat, Oct 4 from New York to Chicago, returning Wed, Oct 8, priced at $76 found 1 hour ago
Southwest Airlines
Sat, Jan 10 - Wed, Jan 14
DAL
Dallas
MDW
Chicago
$127 Roundtrip, found 6 days ago
$127
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sat, Jan 10 from Dallas to Chicago, returning Wed, Jan 14, priced at $127 found 6 days ago
American Airlines
Tue, Oct 21 - Wed, Oct 22
ATL
Atlanta
RFD
Rockford
$139 Roundtrip, just found
$139
Roundtrip
just found
Select American Airlines flight, departing Tue, Oct 21 from Atlanta to Rockford, returning Wed, Oct 22, priced at $139 just found
Contour Airlines
Sun, Oct 5 - Wed, Oct 8
DFW
Dallas
ORD
Chicago
$189 Roundtrip, just found
$189
Roundtrip
just found
Select Contour Airlines flight, departing Sun, Oct 5 from Dallas to Chicago, returning Wed, Oct 8, priced at $189 just found

Find the cheapest month to fly from Columbus (CMH) to Chicago (ORD)

July is typically the cheapest month to fly

From $77 - $262 per traveler.

Tips to find the cheapest flights to Oak Park

The cheapest day to fly

Get started finding a cheap flight to Oak Park on Expedia by either choosing a deal on this page or entering into the search bar your travel dates, origin airport, and whether you want roundtrip or one-way airfare. You can filter for flexibility, number of stops, airline, and departure/arrival times to find the best flight for you.

The cheapest month to fly

October is the cheapest month to fly to Oak Park. This coincides with the low season when fewer people travel. Whichever month you travel in, though, be sure to book at least a month in advance if you want to score cheap tickets to Oak Park. ARC's data shows that domestic flights booked 28 days or more before departure are typically 24% cheaper than those booked last minute.

The most affordable time to book a flight

Typically, a Sunday can be the cheapest time to book a flight to Oak Park, according to ARC’s data. On average, you could save between 6% and 13% by booking on a Sunday instead of a Friday, which is the most expensive day to make a reservation.

The cheapest round-trip tickets to Oak Park

The lowest price for round-trip flights to Oak Park in 2025 starts from from $76, while one-way tickets start from from $28. Expedia's effective search tool is one of the best ways to find a budget airfare. Simply enter your dates, and within seconds, it'll show you a vast selection of the cheapest flights to Oak Park. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to Oak Park

Spirit Airlines, Frontier Airlines, Southwest Airlines, American Airlines, United, Contour Airlines are just some of the airlines that can typically offer cheap tickets to Oak Park. You can find their most affordable flights by using the “airline” search filter and then sorting prices from low to high. As a trusted partner of the world's leading airlines, Expedia offers you some of the best airfare deals to Oak Park and countless more destinations worldwide.

The most affordable airports to fly into

To view the cheapest airports to fly into for Oak Park, simply order your search results from lowest to highest price. Expedia's search tool compares flight prices for all airports close to your destination, so you don't have to manually search them one by one to find the cheapest flight to Oak Park. If you have a preferred place to fly into, take advantage of the “arrival airport” filter to narrow down your search on Expedia.

Save with a package

With Expedia's amazing package deals, you could save hundreds of dollars by booking your Oak Park plane tickets together with your accommodations, car rental, or activities. Just select the search wizard's “package” option to view some of the cheapest deals. Look out for the green savings label to see how much you're saving.

Date flexibility for the cheapest flights to Oak Park

If you can be flexible with your travel dates, it's a good idea to broaden your search by comparing prices on different days. This will open up more options, meaning you could uncover a less expensive flight to Oak Park.

Stopover savings

The cheapest tickets to Oak Park are sometimes those with a stopover. Book one of these flights, and you'll change planes at an airport en route to Oak Park. While the overall travel time might be longer than a non-stop flight, you may decide it's worth it for the money saved.

Get Expedia's Price Drop Protection

Price Drop Protection means that if your flight gets cheaper after booking, you'll be credited the difference*. This gives you peace of mind that you're getting one of the cheapest flights to Oak Park for your chosen departure. Expedia's Price Drop Protection is available for a small fee but is free to One Key Gold and Platinum tier members.

*Terms apply.

Use our Price Tracking feature

Expedia's Price Tracking feature is another great tool that removes the guesswork from finding cheap flights to Oak Park. Simply download the free Expedia app to your smart device and activate Oak Park flight price alerts for your travel dates. There's even a price predictor tool that uses historical data to indicate the best time to book, giving you peace of mind that you'll nab the lowest prices.

Book with Expedia

As well as Price Drop Protection and Price Tracking, Expedia's close partnership with a vast selection of the world's leading airlines means you're sure to find cheap flights to Oak Park. Plus, the One Key rewards program lets you earn real cash rewards on most bookings that you can use to save money on future trips. Best of all, it's free to join, and members often unlock exclusive discounts, too.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

Frequently asked questions

What month is the cheapest to fly to Oak Park?
October is the cheapest month to travel to Oak Park. Demand is lower then, so you're likely to snag a great deal. Organizing your trip outside of major holidays and school breaks can also help you save.
Which US cities have the cheapest flights to Oak Park?
Score cheap flights to Oak Park from New York, Washington and Dallas. These cities typically offer the best fares to this top destination. But bear in mind that seasonality, demand and stopovers will also influence rates, so remain flexible and book when you see a bargain.
Which US cities fly direct to Oak Park?
There are 150 US destinations that you can fly to Oak Park directly from. Compare your options by using the "Direct flights only" filter on Expedia and choose the best starting point for your trip. Here are a few of the leading cities to head out from:

  • New York
  • Washington
  • Dallas
  • Boston
  • Phoenix

How to find a cheap flight to Oak Park?
Book early to score cheap flights to Oak Park. Also, consider visiting during off-peak months like January and February. If you jet off on a Thursday, you can save an average of 16% compared to departing on a Sunday.* Save time searching every day and set up a price alert on the Expedia app. We'll let you know when fares change.*Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
How to get a cheap last-minute flight to Oak Park?
Staying flexible with your travel plans can help you find last-minute deals on cheap flights to Oak Park. To see all the available options, try exploring different ticket types, changing your Oak Park vacation dates, jetting out of an alternative airport or using another carrier.
How far in advance should I book a flight to Oak Park?
Book your flight to Oak Park two to four months ahead if you're jetting in from an international destination. For domestic travel, the general guideline is 28 days in advance. Bigger savings and a greater choice of travel dates, times and seating options are some of the great reasons to book early.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which day of the week is the cheapest day to buy a plane ticket to Oak Park?
You'll save an average of 8% if you purchase tickets on a Sunday rather than Fridays, which tend to be the most expensive day to book.* When it comes to snapping up a cheap flight to Oak Park, the key is good timing.*Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which airlines fly to Oak Park?
Oak Park has connections to 216 airports worldwide through 44 airlines, with O'Hare Intl. Airport (ORD) as its chief entry point. Consider these top airlines to Oak Park when planning your trip:

  • United Airlines
  • American Airlines
  • Delta Air Lines
  • Alaska Airlines

Where do you fly into Oak Park?
Oak Park's main point of arrival is Midway Intl. Airport (MDW). If you want other nearby options when flying to Oak Park, consider O'Hare Intl. Airport (ORD), Lewis University Airport (LOT) or Chicago Executive Airport (PWK). It's also possible to fly to Oak Park through Dupage Airport (DPA).
How far is the airport from central Oak Park?
If you're jetting into Midway Intl. Airport (MDW), you'll be about 7 mi south of the center of Oak Park.
Can I save money by booking an Oak Park trip package?
Bundle your flight and hotel and you could save hundreds of dollars. Better yet, you can add extras like car rentals and tours to your Oak Park flight and hotel package deal. With Expedia, it's simple to organize all your Oak Park travel arrangements in one place.
Can I change or cancel my flight to Oak Park?
You can typically change or cancel your flight to Oak Park within 24 hours of booking. However, be mindful that some flights are non-refundable. In those cases, you may receive a credit toward future flights rather than a direct refund. It's important to check the airline's terms of service in your itinerary for exact details. Use Expedia's "No cancel fee" or "Changes included" filters when you search to find cheap flights to Oak Park with flexible change policies. For additional information, browse our Customer Service Portal.
How far is ORD from central Oak Park?
If you plan on staying in central Oak Park, it's a good idea to arrange how you'll get into the city before you arrive. The downtown area is 9 miles from ORD.
What airport is best to fly into Oak Park?
There are two major airports that service Oak Park. ORD is approximately 9 miles from the downtown area, while Midway Intl. Airport (MDW) is around 7 miles away. As soon as you check prices and find out where you're staying, you'll have a better idea of which to touchdown at.
How many nonstop flights are there to Oak Park?
With approximately 7,564 nonstop flights operating every week, you'll be hitting the tarmac in Oak Park before you can ask, "Are we there yet?"
Where are the most popular flights to Oak Park departing from?
Travelers frequently depart from New York, Washington and Dallas airports when going to Oak Park.
Flights to Oak Park information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Destination city name
Chicago
Roundtrip price
$70

Trending flights to Oak Park

Prices were available within the past 7 days and start at $28 for one-way flights and $76 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Sat, Oct 4 - Wed, Oct 8
LGA
New York
ORD
Chicago
$76 Roundtrip, found 1 hour ago
$76
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sat, Oct 4 from New York to Chicago, returning Wed, Oct 8, priced at $76 found 1 hour ago

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*Available to One Key members.