$28 Cheap Flights to Countryside, IL

View $28 flight on Tue, Mar 17, 2026Opens in a new window

Popular airlines to Countryside

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Today's featured flight deals to Countryside

Nonstop
Carry-on included
Lower price than typical

How much is the cheapest flight to Countryside?

Prices were available within the past 7 days and start at $28 for one-way flights and $56 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Mon, Mar 16 - Tue, Mar 24
JFK
New York
ORD
Chicago
$56 Roundtrip, just found
$56
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, Mar 16 from New York to Chicago, returning Tue, Mar 24, priced at $56 just found
Spirit Airlines
Wed, Mar 18 - Wed, Mar 25
EWR
New York
ORD
Chicago
$58 Roundtrip, just found
$58
Roundtrip
just found
Select Spirit Airlines flight, departing Wed, Mar 18 from New York to Chicago, returning Wed, Mar 25, priced at $58 just found
American Airlines
Tue, Apr 14 - Sat, Apr 18
EWR
New York
RFD
Rockford
$147 Roundtrip, found 20 hours ago
$147
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Tue, Apr 14 from New York to Rockford, returning Sat, Apr 18, priced at $147 found 20 hours ago
Delta
Sat, May 2 - Wed, May 6
LGA
New York
ORD
Chicago
$147 Roundtrip, just found
$147
Roundtrip
just found
Select Delta flight, departing Sat, May 2 from New York to Chicago, returning Wed, May 6, priced at $147 just found
United
Wed, May 6 - Sun, May 10
EWR
New York
ORD
Chicago
$147 Roundtrip, just found
$147
Roundtrip
just found
Select United flight, departing Wed, May 6 from New York to Chicago, returning Sun, May 10, priced at $147 just found

Alternative airports near Countryside

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 32 minutes. Flights from $257
ORD
O'Hare Intl.
Cheapest
Average driving time to city center32 min
Flights from $257
Select flight to Midway Intl. MDW. Cheapest and Closest option available. Average driving time to city center is 17 minutes. Flights from $257
MDW
Midway Intl.
CheapestClosest
Average driving time to city center17 min
Flights from $257

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

July is typically the cheapest month to fly

From $77 - $303 per traveler.

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Frequently asked questions

What month is the cheapest to fly to Countryside?
September is the cheapest month to fly to Countryside, with average fares around $403. This month is often less crowded, which helps keep prices down. You can also look for good deals in January, February, and April.*Prices based on flights available on Expedia in the last year.
Which US cities have the cheapest flights to Countryside?
You can find some of the cheapest flights to Countryside from these US cities:

  • Burlington (BRL, BTV)
  • Quincy (UIN)
  • Owensboro (OWB)
  • Kirksville (IRK)
  • Manistee (MBL)

with fares typically starting around $39.
Which US cities fly direct to Countryside?
Direct flights to airports near Countryside are available from these US cities:To O'Hare Intl. (ORD)
  • New York (JFK, LGA)
  • Newark (EWR)
  • Los Angeles (LAX)
  • Dallas (DAL, DFW)
  • Houston (IAH)

To Midway Intl. (MDW)
  • Atlanta (ATL)
  • Dallas (DAL, DFW)
  • Orlando (MCO)
  • Phoenix (PHX)
  • Los Angeles (LAX)

To General Mitchell Intl. (MKE)
  • Chicago (MDW, ORD)
  • Denver (DEN)
  • New York (JFK, LGA)
  • Newark (EWR)
  • Phoenix (PHX)

How to find a cheap flight to Countryside?
To find a cheap flight to Countryside, be flexible with your dates. Traveling in the off-season or shoulder season can help you save. Mid-week flights are usually less expensive, too. Use flight search engines, like Expedia, to compare airlines, flight times and routes all in one place to find affordable rates. You may find that flights with layovers are cheaper than direct flights. You can also set up Price Tracking and receive alerts when fares go up or down.
Which airlines fly to Countryside?
Several airlines offer flights to Countryside:

  • American Airlines
  • Delta
  • Frontier Airlines
  • Spirit Airlines
  • United
  • United Airlines
  • Volaris

Where do you fly into Countryside?
If you're heading to Countryside, you have several airport options:

  • The closest major airport is Chicago, IL (ORD-O'Hare Intl.), about 15 miles from the city center, which is a hub for United, American Airlines, and Delta, with other airlines like Frontier Airlines, Air Canada also operating here.
  • Milwaukee, WI (MKE-General Mitchell Intl.) is another option, about 82 miles away, serving as a hub for United, Delta, and WN, with American Airlines, Alaska Airlines also operating here.
  • Chicago, IL (MDW-Midway Intl.), about 10 miles away, serving as a hub for WN, Delta, and Frontier Airlines, with Volaris, Porter Airlines also operating here.
  • South Bend, IN (SBN-South Bend Intl.), about 108 miles away, serving as a hub for United, American Airlines, and Delta, with MX, OO also operating here.

What is the cheapest airport to fly to in Countryside?
The most affordable airport to fly into in Countryside is typically Chicago, IL (ORD-O'Hare Intl.), which is about 15 miles from the city center. This airport can be a convenient and budget-friendly choice for your travels.*Prices based on flights available on Expedia in the last year.
Which budget airlines fly to Countryside?
For budget travel to Countryside, there are 13 low-cost airlines to choose from, including:

  • Southwest Airlines: serves Chicago (MDW), Chicago (ORD), Milwaukee (MKE)
  • Spirit Airlines: serves Chicago (ORD), Milwaukee (MKE)
  • Frontier Airlines: serves Chicago (MDW), Chicago (ORD), Milwaukee (MKE)
  • Volaris: serves Chicago (MDW), Chicago (ORD)
  • JetBlue Airways: serves Chicago (ORD), Milwaukee (MKE)
  • Viva Aerobus: flies to Chicago (ORD)
  • Sun Country Airlines: serves Chicago (ORD), Milwaukee (MKE)
  • WestJet: serves Chicago (MDW), Chicago (ORD), South Bend (SBN), Milwaukee (MKE)
  • Breeze: flies to South Bend (SBN)
  • Arajet: flies to Chicago (ORD)

What is the best month to visit Countryside?
The best month to visit Countryside depends on your priorities, whether you want ideal weather, fewer crowds, or the lowest prices. If affordability matters most, look for cheap March flights outside of peak season.
How far in advance should I book a flight to Countryside?
For domestic travel to Countryside, booking 1-2 months in advance can help you find the best prices. For international flights to Countryside, aim to book around 1 month ahead to get cheaper fares. For added peace of mind, use Expedia's Price Drop Protection™ when you make your booking. It's free to use for Gold and Platinum members on the Expedia app. Once a qualifying flight is purchased, we'll automatically check your flight on Expedia until the day of your departure and notify you if there are price changes. If your flight price drops after you book, we'll automatically award the price difference in OneKeyCash™* into your One Key account after your trip ends.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What day of the week is cheapest day to buy a plane ticket to Countryside?
Saturday is typically the cheapest day to buy a plane ticket to Countryside, with an average price of around $396. This is likely because many travelers prefer to fly during the week, leaving weekends less crowded and more affordable. If Saturday doesn't work for you, consider flying on Friday or Sunday as alternatives. Use Expedia's Price Tracking tool to monitor prices for your trip and receive alerts when fares go up or down.*Cheapest day to book based on flights available on Expedia in the last year.
What is the most expensive month to fly to Countryside?
July is typically the most expensive month to fly to Countryside, with average return ticket prices around $471. This is about 7% higher than the average price throughout the year, as summer vacations lead to increased demand. For better deals, consider planning your trip in September or October when prices are generally lower.*Prices based on flights available on Expedia in the last year.
How far is the airport from central Countryside?
Countryside is served by 2 airports:

  • Chicago, IL (MDW-Midway Intl.): 10 miles southwest
  • Chicago, IL (ORD-O'Hare Intl.): 20 miles west

These options give you flexibility when planning your trip.
How can I track flight prices to Countryside?
Our Price Tracking tool allows you to monitor fares to Countryside. You can view flight price history and see predictions of future prices as available. When you're signed into your Expedia account, you can set up flight price alerts too. This way, you'll receive notifications when prices go up or down, so you know when it's the right time to book.
How to get a cheap last-minute flight to Countryside?
It is possible to find cheap, last-minute flights to Countryside, especially if you can be flexible with your dates, times and route. Whether you're planning a spontaneous getaway or need to travel for business, there are plenty of last-minute flight deals on Expedia. You can also bundle your flight and hotel for even more savings with a package deal.
Can I earn miles booking a flight to Countryside with Expedia?
You can earn miles when booking a flight to Countryside on Expedia. Before confirming your booking, just select the frequent flyer program name and enter your program number. For even more rewards, join One Key™—our free travel rewards program. One Key members earn OneKeyCash™* on eligible bookings for every dollar spent.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
Can I save money by booking a Countryside trip package?
Book a Countryside flight and hotel package deal on Expedia, and you can make significant savings. It's simple to bundle your accommodations and flights, and you can also add car rentals and activities to create your own customized Countryside trip. Plus, nothing beats the convenience of booking everything in the same place.
Can I change or cancel my flight to Countryside?
It's often possible to cancel or change your flight to Countryside using Expedia. Many airlines let you cancel your flights for free within 24 hours of booking. However, some flights are non-refundable, and airlines may offer to reschedule your flight rather than provide a direct refund. To find affordable flights to Countryside with flexible change policies, select "No cancel fee" or "Changes included" when you search. Need more information? Visit our Customer Service Portal.

*Flight schedules are subject to change.

Book with confidence

Tips to find the cheapest flights to Countryside

The cheapest day to fly

Get started finding a cheap flight to Countryside 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

March is the cheapest month to fly to Countryside. 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 Countryside. 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 Countryside, 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 Countryside

The lowest price for round-trip flights to Countryside in 2026 starts from from $56, 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 Countryside. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to Countryside

Frontier Airlines, Spirit Airlines, American Airlines, JetBlue Airways, Delta, United are just some of the airlines that can typically offer cheap tickets to Countryside. 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 Countryside and countless more destinations worldwide.

The most affordable airports to fly into

To view the cheapest airports to fly into for Countryside, 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 Countryside. 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 Countryside 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 Countryside

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 Countryside.

Stopover savings

The cheapest tickets to Countryside are sometimes those with a stopover. Book one of these flights, and you'll change planes at an airport en route to Countryside. 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 Countryside 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 Countryside. Simply download the free Expedia app to your smart device and activate Countryside 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 Countryside. 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.

Tips to find the cheapest flights to Countryside

Travel information

Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Roundtrip price
$56

Trending flights to Countryside

Prices were available within the past 7 days and start at $28 for one-way flights and $56 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Mon, Mar 16 - Tue, Mar 24
JFK
New York
ORD
Chicago
$56 Roundtrip, just found
$56
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, Mar 16 from New York to Chicago, returning Tue, Mar 24, priced at $56 just found

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*Available to One Key members.