$56 Cheap Flights to Countryside, IL

Flights to Countryside at a glance

Traveling to Countryside is easy; simply choose between full-service and budget airlines. Compare flight durations and select the option that best fits your budget, schedule, and plans to explore the city’s renowned attractions and neighborhoods.

• Major airports near Countryside: O'Hare International Airport (ORD), Midway International Airport (MDW)
• Closest airport to Countryside: Midway International Airport, MDW (around 7 miles)
• Flights per week: 9,800+ flights arriving across Countryside airports
• Number of airlines that fly to Countryside: around 75+ carriers

Popular airports near Countryside

Countryside is a lively city ideal for family getaways, outdoor activities, and sports vacations. Visitors are drawn to Countryside for its family-friendly atmosphere, business opportunities, and recreational options. The city is conveniently accessible via two major airports.

• O'Hare International Airport (ORD): Situated in Cook County, Illinois, approximately 15 miles from Countryside, O'Hare is a bustling hub for both domestic and international travel. It offers connections to over 285 domestic cities and more than 315 international destinations. Travelers can opt for first class, premium economy, or business class seating for enhanced comfort based on their airline and route. Notable airlines operating here include American Airlines, United, and Frontier Airlines.
• Midway International Airport (MDW): Located in Cook County, Illinois, just about 7 miles from Countryside, Midway caters to both domestic and international flights. It connects to around 130 domestic cities and 30 international locations. Travelers have the option to upgrade to premium economy or first class seating for a more comfortable journey, depending on their airline and route. Key airlines servicing this airport include Southwest Airlines, Frontier Airlines, and Delta.

Top routes to Countryside

• New York (JFK/LGA) to Countryside (ORD/MDW), with one-way fares starting at around $45
• Los Angeles (LAX) to Countryside (ORD/MDW), with one-way flight options from around $80
• Boston (BOS) to Countryside (ORD/MDW), with one-way fares starting at around $50
• Orlando (MCO) to Countryside (ORD/MDW), with one-way flight options from around $45
• Atlanta (ATL) to Countryside (ORD/MDW), with one-way tickets available from around $40

Cheapest routes to Countryside

• Newark (EWR) to Countryside (ORD/MDW), with budget one-way fares from around $30
• Dallas (DFW/DAL) to Countryside (ORD/MDW), with budget one-way fares from around $35
• Atlanta (ATL) to Countryside (ORD/MDW), with cheap one-way fares from around $40
• Minneapolis (MSP) to Countryside (ORD/MDW), with low one-way fares from around $40
• Nashville (BNA) to Countryside (ORD/MDW), with budget one-way fares from around $40

*Flight times and fares vary by season and availability and are based on one-way routes

Top airlines with flights to Countryside

• American Airlines: Operating flights to O'Hare International Airport (ORD), American Airlines represents about 31% of arrivals in Countryside. The typical one-way ticket costs around $390, with premium options like premium economy, business, and first class available on select routes.
• United: Also servicing O'Hare International Airport (ORD), United Airlines accounts for roughly 31% of arrivals to Countryside. The average fare for a one-way ticket is about $380, and premium cabin options may include premium economy, business, and first class depending on the route.
• Southwest Airlines: This airline operates flights to both O'Hare International Airport (ORD) and Midway International Airport (MDW), contributing to approximately 12% of arrivals in Countryside. The average one-way fare is around $220, offering a budget-friendly choice for travelers.
• Delta: Serving O'Hare International Airport (ORD) and Midway International Airport (MDW), Delta makes up about 8% of arrivals to Countryside. Expect an average one-way fare of around $290, with options for premium economy, business, and first class depending on the route.
• Frontier Airlines: Operating flights to both O'Hare International Airport (ORD) and Midway International Airport (MDW), Frontier Airlines accounts for around 4% of arrivals in Countryside. The average one-way fare is approximately $160, making it a cost-effective travel option.

Best time to fly to Countryside

The most popular months for travelers to fly to Countryside are January, March, and April, when peak temperatures in Countryside can reach up to 48.6°F in April. If you prefer quieter travel, consider September, the least busy time to visit with temperatures around 67.3°F and typically the lowest average one-way fare (around $200), roughly 10% cheaper than the yearly average. Looking for additional cheaper months to fly? October, November, and May offer average one-way fares roughly ranging from $201 to $214, making them good options for flexible travelers.

*Average one-way fare is based on Expedia flight booking data from January 2025 to April 2026 for the specified route and travel class and may change depending on availability, dates, and demand.

How to save money on a flight to Countryside

Getting some of the best deals on flights to Countryside is all about timing and flexibility. Here are some key tips to help you save:

1. Compare flight options—use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
2. Set up price alerts—as an Expedia member you can use Price Tracking to receive notifications when flight prices change.
3. Bundle and save—book a flight and unlock a hotel deal on Expedia.*
4. Think about luggage-nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your baggage allowance before confirming your booking to avoid excess baggage fees at the airport.
5. Earn miles—you can earn airline miles when you book your Countryside flight with Expedia. Just select your frequent flyer program and enter your program number when confirming your booking.

*For members. Select hotels.

Arriving in Countryside

Countryside welcomes travelers through its range of transport options based on price, convenience, and proximity. Here's how to reach Countryside efficiently:

• Public transportation: From O'Hare International Airport, O'Hare Station, a metro station, is located about 0.1 miles away by walking, while Rosemont Station, a train station, is about 2.2 miles from the airport and is typically reached by car.
• Hotel transfer: Transfers offer a convenient way to reach your hotel in Countryside, with options including free hotel shuttles and private rides, which can be arranged in advance.
• Car rental: Renting a car in Countryside is a good option if you plan to explore and sightsee beyond the city. Browse cheap car rentals in Countryside on Expedia.
• Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.

Where to stay in and around Countryside

• Chicago: Chicago is a vibrant metropolis that serves as the heart of the region. Travelers come to Chicago for its family-friendly activities, outdoor experiences, and dynamic city life. You can explore bustling shopping areas, enjoy entertainment at renowned arenas, or catch a show at the theater. Nearby landmarks include impressive sports facilities and urban parks. Highlights to discover include the Griffin Museum of Science and Industry, perfect for families and culture enthusiasts; the iconic 875 North Michigan Avenue skyscraper; and the lively Michigan Avenue, a must-see street that embodies the city's spirit.
• Homer Glen: Located 12 miles away from Countryside, Homer Glen is a charming city that offers a delightful mix of family-friendly activities, outdoor spaces, and entertainment options. This community is home to various venues including theaters and music concert locations, making it an ideal spot for cultural experiences. Visitors can enjoy the beautiful Morton Arboretum, which is perfect for outdoor adventures, or attend events at the Tinley Park Convention Center. For a taste of history, Lewis University presents a unique cultural vacation opportunity, showcasing the area's educational heritage.
• Summit: Summit is located 4 miles drive away from Countryside and is known for its active, family-oriented atmosphere. This city features sports facilities and urban parks, making it ideal for outdoor enthusiasts. Visitors can enjoy educational experiences at the University of Illinois Chicago, or have fun at the Wintrust Arena, which hosts various entertainment shows. Additionally, the Wintrust Sports Complex offers excellent opportunities for sports fans. Summit’s blend of activities makes it a great destination for travelers looking for a lively experience close to Countryside.

Tips for short-haul flights to Countryside

For quick getaways, efficiency is key. Here is how to make your short-haul journey smoother:

• Pack light and skip checked bags—when flying with budget airlines, it's often more economical to travel with just a carry-on. Maximize your space by bringing mini toiletries, wearing your bulkiest clothing, and planning your outfits strategically. This approach also helps you avoid the wait at baggage claim upon arrival.
• Bring your own entertainment—many short-haul flights may lack in-flight entertainment options. To keep yourself engaged, download TV shows, movies, music, or podcasts ahead of time, and consider bringing a book. Remember to fully charge your devices before you board.
• Arrive at the airport in plenty of time—even for short or domestic flights, it's wise to arrive at least 1.5 to 2 hours prior to departure, taking into account traffic and security lines.
• Bring your own snacks and water—pack some snacks and a refillable water bottle to stay hydrated and save money at the airport.

Tips for long-haul flights to Countryside

Flying long-haul sometimes requires extra planning to ensure a comfortable journey:

• Select your seat in advance—for longer flights, choosing your seat is essential for comfort. Full-service airlines typically allow you to select your seat for free once online check-in opens, which is usually 24–48 hours before your flight. Some airlines even permit seat selection earlier than this.
• Arrive at the airport in plenty of time—aim to arrive at the airport at least 3 hours before departure for international flights to ensure you have enough time for check-in, security, and immigration.
• Relax at the airport—if you find yourself with extra time, take the opportunity to browse the shops, grab a coffee, or unwind at the gate or in a departure lounge if you have access. Airport Wi-Fi is generally free and available.
• Adjust to the new time zone mid-flight—begin syncing your body clock by changing your watch and sleep schedule to align with your destination's time zone. Try to either sleep or stay awake during the flight according to the local time at your arrival destination to help minimize jet lag.

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

October 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 $118, while one-way tickets start from from $56. 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, American Airlines, Southwest Airlines, United, Delta 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.