View of a serene sunset over the Mississippi River with a bridge and a boat, Chester, United States.

$38 Cheap Flights to Chester, IL

Popular airlines to Chester

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How much is the cheapest flight to Chester?

Prices were available within the past 7 days and start at $38 for one-way flights and $76 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

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What you need to know for your flight to Chester

Flights to Chester at a glance

Traveling to Chester is easy, with a full-service airline providing comfortable flights that allow you to explore the city’s iconic attractions and charming neighborhoods.

  • Major airport near Chester: Williamson County Regional Airport (MWA)
  • Flights per week: 8 flights arriving at Chester airport
  • Number of airlines that fly to Chester: around 1 carrier

Popular airport near Chester

Chester is a charming city perfect for those seeking outdoor adventures, scenic landscapes, romance, wellness, and relaxation. Travelers flock to Chester for its beautiful surroundings and active pursuits, with a major airport conveniently serving the area.

  • Williamson County Regional Airport (MWA): Situated in Williamson County, Illinois, approximately 46 miles from Chester, this airport primarily operates domestic flights, with Contour Airlines being a prominent carrier here.

Top routes to Chester

  • Chicago (ORD) to Chester (MWA), with one-way flights starting at around $70

Cheapest routes to Chester

  • Chicago (ORD) to Chester (MWA), with low-cost one-way tickets from around $70

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

Top airlines with flights to Chester

  • Contour Airlines: Operating flights to Williamson County Regional Airport (MWA), Contour Airlines handles nearly all incoming flights to {short_name}. The typical one-way ticket costs around $100.

Best time to fly to Chester

The most popular months for travelers to fly to Chester are January, March, and April, when peak temperatures in Chester can reach up to 56.1°F in April. If you prefer quieter travel, consider May, the least busy and relatively cheaper time to visit with fewer crowds and temperatures around 66°F. For better deals, December usually offers the lowest average one-way fare around $80, roughly 28% cheaper than the yearly average.

calendar iconMonthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinesscrowd level iconDemandprice iconAverage one-way Fare
January32.9°F (0.5°C)Light RainMostly SunnyHigh$115
February36.0°F (2.2°C)Light RainMostly SunnyAverage$113
March46.9°F (8.3°C)Light RainMostly SunnyHigh$110
April56.1°F (13.4°C)Light RainMostly SunnyHigh$106
May66.0°F (18.9°C)Light RainMostly SunnyLow$114
June75.4°F (24.1°C)Light RainMostly SunnyAverage$123
July78.1°F (25.6°C)Light RainMostly SunnyLow$118
August76.1°F (24.5°C)Light RainMostly SunnyLow$125
September70.2°F (21.2°C)Light RainMostly SunnyAverage$127
October58.5°F (14.7°C)Light RainMostly SunnyAverage$113
November46.2°F (7.9°C)Light RainMostly SunnyAverage$105
December38.5°F (3.6°C)Light RainMostly SunnyAverage$80

*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 Chester

Getting some of the best deals on flights to Chester 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*, or explore our Chester hotel and flight deals.
  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 Chester flight with Expedia. Just select your frequent flyer program and enter your program number when confirming your booking.

*For members. Select hotels.

Arriving in Chester

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

  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Chester, with private rides that can be arranged in advance.
  • Car rental: Renting a car in Chester is a good option if you plan to explore and sightsee beyond the city. Browse cheap car rentals in Chester 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 Chester

  • Ste Genevieve: Located 36 miles drive away from Chester, Ste Genevieve offers a delightful blend of outdoor adventures and romantic getaways. This charming city is known for its scenic landscapes and recreational areas, including the stunning Hawn State Park, which is perfect for nature enthusiasts. History buffs will appreciate the Ste. Genevieve Historic District, showcasing the rich cultural heritage of the area. Families can enjoy a day at Pere Marquette Park, where eco-friendly activities abound amid beautiful surroundings. Ste Genevieve is an excellent destination for those looking to immerse themselves in nature and history.
  • Bremen: Situated in the area of Chester, Bremen is a quaint village that invites travelers to explore its unique cultural landmarks. A visit to the Mary’s River Covered Bridge offers a glimpse into the region’s history, while the Popeye Museum celebrates the beloved cartoon character with fun exhibits. For those interested in historical sites, the Kaskaskia Bell adds a touch of local lore to your itinerary. Bremen’s charming atmosphere makes it a great spot for a leisurely afternoon of exploration and appreciation of its heritage.
  • St Mary: St Mary is located 13 miles drive away from Chester and is an ideal destination for those seeking outdoor activities and adventure. Golf enthusiasts can enjoy the local courses, while the picturesque Mitchell Island provides a serene beach escape. History lovers will find Fort Kaskaskia intriguing, showcasing the area’s rich past. Elzie C. Segar Memorial Park is perfect for families, offering recreational spaces in a lovely urban setting. St Mary’s diverse offerings make it a wonderful spot for outdoor fun and cultural exploration.

Tips for short-haul flights to Chester

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 space by using mini toiletries, wearing your heaviest clothing, and planning your outfits wisely. This approach also allows you to avoid the wait at baggage claim upon arrival.
  • Bring your own entertainment—many short-haul flights may lack in-flight entertainment options. To stay 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 advisable to arrive at least 1.5 to 2 hours before your departure, accounting for traffic and security lines.
  • Bring your own snacks and water—pack some snacks and a refillable water bottle to keep hydrated and save money while at the airport.

Tips for long-haul flights to Chester

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 often provide free seat selection once online check-in opens, typically 24–48 hours before your flight. Some airlines allow seat selection even earlier than that.
  • Arrive at the airport in plenty of time—make sure to arrive at least 3 hours prior to departure for international flights to accommodate check-in, security, and immigration processes.
  • Relax at the airport—if you have some extra time, take the opportunity to browse the shops, find a coffee shop, or unwind at the gate or in a departure lounge if you have access. Airport Wi-Fi is generally free and readily available.
  • Adjust to the new time zone mid-flight—begin syncing your body clock by changing your watch and modifying your sleep schedule to align with your destination's time zone. Aim to sleep or stay awake during the flight according to the local time at your arrival destination to help minimize jet lag.

Frequently asked questions

What month is the cheapest to fly to Chester?
The cheapest month to fly to Chester is July when there's less demand. Off-peak months are typically when you'll find cheap flights. To keep costs down, avoid flying during public and school holidays.
Which US cities have the cheapest flights to Chester?
Typically, you'll find that Chicago, Dallas and Denver offer cheap flights to Chester. However, being flexible is always key to scoring yourself the best deals. Book during the off-peak season or midweek to keep costs to a minimum.
Which US cities fly direct to Chester?
Pick from 55 US cities offering direct flights to Chester. When you book on Expedia, click on "Direct flights only" to compare nonstop itineraries. Fly to Chester from any of these leading cities:

  • Chicago
  • Dallas
  • Denver
  • New York
  • Atlanta

How to find a cheap flight to Chester?
Book your trip early to maximize your chances of getting cheap flights to Chester. Also, consider traveling during off-peak months like December and January. If you jet off on a Thursday, you can save 16% on average compared to departing on a Sunday.* Save time checking every day and track your flight prices using 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 Chester?
Staying flexible about your plans may help you to secure last-minute offers on cheap flights to Chester. To view all the available options, try exploring different ticket types, changing your Chester vacation dates, leaving from an alternative airport or going with another airline.
How far in advance should I book a flight to Chester?
Secure the departure dates you want and a price you'll love by booking your domestic flight to Chester up to 28 days in advance. Search for tickets between two and four months ahead if you're flying to Chester from an international destination.**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 Chester?
Sundays are usually the best day to book a cheap flight to Chester, with savings of around 8% on average compared to Fridays. If you choose to purchase tickets on a Friday, be ready to pay a higher price as this is often the most expensive day.**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 Chester?
Whether you want to sit in a premium seat or save dollars in economy, these top airlines will get you to Chester:

  • American Airlines - 927 flights to Chester each month, including 927 flights to Lambert-St. Louis Intl. Airport (STL) per month.
  • Delta Air Lines - 637 flights to Chester each month, including 637 flights to Lambert-St. Louis Intl. Airport (STL) per month.

Where do you fly into Chester?
The main hub when you fly to Chester is Williamson County Regional Airport (MWA), but there are other nearby options like Cape Girardeau Municipal Airport (CGI) and Carbondale, IL (MDH-Southern Illinois). You can also land at MidAmerica-St. Louis Airport (BLV) and St. Louis Downtown Airport (CPS) when flying to Chester.
How far is the airport from central Chester?
If you're flying into Williamson County Regional Airport (MWA), you'll be around 45 mi east of central Chester.
Can I save money by booking a Chester trip package?
Book a Chester flight and hotel package deal on Expedia, and you can make significant savings. It's a breeze to bundle your hotel and flight, and you can even add tours and car rentals to create your own personalized Chester getaway. Plus, nothing beats the convenience of booking everything in one place.
Can I change or cancel my flight to Chester?
If you bought your flight to Chester within the last 24 hours, you can usually cancel or change it without fees. After that, additional charges may apply depending on the airline's terms of service. To learn more, check out our Customer Service Portal. Keep in mind that some flights are non-refundable, so you may be offered a credit for a future flight instead of a direct refund. When browsing Expedia, check the "Changes included" or "No cancel fee" boxes to see fares with flexible change policies.

*Flight schedules are subject to change.

*Available to One Key members.

 

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Travel information

Destination airport
Lambert-St. Louis Intl.
Destination airport IATA code
STL
Destination city name
St. Louis
Roundtrip price
$76

Trending flights to Chester

Prices were available within the past 7 days and start at $38 for one-way flights and $76 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

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