A wooden staircase ascending a sandy hill with sparse vegetation.

$25 Cheap Flights to Chesterton, IN

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Popular airlines to Chesterton

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Today's featured flight deals to Chesterton

NonstopCarry-on includedLower price than typical

How much is the cheapest flight to Chesterton?

Prices were available within the past 7 days and start at $25 for one-way flights and $54 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Delta
JetBlue Airways
United
Southwest Airlines

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

From $91 - $117 per traveler.

What you need to know for your flight to Chesterton

Flights to Chesterton at a glance

Traveling to Chesterton is easy. You can choose from either full-service or budget airlines. Compare flight times and select the best option that fits your budget and schedule as you plan to explore the city's renowned attractions and neighborhoods. Look for cheap flights to Chesterton for the best deals.

  • Major airport near Chesterton: Midway International Airport (MDW)
  • Flights per week: 1,650+ flights arriving at Chesterton airport
  • Number of airlines that fly to Chesterton: around 10+ carriers

Popular airport near Chesterton

Chesterton is a charming city perfect for outdoor enthusiasts and those seeking picturesque scenery, romantic getaways, or family adventures. With a major airport nearby, it's easy for travelers to search for the closest airport and plan their journey to this delightful destination.

  • Midway International Airport (MDW): Situated in Cook County, Illinois, approximately 37 miles from Chesterton, this airport provides access to both domestic and international flights, with connections to over 130 domestic cities and 30 international locales. Passengers have the option to enhance their travel experience by upgrading to premium economy or first class seating, depending on the airline and route. Notable carriers operating at this airport include Southwest Airlines, Frontier Airlines, and Delta.

Top routes to Chesterton

  • Atlanta (ATL) to Chesterton (MDW), with one-way tickets available from around $40
  • Orlando (MCO) to Chesterton (MDW), with one-way tickets available from around $45
  • Dallas (DFW/DAL) to Chesterton (MDW), with one-way fares starting at around $35
  • Phoenix (PHX) to Chesterton (MDW), with one-way fares starting at around $50
  • New York (JFK/LGA) to Chesterton (MDW), with one-way airfare from around $70

Cheapest routes to Chesterton

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

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

Top airlines with flights to Chesterton

  • Southwest Airlines: Operating flights to Midway International Airport (MDW), Southwest Airlines is responsible for about 75% of arrivals to Chesterton, with the average one-way fare being around $210.
  • Delta: Also servicing Midway International Airport (MDW), Delta accounts for roughly 12% of arrivals in Chesterton. The average one-way fare is about $230, with options for premium economy and first class available on select routes.
  • Frontier Airlines: Flying into Midway International Airport (MDW), Frontier Airlines makes up approximately 10% of Chesterton's arrivals, offering competitive average one-way fares around $160.
  • Volaris: With flights to Midway International Airport (MDW), Volaris represents about 2% of arrivals to Chesterton, featuring an average one-way fare of approximately $270.
  • Porter Airlines: Serving Midway International Airport (MDW), Porter Airlines constitutes around 1% of arrivals to Chesterton, with an average one-way fare estimated at $190.

How to save money on a flight to Chesterton

Getting some of the best deals on flights to Chesterton 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 Chesterton 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 Chesterton flight with Expedia. Just select your frequent flyer program and enter your program number when confirming your booking.

*For members. Select hotels.

Arriving in Chesterton

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

  • Public transportation: From Midway International Airport, Midway Station (a metro station) is located about 0.2 miles away by walking, while for train travel, Chicago Ashburn Station is about 4.1 miles from the airport by car. If you're heading to the waterfront, Lyons Seaport, a seaport, is situated approximately 7.2 miles away by car.
  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Chesterton, with options including free hotel shuttles and private rides, which can be arranged in advance.
  • Car rental: Renting a car in Chesterton is a good option if you plan to explore and sightsee beyond the city. Browse cheap car rentals in Chesterton 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 around Chesterton

  • Michigan City: Located 11 miles drive away from Chesterton, Michigan City is a delightful destination for those seeking scenic beauty and outdoor adventures. Visitors can explore the picturesque Lake View Beach, perfect for a relaxing day by the water, or wander through the enchanting Friendship Botanic Gardens, ideal for families and couples alike. For nature lovers, the Ambler Flatwoods Nature Preserve offers a tranquil escape where you can immerse yourself in the area's natural splendor. Experience a blend of leisure and exploration in this charming city.
  • Portage: Portage is located 6 miles drive away from Chesterton and is a city full of outdoor excitement and scenic landscapes. The renowned Indiana Dunes National Park provides thrilling opportunities for adventure and sightseeing, while the Portage Lakefront Beach invites you to unwind by the water. For a taste of local community life, Founders' Square Park offers a modern gathering space. Whether you're in search of recreation or relaxation, Portage has something for everyone.
  • Valparaiso: Valparaiso is located 10 miles drive away from Chesterton and showcases a vibrant mix of culture and outdoor activities. Nature enthusiasts can visit the stunning Indiana Dunes National Park for unforgettable adventures and stunning views. The historic Valparaiso University adds a cultural touch to your visit, while the Memorial Opera House offers a glimpse into the city’s artistic heritage. With its charming atmosphere, Valparaiso invites travelers to explore both its natural and cultural offerings.

Tips for short-haul flights to Chesterton

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

  • Pack light and skip checked bags—with budget airlines, traveling with just a carry-on is often more economical. Maximize space by using mini toiletries, wearing your bulkiest clothing, and planning versatile outfits. This strategy also helps you avoid the hassle of waiting at baggage claim upon arrival.
  • Bring your own entertainment—many short-haul flights may lack in-flight entertainment options. Download your favorite TV shows, movies, music, or podcasts ahead of time, and consider bringing a book for added enjoyment. Remember to charge your devices fully 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, taking into account potential traffic and security lines.
  • Bring your own snacks and water—pack some snacks and a refillable water bottle to stay hydrated and save money while at the airport.

Tips for long-haul flights to Chesterton

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

  • Select your seat in advance—for longer flights, choosing your seat is crucial for comfort. Full-service airlines often provide the option to select seats for free once online check-in opens, typically 24–48 hours before your flight. Some airlines may allow seat selection even earlier.
  • Arrive at the airport in plenty of time—make sure to arrive at the airport 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 explore 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. Aim to either 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 Chesterton?
Schedule your trip for November if you're looking for a good price on your fare. It's the cheapest month to fly to Chesterton. If possible, avoid traveling during peak periods such as school vacation time or public holidays.
Which US cities have the cheapest flights to Chesterton?
Generally, New York, Washington and Dallas have cheap flights to Chesterton. Flexibility, however, is the secret to landing a bargain. Plan your escape midweek or during the low season to keep costs down.
Which US cities fly direct to Chesterton?
There are 150 US destinations where you can fly to Chesterton directly from. Explore the options by using the "Direct flights only" box on Expedia and pick the best departure point for your trip. Here are some of the leading cities to leave from:
  • New York
  • Washington
  • Dallas
  • Boston
  • Phoenix
How to find a cheap flight to Chesterton?
To lock in cheap flights to Chesterton, book in advance and travel during the off-peak months of December and January. Want another helpful tip? Jet off on a Thursday and save around 16% on average compared to those who travel on a Sunday.* Set a price alert on the Expedia app and we'll let you know as soon as your fares go down.*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 Chesterton?
Staying flexible about your travel plans can help you to secure last-minute offers on cheap flights to Chesterton. To view all the available options, try looking at different ticket types, changing your Chesterton vacation dates, flying out of an alternative airport or going with another airline.
How far in advance should I book a flight to Chesterton?
To pick up some of the best deals on domestic journeys, book your flight to Chesterton 28 days ahead of your travel dates. For international flights, search for your ticket between two and four months in advance. This improves your chances of locking in the departure dates and seats you want.**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 Chesterton?
Sundays are usually the best day to book a cheap flight to Chesterton, with savings of about 8% on average compared to a Friday. If you decide to buy tickets on a Friday, expect 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 Chesterton?
There are 44 airlines that connect Chesterton with 216 airports across the world. The key point of arrival to this city is O'Hare Intl. Airport (ORD). Fly with any of these top airlines to Chesterton:
  • United Airlines
  • American Airlines
  • Delta Air Lines
  • Alaska Airlines
Where do you fly into Chesterton?
Chesterton's main point of arrival is Midway Intl. Airport (MDW). If you're looking for more nearby choices when flying to Chesterton, consider South Bend Intl. Airport (SBN), O'Hare Intl. Airport (ORD) or Valparaiso, IN (VPZ-Porter County Municipal). You can also opt to fly to Chesterton through Michigan City, IN (MGC-Michigan City Municipal).
How far is the airport from central Chesterton?
Flying into Midway Intl. Airport (MDW) puts you about 35 mi west of the center of Chesterton.
Can I save money by booking a Chesterton trip package?
You could possibly save hundreds of dollars if you choose a Chesterton flight and hotel package deal on Expedia. And you'll save time and hassle by having all your travel arrangements in the same place. Try bundling flights and hotels with extras such as car rentals and tours for your own personalized Chesterton getaway.
Can I change or cancel my flight to Chesterton?
You can often cancel or change your flight to Chesterton within 24 hours of booking. However, be mindful that some fares are non-refundable. In those cases, you may be issued credit for future flights rather than a direct refund. Be sure to check the airline's rules and restrictions in your itinerary for exact details. Use Expedia's "No cancel fee" or "Changes included" filters during your search to secure cheap flights to Chesterton with flexible change policies. For additional information, head to our Customer Service Portal.

*Flight schedules are subject to change.

*Available to One Key members.

Book with confidence

Tips to find the cheapest flights to Chesterton

The cheapest day to fly

Get started finding a cheap flight to Chesterton 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

November is the cheapest month to fly to Chesterton. 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 Chesterton. 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 Chesterton, 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 Chesterton

The lowest price for round-trip flights to Chesterton in 2026 starts from from $54, while one-way tickets start from from $25. 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 Chesterton. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to Chesterton

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

The most affordable airports to fly into

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

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 Chesterton.

Stopover savings

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

Travel information

Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Roundtrip price
$98

Trending flights to Chesterton

Prices were available within the past 7 days and start at $25 for one-way flights and $54 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines

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