$53 Cheap Flights to Chesterton, IN

Popular airlines to Chesterton

  • Plan, book, fly with confidence

  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 30% on select hotels after you book a flight*
  • one key icon
    Earn twice
    Earn your airline miles on top of our OneKeyCash

How much is the cheapest flight to Chesterton?

Prices were available within the past 7 days and start at $53 for one-way flights and $106 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
American Airlines
Delta
United
Southwest Airlines

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

June is typically the cheapest month to fly

From $77 - $248 per traveler.

Graph displaying average flight prices per month

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

September 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 2025 starts from from $106, while one-way tickets start from from $53. 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

Spirit Airlines, Delta, American Airlines, JetBlue Airways, 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.

Frequently asked questions

What month is the cheapest to fly to Chesterton?
October is typically the cheapest month for flights to Chesterton*. Look out for affordable flights during this time as you may be able to snag a great discount. *Cheapest month to fly is based on the month with the cheapest flight found on Expedia.com in the next 330 days.
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.
Flights to Chesterton information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Roundtrip price
$71

Trending flights to Chesterton

Prices were available within the past 7 days and start at $53 for one-way flights and $106 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines

Explore a world of travel with Expedia

*Available to One Key members.