$28 Cheap Flights to Chesterton, IN

View $28 flight on Tue, May 19, 2026Opens in a new window

Popular airlines to Chesterton

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How much is the cheapest flight to Chesterton?

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
Tue, Jun 16 - Tue, Jun 23
LAX
Los Angeles
ORD
Chicago
$68 Roundtrip, just found
$68
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Jun 16 from Los Angeles to Chicago, returning Tue, Jun 23, priced at $68 just found
Spirit Airlines
Wed, Apr 29 - Tue, May 5
DFW
Dallas
ORD
Chicago
$81 Roundtrip, found 2 hours ago
$81
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Wed, Apr 29 from Dallas to Chicago, returning Tue, May 5, priced at $81 found 2 hours ago
United
Wed, May 13 - Tue, May 19
EWR
New York
ORD
Chicago
$155 Roundtrip, just found
$155
Roundtrip
just found
Select United flight, departing Wed, May 13 from New York to Chicago, returning Tue, May 19, priced at $155 just found
Southwest Airlines
Wed, May 13 - Wed, May 20
LGA
New York
MDW
Chicago
$155 Roundtrip, found 3 hours ago
$155
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Wed, May 13 from New York to Chicago, returning Wed, May 20, priced at $155 found 3 hours ago
American Airlines
Tue, Jun 30 - Fri, Jul 3
EWR
New York
RFD
Rockford
$176 Roundtrip, found 3 hours ago
$176
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Tue, Jun 30 from New York to Rockford, returning Fri, Jul 3, priced at $176 found 3 hours ago

Frequently asked questions

What month is the cheapest to fly to Chesterton?
Schedule your trip for June 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.

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Travel information

Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Roundtrip price
$68

Trending flights to Chesterton

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
Tue, May 5 - Tue, May 12
IAH
Houston
ORD
Chicago
$56 Roundtrip, found 2 hours ago
$56
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Tue, May 5 from Houston to Chicago, returning Tue, May 12, priced at $56 found 2 hours ago

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