$49 Cheap Flights to Oskaloosa, IA

View $49 flight on Sat, May 23, 2026Opens in a new window

Popular airlines to Oskaloosa

How much is the cheapest flight to Oskaloosa?

Prices were available within the past 7 days and start at $49 for one-way flights and $93 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Contour Airlines
Thu, Jul 16 - Mon, Jul 20
ORD
Chicago
BRL
Burlington
$98 Roundtrip, found 2 hours ago
$98
Roundtrip
found 2 hours ago
Select Contour Airlines flight, departing Thu, Jul 16 from Chicago to Burlington, returning Mon, Jul 20, priced at $98 found 2 hours ago
Frontier Airlines
Wed, Jun 24 - Wed, Jul 1
DEN
Denver
DSM
Des Moines
$112 Roundtrip, found 6 hours ago
$112
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Wed, Jun 24 from Denver to Des Moines, returning Wed, Jul 1, priced at $112 found 6 hours ago
American Airlines
Tue, May 19 - Mon, Jun 8
ORD
Chicago
DSM
Des Moines
$225 Roundtrip, found 5 hours ago
$225
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Tue, May 19 from Chicago to Des Moines, returning Mon, Jun 8, priced at $225 found 5 hours ago
United
Wed, Aug 19 - Tue, Aug 25
DEN
Denver
DSM
Des Moines
$261 Roundtrip, found 1 hour ago
$261
Roundtrip
found 1 hour ago
Select United flight, departing Wed, Aug 19 from Denver to Des Moines, returning Tue, Aug 25, priced at $261 found 1 hour ago
Southwest Airlines
Tue, Jun 9 - Tue, Jun 16
DEN
Denver
DSM
Des Moines
$261 Roundtrip, found 23 hours ago
$261
Roundtrip
found 23 hours ago
Select Southwest Airlines flight, departing Tue, Jun 9 from Denver to Des Moines, returning Tue, Jun 16, priced at $261 found 23 hours ago

Frequently asked questions

What month is the cheapest to fly to Oskaloosa?
The cheapest month to fly to Oskaloosa is July when demand is low. Off-peak months are often 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 Oskaloosa?
Score cheap flights to Oskaloosa from Chicago, Denver and Atlanta. These cities generally offer the lowest fares to this exciting destination. But bear in mind that stopovers, seasonality and demand will also influence rates, so stay flexible and book when prices are right.
Which US cities fly direct to Oskaloosa?
There are 21 US destinations you're able to fly to Oskaloosa nonstop from. Explore the options by using the "Direct flights only" box on Expedia and find the best starting point for you. Here are several of the major cities to head out from:

  • Chicago
  • Denver
  • Atlanta
  • Dallas
  • Detroit

How to find a cheap flight to Oskaloosa?
To lock in cheap flights to Oskaloosa, book in advance and visit during the off-peak months of January and March. Want a handy tip? Depart on a Thursday and save around 16% on average compared to traveling on a Sunday.* Opt to receive price alerts on the Expedia app and we'll get in touch as soon as your fares drop.*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 Oskaloosa?
While booking in advance is generally the best way to save money, don't worry if your Oskaloosa getaway is last minute. You can still find cheap flights to Oskaloosa, especially if your plans have a little leeway. Try changing your trip dates, looking at different ticket types or jetting out of an alternative airport.
How far in advance should I book a flight to Oskaloosa?
To pick up the best deals on domestic journeys, book your flight to Oskaloosa 28 days ahead of your travel dates. For international flights, it's between two and four months in advance. This boosts your chances of securing your preferred departure dates, times and seats.**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 Oskaloosa?
You can usually find cheap flights to Oskaloosa on a Sunday. You'll save about 8% on average compared to those who book on a Friday, which is typically the most expensive day to purchase tickets.**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 Oskaloosa?
Grab a seat with one of these airlines and dynamic Oskaloosa will be all yours to explore:

  • American Airlines - 407 flights to Oskaloosa each month, including 407 flights to Des Moines Intl. Airport (DSM) per month.
  • Delta Air Lines - 320 flights to Oskaloosa each month, including 320 flights to Des Moines Intl. Airport (DSM) per month.
  • United Airlines - 294 flights to Oskaloosa each month, including 294 flights to Des Moines Intl. Airport (DSM) per month.

Where do you fly into Oskaloosa?
If you're flying to Oskaloosa, the main airport to disembark at is Ottumwa, IA (OTM-Ottumwa Industrial). Alternatively, you could fly to Oskaloosa via Marshalltown, IA (MIW-Marshalltown Municipal).
How far is the airport from central Oskaloosa?
Touching down at Ottumwa, IA (OTM-Ottumwa Industrial) puts you around 17 mi southeast of the center of Oskaloosa.
Can I save money by booking an Oskaloosa trip package?
You could potentially save hundreds of dollars if you secure an Oskaloosa flight and hotel package deal on Expedia. And you'll make life easier by having all your travel plans in one place. Try bundling hotels and flights with extras like tours and activities for your own customized Oskaloosa escape.
Can I change or cancel my flight to Oskaloosa?
It's usually possible to cancel or change your flight to Oskaloosa. Many airlines let you cancel your flights for free within 24 hours of booking. However, some flights are non-refundable, and airlines may issue you a credit toward future travel instead of a direct refund. To find cheap flights to Oskaloosa with flexible change policies, pick "Changes included" or "No cancel fee" during your search. Want more details? Check out our Customer Service Portal.

*Flight schedules are subject to change.

*Available to One Key members.

 

Travel information

Destination airport
Southeast Iowa Regional
Destination airport IATA code
BRL
Destination city name
Burlington
Roundtrip price
$92

Trending flights to Oskaloosa

Prices were available within the past 7 days and start at $49 for one-way flights and $93 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Contour Airlines
Fri, Jul 17 - Fri, Jul 17
ORD
Chicago
BRL
Burlington
$93 Roundtrip, found 2 hours ago
$93
Roundtrip
found 2 hours ago
Select Contour Airlines flight, departing Fri, Jul 17 from Chicago to Burlington, returning Fri, Jul 17, priced at $93 found 2 hours ago

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