$29 Cheap Flights to Oakville, CT

View $29 flight on Fri, May 8, 2026Opens in a new window

Popular airlines to Oakville

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How much is the cheapest flight to Oakville?

Prices were available within the past 7 days and start at $29 for one-way flights and $58 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Avelo Airlines
Sat, May 23 - Tue, May 26
MCO
Orlando
HVN
New Haven
$73 Roundtrip, found 5 hours ago
$73
Roundtrip
found 5 hours ago
Select Avelo Airlines flight, departing Sat, May 23 from Orlando to New Haven, returning Tue, May 26, priced at $73 found 5 hours ago
Frontier Airlines
Sat, May 9 - Fri, May 15
MCO
Orlando
BDL
Hartford
$93 Roundtrip, found 3 hours ago
$93
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, May 9 from Orlando to Hartford, returning Fri, May 15, priced at $93 found 3 hours ago
Breeze Airways
Thu, May 28 - Sun, May 31
MCO
Orlando
HVN
New Haven
$102 Roundtrip, found 2 hours ago
$102
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Thu, May 28 from Orlando to New Haven, returning Sun, May 31, priced at $102 found 2 hours ago
Southwest Airlines
Sat, May 30 - Tue, Jun 2
TPA
Tampa
BDL
Hartford
$187 Roundtrip, found 9 hours ago
$187
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Sat, May 30 from Tampa to Hartford, returning Tue, Jun 2, priced at $187 found 9 hours ago
JetBlue Airways
Wed, May 20 - Wed, May 27
TPA
Tampa
BDL
Hartford
$197 Roundtrip, found 1 hour ago
$197
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Wed, May 20 from Tampa to Hartford, returning Wed, May 27, priced at $197 found 1 hour ago

Alternative airports near Oakville

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Bradley Intl. BDL. Cheapest option available. Average driving time to city center is 59 minutes. Flights from $257
BDL
Bradley Intl.
Cheapest
Average driving time to city center59 min
Flights from $257

Frequently asked questions

What month is the cheapest to fly to Oakville?
The cheapest month to fly to Oakville is May when there's less demand. Off-peak months are often when you'll find cheap fares. To save money, avoid flying during major holidays and school breaks.
Which US cities have the cheapest flights to Oakville?
Washington, Chicago and Orlando typically have cheap flights to Oakville. Bear in mind that fares vary based on factors like demand, time of year and number of stopovers.
Which US cities fly direct to Oakville?
There are 32 US cities that you can fly to Oakville nonstop from. Compare your options by using the "Direct flights only" filter on Expedia and pick the best starting point for you. Here are some of the major cities to jet off from:

  • Washington
  • Chicago
  • Orlando
  • Atlanta
  • Charlotte

How to find a cheap flight to Oakville?
Jetting off in the low season and booking early are two good ways to snag cheap flights to Oakville. Or, consider flying on a Thursday, which, on average, is 16% cheaper than leaving on a Sunday.* Want to be the first to know as soon as fares drop? Set up price tracking on the Expedia app to get real-time updates.*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 Oakville?
While booking in advance is generally the best way to save money, don't panic if your Oakville getaway is last minute. It's still possible to find cheap flights to Oakville, especially if your plans have a little wiggle room. Try changing your trip dates, exploring different ticket types or flying out of another airport.
How far in advance should I book a flight to Oakville?
Lock in your flight to Oakville two to four months ahead if you're coming in from an international destination. For domestic travel, the usual timeframe is 28 days in advance. Lower fares and a greater choice of departure dates, times and seating options are just some of the advantages of booking early.**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 Oakville?
You'll save an average of 8% if you purchase plane tickets on a Sunday instead of Fridays, which tend to be the most expensive day to book.* When it comes to scoring a cheap flight to Oakville, it's all about timing.*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 Oakville?
Choose from these two top airlines that operate flights to Oakville:

  • American Airlines - 611 flights to Oakville each month, including 611 flights to Bradley Intl. Airport (BDL) per month.
  • Delta Air Lines - 359 flights to Oakville each month, including 359 flights to Bradley Intl. Airport (BDL) per month.

Where do you fly into Oakville?
When flying to Oakville, the main airport to touch down at is Tweed - New Haven Regional Airport (HVN). You can also head to nearby hubs like Hartford, CT (HFD-Hartford - Brainard), Bradley Intl. Airport (BDL) or Westchester County Airport (HPN). An additional option worth keeping in mind when you fly to Oakville is MacArthur Airport (ISP).
Can I save money by booking an Oakville trip package?
You could possibly save hundreds of dollars if you secure an Oakville flight and hotel package deal on Expedia. And you'll save yourself hassle by having all your travel arrangements in one place. Try bundling flights and hotels with add-ons like tours and activities for your own customized Oakville escape.
Can I change or cancel my flight to Oakville?
You can typically change or cancel your flight to Oakville within 24 hours of booking. However, be mindful that some flights are non-refundable. In those cases, you may be issued a credit toward future travel rather than a direct refund. It's important to check the airline's terms and conditions in your itinerary for specific details. You can use Expedia's "No cancel fee" or "Changes included" filters when you search to find cheap flights to Oakville with flexible change policies. For more information, browse our Customer Service Portal.

*Flight schedules are subject to change.

*Available to One Key members.

 

Travel information

Destination airport
Tweed - New Haven Regional
Destination airport IATA code
HVN
Destination city name
New Haven
Roundtrip price
$57

Trending flights to Oakville

Prices were available within the past 7 days and start at $29 for one-way flights and $58 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Avelo Airlines
Fri, May 8 - Sun, May 10
RDU
Raleigh
HVN
New Haven
$58 Roundtrip, just found
$58
Roundtrip
just found
Select Avelo Airlines flight, departing Fri, May 8 from Raleigh to New Haven, returning Sun, May 10, priced at $58 just found

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