Cheap Flights to Town of Southold Town from $28

View $28 flight on Fri, Mar 27, 2026Opens in a new window

Popular airlines to Town of Southold Town

  • United

  • Spirit Airlines

  • American Airlines

  • Delta

  • Frontier Airlines

  • Alaska Airlines

  • JetBlue Airways

  • Be in the know

    Get alerts if flight prices drop or rise*

  • Book smarter

    Save up to 30% on select hotels after you book a flight*

  • Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Today's featured flight deals to Town of Southold Town

Nonstop
Carry-on included
Lower price than typical

How much is the cheapest flight to Town of Southold Town?

Prices were available within the past 7 days and start at $28 for one-way flights and $58 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Thu, Feb 26 - Mon, Mar 9
MCO
Orlando
ISP
Islip
$77 Roundtrip, found 1 day ago
$77
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Feb 26 from Orlando to Islip, returning Mon, Mar 9, priced at $77 found 1 day ago
Breeze Airways
Wed, May 6 - Sat, May 9
MCO
Orlando
HVN
New Haven
$82 Roundtrip, found 1 day ago
$82
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, May 6 from Orlando to New Haven, returning Sat, May 9, priced at $82 found 1 day ago
Frontier Airlines
Wed, Mar 4 - Sun, Mar 8
MCO
Orlando
ISP
Islip
$82 Roundtrip, found 2 days ago
$82
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Mar 4 from Orlando to Islip, returning Sun, Mar 8, priced at $82 found 2 days ago
Frontier Airlines
Mon, Mar 2 - Mon, Mar 9
MCO
Orlando
ISP
Islip
$87 Roundtrip, found 1 day ago
$87
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Mar 2 from Orlando to Islip, returning Mon, Mar 9, priced at $87 found 1 day ago
Frontier Airlines
Wed, Apr 1 - Sat, Apr 11
MCO
Orlando
ISP
Islip
$97 Roundtrip, found 9 hours ago
$97
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Wed, Apr 1 from Orlando to Islip, returning Sat, Apr 11, priced at $97 found 9 hours ago
Frontier Airlines
Fri, Apr 17 - Mon, Apr 20
MCO
Orlando
ISP
Islip
$98 Roundtrip, found 1 hour ago
$98
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, Apr 17 from Orlando to Islip, returning Mon, Apr 20, priced at $98 found 1 hour ago
Avelo Airlines
Thu, May 28 - Sun, May 31
MCO
Orlando
HVN
New Haven
$100 Roundtrip, found 6 hours ago
$100
Roundtrip
found 6 hours ago
Select Avelo Airlines flight, departing Thu, May 28 from Orlando to New Haven, returning Sun, May 31, priced at $100 found 6 hours ago
Breeze Airways
Thu, May 28 - Sun, May 31
MCO
Orlando
HVN
New Haven
$102 Roundtrip, found 6 hours ago
$102
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Thu, May 28 from Orlando to New Haven, returning Sun, May 31, priced at $102 found 6 hours ago
Breeze Airways
Fri, May 8 - Sun, May 17
MCO
Orlando
HVN
New Haven
$103 Roundtrip, found 3 days ago
$103
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, May 8 from Orlando to New Haven, returning Sun, May 17, priced at $103 found 3 days ago
Southwest Airlines
Wed, Apr 1 - Tue, Apr 14
MCO
Orlando
ISP
Islip
$182 Roundtrip, found 9 hours ago
$182
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Wed, Apr 1 from Orlando to Islip, returning Tue, Apr 14, priced at $182 found 9 hours ago

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now

Airports in Town of Southold Town

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

Select flight to MacArthur ISP. Flights from $802
ISP
MacArthur
Flights from $802
Select flight to Tweed - New Haven Regional HVN. Cheapest option available. Flights from $599
HVN
Tweed - New Haven Regional
Cheapest
Flights from $599

Trending flights to Town of Southold Town

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sat, Apr 4 - Sat, Apr 11
TPA
Tampa
ISP
Islip
$58 Roundtrip, found 5 hours ago
$58
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sat, Apr 4 from Tampa to Islip, returning Sat, Apr 11, priced at $58 found 5 hours ago

Frequently asked questions

How do I find cheap flights to Town of Southold Town that have flexible change policies?
It's as easy as 1-2-3 with Expedia. First, enter your travel dates and destination and hit "Search." Second step: Check "No change fee" directly below the "Flexible change policies" filter on the left-hand side of your screen. Step 3. Reserve your flexible and cheap fare to Town of Southold Town.
Which airlines fly to Town of Southold Town?
Pack your suitcase and choose between these popular airlines that fly into or near Town of Southold Town:

  • Southwest Airlines - 156 flights to or near Town of Southold Town each month, including 156 flights to MacArthur Airport (ISP) per month.
  • Frontier Airlines - 151 flights to or near Town of Southold Town each month, including 151 flights to MacArthur Airport (ISP) per month.
  • Breeze Airways - 56 flights to or near Town of Southold Town each month, including 56 flights to MacArthur Airport (ISP) per month.

How can I find cheap tickets to Town of Southold Town?
A good strategy for nabbing cheap fares is to be flexible with your travel dates. Begin with searching for your flight to Town of Southold Town, then click on the "flexible dates" box for a list of prices for nearby days. Another good tip? Book well in advance. For an idea of fares, $58 was the lowest price for a flight to Town of Southold Town in the last seven days.
How much is a flight to Town of Southold Town?
One-way flights leaving Orlando (MCO) sold for as little as $28 in the last seven days. During this period, the price of a return ticket to Town of Southold Town ranged between $58 and $182. If you find a deal, grab it quickly — these prices don't wait around for long.
What are the most popular airports to fly into in Town of Southold Town?
Fly into MacArthur Airport (ISP) and experience everything that Town of Southold Town has to offer. As the region's main point of entry, about 364 flights touch down here each month.
When is the cheapest time to fly to Town of Southold Town?
Fly out on a Tuesday to better your chances of bagging the cheapest airfare to Town of Southold Town. Mondays are usually the next most affordable day to depart. Saturday is typically the costliest day to fly anywhere.
How much is a plane ticket to Town of Southold Town?
In the last seven days, seats to Town of Southold Town fluctuated between $58 and $182. Prices tend to rise over time, so pick up an awesome deal today.
What months are the cheapest to book a flight to Town of Southold Town?
The most affordable month to book a fabulous deal to Town of Southold Town is February, whereas the priciest month is December. Try to avoid this month if you're counting your pennies.
How long is a flight to Town of Southold Town?
Whether or not you'll have time to binge-watch your favorite series depends on where you're coming from. To give you a rough estimate, here are the average flight times for some leading domestic routes to Town of Southold Town:

  • Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall) to MacArthur Airport (ISP) - 1 hour and 20 minutes
  • Orlando, FL (MCO-Orlando Intl.) to MacArthur Airport (ISP) - 2 hours and 44 minutes
  • Fort Lauderdale, FL (FLL-Fort Lauderdale - Hollywood Intl.) to MacArthur Airport (ISP) - 2 hours and 26 minutes

Book with confidence

Enjoy extra legroom, flight flexibility, and a seamless travel experience.

Travel information

*Flight schedules are subject to change.

*Flight schedules are subject to change.

Explore a world of travel with Expedia

*Available to One Key members.