$48 Cheap flights to Town of Southold Town

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Top places to visit in Town of Southold Town

An aerial view of a harbor with boats, a ship, and a dock extending into the water.
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Greenport

Greenport
A calm lake with a forest in the background during sunset.
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Southold

Southold
A lighthouse on a rocky outcrop with a boat in the water.
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Orient

Orient

Cheap flights to Town of Southold Town from $48 One Way, $98 Round Trip

$98 return flights and $48 one-way flights to Town of Southold Town were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Aug 26 - Thu, Aug 27
MCO
Orlando
HVN
New Haven
$98 Roundtrip, found 10 hours ago
$98
Roundtrip
found 10 hours ago
Select Avelo Airlines flight, departing Wed, Aug 26 from Orlando to New Haven, returning Thu, Aug 27, priced at $98 found 10 hours ago
Wed, Sep 2 - Sat, Sep 5
MCO
Orlando
HVN
New Haven
$101 Roundtrip, found 9 hours ago
$101
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Wed, Sep 2 from Orlando to New Haven, returning Sat, Sep 5, priced at $101 found 9 hours ago
Tue, Sep 1 - Wed, Sep 2
MCO
Orlando
HVN
New Haven
$111 Roundtrip, found 3 hours ago
$111
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Tue, Sep 1 from Orlando to New Haven, returning Wed, Sep 2, priced at $111 found 3 hours ago
Thu, Sep 3 - Sat, Sep 5
MCO
Orlando
HVN
New Haven
$112 Roundtrip, found 9 hours ago
$112
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Thu, Sep 3 from Orlando to New Haven, returning Sat, Sep 5, priced at $112 found 9 hours ago
Fri, Sep 11 - Mon, Sep 14
MCO
Orlando
ISP
Islip
$115 Roundtrip, found 3 hours ago
$115
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Fri, Sep 11 from Orlando to Islip, returning Mon, Sep 14, priced at $115 found 3 hours ago
Thu, Oct 1 - Sun, Oct 4
ORD
Chicago
HVN
New Haven
$118 Roundtrip, just found
$118
Roundtrip
just found
Select Avelo Airlines flight, departing Thu, Oct 1 from Chicago to New Haven, returning Sun, Oct 4, priced at $118 just found
Fri, Sep 4 - Sun, Sep 6
ORD
Chicago
HVN
New Haven
$119 Roundtrip, just found
$119
Roundtrip
just found
Select Avelo Airlines flight, departing Fri, Sep 4 from Chicago to New Haven, returning Sun, Sep 6, priced at $119 just found
Fri, Aug 21 - Mon, Aug 24
ORD
Chicago
HVN
New Haven
$130 Roundtrip, found 1 hour ago
$130
Roundtrip
found 1 hour ago
Select Avelo Airlines flight, departing Fri, Aug 21 from Chicago to New Haven, returning Mon, Aug 24, priced at $130 found 1 hour ago
Thu, Aug 27 - Mon, Aug 31
ORD
Chicago
HVN
New Haven
$132 Roundtrip, just found
$132
Roundtrip
just found
Select Avelo Airlines flight, departing Thu, Aug 27 from Chicago to New Haven, returning Mon, Aug 31, priced at $132 just found
Fri, Aug 14 - Mon, Aug 24
ORD
Chicago
HVN
New Haven
$136 Roundtrip, found 2 days ago
$136
Roundtrip
found 2 days ago
Select Avelo Airlines flight, departing Fri, Aug 14 from Chicago to New Haven, returning Mon, Aug 24, priced at $136 found 2 days ago
Thu, Aug 20 - Mon, Aug 24
ORD
Chicago
HVN
New Haven
$140 Roundtrip, found 2 hours ago
$140
Roundtrip
found 2 hours ago
Select Avelo Airlines flight, departing Thu, Aug 20 from Chicago to New Haven, returning Mon, Aug 24, priced at $140 found 2 hours ago
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Find The Perfect Hotel For After Your Flight

Score Epic Town of Southold Town Accommodation Deals

Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
$387 nightly
The price is $442 total per night from Aug 18 to Aug 19
$442 total
Aug 18 - Aug 19
Total with taxes and fees
Book a stay at this beach hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
Opens in a new windowSound View Greenport
Zey Hotel

Zey Hotel

3.5 out of 5
439 Main Street Greenport NY
$243 nightly
The price is $278 total per night from Aug 17 to Aug 18
$278 total
Aug 17 - Aug 18
Total with taxes and fees
Book a stay at this boutique hotel in Greenport. Enjoy free parking, free bicycles on site, and daily housekeeping. Popular attractions Greenport Harbor Brewing ...
9.2/10 Wonderful! (364 reviews)
"Room clean, bed comfy, high quality towels, friendly and accommodating customer service. Great areas in hotel to sit, read, relax Great location"

Reviewed on Jul 31, 2026

Opens in a new windowZey Hotel
North Fork Resort

North Fork Resort

3 out of 5
690 Queen St Greenport NY
$481 nightly
The price is $550 total per night from Aug 17 to Aug 18
$550 total
Aug 17 - Aug 18
Total with taxes and fees
Stay at this cottage in Greenport. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Railroad Museum of Long Island and Greenport Farmers' ...
9.4/10 Exceptional! (41 reviews)
"Very nice units. Pool area and outdoor space around pool also very nice. Also excellent location and Greenport is a fantastic town Lot of work still being done on the property. Once completed the place will be great."

Reviewed on Jul 29, 2026

Opens in a new windowNorth Fork Resort
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The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
$345 nightly
The price is $391 total per night from Sep 1 to Sep 2
$391 total
Sep 1 - Sep 2
Total with taxes and fees
Stay at this hotel in Southold. Enjoy free WiFi, free bicycles on site, and a business center. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.4/10 Exceptional! (310 reviews)
"We stayed at the Shoals for 3 nights. Something I didn't realize was that there are no rooms directly facing the water - all rooms look out to the parking lot. The property and rooms were very clean and very well maintained, however many things were lacking. 1.) MAJOR concern: We asked for a pack ..."

Reviewed on Jul 30, 2026

Opens in a new windowThe Shoals Suites and Slips
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Need a Car For After Your Flight?

Economy

Chevrolet Spark
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass
  • 5 people
Jeep Compass
SUV Jeep Compass

Town of Southold Town

Orbitz uses cutting edge mobile technology to help get you the best deals on Town of Southold Town flights. We offer guaranteed low prices on air tickets that can be combined with hotels and car rentals to save you even more money.

Find Cheap Town of Southold Town Flights And Hotel Rooms Using Our Mobile App

Orbitz not only guarantees low prices for flights to Town of Southold Town, we also offer Mobile Steals on our Orbitz on the Go mobile app where you can find great mobile-only deals on hotel rooms in the area.

Use the Orbitz Flight Matrix To Save Big On Car Rental

Discount flights to Town of Southold Town can be combined with car rental to get you additional savings. Just use our Flight Matrix to see how your budget air ticket can be combined with a car rental to make your trip not only inexpensive but also more convenient.

Use Multiple Airlines To Ensure You Get The Best Deal

Orbitz allows you to use multiple airlines for flights to Town of Southold Town. By using a combination of airlines for discount flights you are guaranteed to get the lowest fares each way and get the schedule that is most convenient for you.

Store Your Frequent Flyer Information on Orbitz For Easy Access

Booking with Orbitz will still allow you to apply miles for flights to Town of Southold Town to your frequent flyer program. Not only that, but your frequent flyer information will be safely stored on our website, so it will be easy to access the next time you book a discount air ticket with Orbitz.

Frequently asked questions

Which airlines fly to Town of Southold Town?
Booking a flight to Town of Southold Town is easy — simply choose from 23 airlines that fly into MacArthur Airport (ISP). When you've finalized your sightseeing itinerary and packed your suitcase, these leading domestic carriers will welcome you on board:

  • Southwest Airlines - 73 flights to Town of Southold Town per month
  • Frontier Airlines - 38 flights to Town of Southold Town per month
  • Breeze Airways - 1 flights to Town of Southold Town per month

How much is a flight to Town of Southold Town?
Plenty of fantastic deals were up for the taking this week, with return flights to Town of Southold Town ranging from $98 to $140. But it was jet-setters beginning their trip from Orlando (MCO) who landed the really big bargains. One-way fares to Town of Southold Town started at just $48.
How to book the cheapest flight to Town of Southold Town?
Scoring cheap flights to Town of Southold Town is as simple as booking with Orbitz. But if you're eager to make sure you're walking away with the best flight deals around, here are some suggestions to follow:

  • Depending on where you're leaving from, choose the 'Nearby airports' function (located under the departure and arrival options). In some instances, other departure points will have cheaper fares.
  • Similarly, click on the 'Show flexible dates' option to bring up the airfares on days around your selected departure. You may be able to pick up cheaper flight deals if you're flexible with your schedule.
  • To filter your results, click on 'Show options.' You can search based on airlines, seating class, nonstop flights and refundable flights. You can also choose whether you want to fly in the morning, afternoon or evening under 'Sort & Filter' to the left.
  • The early bird gets the best savings, so purchase your seats once you've settled on your travel dates. The most affordable airfares are quick to go and prices normally climb as the departure date nears.
  • Save on your trip by bundling your hotel, flights and car rental into one convenient package deal. Your credit card will thank you.
  • Flying during the busy season can mean steep airfares. If possible, plan your trip outside of popular dates, such as Christmas, New Year's Eve and Easter.

What is the best time to book a flight to Town of Southold Town?
Book in January, February or August for the best flight prices to Town of Southold Town. Once you've found a bargain, snap it up — cheap flights tend to pop up and vanish at the tap of a button.
What day of the week is the cheapest to book a flight to Town of Southold Town?
If you're after low-cost fares to Town of Southold Town, the best days to book are Tuesdays, Wednesdays and Saturdays. With Orbitz (and some good timing!), a fabulous flight deal will be all yours.
What is the cheapest day of the week to fly to Town of Southold Town?
You can grab cheap flights to Town of Southold Town by hopping on a plane on a Monday, according to Orbitz data from 2020. Tuesday is also more affordable, while Saturday has the most expensive ticket prices. Whether you prefer to stretch your travel budget or fly out on any day that's convenient, you'll always find a good deal with Orbitz.
What is the cheapest month to fly to Town of Southold Town?
Travel sometime in August if you don't want to eat into your budget. Orbitz data has found that it's generally the best month for cheap flights to Town of Southold Town. June is when fares are at their most expensive.
Which airlines allow free cancellation?
Flexibility is important these days, that's why Orbitz lets you search for flights that won't slap on fees for any amendments. Add your departure and arrival destinations, then click on "Filter by flexible change policies." We'll show you options that include free cancellation within 24 hours of booking and no change fees.
What do I need for the flight to Town of Southold Town?
There's so much to plan for any big journey, so it's nice to get some help before you set out. Here are a few suggestions to ensure you're prepared for departure:

  • Make sure you've got your travel papers and identification. For overseas trips, you'll need to take your passport. When booking your flights, always use the same details that are listed on your current ID.
  • Stock your carry-on bag with activities and snacks and you'll easily pass the time on your medium-haul flight. If you get the chance, join the airport's Wi-Fi and download your favorite podcast or playlist to your phone or tablet before take off.
  • Both air conditioning and high altitudes can create a cool environment. No matter what the weather is outside, pack a sweater to keep nice and warm during your flight.

How do I get cheap first-class/business deals to Town of Southold Town?
Experienced travelers have a way of finding business or first-class flights to Town of Southold Town that don't cost a packet. Be like them with these practical tips:

  • Be flexible with your travel dates and wait for huge sales on business or first-class airfares.
  • Many low-cost airlines offer excellent business or premium-class seating without the hefty fees.
  • Make the most of your airline's customer loyalty program and use points to upgrade your seat. Alternatively, you can try bidding for an upgrade in online auctions.

What is the best time to go to Town of Southold Town?
Anytime is an awesome time to experience Town of Southold Town, though May, June and August are the busiest months. Like most of the Northern Hemisphere, summertime begins June 20. If you'd prefer to spend most of your days in a light T-shirt than a winter coat, this time of year would be ideal. Expect average daytime highs of 75 ºF and nightly lows around 70 ºF.
Travel tips for Town of Southold Town

  • Downtown Town of Southold Town has plenty of renowned attractions. Drawcards like Kontokosta Winery and 67 Steps Beach will keep your feet moving and your adventurous spirit happy.
  • You'll find fun day trip adventures a short commute from the center. Head for Yale University first and after that, Montauk Point Lighthouse.
  • When you want to explore other parts of Suffolk County, arrange a car rental and head in the direction of Northport. Islandia is another major city with loads to do and see.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.