Cheap flights To Anna Maria Island (PIE) from $73

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Cheap Flights to Anna Maria Island from $73 One Way, $142 Round Trip

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, Sep 16 - Sat, Sep 26
BDL
Bradley Intl.
SRQ
Sarasota-Bradenton Intl.
$142 Roundtrip, found 1 day ago
$142
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Sep 16 from Bradley Intl. to Sarasota-Bradenton Intl., returning Sat, Sep 26, priced at $142 found 1 day ago
Wed, Sep 16 - Sat, Sep 26
BDL
Bradley Intl.
SRQ
Sarasota-Bradenton Intl.
$147 Roundtrip, found 1 day ago
$147
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Sep 16 from Bradley Intl. to Sarasota-Bradenton Intl., returning Sat, Sep 26, priced at $147 found 1 day ago
Wed, Sep 16 - Sat, Sep 26
BDL
Bradley Intl.
SRQ
Sarasota-Bradenton Intl.
$152 Roundtrip, found 1 day ago
$152
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Sep 16 from Bradley Intl. to Sarasota-Bradenton Intl., returning Sat, Sep 26, priced at $152 found 1 day ago
Wed, Sep 16 - Sat, Sep 19
BDL
Bradley Intl.
SRQ
Sarasota-Bradenton Intl.
$154 Roundtrip, found 15 hours ago
$154
Roundtrip
found 15 hours ago
Select Breeze Airways flight, departing Wed, Sep 16 from Bradley Intl. to Sarasota-Bradenton Intl., returning Sat, Sep 19, priced at $154 found 15 hours ago
Wed, Aug 5 - Wed, Aug 12
BDL
Bradley Intl.
SRQ
Sarasota-Bradenton Intl.
$162 Roundtrip, found 12 hours ago
$162
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Wed, Aug 5 from Bradley Intl. to Sarasota-Bradenton Intl., returning Wed, Aug 12, priced at $162 found 12 hours ago
Sat, Jul 4 - Wed, Sep 9
BDL
Bradley Intl.
SRQ
Sarasota-Bradenton Intl.
$166 Roundtrip, found 1 day ago
$166
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Jul 4 from Bradley Intl. to Sarasota-Bradenton Intl., returning Wed, Sep 9, priced at $166 found 1 day ago
Wed, Aug 5 - Wed, Aug 12
BDL
Bradley Intl.
SRQ
Sarasota-Bradenton Intl.
$167 Roundtrip, found 12 hours ago
$167
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Wed, Aug 5 from Bradley Intl. to Sarasota-Bradenton Intl., returning Wed, Aug 12, priced at $167 found 12 hours ago
Wed, Sep 16 - Sat, Sep 19
BDL
Bradley Intl.
SRQ
Sarasota-Bradenton Intl.
$168 Roundtrip, found 15 hours ago
$168
Roundtrip
found 15 hours ago
Select Breeze Airways flight, departing Wed, Sep 16 from Bradley Intl. to Sarasota-Bradenton Intl., returning Sat, Sep 19, priced at $168 found 15 hours ago
Wed, Sep 16 - Sat, Sep 19
BDL
Bradley Intl.
SRQ
Sarasota-Bradenton Intl.
$170 Roundtrip, found 15 hours ago
$170
Roundtrip
found 15 hours ago
Select Breeze Airways flight, departing Wed, Sep 16 from Bradley Intl. to Sarasota-Bradenton Intl., returning Sat, Sep 19, priced at $170 found 15 hours ago
Wed, Aug 5 - Wed, Aug 12
BDL
Bradley Intl.
SRQ
Sarasota-Bradenton Intl.
$172 Roundtrip, found 12 hours ago
$172
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Wed, Aug 5 from Bradley Intl. to Sarasota-Bradenton Intl., returning Wed, Aug 12, priced at $172 found 12 hours ago

Anna Maria Island Flight Information

Traveling To
Anna Maria Island
Destination Airport IATA Code
PIE
Number of Airlines Serving
Airlines
Breeze Airways
Flight Price
$142
Earliest Departing Flight
Latest Departing Flight

Book Your Flight & Hotel Together & Save

Anna Maria Island economy flight packages

Price found within the past 48 hours. Click for updated prices.
Cedar Cove Resort and Cottages
3.0-star property

Cedar Cove Resort and Cottages

Jul 9 - Jul 14

5 night stay

Chicago (CHI) to Tampa (TPA)

American Airlines • Coach

Tampa (TPA) to Chicago (CHI)

Southwest Airlines • Coach
Save 100% on your flight
Price was $1,431, price is now $944 per person
$944
per person
found 1 day ago
The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5-star property

The Residences at Siesta Key Beach by Hyatt Vacation Club

Jun 21 - Jun 25

4 night stay

Chicago (CHI) to Tampa (TPA)

Southwest Airlines • Coach

Tampa (TPA) to Chicago (CHI)

Frontier Airlines • Coach
Save 100% on your flight
Price was $2,556, price is now $1,635 per person
$1,635
per person
found 1 day ago
Resort Sixty-Six
2.5-star property

Resort Sixty-Six

Jun 20 - Jun 27

7 night stay

New York (JFK) to Tampa (TPA)

Delta • Roundtrip • Coach
Save 100% on your flight
Price was $1,534, price is now $1,022 per person
$1,022
per person
found 1 day ago
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See all available trips from Chicago to Anna Maria Island
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Anna Maria Island premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Barrymore Hotel Tampa Riverwalk
3.0-star property

The Barrymore Hotel Tampa Riverwalk

8.6/10 Excellent! (2,602 reviews)

Jun 28 - Jul 2

4 night stay

New York (NYC) to Tampa (TPA)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,048, price is now $892 per person
$892
per person
found 1 day ago
The price of the hotel stay did not meet our expectations for the quality provided. For what we paid, we anticipated a better room and a more welcoming atmosphere. We also noticed that the cleaning staff were not very friendly and did not attend to basic housekeeping tasks such as making the beds or refilling soaps. The condition of the bed even appeared as though it had been previously used, Due to the lack of attention to detail and the overall unwelcoming attitude, only minimal cash tips were given.

Reviewed on May 4, 2026

Hyatt Place Tampa Downtown
3.0-star property

Hyatt Place Tampa Downtown

9.4/10 Exceptional! (2,064 reviews)

Jun 28 - Jul 2

4 night stay

New York (NYC) to Tampa (TPA)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,128, price is now $958 per person
$958
per person
found 1 day ago
Beautiful rooms, friendly staff, great food.

Reviewed on Apr 14, 2026

Hyatt House Tampa Downtown
3.5-star property

Hyatt House Tampa Downtown

9.4/10 Exceptional! (1,220 reviews)

Jun 28 - Jul 2

4 night stay

New York (NYC) to Tampa (TPA)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,080, price is now $923 per person
$923
per person
found 1 day ago
Breakfast time changed without information to guests

Reviewed on Jan 26, 2025

Don't see what you're looking for?
See all available trips from New York to Anna Maria Island
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Anna Maria Island

Get the absolute lowest prices on flights to Anna Maria Island by shopping with Orbitz. Orbitz is the most efficient travel planner around, allowing you to search, compare and book discount domestic and international flights fast. With cutting-edge mobile tools and access to frequent flier rewards programs, we have everything you need for both your routine and holiday excursions.

Book Your Flight To Anna Maria Island Using Your Mobile Device

New mobile app tools enable those with hand-held devices to scout out the best bargains and to secure tickets from any location. If you have an iPhone, iPad or Android device, you may take advantage of special discounts, only available to mobile device customers, when you book hotel rooms or car rentals on the same day as booking Anna Maria Island flights.

Avoid Check-In Hassles When Traveling On Flights to Anna Maria Island

Orbitz also provides an array of resources that can help you eliminate most check-in hassles. Detailed baggage information is continually available for Anna Maria Island flights. Mobile apps can also be used to share travel itineraries with family members or business associates.

Keeping Everyone Up To Date

When you download the free Orbitz mobile phone app, you can get regular and free flight updates. These will keep you informed of important scheduling changes. Updates can even be sent to several contacts, helping to keep everyone current on anticipated arrival times and all other relevant flight details.

Orbitz makes traveling on a budget very easy to do. We provide everything you need to plan your ideal trip from start to finish. Getting there and back again is a snap when you book your Anna Maria Island flight using Orbitz.

Frequently asked questions

How much is a flight to Anna Maria Island?
This week, prices fluctuated between $142 and $172 for a return flight to Anna Maria Island. One-way tickets originating from Hartford (BDL) dropped down to $73 during the same period.
How to book the cheapest flight to Anna Maria Island?
With some of the most competitive flight deals around, you're guaranteed value for money with Orbitz. The following suggestions will help you land cheap flights to Anna Maria Island — and leave you with more cash to splash:

  • Depending on your place of departure, choose the 'Nearby airports' function (located under the departure and arrival form fields). At times, alternative departure points offer better priced fares.
  • If you're flexible with your travel itinerary, click on the 'Show flexible dates' option. You'll see the flight deals for the days around your chosen departure. Ticket prices often vary depending on what day it is.
  • To refine your results, hit '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.
  • Once you've sorted out your travel dates, don't delay booking. Prices generally get more expensive as the departure date nears.
  • Consider bundling your hotels, flights and car rentals into a package with Orbitz to get more for your money.
  • Don't fly during the busy season if you can. By steering clear of summer, school vacations and other popular dates, you can save plenty on your airfare.

What is the best time to book a flight to Anna Maria Island?
Catch a bargain and secure your seats to Anna Maria Island in January. If you've missed this month, fear not. February and August often have affordable airfares as well. Just be careful you don't snooze on a sale — cheap flights appear and vanish in an instant!
What day of the week is the cheapest to book a flight to Anna Maria Island?
In general, Tuesdays, Wednesdays and Saturdays are the cheapest days to book flights to Anna Maria Island. If you're looking for the most competitive airfares, search across those days and you're likely to pick up a fantastic flight deal.
What is the cheapest day of the week to fly to Anna Maria Island?
Everybody enjoys saving money, so we recommend flying out early in the week for cheap flights to Anna Maria Island. Orbitz data from 2020 shows you can pick up the best prices on flights taking off on Mondays. Tuesdays are the next most affordable day, while Saturdays are likely to cost an arm and a leg. Many passengers like to start their vacation when the working week is over, so leave those Saturdays for catching up with friends.
What is the cheapest month to fly to Anna Maria Island?
You can jet for less in August. This is generally an excellent month to get on a plane if you're looking for cheap flights to Anna Maria Island, according to Orbitz data. The most expensive time to fly is June, so avoid this month if you're watching your pennies.
Which airlines allow free cancellation?
Flexibility is more important than ever, that's why Orbitz lets you search for carriers that won't slap you with a fee for any amendments. Add your departure and arrival destinations, then choose "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 Anna Maria Island?
From onboard entertainment to travel necessities like noise-canceling headphones, there are a number of things a frequent flyer won't leave home without. To make sure you're organized for your flight, have a look at this helpful list:

  • Make sure you've packed your travel documents and some identification. For international journeys, you'll need your passport. When reserving your seats, always use the exact details written on your current ID.
  • A well-stocked carry-on bag is important for any medium-haul journey. With a few hours or more to kill, you'll need something to keep you busy on your trip. We suggest a good book (or trashy magazine), and something to nibble on.
  • Together, air conditioning and high altitudes make for a chilly environment. No matter what the season is in Anna Maria Island, carry an extra layer with you to keep nice and warm during the journey.

How many direct flights are there to Anna Maria Island?
Every month, there are 80 direct flights to Anna Maria Island. Take your pick of an impressive range of airline companies, including Southwest Airlines, Delta Air Lines and American Airlines. Other carriers that fly nonstop are Allegiant Air, United Airlines and JetBlue Airways.
How do I get cheap first-class/business deals to Anna Maria Island?
If you think a business or first-class ticket is beyond your reach, you may want to think again. Here are some top tips to help you pick up a premium flight to Anna Maria Island for a whole lot less:

  • Flexibility is key. By being open to a range of travel dates, you'll have a better chance of picking up a deal on business or first-class airfares.
  • Plenty of budget airlines nowadays have outstanding business-class seating that doesn't cost a bundle.
  • Make a bid for an upgrade. Some carriers hold online auctions that let you offer a price for a seat at the front of the plane. You can also try upgrading with points earned through a loyalty scheme.

What is the best time to go to Anna Maria Island?
There's loads of fun to be had no matter what time of year you visit Anna Maria Island, but January, February and March are the busiest months. Like to fill your itinerary with plenty of warm-weather experiences? Plan your getaway around June 20. This is when summer starts in the Northern Hemisphere. Expect the mercury to span between 80 ºF and 90 ºF at this time of year.

More to Explore

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.