Cheap flights To Anna Maria Island (PIE) from $66

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Cheap Flights to Anna Maria Island from $66 One Way, $117 Round Trip

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

Tue, Dec 9 - Thu, Dec 11
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$117 Roundtrip, found 5 days ago
$117
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Tue, Dec 9 from Logan Intl. to Sarasota-Bradenton Intl., returning Thu, Dec 11, priced at $117 found 5 days ago
Mon, Nov 3 - Wed, Nov 19
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$119 Roundtrip, found 5 days ago
$119
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Mon, Nov 3 from Logan Intl. to Sarasota-Bradenton Intl., returning Wed, Nov 19, priced at $119 found 5 days ago
Sat, Dec 6 - Sat, Dec 13
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$119 Roundtrip, found 4 days ago
$119
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Sat, Dec 6 from Logan Intl. to Sarasota-Bradenton Intl., returning Sat, Dec 13, priced at $119 found 4 days ago
Sat, Nov 1 - Wed, Nov 5
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$134 Roundtrip, found 6 days ago
$134
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Sat, Nov 1 from Logan Intl. to Sarasota-Bradenton Intl., returning Wed, Nov 5, priced at $134 found 6 days ago
Mon, Nov 3 - Wed, Nov 5
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$136 Roundtrip, found 6 days ago
$136
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Mon, Nov 3 from Logan Intl. to Sarasota-Bradenton Intl., returning Wed, Nov 5, priced at $136 found 6 days ago
Sat, Nov 1 - Mon, Nov 3
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$138 Roundtrip, found 6 days ago
$138
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Nov 1 from Logan Intl. to Sarasota-Bradenton Intl., returning Mon, Nov 3, priced at $138 found 6 days ago
Sat, Dec 6 - Fri, Dec 12
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$139 Roundtrip, just found
$139
Roundtrip
just found
Select JetBlue Airways flight, departing Sat, Dec 6 from Logan Intl. to Sarasota-Bradenton Intl., returning Fri, Dec 12, priced at $139 just found
Sat, Nov 15 - Mon, Nov 17
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$143 Roundtrip, found 6 days ago
$143
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Sat, Nov 15 from Logan Intl. to Sarasota-Bradenton Intl., returning Mon, Nov 17, priced at $143 found 6 days ago
Sat, Jan 17 - Tue, Jan 20
ORD
O'Hare Intl.
SRQ
Sarasota-Bradenton Intl.
$145 Roundtrip, found 5 days ago
$145
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Jan 17 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Tue, Jan 20, priced at $145 found 5 days ago
Sat, Jan 17 - Tue, Jan 20
ORD
O'Hare Intl.
SRQ
Sarasota-Bradenton Intl.
$148 Roundtrip, found 5 days ago
$148
Roundtrip
found 5 days ago
Select United flight, departing Sat, Jan 17 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Tue, Jan 20, priced at $148 found 5 days ago

Anna Maria Island Flight Information

Traveling To
Anna Maria Island
Destination Airport IATA Code
PIE
Number of Airlines Serving
Airlines
Frontier Airlines, JetBlue Airways, United, American Airlines, Southwest Airlines, Delta, Breeze Airways
Flight Price
$117
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.
Resort Sixty-Six
2.5-star property

Resort Sixty-Six

Dec 6 - Dec 13

7 night stay

Detroit (DTW) to Sarasota (SRQ)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $849, price is now $498 per person
$498
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

Dec 4 - Dec 7

3 night stay

Boston (BOS) to Sarasota (SRQ)

JetBlue Airways • Non-stop • Coach

Sarasota (SRQ) to Boston (BOS)

American Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,240, price is now $793 per person
$793
per person
found 1 day ago
Tropic Isle at Anna Maria Island Inn
4.0-star property

Tropic Isle at Anna Maria Island Inn

Dec 4 - Dec 7

3 night stay

Boston (BOS) to Sarasota (SRQ)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $911, price is now $600 per person
$600
per person
found 23 hours ago
Don't see what you're looking for?
See all available trips from Detroit to Anna Maria Island
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Anna Maria Island first class flight packages

Price found within the past 48 hours. Click for updated prices.
Residence Inn by Marriott Clearwater Beach
3.0-star property

Residence Inn by Marriott Clearwater Beach

8.8/10 Excellent! (1,011 reviews)

Dec 6 - Dec 13

7 night stay

Boston (BOS) to Tampa (TPA)

Delta • Roundtrip • FirstClass
Price was $1,409, price is now $1,212 per person
$1,212
per person
found 15 hours ago
Clean rooms. Nice staff

Reviewed on Sep 28, 2025

The Westin Sarasota
4.0-star property

The Westin Sarasota

9/10 Wonderful! (1,108 reviews)

Dec 6 - Dec 13

7 night stay

Boston (BOS) to Tampa (TPA)

Delta • Roundtrip • FirstClass
Price was $1,766, price is now $1,274 per person
$1,274
per person
found 15 hours ago
$50 per valet without other option is too high

Reviewed on Sep 8, 2025

AC Hotel Clearwater Beach
3.5-star property

AC Hotel Clearwater Beach

9/10 Wonderful! (888 reviews)

Dec 6 - Dec 13

7 night stay

Boston (BOS) to Tampa (TPA)

Delta • Roundtrip • FirstClass
Price was $1,485, price is now $1,283 per person
$1,283
per person
found 15 hours ago
Great location - 1 minute from the beach. Clean brand new rooms.

Reviewed on Sep 21, 2025

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

Orbitz provides convenient, one-stop shopping for travelers looking for budget flights to Anna Maria Island or any other low fare domestic or international air travel.

Innovative Orbitz Tools for the Trip Planner on the Move

Now it is even faster to find exclusive deals and book cheap Anna Maria Island flights from any location with our new Orbitz apps. These cutting-edge mobile tools are available free to anyone with an Android device, iPad, or iPhone. Look up Anna Maria Island's most popular attractions, best restaurants, and entertainment venues or check on your flights to Anna Maria Island and make changes to your itinerary while waiting in line for your latte.

Stay on Budget, Earn Miles with Bargain Anna Maria Island Flights

You can find amazing discount fares with Orbitz’s guaranteed low prices or take advantage of last-minute sales and special travel packages. You can also earn points towards your airline frequent flyer programs when you book qualified flights to Anna Maria Island. That means you can rack up money-saving points and miles for future use while saving money now.

We Are Just a Phone Call Away If You Need Us

Booking, changing, or canceling your Anna Maria Island flights is a breeze with Orbitz’s online and mobile tools, but that doesn't mean that we leave you hanging if you want to speak with one of our representatives. If you need help, just contact our Customer Service by email or phone. To enjoy a less stressful trip, be sure to sign up for instant alerts so we can send you any updates or delays relating to your flights to Anna Maria Island to your mobile phone or email.

Frequently asked questions

How much is a flight to Anna Maria Island?
This week, prices fluctuated between $117 and $148 for a return flight to Anna Maria Island. One-way tickets originating from Chicago (ORD) dropped down to $66 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.