Cheap flights To Anna Maria Island (PIE) from $48

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Cheap Flights to Anna Maria Island from $48 One Way, $81 Round Trip

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

Sun, Jan 10 - Thu, Jan 14
CAK
Akron-Canton
PIE
St. Petersburg-Clearwater Intl.
$81 Roundtrip, found 3 hours ago
$81
Roundtrip
found 3 hours ago
Select Allegiant Air flight, departing Sun, Jan 10 from Akron-Canton to St. Petersburg-Clearwater Intl., returning Thu, Jan 14, priced at $81 found 3 hours ago
Sun, Jan 17 - Sun, Jan 24
CAK
Akron-Canton
PIE
St. Petersburg-Clearwater Intl.
$83 Roundtrip, found 22 hours ago
$83
Roundtrip
found 22 hours ago
Select Allegiant Air flight, departing Sun, Jan 17 from Akron-Canton to St. Petersburg-Clearwater Intl., returning Sun, Jan 24, priced at $83 found 22 hours ago
Sun, Dec 6 - Thu, Dec 10
CAK
Akron-Canton
PIE
St. Petersburg-Clearwater Intl.
$90 Roundtrip, found 6 hours ago
$90
Roundtrip
found 6 hours ago
Select Allegiant Air flight, departing Sun, Dec 6 from Akron-Canton to St. Petersburg-Clearwater Intl., returning Thu, Dec 10, priced at $90 found 6 hours ago
Sun, Nov 1 - Wed, Nov 4
CVG
Cincinnati - Northern Kentucky Intl.
PIE
St. Petersburg-Clearwater Intl.
$91 Roundtrip, found 22 hours ago
$91
Roundtrip
found 22 hours ago
Select Allegiant Air flight, departing Sun, Nov 1 from Cincinnati - Northern Kentucky Intl. to St. Petersburg-Clearwater Intl., returning Wed, Nov 4, priced at $91 found 22 hours ago
Mon, Oct 26 - Fri, Oct 30
CAK
Akron-Canton
PIE
St. Petersburg-Clearwater Intl.
$92 Roundtrip, found 5 days ago
$92
Roundtrip
found 5 days ago
Select Allegiant Air flight, departing Mon, Oct 26 from Akron-Canton to St. Petersburg-Clearwater Intl., returning Fri, Oct 30, priced at $92 found 5 days ago
Mon, Jan 18 - Thu, Jan 21
CAK
Akron-Canton
SRQ
Sarasota-Bradenton Intl.
$93 Roundtrip, found 1 day ago
$93
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Mon, Jan 18 from Akron-Canton to Sarasota-Bradenton Intl., returning Thu, Jan 21, priced at $93 found 1 day ago
Fri, Oct 30 - Fri, Nov 6
CAK
Akron-Canton
PIE
St. Petersburg-Clearwater Intl.
$94 Roundtrip, found 5 days ago
$94
Roundtrip
found 5 days ago
Select Allegiant Air flight, departing Fri, Oct 30 from Akron-Canton to St. Petersburg-Clearwater Intl., returning Fri, Nov 6, priced at $94 found 5 days ago
Sun, Nov 1 - Fri, Nov 20
CVG
Cincinnati - Northern Kentucky Intl.
PIE
St. Petersburg-Clearwater Intl.
$97 Roundtrip, found 2 days ago
$97
Roundtrip
found 2 days ago
Select Allegiant Air flight, departing Sun, Nov 1 from Cincinnati - Northern Kentucky Intl. to St. Petersburg-Clearwater Intl., returning Fri, Nov 20, priced at $97 found 2 days ago
Sun, Jan 17 - Thu, Jan 28
CAK
Akron-Canton
PIE
St. Petersburg-Clearwater Intl.
$98 Roundtrip, found 1 day ago
$98
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Sun, Jan 17 from Akron-Canton to St. Petersburg-Clearwater Intl., returning Thu, Jan 28, priced at $98 found 1 day ago
Thu, Oct 1 - Sun, Oct 4
SWF
Stewart Intl.
PIE
St. Petersburg-Clearwater Intl.
$117 Roundtrip, found 5 days ago
$117
Roundtrip
found 5 days ago
Select Allegiant Air flight, departing Thu, Oct 1 from Stewart Intl. to St. Petersburg-Clearwater Intl., returning Sun, Oct 4, priced at $117 found 5 days ago

Anna Maria Island Flight Information

Traveling To
Anna Maria Island
Destination Airport IATA Code
PIE
Number of Airlines Serving
Airlines
Allegiant Air
Flight Price
$81
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.
Ocean Club Treasure Island Hotel
4.0-star property

Ocean Club Treasure Island Hotel

Oct 7 - Oct 11

4 night stay

Chicago (CHI) to Tampa (TPA)

American Airlines • Coach

Tampa (TPA) to Chicago (CHI)

Frontier Airlines • Coach
Save 100% on your flight
Price was $1,079, price is now $742 per person
$742
per person
found 1 day ago
Cedar Cove Resort and Cottages
3.0-star property

Cedar Cove Resort and Cottages

Sep 24 - Sep 28

4 night stay

Chicago (CHI) to Tampa (TPA)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,446, price is now $831 per person
$831
per person
found 1 day ago
Landing Tampa Westshore
4.5-star property

Landing Tampa Westshore

Oct 8 - Oct 15

7 night stay

Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,549, price is now $1,039 per person
$1,039
per person
found 4 hours ago
Don't see what you're looking for?
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.
ChartHouse Clearwater Beach Marina Hotel
2.0-star property

ChartHouse Clearwater Beach Marina Hotel

9.6/10 Exceptional! (1,341 reviews)

Oct 8 - Oct 11

3 night stay

New York (NYC) to Tampa (TPA)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $851, price is now $693 per person
$693
per person
found 6 hours ago

Wyndham Grand Clearwater Beach
4.0-star property

Wyndham Grand Clearwater Beach

9.4/10 Exceptional! (3,672 reviews)

Oct 8 - Oct 11

3 night stay

New York (NYC) to Tampa (TPA)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,151, price is now $860 per person
$860
per person
found 6 hours ago
Evan was extremely hospitable! Trish also provided excellent customer service and went above and beyond to make sure our room was clean and comfortable for the remainder of our stay! Beautiful property and smells amazing!

Reviewed on Aug 17, 2026

Barefoot Beach Club
2.5-star property

Barefoot Beach Club

9.4/10 Exceptional! (1,398 reviews)

Oct 8 - Oct 11

3 night stay

New York (NYC) to Tampa (TPA)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $869, price is now $712 per person
$712
per person
found 6 hours ago

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

When you plan to buy tickets for flights to Anna Maria Island, you don’t have to look any further than Orbitz! We offer bargain rates and low fares on thousands of flights.

Reliable Customer Service

Along with our low prices, Orbitz is well known for exceptional customer care. We make it simple to find the best Anna Maria Island flights for you. If you need to cancel your booking or change your flight plans, simply contact our Customer Service department to make any adjustments.

Bargain Tickets for Anna Maria Island Flights

Orbitz offers deeply discounted flights to Anna Maria Island, and we provide the resources to research your travel destination and plan your complete itinerary.

Use Orbitz to Earn Points with Your Frequent Flyer Program

Saving your frequent flyer miles for your flights to Anna Maria Island? You can use Orbitz to make your budget ticket reservation for all your flights and still earn points or miles on your frequent flyer program! Just enter your program account number while you’re booking your ticket to have your points added automatically, every time you book with Orbitz.

Convenient Travel Planning Services

If you like the ease of making your travel plans on the move, you’ll love the free Orbitz apps for iPhones, iPads, and Android devices. You can use these apps to review your travel reservations or make a change to your itinerary. Orbitz also offers additional travel assistance such as free mobile alerts that keep you up-to-date about sudden changes to your upcoming flights. You can also browse Orbitz easily on your smartphone by using the mobile version of the website to find budget Anna Maria Island flights.

Frequently asked questions

How much is a flight to Anna Maria Island?
This week, prices fluctuated between $81 and $117 for a return flight to Anna Maria Island. One-way tickets originating from Akron (CAK) dropped down to $48 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.