$106 Cheap flight deals from Chicago (CHI) to Anna Maria Island (PIE)
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This Weekend's Flight Deals from Chicago to Anna Maria Island
This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Airfares from $106 One Way, $211 Round Trip from Chicago to Anna Maria Island
Prices starting at $211 for return flights and $106 for one-way flights to Anna Maria Island were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Anna Maria Island economy flight packages
DoubleTree by Hilton Tampa Rocky Point Waterfront
Dec 10 - Dec 13
Chicago (CHI) to Sarasota (SRQ)
Sarasota (SRQ) to Chicago (CHI)
Reviewed on Jan 3, 2025
The Residences at Siesta Key Beach by Hyatt Vacation Club
Dec 20 - Dec 27
Chicago (CHI) to Sarasota (SRQ)
Reviewed on May 10, 2025
More About Flying To Anna Maria Island from Chicago
Route Information for Flights from Chicago to Anna Maria Island
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | PIE |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Anna Maria Island
It has never been easier to find cheap Chicago to Anna Maria Island flights. Orbitz has some of the best deals around to save you more money on your flight, hotel, and vacation package for the trip you have been waiting for.
Plan Your Chicago to Anna Maria Island Flights on the Go
Orbitz offers cutting-edge mobile tools that let you search and book flights anywhere. All you need is a smartphone or mobile device to find discounts on flights from Chicago to Anna Maria Island. Use the app to check to make sure your flight is on time or book a last-minute cheap hotel room.
Get the Best Deals on Chicago to Anna Maria Island Flights
Finding great deals on flights from Chicago to Anna Maria Island is a snap with Orbitz. With our guaranteed low prices, you don’t have to worry if you are getting the best prices on air tickets, hotels, and cruises. And with all that money you saved, you can enjoy your Anna Maria Island vacation even more.
Pile Up Miles With Discount Air Tickets
Not only can you find great bargains on Chicago to Anna Maria Island flights, but you can rack up frequent flyer miles on the flights too. Enter your frequent flyer number on qualified flights when booking for Orbitz to see the miles pile up in your account.
Flight Alerts Keep You Informed
Stay on top of the latest updates for flights from Chicago to Anna Maria Island. We send you free email and mobile alerts to keep you informed about delays to Chicago to Anna Maria Island flights.
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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.