$92 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 $92 One Way, $280 Round Trip from Chicago to Anna Maria Island
Prices starting at $280 for return flights and $92 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
Candlewood Suites Safety Harbor - Clearwater NE by IHG
Feb 20 - Feb 22
Chicago (CHI) to Tampa (TPA)
Reviewed on Jun 25, 2024
Saddlebrook Resort
Feb 11 - Feb 15
Chicago (CHI) to Tampa (TPA)
Tampa (TPA) to Chicago (CHI)
Hotel Tampa Riverwalk
Feb 6 - Feb 12
Chicago (CHI) to Sarasota (SRQ)
Reviewed on Dec 16, 2025
Anna Maria Island first class flight packages
SkyBeach Resort
Feb 3 - Feb 8
Chicago (CHI) to Tampa (TPA)
Reviewed on Apr 9, 2025
Ocean Club Treasure Island Hotel
Feb 3 - Feb 8
Chicago (CHI) to Tampa (TPA)
Reviewed on Dec 4, 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
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Find Low Prices in One Place
Booking a trip from Chicago to Anna Maria Island has never been easier. Not only will you find great deals on flights, we offer bargains on cruises, car rentals, top-notch hotels, and more. You can also research and add local activities in Anna Maria Island to your flight or hotel reservation to keep the kids happy and active.
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Don’t Miss out on Miles
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Anna Maria Island Airports
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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.