$82 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 $82 One Way, $159 Round Trip from Chicago to Anna Maria Island
Prices starting at $159 for return flights and $82 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
voco Sarasota by IHG
Aug 29 - Sep 2
Chicago (CHI) to Tampa (TPA)
Tampa (TPA) to Chicago (CHI)
Reviewed on Jun 30, 2024
Ocean Club Treasure Island Hotel
Sep 15 - Sep 19
Chicago (CHI) to Tampa (TPA)
Tampa (TPA) to Chicago (CHI)
Reviewed on Apr 29, 2025
The Avalon Club
Aug 29 - Sep 1
Chicago (CHI) to Tampa (TPA)
Reviewed on Jun 7, 2024
Anna Maria Island first class flight packages
Hotel Alba, Tapestry Collection by Hilton
Sep 13 - Sep 17
Chicago (ORD) to Sarasota (SRQ)
Sarasota (SRQ) to Chicago (ORD)
Reviewed on Jul 27, 2025
The Pointe Condos by Barsala
Sep 13 - Sep 17
Chicago (ORD) to Sarasota (SRQ)
Sarasota (SRQ) to Chicago (ORD)
Reviewed on Oct 25, 2022
The Westshore Grand, A Tribute Portfolio Hotel, Tampa
Sep 13 - Sep 17
Chicago (ORD) to Sarasota (SRQ)
Sarasota (SRQ) to Chicago (ORD)
Reviewed on Jun 22, 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 | 1052 mi |
Direct Flight Airlines | Air Canada, Emirates, Air New Zealand, United Airlines |
Earliest Flight Arrival | 7:10PM UTC |
Latest Flight Arrival | 7:10PM UTC |
Chicago to Anna Maria Island
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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.