$50 Cheap flight deals from Chicago (CHI) to Anna Maria (TPA)

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This Weekend's Flight Deals from Chicago to Anna Maria

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.

Fri, Jul 4 - Fri, Aug 1
ORD
O'Hare Intl.
TPA
Tampa Intl.
$150 Roundtrip, just found
$150
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Jul 4 from O'Hare Intl. to Tampa Intl., returning Fri, Aug 1, priced at $150 just found
Sat, Jul 5 - Thu, Jul 24
MDW
Midway Intl.
TPA
Tampa Intl.
$174 Roundtrip, found 3 hours ago
$174
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, Jul 5 from Midway Intl. to Tampa Intl., returning Thu, Jul 24, priced at $174 found 3 hours ago
Sat, Jul 5 - Tue, Jul 22
ORD
O'Hare Intl.
SRQ
Sarasota-Bradenton Intl.
$445 Roundtrip, found 3 days ago
$445
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Jul 5 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Tue, Jul 22, priced at $445 found 3 days ago
Fri, Jul 4 - Wed, Jul 23
MDW
Midway Intl.
SRQ
Sarasota-Bradenton Intl.
$701 Roundtrip, found 1 day ago
$701
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Jul 4 from Midway Intl. to Sarasota-Bradenton Intl., returning Wed, Jul 23, priced at $701 found 1 day ago

Airfares from $50 One Way, $98 Round Trip from Chicago to Anna Maria

Prices starting at $98 for return flights and $50 for one-way flights to Anna Maria were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon, Sep 29 - Fri, Oct 3
MDW
Chicago
TPA
Tampa
$98 Roundtrip, found 3 hours ago
$98
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Mon, Sep 29 from Chicago to Tampa, returning Fri, Oct 3, priced at $98 found 3 hours ago
Sun, Oct 12 - Thu, Oct 23
ORD
Chicago
TPA
Tampa
$98 Roundtrip, just found
$98
Roundtrip
just found
Select Frontier Airlines flight, departing Sun, Oct 12 from Chicago to Tampa, returning Thu, Oct 23, priced at $98 just found
Sat, Oct 11 - Tue, Oct 14
ORD
Chicago
TPA
Tampa
$157 Roundtrip, just found
$157
Roundtrip
just found
Select United flight, departing Sat, Oct 11 from Chicago to Tampa, returning Tue, Oct 14, priced at $157 just found
Thu, Sep 4 - Tue, Sep 9
MDW
Chicago
TPA
Tampa
$157 Roundtrip, found 23 hours ago
$157
Roundtrip
found 23 hours ago
Select Southwest Airlines flight, departing Thu, Sep 4 from Chicago to Tampa, returning Tue, Sep 9, priced at $157 found 23 hours ago
Wed, Oct 22 - Wed, Nov 12
ORD
Chicago
TPA
Tampa
$157 Roundtrip, found 4 hours ago
$157
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Wed, Oct 22 from Chicago to Tampa, returning Wed, Nov 12, priced at $157 found 4 hours ago

Anna Maria economy flight packages

Price found within the past 48 hours. Click for updated prices.
Barsala At The Wayland Condos
4.0-star property

Barsala At The Wayland Condos

7.8/10 Good! (9 reviews)

Aug 16 - Aug 22

6 night stay

Chicago (ORD) to Tampa (TPA)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 23 hours ago
Ocean Club Treasure Island Hotel
4.0-star property

Ocean Club Treasure Island Hotel

9.6/10 Exceptional! (499 reviews)

Aug 10 - Aug 15

5 night stay

Chicago (CHI) to Tampa (TPA)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 13 hours ago
This was our second time staying at this property. We stayed for eight nights this time. The rooms are lovely but our stay was not nearly as enjoyable as the first time a year ago. There were a lot of children there during our stay. It was practically impossible to use the pool because the kids took over with their inflatables and games. We will likely look elsewhere next time due to the volume of children.

Reviewed on Apr 29, 2025

Cedar Cove Resort and Cottages
3.0-star property

Cedar Cove Resort and Cottages

9.2/10 Wonderful! (445 reviews)

Aug 18 - Aug 23

5 night stay

Chicago (CHI) to Sarasota (SRQ)

Frontier Airlines • Coach

Sarasota (SRQ) to Chicago (CHI)

Spirit Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
had a great time and very friendly staff

Reviewed on Nov 30, 2024

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Anna Maria packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
The Westin Sarasota
4.0-star property

The Westin Sarasota

9/10 Wonderful! (1,013 reviews)

Aug 18 - Aug 24

6 night stay

Chicago (ORD) to Tampa (TPA)

Delta • Non-stop roundtrip • PremiumEconomy
per person
found 3 hours ago
Entrance to the building to park is a mess

Reviewed on Mar 20, 2025

Ocean Club Treasure Island Hotel
4.0-star property

Ocean Club Treasure Island Hotel

9.6/10 Exceptional! (499 reviews)

Aug 18 - Aug 24

6 night stay

Chicago (ORD) to Tampa (TPA)

Delta • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
per person
found 3 hours ago
This was our second time staying at this property. We stayed for eight nights this time. The rooms are lovely but our stay was not nearly as enjoyable as the first time a year ago. There were a lot of children there during our stay. It was practically impossible to use the pool because the kids took over with their inflatables and games. We will likely look elsewhere next time due to the volume of children.

Reviewed on Apr 29, 2025

The Avalon Club
4.0-star property

The Avalon Club

9.6/10 Exceptional! (421 reviews)

Aug 18 - Aug 24

6 night stay

Chicago (ORD) to Tampa (TPA)

Delta • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
per person
found 3 hours ago
This hotel is very clean. It comes with everything that you can possibly need just like home. Staff is friendly, welcoming and very helpful. I will definitely stay here again.

Reviewed on Jun 7, 2024

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More About Flying To Anna Maria from Chicago

Route Information for Flights from Chicago to Anna Maria

Origin Airport IATA Code
CHI
Destination Airport IATA Code
TPA
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Anna Maria

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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.