$34 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.

Sat, Jan 31 - Sat, Feb 7
ORD
O'Hare Intl.
TPA
Tampa Intl.
$144 Roundtrip, just found
$144
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Jan 31 from O'Hare Intl. to Tampa Intl., returning Sat, Feb 7, priced at $144 just found
Sat, Jan 31 - Sun, Feb 1
MDW
Midway Intl.
TPA
Tampa Intl.
$338 Roundtrip, just found
$338
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Jan 31 from Midway Intl. to Tampa Intl., returning Sun, Feb 1, priced at $338 just found
Fri, Jan 30 - Sun, Feb 1
ORD
O'Hare Intl.
SRQ
Sarasota-Bradenton Intl.
$452 Roundtrip, found 5 days ago
$452
Roundtrip
found 5 days ago
Select American Airlines flight, departing Fri, Jan 30 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Sun, Feb 1, priced at $452 found 5 days ago
Sun, Feb 1 - Wed, Feb 18
MDW
Midway Intl.
SRQ
Sarasota-Bradenton Intl.
$503 Roundtrip, found 3 days ago
$503
Roundtrip
found 3 days ago
Select Delta flight, departing Sun, Feb 1 from Midway Intl. to Sarasota-Bradenton Intl., returning Wed, Feb 18, priced at $503 found 3 days ago

Airfares from $34 One Way, $57 Round Trip from Chicago to Anna Maria

Prices starting at $57 for return flights and $34 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.

Tue, Feb 24 - Wed, Mar 11
ORD
Chicago
TPA
Tampa
$57 Roundtrip, found 4 hours ago
$57
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Tue, Feb 24 from Chicago to Tampa, returning Wed, Mar 11, priced at $57 found 4 hours ago
Mon, Mar 2 - Wed, Mar 11
ORD
Chicago
TPA
Tampa
$59 Roundtrip, found 10 hours ago
$59
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Mon, Mar 2 from Chicago to Tampa, returning Wed, Mar 11, priced at $59 found 10 hours ago
Tue, Feb 24 - Wed, Feb 25
ORD
Chicago
TPA
Tampa
$68 Roundtrip, found 1 hour ago
$68
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Tue, Feb 24 from Chicago to Tampa, returning Wed, Feb 25, priced at $68 found 1 hour ago
Sat, Feb 21 - Sat, Feb 28
MDW
Chicago
TPA
Tampa
$138 Roundtrip, found 2 days ago
$138
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Feb 21 from Chicago to Tampa, returning Sat, Feb 28, priced at $138 found 2 days ago
Tue, Mar 10 - Wed, Mar 11
MDW
Chicago
TPA
Tampa
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Mar 10 from Chicago to Tampa, returning Wed, Mar 11, priced at $157 found 1 day ago

Anna Maria economy flight packages

Price found within the past 48 hours. Click for updated prices.
Lemon Bay Motel
2.0-star property

Lemon Bay Motel

8.4/10 Very Good! (39 reviews)

Mar 3 - Mar 10

7 night stay

Chicago (CHI) to Sarasota (SRQ)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $570, price is now $340 per person
$340
per person
found 1 day ago
The owner was very nice, room very clean and updated, close to the beach

Reviewed on Aug 19, 2025

voco Sarasota by IHG
3.5-star property

voco Sarasota by IHG

9.2/10 Wonderful! (1,001 reviews)

Mar 19 - Mar 23

4 night stay

Chicago (CHI) to Tampa (TPA)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,120, price is now $713 per person
$713
per person
found 1 day ago
Hotel was great. They are close to restaurants and have a shuttle that will take you places like St Armand’s Circle. They also have beach towels, chairs and umbrellas that you can use at the beach. We would stay at hotel again for sure.

Reviewed on Jun 30, 2024

Mar Bay Motel &Suites
2.0-star property

Mar Bay Motel &Suites

8.6/10 Excellent! (60 reviews)

Mar 12 - Mar 15

3 night stay

Chicago (CHI) to Tampa (TPA)

Frontier Airlines • Non-stop roundtrip • Coach
Price was $633, price is now $406 per person
$406
per person
found 1 day ago
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Anna Maria first class flight packages

Price found within the past 48 hours. Click for updated prices.
Lemon Bay Motel
2.0-star property

Lemon Bay Motel

8.4/10 Very Good! (39 reviews)

Mar 11 - Mar 18

7 night stay

Chicago (ORD) to Sarasota (SRQ)

Delta • Non-stop • FirstClass

Sarasota (SRQ) to Chicago (ORD)

United • Non-stop • FirstClass
Price was $1,295, price is now $1,000 per person
$1,000
per person
found 2 days ago
The owner was very nice, room very clean and updated, close to the beach

Reviewed on Aug 19, 2025

Escape Coastal Resort on Casey Key
2.5-star property

Escape Coastal Resort on Casey Key

9.8/10 Exceptional! (229 reviews)

Mar 11 - Mar 18

7 night stay

Chicago (ORD) to Sarasota (SRQ)

Delta • Non-stop • FirstClass

Sarasota (SRQ) to Chicago (ORD)

United • Non-stop • FirstClass
Price was $2,315, price is now $1,925 per person
$1,925
per person
found 2 days ago
Could hear noise from other rooms at times. Other than that the place is amazing.

Reviewed on Aug 28, 2025

Fairfield Inn & Suites by Marriott Venice
2.5-star property

Fairfield Inn & Suites by Marriott Venice

9.2/10 Wonderful! (989 reviews)

Mar 11 - Mar 18

7 night stay

Chicago (ORD) to Sarasota (SRQ)

Delta • Non-stop • FirstClass

Sarasota (SRQ) to Chicago (ORD)

United • Non-stop • FirstClass
Price was $2,447, price is now $2,153 per person
$2,153
per person
found 2 days ago
It was a great hotel and a delicious breakfast!

Reviewed on Sep 15, 2025

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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.