$30 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.

Sun, Jan 11 - Sat, Jan 17
ORD
O'Hare Intl.
TPA
Tampa Intl.
$171 Roundtrip, found 4 hours ago
$171
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sun, Jan 11 from O'Hare Intl. to Tampa Intl., returning Sat, Jan 17, priced at $171 found 4 hours ago
Sat, Jan 10 - Thu, Jan 15
MDW
Midway Intl.
TPA
Tampa Intl.
$185 Roundtrip, found 1 day ago
$185
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Jan 10 from Midway Intl. to Tampa Intl., returning Thu, Jan 15, priced at $185 found 1 day ago
Sun, Jan 11 - Wed, Jan 21
RFD
Greater Rockford
TPA
Tampa Intl.
$233 Roundtrip, found 6 days ago
$233
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sun, Jan 11 from Greater Rockford to Tampa Intl., returning Wed, Jan 21, priced at $233 found 6 days ago
Sun, Jan 11 - Fri, Jan 16
ORD
O'Hare Intl.
SRQ
Sarasota-Bradenton Intl.
$365 Roundtrip, found 1 day ago
$365
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sun, Jan 11 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Fri, Jan 16, priced at $365 found 1 day ago

Airfares from $30 One Way, $59 Round Trip from Chicago to Anna Maria

Prices starting at $59 for return flights and $30 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.

Sun, Feb 1 - Sat, Feb 7
ORD
Chicago
TPA
Tampa
$59 Roundtrip, found 8 hours ago
$59
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Sun, Feb 1 from Chicago to Tampa, returning Sat, Feb 7, priced at $59 found 8 hours ago
Tue, Jan 20 - Sat, Jan 24
ORD
Chicago
TPA
Tampa
$104 Roundtrip, found 20 hours ago
$104
Roundtrip
found 20 hours ago
Select Spirit Airlines flight, departing Tue, Jan 20 from Chicago to Tampa, returning Sat, Jan 24, priced at $104 found 20 hours ago
Sat, Jan 24 - Tue, Jan 27
MDW
Chicago
TPA
Tampa
$128 Roundtrip, found 1 day ago
$128
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Jan 24 from Chicago to Tampa, returning Tue, Jan 27, priced at $128 found 1 day ago
Sat, Feb 14 - Wed, Feb 18
MDW
Chicago
TPA
Tampa
$156 Roundtrip, found 5 days ago
$156
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Sat, Feb 14 from Chicago to Tampa, returning Wed, Feb 18, priced at $156 found 5 days ago
Wed, Feb 25 - Tue, Mar 3
RFD
Rockford
TPA
Tampa
$157 Roundtrip, found 3 days ago
$157
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Feb 25 from Rockford to Tampa, returning Tue, Mar 3, priced at $157 found 3 days ago

Anna Maria economy flight packages

Price found within the past 48 hours. Click for updated prices.
Island Grand at TradeWinds
4.0-star property

Island Grand at TradeWinds

7.4/10 Good! (1,005 reviews)

Feb 5 - Feb 11

6 night stay

Chicago (CHI) to Tampa (TPA)

Frontier Airlines • Non-stop • Coach

Tampa (TPA) to Chicago (CHI)

Spirit Airlines • Non-stop • Coach
Price was $1,193, price is now $788 per person
$788
per person
found 1 day ago
To start off, there was ALWAYS a line for the elevator (at least one in our building was broken.) Also, the elevators that did work were slow and had no AC. Our room was not the cleanest & we didn’t notice how bad it really was until we were unpacked. Not wanting to have to move rooms, we left it alone. There was quite a bit of dust everywhere and we found a cockroach behind the couch that was still alive. Our tv quit working one night and while it took maintenance a while to get there, he very kindly found us a new tv to replace our broken one. For the price, I expected it to be cleaner and better quality all around.

Reviewed on Aug 4, 2025

The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5-star property

The Residences at Siesta Key Beach by Hyatt Vacation Club

9.6/10 Exceptional! (294 reviews)

Feb 6 - Feb 10

4 night stay

Chicago (CHI) to Sarasota (SRQ)

American Airlines • Non-stop • Coach

Sarasota (SRQ) to Chicago (CHI)

Spirit Airlines • Non-stop • Coach
Save 100% on your flight
Price was $2,410, price is now $1,446 per person
$1,446
per person
found 20 hours ago
We had a fantastic vacation at the Hyatt. The rooms are immaculate and have everything you need for your vacation. Beach staff was wonderful with daily umbrella service and the continental breakfast was very convenient. We look forward to returning!

Reviewed on May 10, 2025

Ocean Club Treasure Island Hotel
4.0-star property

Ocean Club Treasure Island Hotel

9.6/10 Exceptional! (712 reviews)

Feb 5 - Feb 11

6 night stay

Chicago (CHI) to Tampa (TPA)

Frontier Airlines • Non-stop • Coach

Tampa (TPA) to Chicago (CHI)

Spirit Airlines • Non-stop • Coach
Price was $1,733, price is now $1,131 per person
$1,131
per person
found 1 day ago
Great spot, had a great time

Reviewed on Dec 4, 2025

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Anna Maria first class flight packages

Price found within the past 48 hours. Click for updated prices.
FUSION Resort Waterfront Suites
3.5-star property

FUSION Resort Waterfront Suites

9.2/10 Wonderful! (1,097 reviews)

Feb 12 - Feb 15

3 night stay

Chicago (ORD) to Tampa (TPA)

American Airlines • Non-stop roundtrip • FirstClass
Price was $1,707, price is now $1,376 per person
$1,376
per person
found 1 hour ago
Room wasn’t ready when we arrived, we had to wait 45 minutes. The front desk lady didn’t have a name tag so I couldn’t addressed her properly. She didn’t have good communication skills. Richard was awesome he had to take over and helped her. Other than that was a great clean place to stay.

Reviewed on Jul 2, 2024

The Avalon Club
4.0-star property

The Avalon Club

9.4/10 Exceptional! (481 reviews)

Feb 12 - Feb 15

3 night stay

Chicago (ORD) to Tampa (TPA)

American Airlines • Non-stop roundtrip • FirstClass
Price was $2,108, price is now $1,713 per person
$1,713
per person
found 1 hour ago
You can walk to different restaurants. The only bad thing is that the bed in the master bedroom was not in good condition and the metal base was broken. I had to move to another room within the same unit.

Reviewed on Aug 17, 2025

The Akoya Pearl - 2 Beach Homes Steps From CWB
2.0-star property

The Akoya Pearl - 2 Beach Homes Steps From CWB

No reviews

Feb 12 - Feb 15

3 night stay

Chicago (ORD) to Tampa (TPA)

American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $11,692, price is now $9,575 per person
$9,575
per person
found 1 hour ago
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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.