$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 - Tue, Jan 13
ORD
O'Hare Intl.
TPA
Tampa Intl.
$218 Roundtrip, just found
$218
Roundtrip
just found
Select Spirit Airlines flight, departing Sun, Jan 11 from O'Hare Intl. to Tampa Intl., returning Tue, Jan 13, priced at $218 just found
Sat, Jan 10 - Tue, Jan 13
MDW
Midway Intl.
TPA
Tampa Intl.
$265 Roundtrip, found 1 day ago
$265
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Jan 10 from Midway Intl. to Tampa Intl., returning Tue, Jan 13, priced at $265 found 1 day ago
Sun, Jan 11 - Wed, Jan 14
ORD
O'Hare Intl.
SRQ
Sarasota-Bradenton Intl.
$426 Roundtrip, found 4 days ago
$426
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sun, Jan 11 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Wed, Jan 14, priced at $426 found 4 days ago
Fri, Jan 9 - Thu, Jan 15
RFD
Greater Rockford
TPA
Tampa Intl.
$627 Roundtrip, found 1 day ago
$627
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Jan 9 from Greater Rockford to Tampa Intl., returning Thu, Jan 15, priced at $627 found 1 day ago

Airfares from $30 One Way, $63 Round Trip from Chicago to Anna Maria

Prices starting at $63 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.

Sat, Jan 31 - Thu, Feb 5
ORD
Chicago
TPA
Tampa
$63 Roundtrip, found 1 day ago
$63
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Jan 31 from Chicago to Tampa, returning Thu, Feb 5, priced at $63 found 1 day ago
Tue, Feb 3 - Tue, Feb 10
ORD
Chicago
TPA
Tampa
$87 Roundtrip, found 1 hour ago
$87
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Tue, Feb 3 from Chicago to Tampa, returning Tue, Feb 10, priced at $87 found 1 hour ago
Sat, Jan 24 - Tue, Jan 27
MDW
Chicago
TPA
Tampa
$128 Roundtrip, found 6 days ago
$128
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Jan 24 from Chicago to Tampa, returning Tue, Jan 27, priced at $128 found 6 days ago
Mon, Mar 9 - Thu, Mar 12
RFD
Rockford
TPA
Tampa
$145 Roundtrip, found 7 hours ago
$145
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Mon, Mar 9 from Rockford to Tampa, returning Thu, Mar 12, priced at $145 found 7 hours ago
Wed, Mar 11 - Mon, Mar 16
ORD
Chicago
TPA
Tampa
$145 Roundtrip, just found
$145
Roundtrip
just found
Select Southwest Airlines flight, departing Wed, Mar 11 from Chicago to Tampa, returning Mon, Mar 16, priced at $145 just found

Anna Maria economy flight packages

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

Mar Bay Motel &Suites

8.6/10 Excellent! (60 reviews)

Feb 11 - Feb 15

4 night stay

Chicago (CHI) to Tampa (TPA)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $715, price is now $438 per person
$438
per person
found 14 hours ago
The Beach Haven Resort
2.0-star property

The Beach Haven Resort

9.4/10 Exceptional! (157 reviews)

Feb 17 - Feb 24

7 night stay

Chicago (CHI) to Tampa (TPA)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,232, price is now $668 per person
$668
per person
found 13 hours ago
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 7 - Feb 11

4 night stay

Chicago (ORD) to Sarasota (SRQ)

United • Roundtrip • Coach
Save 100% on your flight
Price was $2,624, price is now $1,612 per person
$1,612
per person
found 6 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

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Anna Maria packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Plaza Beach Hotel Beachfront Resort
3.0-star property

Plaza Beach Hotel Beachfront Resort

9/10 Wonderful! (1,000 reviews)

Feb 11 - Feb 15

4 night stay

Chicago (CHI) to Tampa (TPA)

Delta • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,333, price is now $975 per person
$975
per person
found 5 hours ago
Perfect little spot directly on the beach. Loved the easy access and all of the amenities. We will absolutely stay here again.

Reviewed on Jul 21, 2024

The Westin Tampa Bay
4.0-star property

The Westin Tampa Bay

8.4/10 Very Good! (1,047 reviews)

Feb 26 - Mar 4

6 night stay

Chicago (CHI) to Tampa (TPA)

Delta • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,830, price is now $1,281 per person
$1,281
per person
found 11 hours ago
The hotel does not have a pool at this time it's under construction, which also causes quite a bit of noise throughout the day.

Reviewed on Nov 10, 2025

FUSION Resort Waterfront Suites
3.5-star property

FUSION Resort Waterfront Suites

9.2/10 Wonderful! (1,097 reviews)

Feb 11 - Feb 15

4 night stay

Chicago (CHI) to Tampa (TPA)

Delta • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,444, price is now $1,036 per person
$1,036
per person
found 5 hours 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

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Anna Maria first class flight packages

Price found within the past 48 hours. Click for updated prices.
Sleep Inn near Busch Gardens/USF
2.5-star property

Sleep Inn near Busch Gardens/USF

7.8/10 Good! (1,003 reviews)

Feb 26 - Mar 4

6 night stay

Chicago (CHI) to Sarasota (SRQ)

Delta • Non-stop roundtrip • FirstClass
Price was $1,206, price is now $999 per person
$999
per person
found 11 hours ago
The room was very clean, and the front desk staff was friendly. I can’t complain about a last-minute one-night stay. I would use this place again if needed.

Reviewed on Dec 7, 2025

Hotel Tampa Riverwalk
4.0-star property

Hotel Tampa Riverwalk

7/10 Good! (1,744 reviews)

Feb 26 - Mar 4

6 night stay

Chicago (CHI) to Sarasota (SRQ)

Delta • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $2,209, price is now $1,521 per person
$1,521
per person
found 11 hours ago
Very old room, bad air conditioning

Reviewed on Dec 16, 2025

Aloft Tampa Midtown
3.0-star property

Aloft Tampa Midtown

8.2/10 Very Good! (510 reviews)

Feb 26 - Mar 4

6 night stay

Chicago (CHI) to Sarasota (SRQ)

Delta • Non-stop roundtrip • FirstClass
Price was $1,567, price is now $1,315 per person
$1,315
per person
found 11 hours ago
The Aloft looks great. There was little/ no signage in the atrium and there were two desks for two different hotels and often only one person on the phone at one or the other. The music in the common areas is too loud and obnoxious - it was hard to take a phone call over the music. The faucets in the rooms don’t fit the sink. EVERY TIME we used the faucet, the water FLOODED the counter top and tan down the back making a puddle on the back of the wall and floor. Coworkers confirmed it was the same in their rooms. The faucets in the mens bathroom of the conference center on the too floor did the same. The toilets in the ladies room top floor conference center didn’t have enough water pressure to flush everything down. After they were used the first time in the morning they were full of grossness the rest of the day. We tried manually flushing 2-3 times and it helped a little, but it was gross. Catering staff in conference center and breakfast staff was great, very attentive. Food was good. We were also charged for overnight parking each night I stayed at the hotel even though my husband had the car in Orlando half of the days. We were told that they charged approximately $40 overnight each time the valet “touched” the car. So when my husband dropped me off and left a couple hours later we were charged the overnight amount instead of the significantly smaller $7 restaurant visit fee. We spent almost an hour trying to fix this with the front desk staff. Ridiculous!

Reviewed on Feb 20, 2022

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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.