$29 Cheap flight deals from Chicago (CHI) to Florida Gulf Coast (TPA)
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This Weekend's Flight Deals from Chicago to Florida Gulf Coast
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.
ORD
O'Hare Intl.
TPA
Tampa Intl.
$196 Roundtrip, found 2 hours ago
$196
Roundtrip
found 2 hours ago
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$221 Roundtrip, found 1 hour ago
$221
Roundtrip
found 1 hour ago
MDW
Midway Intl.
TPA
Tampa Intl.
$280 Roundtrip, found 1 day ago
$280
Roundtrip
found 1 day ago
RFD
Greater Rockford
TPA
Tampa Intl.
$326 Roundtrip, found 4 days ago
$326
Roundtrip
found 4 days ago
Airfares from $29 One Way, $59 Round Trip from Chicago to Florida Gulf Coast
Prices starting at $59 for return flights and $29 for one-way flights to Florida Gulf Coast were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
ORD
Chicago
RSW
Fort Myers
$59 Roundtrip, just found
$59
Roundtrip
just found
ORD
Chicago
TPA
Tampa
$87 Roundtrip, found 5 days ago
$87
Roundtrip
found 5 days ago
MDW
Chicago
TPA
Tampa
$128 Roundtrip, found 2 days ago
$128
Roundtrip
found 2 days ago
MDW
Chicago
RSW
Fort Myers
$156 Roundtrip, found 3 hours ago
$156
Roundtrip
found 3 hours ago
RFD
Rockford
TPA
Tampa
$157 Roundtrip, found 2 days ago
$157
Roundtrip
found 2 days ago
Florida Gulf Coast economy flight packages
Price found within the past 48 hours. Click for updated prices.
3.5-star property
voco Sarasota by IHG
9.2/10 Wonderful! (1,001 reviews)
Feb 25 - Mar 1
4 night stay
Chicago (CHI) to Tampa (TPA)
Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,291, price is now $730 per person
$730
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
3.5-star property
The Residences at Siesta Key Beach by Hyatt Vacation Club
9.6/10 Exceptional! (294 reviews)
Mar 6 - Mar 8
2 night stay
Chicago (CHI) to Sarasota (SRQ)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,663, price is now $997 per person
$997
per person
found 1 day 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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View all tripsFlorida Gulf Coast packages with premium economy flights
Price found within the past 48 hours. Click for updated prices.
4.0-star property
The Westin Tampa Bay
8.4/10 Very Good! (1,047 reviews)
Feb 23 - Feb 26
3 night stay
Chicago (MDW) to Tampa (TPA)
Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,085, price is now $794 per person
$794
per person
found 1 day 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
3.5-star property
FUSION Resort Waterfront Suites
9.2/10 Wonderful! (1,097 reviews)
Feb 23 - Feb 26
3 night stay
Chicago (MDW) to Tampa (TPA)
Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,117, price is now $826 per person
$826
per person
found 1 day 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
4.0-star property
The Avalon Club
9.4/10 Exceptional! (481 reviews)
Feb 23 - Feb 26
3 night stay
Chicago (MDW) to Tampa (TPA)
Delta • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,417, price is now $1,076 per person
$1,076
per person
found 1 day 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
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View all tripsFlorida Gulf Coast first class flight packages
Price found within the past 48 hours. Click for updated prices.
3.0-star property
The Beachview Inn Clearwater Beach
7.2/10 Good! (1,004 reviews)
Feb 26 - Mar 3
5 night stay
Chicago (CHI) to Tampa (TPA)
American Airlines • Non-stop • FirstClass
Tampa (TPA) to Chicago (CHI)
Delta • Non-stop • FirstClass
Price was $1,648, price is now $1,274 per person
$1,274
per person
found 1 day ago
We have stayed her at least 6 times over the last 8 years. To know about the hotel-it's basic, but people are friendly, our room was clean (and ocean front), and location is a 10/10. The price is right especially given the location. We love the pool deck, but our only suggestion would be to just clean the pool a bit from sand, etc like in previous years.
Reviewed on Nov 11, 2025
4.0-star property
The Avalon Club
9.4/10 Exceptional! (481 reviews)
Feb 26 - Mar 3
5 night stay
Chicago (CHI) to Tampa (TPA)
American Airlines • Non-stop • FirstClass
Tampa (TPA) to Chicago (CHI)
Delta • Non-stop • FirstClass
Price was $3,082, price is now $2,307 per person
$2,307
per person
found 1 day 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
2.0-star property
ChartHouse Clearwater Beach Marina Hotel
9.6/10 Exceptional! (531 reviews)
Feb 26 - Mar 3
5 night stay
Chicago (CHI) to Tampa (TPA)
American Airlines • Non-stop • FirstClass
Tampa (TPA) to Chicago (CHI)
Delta • Non-stop • FirstClass
Price was $1,693, price is now $1,288 per person
$1,288
per person
found 1 day ago
Todo perfecto y el trato increible
Reviewed on Oct 24, 2025
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View all tripsMore About Flying To Florida Gulf Coast from Chicago
Route Information for Flights from Chicago to Florida Gulf Coast
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | TPA |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Florida Gulf Coast
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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.