$80 Cheap flight deals from Chicago (CHI) to Holiday (TPA)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

This Weekend's Flight Deals from Chicago to Holiday

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, May 16 - Tue, May 19
MDW
Midway Intl.
TPA
Tampa Intl.
$315 Roundtrip, just found
$315
Roundtrip
just found
Select Southwest Airlines flight, departing Sat, May 16 from Midway Intl. to Tampa Intl., returning Tue, May 19, priced at $315 just found
Sat, May 16 - Mon, May 18
RFD
Greater Rockford
TPA
Tampa Intl.
$326 Roundtrip, found 5 days ago
$326
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, May 16 from Greater Rockford to Tampa Intl., returning Mon, May 18, priced at $326 found 5 days ago
Fri, May 15 - Sun, May 17
ORD
O'Hare Intl.
TPA
Tampa Intl.
$357 Roundtrip, found 3 hours ago
$357
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Fri, May 15 from O'Hare Intl. to Tampa Intl., returning Sun, May 17, priced at $357 found 3 hours ago

Airfares from $80 One Way, $162 Round Trip from Chicago to Holiday

Prices starting at $162 for return flights and $80 for one-way flights to Holiday 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, Nov 2 - Thu, Nov 5
ORD
Chicago
TPA
Tampa
$162 Roundtrip, found 11 hours ago
$162
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Mon, Nov 2 from Chicago to Tampa, returning Thu, Nov 5, priced at $162 found 11 hours ago
Thu, Oct 29 - Thu, Nov 5
ORD
Chicago
TPA
Tampa
$163 Roundtrip, found 12 hours ago
$163
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Thu, Oct 29 from Chicago to Tampa, returning Thu, Nov 5, priced at $163 found 12 hours ago
Tue, Jul 14 - Tue, Jul 28
ORD
Chicago
TPA
Tampa
$169 Roundtrip, found 1 day ago
$169
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Jul 14 from Chicago to Tampa, returning Tue, Jul 28, priced at $169 found 1 day ago
Wed, Jul 1 - Tue, Jul 7
MDW
Chicago
TPA
Tampa
$173 Roundtrip, found 2 days ago
$173
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Jul 1 from Chicago to Tampa, returning Tue, Jul 7, priced at $173 found 2 days ago
Tue, Jul 14 - Tue, Jul 28
ORD
Chicago
TPA
Tampa
$175 Roundtrip, found 1 day ago
$175
Roundtrip
found 1 day ago
Select United flight, departing Tue, Jul 14 from Chicago to Tampa, returning Tue, Jul 28, priced at $175 found 1 day ago

Holiday economy flight packages

Price found within the past 48 hours. Click for updated prices.
Cedar Cove Resort and Cottages
3.0-star property

Cedar Cove Resort and Cottages

9.2/10 Wonderful! (506 reviews)

Jun 19 - Jun 22

3 night stay

Chicago (CHI) to Tampa (TPA)

American Airlines • Coach

Tampa (TPA) to Chicago (CHI)

Southwest Airlines • Coach
Save 100% on your flight
Price was $1,241, price is now $850 per person
$850
per person
found 1 day ago
Extremely clean. Friendly, helpful staff that went above and beyond. I traveled with my teenage daughter and her friend and we never once felt unsafe. I was fine using the free trolley transportation up and down the island, but the girls talked me into renting a golf cart. That did provide more freedom for our short time there. The resort has golf carts for rent. We will definitely be back!

Reviewed on Aug 10, 2025

Wyndham Grand Clearwater Beach
4.0-star property

Wyndham Grand Clearwater Beach

9.4/10 Exceptional! (3,211 reviews)

Jul 1 - Jul 6

5 night stay

Chicago (CHI) to Tampa (TPA)

American Airlines • Coach

Tampa (TPA) to Chicago (CHI)

Southwest Airlines • Coach
Save 100% on your flight
Price was $1,730, price is now $1,179 per person
$1,179
per person
found 1 day ago
Could not be happier. Staff were attentive, welcoming and super knowledgeable. Property was pristine, amazing amazing location and tons of onsite activities and luxuries. If we could have given ten stars we would have.

Reviewed on Apr 10, 2026

The Avalon Club
4.0-star property

The Avalon Club

9.4/10 Exceptional! (534 reviews)

Jun 19 - Jun 21

2 night stay

Chicago (CHI) to Tampa (TPA)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,307, price is now $932 per person
$932
per person
found 1 day ago
A lot of attention to detail, high quality space with quality things like bedsheets, mattress and pillows. Above all.. incredible staff! Very friendly and thoughtful.

Reviewed on Mar 28, 2026

Don't see what you're looking for?
See all available trips from Chicago to Holiday
View all trips

Holiday first class flight packages

Price found within the past 48 hours. Click for updated prices.
Cedar Cove Resort and Cottages
3.0-star property

Cedar Cove Resort and Cottages

9.2/10 Wonderful! (506 reviews)

Jun 15 - Jun 19

4 night stay

Chicago (ORD) to Tampa (TPA)

American Airlines • Roundtrip • FirstClass
Price was $1,746, price is now $1,438 per person
$1,438
per person
found 14 hours ago
Extremely clean. Friendly, helpful staff that went above and beyond. I traveled with my teenage daughter and her friend and we never once felt unsafe. I was fine using the free trolley transportation up and down the island, but the girls talked me into renting a golf cart. That did provide more freedom for our short time there. The resort has golf carts for rent. We will definitely be back!

Reviewed on Aug 10, 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

9.8/10 Exceptional! (339 reviews)

Jun 15 - Jun 19

4 night stay

Chicago (ORD) to Tampa (TPA)

American Airlines • Roundtrip • FirstClass
Price was $3,015, price is now $2,245 per person
$2,245
per person
found 14 hours ago
Too expensive but large rooms

Reviewed on May 7, 2026

Legacy Hotel at IMG Academy
4.0-star property

Legacy Hotel at IMG Academy

9/10 Wonderful! (1,004 reviews)

Jun 15 - Jun 19

4 night stay

Chicago (ORD) to Tampa (TPA)

American Airlines • Roundtrip • FirstClass
Price was $2,428, price is now $2,030 per person
$2,030
per person
found 14 hours ago
This is our second time we stayed at Legacy and it has turned into one of my wife’s favorites. My only little “oops” is that it would be nice if the clerk that checked us in made it a point to remind us concerning the 25% off a meal at the restaurant, we didn’t see it until we checked out. We also enjoy dining at the restaurant.

Reviewed on Aug 14, 2025

Don't see what you're looking for?
See all available trips from Chicago to Holiday
View all trips

More About Flying To Holiday from Chicago

Route Information for Flights from Chicago to Holiday

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

Chicago to Holiday

Orbitz is the best place to find guaranteed low prices on Chicago to Holiday flights. Because of our cutting-edge mobile tools and low fares on domestic and international flights, Orbitz is the best starting point for travelers.

Find Cheap Chicago to Holiday Flights

Orbitz offers free mobile apps for iPhone and Android devices—a great way to find fantastic deals on flights from Chicago to Holiday. Not only that, but you can check the status of your flight or even book low cost hotel rooms with the apps or on m.orbitz.com.

Get Miles and Points for Your Flight

Simply enter your frequent flyer information while booking to get miles or points for qualifying Chicago to Holiday flights. This information can all be saved in your Orbitz account, which means it will not have to be entered each time you take advantage of a great air fare deal.

Flight Alerts Take Away the Stress

Orbitz does not want travelers to worry on their flights from Chicago to Holiday. We keep you updated on any flight changes for Chicago to Holiday flights with alerts sent directly to your email or a mobile device. These alerts can also be sent to friends and family.

Discount Travel Planning Made Simple

You will have no problems finding budget flights from Chicago to Holiday on Orbitz.com. If your travel plans are flexible, you can search for fares three days before and after a specific date to find the best price.

More Destinations

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.