$69 Cheap Flights from Chicago (MDW) to Tampa (TPA)

View $69 flight on Mon, Dec 8, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Tampa Intl. Airport (TPA)

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Cheap Flights from Chicago to Tampa (MDW-TPA)

Prices were available within the past 7 days and start at $69 for one-way flights and $99 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Tue, Aug 12 - Mon, Sep 22
MDW
Chicago
TPA
Tampa
$99 Roundtrip, found 3 days ago
$99
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Aug 12 from Chicago to Tampa, returning Mon, Sep 22, priced at $99 found 3 days ago
Southwest Airlines
Sat, Nov 1 - Mon, Nov 3
MDW
Chicago
TPA
Tampa
$103 Roundtrip, found 1 day ago
$103
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Nov 1 from Chicago to Tampa, returning Mon, Nov 3, priced at $103 found 1 day ago
Frontier Airlines
Mon, Oct 13 - Mon, Oct 20
MDW
Chicago
TPA
Tampa
$104 Roundtrip, found 3 days ago
$104
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Oct 13 from Chicago to Tampa, returning Mon, Oct 20, priced at $104 found 3 days ago
Southwest Airlines
Sat, Nov 1 - Mon, Nov 3
MDW
Chicago
TPA
Tampa
$108 Roundtrip, found 1 day ago
$108
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Nov 1 from Chicago to Tampa, returning Mon, Nov 3, priced at $108 found 1 day ago
Southwest Airlines
Sat, Nov 1 - Sat, Nov 8
MDW
Chicago
TPA
Tampa
$113 Roundtrip, found 1 day ago
$113
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Nov 1 from Chicago to Tampa, returning Sat, Nov 8, priced at $113 found 1 day ago
Southwest Airlines
Wed, Nov 12 - Mon, Nov 17
MDW
Chicago
TPA
Tampa
$114 Roundtrip, found 3 days ago
$114
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Nov 12 from Chicago to Tampa, returning Mon, Nov 17, priced at $114 found 3 days ago
Southwest Airlines
Fri, Aug 15 - Wed, Aug 20
MDW
Chicago
TPA
Tampa
$116 Roundtrip, found 1 day ago
$116
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Fri, Aug 15 from Chicago to Tampa, returning Wed, Aug 20, priced at $116 found 1 day ago
Southwest Airlines
Tue, Aug 12 - Mon, Sep 22
MDW
Chicago
TPA
Tampa
$116 Roundtrip, found 3 days ago
$116
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Aug 12 from Chicago to Tampa, returning Mon, Sep 22, priced at $116 found 3 days ago
Southwest Airlines
Sat, Nov 1 - Sat, Nov 8
MDW
Chicago
TPA
Tampa
$118 Roundtrip, found 1 day ago
$118
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Nov 1 from Chicago to Tampa, returning Sat, Nov 8, priced at $118 found 1 day ago
Southwest Airlines
Sun, Aug 17 - Fri, Aug 22
MDW
Chicago
TPA
Tampa
$119 Roundtrip, found 1 day ago
$119
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sun, Aug 17 from Chicago to Tampa, returning Fri, Aug 22, priced at $119 found 1 day ago

Find the cheapest month to fly from Chicago (MDW) to Tampa (TPA)

February is typically the cheapest month to fly

From $68 - $392 per traveler.

Graph displaying average flight prices per month

Flights from Chicago (MDW) to Tampa (TPA)
Origin airport
Midway Intl.
Destination airport
Tampa Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$98
Distance
998 mi
Average flight time
3 hours 35 mins

Chicago to Tampa Flights

The cheapest times to fly from Chicago to Tampa

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Tampa are during the month of August. You can find some of the cheapest flights from Chicago to Tampa with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Tampa

Sunday is one of the best days to book for cheap flights from Chicago to Tampa: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Tampa

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Tampa in 2025. You can also book with separate airlines for your outbound and return journeys, from $69 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Tampa flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Tampa airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Tampa Intl. Airport (TPA) cost?
Book cheap return fares starting from $132 from Midway Intl. Airport (MDW) to Tampa Intl. Airport (TPA). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines flight leaving MDW on August 5 2025 and touching down at TPA. The price was last updated on July 9 2025 and has not changed since.
What is the cheapest month to fly from MDW to TPA?
The cheapest flights from MDW to TPA are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Midway Intl. Airport (MDW) to Tampa Intl. Airport (TPA)?
Jump on a direct flight with Southwest Airlines and journey straight from Midway Intl. Airport (MDW) to Tampa Intl. Airport (TPA).
What is the cheapest airline that flies from MDW to TPA?
With prices as low as $66 for a one-way flight from MDW to TPA, Southwest Airlines is currently the cheapest airline operating this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MDW on August 13 2025. Prices were last updated on July 9 2025 and have not changed since.
How many flights per day from Midway Intl. Airport (MDW) to Tampa Intl. Airport (TPA)?
When flying out of Midway Intl. Airport (MDW), you'll have a choice from an average of 4 daily nonstop flights to Tampa Intl. Airport (TPA).
What are the most popular departure times for flights from Midway Intl. Airport (MDW) to Tampa Intl. Airport (TPA)?
The 6 PM departures from MDW to TPA see the highest demand. These flights can come with a higher price due to their popularity. If you want to save on your fare, pick a less crowded time to fly.
What day of the week has the most flights from MDW to TPA?
If you depart on a Friday, you'll get the largest range of options for flights from Midway Intl. Airport (MDW) to Tampa Intl. Airport (TPA).
What is the earliest flight from Midway Intl. Airport (MDW) to Tampa Intl. Airport (TPA)?
The earliest flight leaving Midway Intl. Airport (MDW) is at around 5:25AM UTC-6. Board this plane and you'll touch down at Tampa Intl. Airport (TPA) at approximately 9:05AM UTC-5. The entire trip takes 2h 40m.
How long does it take to fly from Midway Intl. Airport (MDW) to Tampa Intl. Airport (TPA)?
It takes about 2 hours and 37 minutes to travel the 1,000 mi from MDW to TPA.
What is the best time to fly from Midway Intl. Airport (MDW) to Tampa Intl. Airport (TPA)?
To arrive at Tampa Intl. Airport (TPA) without delays, book a flight that takes off from Midway Intl. Airport (MDW) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this time.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Tampa from Midway Intl. Airport (MDW)?
You can touch down at Tampa Intl. Airport (TPA) or Sarasota-Bradenton Intl. Airport (SRQ) when traveling to Tampa on a direct flight from Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Tampa Intl. Airport (TPA) last-minute?
Booking your flight from MDW to TPA shortly before your trip is usually more expensive. However, if you're flexible with your travel times and dates, you could grab a cheap last-minute fare.
Is it cheaper to book a MDW to TPA flight and hotel package?
You'll typically save money by securing a MDW to TPA flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage it all in one convenient place. After choosing your ideal flights and accommodations, consider adding extras such as car rentals, tours and activities.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Tampa Intl. Airport (TPA)?
In most instances, you can modify or cancel your MDW to TPA flight. However, there may be additional fees, especially if you booked more than 24 hours ago. Double-check your itinerary for the airline's fees and policies on flight changes, or if you'd like more details, go to our Customer Service portal.

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