$54 Cheap Flights from Tampa (TPA) to Chicago (MDW)

View $54 flight on Mon, Oct 27, 2025Opens in a new window

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

Cheap Flights from Tampa to Chicago (TPA-MDW)

Prices were available within the past 7 days and start at $54 for one-way flights and $106 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Fri, Nov 14 - Sun, Nov 16
TPA
Tampa
MDW
Chicago
$106 Roundtrip, just found
$106
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Nov 14 from Tampa to Chicago, returning Sun, Nov 16, priced at $106 just found
Frontier Airlines
Fri, Nov 14 - Mon, Nov 17
TPA
Tampa
MDW
Chicago
$107 Roundtrip, found 5 hours ago
$107
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Fri, Nov 14 from Tampa to Chicago, returning Mon, Nov 17, priced at $107 found 5 hours ago
Frontier Airlines
Mon, Nov 3 - Mon, Nov 10
TPA
Tampa
MDW
Chicago
$108 Roundtrip, found 1 day ago
$108
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Nov 3 from Tampa to Chicago, returning Mon, Nov 10, priced at $108 found 1 day ago
Frontier Airlines
Fri, Nov 7 - Fri, Nov 14
TPA
Tampa
MDW
Chicago
$109 Roundtrip, just found
$109
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Nov 7 from Tampa to Chicago, returning Fri, Nov 14, priced at $109 just found
Frontier Airlines
Sun, Nov 16 - Mon, Nov 17
TPA
Tampa
MDW
Chicago
$110 Roundtrip, found 10 hours ago
$110
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Sun, Nov 16 from Tampa to Chicago, returning Mon, Nov 17, priced at $110 found 10 hours ago
Frontier Airlines
Sun, Nov 2 - Mon, Nov 10
TPA
Tampa
MDW
Chicago
$113 Roundtrip, found 1 day ago
$113
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Nov 2 from Tampa to Chicago, returning Mon, Nov 10, priced at $113 found 1 day ago
Frontier Airlines
Sun, Oct 26 - Sun, Nov 9
TPA
Tampa
MDW
Chicago
$115 Roundtrip, found 1 day ago
$115
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Oct 26 from Tampa to Chicago, returning Sun, Nov 9, priced at $115 found 1 day ago
Frontier Airlines
Sun, Oct 26 - Fri, Oct 31
TPA
Tampa
MDW
Chicago
$118 Roundtrip, found 2 days ago
$118
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sun, Oct 26 from Tampa to Chicago, returning Fri, Oct 31, priced at $118 found 2 days ago
Frontier Airlines
Mon, Oct 20 - Sun, Oct 26
TPA
Tampa
MDW
Chicago
$119 Roundtrip, found 2 days ago
$119
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Oct 20 from Tampa to Chicago, returning Sun, Oct 26, priced at $119 found 2 days ago
Southwest Airlines
Tue, Oct 28 - Fri, Oct 31
TPA
Tampa
MDW
Chicago
$143 Roundtrip, found 1 day ago
$143
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Oct 28 from Tampa to Chicago, returning Fri, Oct 31, priced at $143 found 1 day ago

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

September is typically the cheapest month to fly

From $56 - $190 per traveler.

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $78
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $78
Flights from Tampa (TPA) to Chicago (MDW)
Origin airport
Tampa Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$106
Distance
998 mi
Average flight time
2 hours 7 mins

Tampa to Chicago Flights

The cheapest times to fly from Tampa to Chicago

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 Tampa to Chicago are during the month of November. You can find some of the cheapest flights from Tampa to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Tampa to Chicago

Sunday is one of the best days to book for cheap flights from Tampa to Chicago: 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 Tampa to Chicago

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 Tampa to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $54 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 Tampa to Chicago 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 Tampa to Chicago 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 Tampa Intl. Airport (TPA) to Midway Intl. Airport (MDW) cost?
Get a cheap one-way flight from $54 or cheap return flight from $106 from Tampa Intl. Airport (TPA) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Tampa Intl. Airport (TPA) to Midway Intl. Airport (MDW)?
Planning your getaway for November may help you find better deals, as it's the cheapest month for flights between TPA and MDW. You'll typically find the lowest prices during the off-season.
Which airlines fly direct from Tampa Intl. Airport (TPA) to Midway Intl. Airport (MDW)?
You can fly straight from Tampa Intl. Airport (TPA) to Midway Intl. Airport (MDW) on a Southwest Airlines flight.
What is the cheapest airline that flies from Tampa Intl. Airport (TPA) to Midway Intl. Airport (MDW)?
While prices may vary depending on when you travel, Frontier Airlines and Southwest Airlines are popular options for flights between Tampa Intl. Airport (TPA) and Midway Intl. Airport (MDW). You can also compare airlines on Expedia and use the "Sort by" filter to find the cheapest ticket for your TPA to MDW flight.
How many flights per day from Tampa Intl. Airport (TPA) to Midway Intl. Airport (MDW)?
With, on average, 4 nonstop flights departing from Tampa Intl. Airport (TPA) to Midway Intl. Airport (MDW) each day, you'll be on your way in no time.
What are the most popular departure times for flights from Tampa Intl. Airport (TPA) to Midway Intl. Airport (MDW)?
The 7 AM departures from TPA to MDW are the busiest. These flights can come with a higher price due to their popularity. If you're looking to save, book during off-peak hours.
What day of the week has the most flights from TPA to MDW?
Friday offers the most flights from Tampa Intl. Airport (TPA) to Midway Intl. Airport (MDW). Consider jetting off on this day and you'll have the best chance of finding a departure that fits your schedule.
What is the earliest flight from Tampa Intl. Airport (TPA) to Midway Intl. Airport (MDW)?
Tampa Intl. Airport (TPA)'s first flight to Midway Intl. Airport (MDW) leaves at approximately 7:15AM UTC-5. With a total flight time of 2h 50m, you'll land at around 9:05AM UTC-6.
How long does it take to fly from Tampa Intl. Airport (TPA) to Midway Intl. Airport (MDW)?
It takes around 2 hours and 47 minutes to travel the 1,000 mi from TPA to MDW.
What is the best time to fly from Tampa Intl. Airport (TPA) to Midway Intl. Airport (MDW)?
To avoid potential delays on the Tampa Intl. Airport (TPA) to Midway Intl. Airport (MDW) route, aim to travel before 3 PM. Later departures are 22% more likely to be canceled.**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 Chicago from Tampa Intl. Airport (TPA)?
If you're departing on a direct flight from Tampa Intl. Airport (TPA) to Chicago, you'll land at either O'Hare Intl. Airport (ORD) or Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Tampa Intl. Airport (TPA) to Midway Intl. Airport (MDW) last-minute?
Booking your plane ticket from TPA to MDW just before your getaway is typically more expensive. But if you're flexible with your itinerary, you could grab a cheap last-minute fare.
Is it cheaper to book a TPA to MDW flight and hotel package?
Compared with arranging flights and hotels separately, booking a TPA to MDW flight and hotel package with Expedia could result in significant savings. What's more, having everything in one convenient place will take the stress out of planning your trip. Just pick your flights and choose from our wide range of hotels, then tailor your trip with extras like tours, activities and car rentals.
Can I cancel or change the date of my flight from Tampa Intl. Airport (TPA) to Midway Intl. Airport (MDW)?
If you reserved your TPA to MDW flight in the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the fare type you purchased, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal for more information.

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*Available to One Key members.