$67 Cheap Flights from Tampa (TPA) to Chicago (MDW)

View $67 flight on Fri, Oct 17, 2025Opens in a new window

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

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Cheap Flights from Tampa to Chicago (TPA-MDW)

Prices were available within the past 7 days and start at $67 for one-way flights and $114 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Fri, Sep 19 - Fri, Sep 26
TPA
Tampa
MDW
Chicago
$114 Roundtrip, found 2 days ago
$114
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Sep 19 from Tampa to Chicago, returning Fri, Sep 26, priced at $114 found 2 days ago
Frontier Airlines
Thu, Aug 21 - Mon, Aug 25
TPA
Tampa
MDW
Chicago
$122 Roundtrip, found 2 days ago
$122
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Aug 21 from Tampa to Chicago, returning Mon, Aug 25, priced at $122 found 2 days ago
Frontier Airlines
Fri, Oct 31 - Mon, Nov 3
TPA
Tampa
MDW
Chicago
$124 Roundtrip, found 2 days ago
$124
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Oct 31 from Tampa to Chicago, returning Mon, Nov 3, priced at $124 found 2 days ago
Frontier Airlines
Thu, Jul 24 - Fri, Sep 26
TPA
Tampa
MDW
Chicago
$126 Roundtrip, found 3 days ago
$126
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Jul 24 from Tampa to Chicago, returning Fri, Sep 26, priced at $126 found 3 days ago
Frontier Airlines
Thu, Jul 31 - Thu, Aug 7
TPA
Tampa
MDW
Chicago
$129 Roundtrip, found 6 days ago
$129
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Jul 31 from Tampa to Chicago, returning Thu, Aug 7, priced at $129 found 6 days ago
Frontier Airlines
Sun, Aug 31 - Fri, Sep 5
TPA
Tampa
MDW
Chicago
$130 Roundtrip, found 2 days ago
$130
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sun, Aug 31 from Tampa to Chicago, returning Fri, Sep 5, priced at $130 found 2 days ago
Frontier Airlines
Mon, Aug 25 - Tue, Aug 26
TPA
Tampa
MDW
Chicago
$132 Roundtrip, found 2 days ago
$132
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Aug 25 from Tampa to Chicago, returning Tue, Aug 26, priced at $132 found 2 days ago
Frontier Airlines
Thu, Aug 7 - Sat, Aug 16
TPA
Tampa
MDW
Chicago
$132 Roundtrip, found 3 days ago
$132
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Aug 7 from Tampa to Chicago, returning Sat, Aug 16, priced at $132 found 3 days ago
Southwest Airlines
Mon, Oct 6 - Mon, Oct 20
TPA
Tampa
MDW
Chicago
$143 Roundtrip, found 2 days ago
$143
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Mon, Oct 6 from Tampa to Chicago, returning Mon, Oct 20, priced at $143 found 2 days ago
Frontier Airlines
Fri, Sep 26 - Mon, Sep 29
TPA
Tampa
MDW
Chicago
$144 Roundtrip, found 2 days ago
$144
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Sep 26 from Tampa to Chicago, returning Mon, Sep 29, priced at $144 found 2 days ago

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

February is typically the cheapest month to fly

From $68 - $306 per traveler.

Graph displaying average flight prices per month

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. Average driving time to city center is 23 minutes. Flights from $248
ORD
O'Hare Intl.
Average driving time to city center23 min
Flights from $248
Flights from Tampa (TPA) to Chicago (MDW)
Origin airport
Tampa Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$114
Distance
998 mi
Average flight time
2 hours 4 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 September. 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 $67 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?
Cheap round-trip flights from Tampa Intl. Airport (TPA) to Midway Intl. Airport (MDW) start at $98. 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 Frontier Airlines flight leaving TPA on July 31 2025 and touching down at MDW. The price was last updated on July 5 2025 and has not changed since.
What is the cheapest month to fly from TPA to MDW?
Fly direct from TPA to MDW in October to land cheaper tickets. You can find a one-way Frontier Airlines flight for $49 leaving on October 24 2025. This price is based on the cheapest direct flight found on Expedia for this route in the next 330 days. The price was last updated on July 5 2025 and remains unchanged.
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 TPA to MDW?
Travel from TPA to MDW with Frontier Airlines. This airline currently offers the lowest one-way fare for this route, starting from $49. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from TPA on September 26 2025. Prices were last updated on July 5 2025 and have not changed since.
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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