$159 Cheap Flights from Chicago (MDW) to Tallahassee (TLH)

View $159 flight on Tue, Dec 2, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Tallahassee Intl. Airport (TLH)

  • notification illustration

    Be in the know

    Get alerts if flight prices drop or rise*
  • deals illustration

    Book smarter

    Save up to 30% on select hotels after you book a flight*
  • trophy illustration

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Cheap Flights from Chicago to Tallahassee (MDW-TLH)

Prices were available within the past 7 days and start at $159 for one-way flights and $317 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, Dec 3 - Sat, Dec 6
MDW
Chicago
TLH
Tallahassee
$317 Roundtrip, found 1 hour ago
$317
Roundtrip
found 1 hour ago
Select Delta flight, departing Wed, Dec 3 from Chicago to Tallahassee, returning Sat, Dec 6, priced at $317 found 1 hour ago
Delta
Tue, Dec 2 - Wed, Dec 3
MDW
Chicago
TLH
Tallahassee
$348 Roundtrip, found 8 hours ago
$348
Roundtrip
found 8 hours ago
Select Delta flight, departing Tue, Dec 2 from Chicago to Tallahassee, returning Wed, Dec 3, priced at $348 found 8 hours ago
Delta
Sat, Jan 17 - Sun, Jan 18
MDW
Chicago
TLH
Tallahassee
$352 Roundtrip, just found
$352
Roundtrip
just found
Select Delta flight, departing Sat, Jan 17 from Chicago to Tallahassee, returning Sun, Jan 18, priced at $352 just found
Delta
Wed, Nov 26 - Wed, Dec 3
MDW
Chicago
TLH
Tallahassee
$362 Roundtrip, found 1 day ago
$362
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Nov 26 from Chicago to Tallahassee, returning Wed, Dec 3, priced at $362 found 1 day ago
Delta
Tue, Feb 10 - Wed, Mar 4
MDW
Chicago
TLH
Tallahassee
$365 Roundtrip, found 5 days ago
$365
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Feb 10 from Chicago to Tallahassee, returning Wed, Mar 4, priced at $365 found 5 days ago
Delta
Sun, Feb 15 - Wed, Feb 18
MDW
Chicago
TLH
Tallahassee
$372 Roundtrip, found 5 days ago
$372
Roundtrip
found 5 days ago
Select Delta flight, departing Sun, Feb 15 from Chicago to Tallahassee, returning Wed, Feb 18, priced at $372 found 5 days ago
Delta
Tue, Dec 2 - Wed, Dec 3
MDW
Chicago
TLH
Tallahassee
$379 Roundtrip, found 8 hours ago
$379
Roundtrip
found 8 hours ago
Select Delta flight, departing Tue, Dec 2 from Chicago to Tallahassee, returning Wed, Dec 3, priced at $379 found 8 hours ago
Delta
Thu, Nov 27 - Tue, Dec 2
MDW
Chicago
TLH
Tallahassee
$383 Roundtrip, found 17 hours ago
$383
Roundtrip
found 17 hours ago
Select Delta flight, departing Thu, Nov 27 from Chicago to Tallahassee, returning Tue, Dec 2, priced at $383 found 17 hours ago
Delta
Wed, Dec 31 - Wed, Jan 7
MDW
Chicago
TLH
Tallahassee
$385 Roundtrip, found 5 days ago
$385
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Dec 31 from Chicago to Tallahassee, returning Wed, Jan 7, priced at $385 found 5 days ago
Delta
Wed, Dec 3 - Sat, Dec 6
MDW
Chicago
TLH
Tallahassee
$387 Roundtrip, found 1 hour ago
$387
Roundtrip
found 1 hour ago
Select Delta flight, departing Wed, Dec 3 from Chicago to Tallahassee, returning Sat, Dec 6, priced at $387 found 1 hour ago

Find the cheapest month to fly from Chicago (MDW) to Tallahassee (TLH)

October is typically the cheapest month to fly

From $296 - $888 per traveler.

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Tallahassee Intl. Airport (TLH) cost?
Grab a cheap one-way flight from $159 or cheap return flight from $317 from Midway Intl. Airport (MDW) to Tallahassee Intl. Airport (TLH) 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 Midway Intl. Airport (MDW) to Tallahassee Intl. Airport (TLH)?
December is the cheapest month to fly from MDW to TLH. Traveling during quieter months is often the key to better flight prices.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Tallahassee Intl. Airport (TLH)?
Use the filter tool on Expedia to compare different airlines and find the cheapest carrier that'll take you from MDW to TLH. Then, sort your results by "Price (lowest to highest)" to snap up the best deal available.
How many flights per day from Midway Intl. Airport (MDW) to Tallahassee Intl. Airport (TLH)?
Direct flights from Midway Intl. Airport (MDW) to Tallahassee Intl. Airport (TLH) aren't available daily, so you'll have to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your travel dates and choose either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDW to TLH?
Usually you'll find the most flight options available on a Friday. Tuesdays are often the quietest.* But this can vary depending on the airline, time of year and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Tallahassee Intl. Airport (TLH)?
To avoid possible delays on the Midway Intl. Airport (MDW) to Tallahassee Intl. Airport (TLH) route, aim to fly before 3 PM. Flights after this time 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.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Tallahassee Intl. Airport (TLH) last-minute?
Waiting until just before your departure to book your flight from MDW to TLH generally means paying more. While you may find some last-minute deals, they aren't always guaranteed. Keep your travel plans flexible to maximize your chances of snagging a bargain.
Is it cheaper to book a MDW to TLH flight and hotel package?
Opting for a MDW to TLH flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip in one place. Pick from our wide range of accommodations and then add activities, flights and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Tallahassee Intl. Airport (TLH)?
In most instances, you can reschedule or cancel your MDW to TLH flight. However, there may be additional charges, especially if your booking was made over 24 hours ago. Double-check your itinerary for the airline's fees and rules on flight changes, or if you want further information, visit our Customer Service portal.

Travel information

Origin airport
Midway Intl.
Destination airport
Tallahassee Intl.
Airlines serving
Delta
Roundtrip price
$316
Distance
809 mi

Book with confidence

Chicago to Tallahassee Flights

The cheapest times to fly from Chicago to Tallahassee

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

 

The best time to book a flight from Chicago to Tallahassee

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

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 Tallahassee in 2025. You can also book with separate airlines for your outbound and return journeys, from $159 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 Tallahassee 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 Tallahassee 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.

 

Chicago to Tallahassee Flights

Explore a world of travel with Expedia

*Available to One Key members.