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

View $159 flight on Wed, Nov 12, 2025Opens in a new window

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

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Cheap Flights from Tallahassee to Chicago (TLH-MDW)

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
Tue, Dec 16 - Wed, Dec 17
TLH
Tallahassee
MDW
Chicago
$317 Roundtrip, found 13 hours ago
$317
Roundtrip
found 13 hours ago
Select Delta flight, departing Tue, Dec 16 from Tallahassee to Chicago, returning Wed, Dec 17, priced at $317 found 13 hours ago
Delta
Fri, Oct 31 - Sat, Nov 8
TLH
Tallahassee
MDW
Chicago
$352 Roundtrip, just found
$352
Roundtrip
just found
Select Delta flight, departing Fri, Oct 31 from Tallahassee to Chicago, returning Sat, Nov 8, priced at $352 just found
Delta
Wed, Nov 12 - Sat, Nov 15
TLH
Tallahassee
MDW
Chicago
$358 Roundtrip, found 1 day ago
$358
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Nov 12 from Tallahassee to Chicago, returning Sat, Nov 15, priced at $358 found 1 day ago
Delta
Sun, Nov 23 - Sat, Dec 6
TLH
Tallahassee
MDW
Chicago
$362 Roundtrip, found 8 hours ago
$362
Roundtrip
found 8 hours ago
Select Delta flight, departing Sun, Nov 23 from Tallahassee to Chicago, returning Sat, Dec 6, priced at $362 found 8 hours ago
Delta
Tue, Dec 16 - Tue, Dec 23
TLH
Tallahassee
MDW
Chicago
$365 Roundtrip, found 5 days ago
$365
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Dec 16 from Tallahassee to Chicago, returning Tue, Dec 23, priced at $365 found 5 days ago
Delta
Tue, Dec 16 - Wed, Dec 17
TLH
Tallahassee
MDW
Chicago
$387 Roundtrip, found 13 hours ago
$387
Roundtrip
found 13 hours ago
Select Delta flight, departing Tue, Dec 16 from Tallahassee to Chicago, returning Wed, Dec 17, priced at $387 found 13 hours ago
Delta
Tue, Dec 16 - Wed, Dec 31
TLH
Tallahassee
MDW
Chicago
$388 Roundtrip, found 1 hour ago
$388
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Dec 16 from Tallahassee to Chicago, returning Wed, Dec 31, priced at $388 found 1 hour ago
Delta
Wed, Oct 29 - Sat, Nov 8
TLH
Tallahassee
MDW
Chicago
$392 Roundtrip, just found
$392
Roundtrip
just found
Select Delta flight, departing Wed, Oct 29 from Tallahassee to Chicago, returning Sat, Nov 8, priced at $392 just found
Delta
Wed, Dec 10 - Wed, Dec 24
TLH
Tallahassee
MDW
Chicago
$393 Roundtrip, found 4 days ago
$393
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Dec 10 from Tallahassee to Chicago, returning Wed, Dec 24, priced at $393 found 4 days ago
Delta
Wed, Nov 5 - Sat, Nov 8
TLH
Tallahassee
MDW
Chicago
$394 Roundtrip, just found
$394
Roundtrip
just found
Select Delta flight, departing Wed, Nov 5 from Tallahassee to Chicago, returning Sat, Nov 8, priced at $394 just found

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

September is typically the cheapest month to fly

From $296 - $802 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 $392
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $392

Frequently asked questions

How much does a flight from Tallahassee Intl. Airport (TLH) to Midway Intl. Airport (MDW) cost?
Get a cheap one-way flight from $159 or cheap return flight from $317 from Tallahassee Intl. Airport (TLH) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Tallahassee Intl. Airport (TLH) to Midway Intl. Airport (MDW)?
December is the most affordable month to fly from TLH to MDW. Traveling outside of peak seasons is often the key to finding a great deal.
What is the cheapest airline that flies from Tallahassee Intl. Airport (TLH) to Midway Intl. Airport (MDW)?
To find the cheapest airline that'll fly you from TLH to MDW, use Expedia's filter tool. Tailor your search based on what's important to you, such as preferred carriers and seat class. You can then sort your results by "Price (lowest to highest)" to discover the cheapest flight right away.
How many flights per day from Tallahassee Intl. Airport (TLH) to Midway Intl. Airport (MDW)?
There aren't any daily nonstop flights available from Tallahassee Intl. Airport (TLH) to Midway Intl. Airport (MDW). But you can book flights with layovers. Filter your search results on Expedia to include one or two stops, and you'll be on your way before you know it.
What day of the week has the most flights from TLH to MDW?
You'll generally find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can change from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Tallahassee Intl. Airport (TLH) to Midway Intl. Airport (MDW)?
To avoid potential delays on the Tallahassee Intl. Airport (TLH) to Midway Intl. Airport (MDW) route, fly before 3 PM. Later departures have a 22% higher chance of being 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 Tallahassee Intl. Airport (TLH) to Midway Intl. Airport (MDW) last-minute?
Waiting until right before your break to book a ticket from TLH to MDW often results in higher prices. While you might find some last-minute offers, they aren't always guaranteed. Keep your travel schedule open for the best chance of landing a bargain.
Is it cheaper to book a TLH to MDW flight and hotel package?
Securing a TLH to MDW flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip in one place. Pick from our extensive range of stays and then add activities, car rentals and flights to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Tallahassee Intl. Airport (TLH) to Midway Intl. Airport (MDW)?
In most cases, you're able to cancel or reschedule your TLH to MDW flight. However, there may be additional fees, especially if your booking was made over 24 hours ago. Check your itinerary for the airline's rules and fees on flight changes, or if you'd like more details, head to our Customer Service portal.

Travel information

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

Book with confidence

Tallahassee to Chicago Flights

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

 

The best time to book a flight from Tallahassee to Chicago

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

 

Tallahassee to Chicago Flights

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