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Tallahassee

$339+ Cheap flights from Midway (MDW) to Tallahassee (TLH)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/21. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — TLH
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Cheap flight deals from Midway to Tallahassee

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Tallahassee (TLH). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$397
(Delta)

One-way from

$339
(Delta)

Popular in

December

Cheapest in

August

Average price

$605
Provider with most accurate pricing for Chicago Midway-Tallahassee flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Tallahassee flights.
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From Chicago Midway to Tallahassee
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One-way flight from Chicago Midway to Tallahassee
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Highest demand for flights based on searches. 16% potential increase in price ($106 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($27 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find flight deals from Midway to Tallahassee

Cheapest flights from Midway to Tallahassee
Explore the most affordable flight options available from Midway to Tallahassee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 3, 2025.

This Delta deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/206:00 amMDW - TLH
1 stop7h 00mDelta
Fri 11/285:35 amTLH - MDW
1 stop5h 17mDelta
Deal found 11/1$447
This Delta deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/253:25 pmMDW - TLH
1 stop4h 24mDelta
Mon 12/295:26 pmTLH - MDW
1 stop5h 56mDelta
Deal found 11/1$508
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/219:50 amMDW - TLH
1 stop5h 51mDelta
Sun 12/286:00 amTLH - MDW
1 stop4h 05mDelta
Deal found 11/2$588
This Delta deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2012:47 pmMDW - TLH
1 stop4h 31mDelta
Sat 11/225:35 amTLH - MDW
1 stop5h 18mDelta
Deal found 11/1$798
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2710:47 amMDW - TLH
1 stop6h 31mDelta
Sun 11/307:00 amTLH - MDW
1 stop5h 52mDelta
Deal found 11/2$848
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2612:47 pmMDW - TLH
1 stop4h 31mDelta
Sat 11/295:35 amTLH - MDW
1 stop5h 17mDelta
Deal found 11/2$1,058

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Tallahassee that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 3, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Tallahassee that are best for you.

Fly from

Midway

Fly to

Tallahassee

Route

Depart

Return

Price

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

Tue 4/21

1:05 pm-6:44 pm

1 stop4h 39m

Tallahassee

Sat 4/25

10:20 am-4:25 pm

1 stop7h 05m

$397

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

Thu 11/20

6:00 am-2:00 pm

1 stop7h 00m

Tallahassee

Fri 11/28

5:35 am-9:52 am

1 stop5h 17m

$447

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

Thu 12/25

3:25 pm-8:49 pm

1 stop4h 24m

Tallahassee

Mon 12/29

5:26 pm-10:22 pm

1 stop5h 56m

$508

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

Fri 2/6

6:00 am-1:04 pm

1 stop6h 04m

Tallahassee

Mon 2/9

7:29 pm-10:26 pm

1 stop3h 57m

$518

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

Thu 2/12

6:00 am-12:38 pm

1 stop5h 38m

Tallahassee

Sun 2/15

7:23 am-10:15 am

1 stop3h 52m

$559

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

Sun 12/21

6:00 am-12:31 pm

1 stop5h 31m

Tallahassee

Sun 12/28

6:00 am-9:05 am

1 stop4h 05m

$588

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

Thu 11/20

12:47 pm-6:18 pm

1 stop4h 31m

Tallahassee

Sat 11/22

7:00 am-9:53 am

1 stop3h 53m

$798

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

Fri 11/21

12:47 pm-6:18 pm

1 stop4h 31m

$339

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

Sat 12/27

6:00 am-12:31 pm

1 stop5h 31m

$389

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

Thu 11/13

5:34 pm-10:18 pm

1 stop3h 44m

$459

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/31

Showing 1-10 of 15 results
1
2

Compare providers for flights from Midway to Tallahassee

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Tallahassee in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Tallahassee flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Tallahassee flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Tallahassee flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Tallahassee flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Tallahassee flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Midway to Tallahassee

Have a flexible travel schedule? Discover the best time to fly to Tallahassee from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Tallahassee

What is the cheapest month to book a flight from Chicago Midway Airport to Tallahassee?

Currently, May is the cheapest month in which you can book a flight from Chicago Midway Airport to Tallahassee (average of $183). Flying from Chicago Midway Airport to Tallahassee in December is currently the most expensive (average of $698). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

Find useful and relevant information for your journey from Midway to Tallahassee. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Tallahassee from Chicago Midway?

    Most people fly into Tallahassee (TLH) if they book a flight to Tallahassee from Chicago Midway. On average, Tallahassee has 0 inbound flights from Chicago Midway per day from 0 airlines. Tallahassee is conveniently located just 5.0 mi from Tallahassee’s city center.

  • How long is the flight from Chicago Midway Airport to Tallahassee?

    Departing from Chicago Midway Airport to Tallahassee will take you 4h 39m. The distance from Chicago Midway Airport to Tallahassee is about 809 mi.

  • Can I find deals for flights from Midway to Tallahassee that include hotel bookings?

    Yes. In addition to deals on Midway to Tallahassee flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Tallahassee?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Tallahassee.

  • Can I find deals for business class flights from Midway to Tallahassee?

    Yes. Cheapflights offers flight deals from Midway to Tallahassee by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Tallahassee?

    Currently, May is the cheapest month in which you can book a flight from Chicago Midway Airport to Tallahassee (average of $183). Flying from Chicago Midway Airport to Tallahassee in December is currently the most expensive (average of $698). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Tallahassee?

Book flights to Tallahassee if you plan to visit one of these locations
Thomasville
Midway

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