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Tallahassee

$149+ 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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — TLH
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
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 August 14, 2025.

Round-trip from

$342
(Delta)

One-way from

$149
(Delta)

Popular in

December

Cheapest in

August

Average price

$376
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. 13% potential increase in price ($84 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 14, 2025.

This Delta deal was found by Cheapflights users on 8/12. 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 9/176:00 amMDW - TLH
1 stop5h 00mDelta
Fri 9/265:12 pmTLH - MDW
1 stop5h 24mDelta
Deal found 8/12$342
This Delta deal was found by Cheapflights users on 8/12. 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.
Mon 9/86:00 amMDW - TLH
1 stop3h 37mDelta
Mon 9/155:12 pmTLH - MDW
1 stop5h 24mDelta
Deal found 8/12$387
This Delta deal was found by Cheapflights users on 8/12. 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 10/166:00 amMDW - TLH
1 stop26h 18mDelta
Mon 10/205:05 pmTLH - MDW
1 stop6h 09mDelta
Deal found 8/12$393
This Delta deal was found by Cheapflights users on 8/13. 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.
Sat 9/276:00 amMDW - TLH
1 stop6h 35mDelta
Sun 9/2812:45 pmTLH - MDW
1 stop5h 50mDelta
Deal found 8/13$453
This KAYAK deal was found by Cheapflights users on 8/12. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/296:00 amMDW - TLH
1 stop11h 26mDelta
Tue 9/3012:45 pmTLH - MDW
1 stop5h 50mDelta
Deal found 8/12$483
This Delta deal was found by Cheapflights users on 8/11. 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 10/196:00 amMDW - TLH
1 stop4h 30mDelta
Sun 10/266:00 amTLH - MDW
1 stop4h 40mDelta
Deal found 8/11$498
This Delta deal was found by Cheapflights users on 8/13. 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 9/34:25 pmMDW - TLH
1 stop5h 17mDelta
Fri 9/55:10 pmTLH - MDW
1 stop5h 16mDelta
Deal found 8/13$512
This Delta deal was found by Cheapflights users on 8/13. 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 8/2112:43 pmMDW - TLH
1 stop4h 43mDelta
Sat 8/235:40 amTLH - MDW
1 stop4h 56mDelta
Deal found 8/13$527
This Delta deal was found by Cheapflights users on 8/12. 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.
Fri 10/176:23 pmMDW - TLH
2 stops15h 10mDelta
Mon 10/205:05 pmTLH - MDW
1 stop6h 09mDelta
Deal found 8/12$528
This Delta deal was found by Cheapflights users on 8/12. 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.
Fri 11/216:00 amMDW - TLH
1 stop5h 06mDelta
Tue 11/253:40 pmTLH - MDW
1 stop7h 04mDelta
Deal found 8/12$539

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 August 14, 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

Wed 9/17

6:00 am-12:00 pm

1 stop5h 00m

Tallahassee

Fri 9/26

5:12 pm-9:36 pm

1 stop5h 24m

$342

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

Sat 9/20

6:00 am-1:35 pm

1 stop6h 35m

Tallahassee

Fri 9/26

5:12 pm-9:36 pm

1 stop5h 24m

$342

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

Mon 9/8

6:00 am-10:37 am

1 stop3h 37m

Tallahassee

Mon 9/15

5:12 pm-9:36 pm

1 stop5h 24m

$387

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

Thu 10/16

6:00 am-9:18 am

1 stop26h 18m

Tallahassee

Mon 10/20

5:05 pm-10:14 pm

1 stop6h 09m

$393

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

Sat 9/27

6:00 am-1:35 pm

1 stop6h 35m

Tallahassee

Sun 9/28

12:45 pm-5:35 pm

1 stop5h 50m

$453

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

Mon 9/29

6:00 am-6:26 pm

1 stop11h 26m

Tallahassee

Tue 9/30

12:45 pm-5:35 pm

1 stop5h 50m

$483

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

Sun 10/19

6:00 am-11:30 am

1 stop4h 30m

Tallahassee

Sun 10/26

6:00 am-9:40 am

1 stop4h 40m

$498

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

Wed 9/3

4:25 pm-10:42 pm

1 stop5h 17m

Tallahassee

Fri 9/5

5:10 pm-9:26 pm

1 stop5h 16m

$512

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

Fri 8/22

6:04 am-12:01 pm

1 stop4h 57m

Tallahassee

Mon 8/25

5:10 pm-9:44 pm

1 stop5h 34m

$527

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

Thu 8/21

12:43 pm-6:26 pm

1 stop4h 43m

Tallahassee

Sat 8/23

5:40 am-9:36 am

1 stop4h 56m

$527

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 14 results
1
2

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, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Tallahassee (average of $404). Flying from Chicago Midway Airport to Tallahassee in December is currently the most expensive (average of $551). 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.

Reviews of airlines servicing Tallahassee

Get insights into the airlines that provide service to Tallahassee. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Tallahassee. Reviews last updated August 14, 2025.
Read reviews from past customers who have flown Delta from Chicago Midway Airport to Tallahassee. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,980 reviews

Boarding

8.2

Entertainment

7.9

Overall

8.0

Comfort

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Delta
8.0
Very good
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Boarding

8.2

Entertainment

7.9

Overall

8.0

Comfort

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.

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 1 airline. Tallahassee is conveniently located just 5.0 mi from Tallahassee’s city center.

  • 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, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Tallahassee (average of $404). Flying from Chicago Midway Airport to Tallahassee in December is currently the most expensive (average of $551). 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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Top airline flying from Midway to Tallahassee

Discover the top airline that operate flights from Midway to Tallahassee. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$401Average$618FlexibilityNo cancel feeOn-timeN/A

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