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$309+ Cheap flights from Tallahassee (TLH) to Midway (MDW)

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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
TLH — MDW
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Find flight deals from Tallahassee to Midway

Cheapest flights from Tallahassee to Midway
Explore the most affordable flight options available from Tallahassee to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This Delta deal was found by Cheapflights users on 10/29. 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 12/215:26 pmTLH - MDW
1 stop5h 56mDelta
Wed 1/76:45 amMDW - TLH
1 stop5h 40mDelta
Deal found 10/29$362
This Delta deal was found by Cheapflights users on 10/30. 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 12/245:26 pmTLH - MDW
1 stop5h 56mDelta
Tue 12/309:50 amMDW - TLH
1 stop5h 51mDelta
Deal found 10/30$387
This Delta deal was found by Cheapflights users on 10/29. 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 12/205:26 pmTLH - MDW
1 stop5h 56mDelta
Thu 1/86:45 amMDW - TLH
1 stop5h 40mDelta
Deal found 10/29$407
This Delta deal was found by Cheapflights users on 10/29. 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 11/137:00 amTLH - MDW
1 stop3h 52mDelta
Mon 11/175:34 pmMDW - TLH
1 stop3h 44mDelta
Deal found 10/29$487
This Delta deal was found by Cheapflights users on 10/29. 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 11/205:35 amTLH - MDW
1 stop5h 17mDelta
Sun 11/236:00 amMDW - TLH
1 stop4h 34mDelta
Deal found 10/29$577
This Delta deal was found by Cheapflights users on 10/28. 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 11/1312:37 pmTLH - MDW
1 stop5h 01mDelta
Wed 11/266:00 amMDW - TLH
1 stop7h 00mDelta
Deal found 10/28$598
This Delta deal was found by Cheapflights users on 10/29. 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 11/16:00 amTLH - MDW
1 stop4h 45mDelta
Wed 11/510:40 amMDW - TLH
1 stop6h 51mDelta
Deal found 10/29$637
This Delta deal was found by Cheapflights users on 10/30. 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 12/286:00 amTLH - MDW
1 stop4h 05mDelta
Fri 1/26:00 amMDW - TLH
1 stop5h 31mDelta
Deal found 10/30$667
This Delta deal was found by Cheapflights users on 10/29. 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.
Tue 11/255:35 amTLH - MDW
1 stop5h 17mDelta
Fri 11/286:00 amMDW - TLH
1 stop3h 47mDelta
Deal found 10/29$668
This Delta deal was found by Cheapflights users on 10/30. 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 11/177:08 pmTLH - MDW
1 stop5h 32mDelta
Thu 11/2010:47 amMDW - TLH
1 stop6h 31mDelta
Deal found 10/30$707
This Delta deal was found by Cheapflights users on 10/29. 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 11/2911:35 amTLH - MDW
1 stop6h 03mDelta
Sat 12/64:29 pmMDW - TLH
1 stop4h 54mDelta
Deal found 10/29$893

Cheap flight deals from Tallahassee to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Tallahassee (TLH) to Midway (MDW). 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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$317
(Delta)

One-way from

$309
(Delta)

Popular in

January

Cheapest in

April

Average price

$888
Provider with most accurate pricing for Tallahassee-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Tallahassee-Chicago Midway flights.
Search Deals
From Tallahassee to Chicago Midway
Search Deals
One-way flight from Tallahassee to Chicago Midway
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($102 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($38 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Tallahassee to Midway 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 October 30, 2025.
Use the filters below to find and compare flights from Tallahassee to Chicago Midway Airport that are best for you.

Fly from

Tallahassee

Fly to

Midway

Route

Depart

Return

Price

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Wed 1/14

5:50 pm-10:09 pm

1 stop5h 19m

Chicago Midway

Wed 1/21

10:46 am-6:42 pm

1 stop6h 56m

$317

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Sun 12/21

5:26 pm-10:22 pm

1 stop5h 56m

Chicago Midway

Wed 1/7

6:45 am-1:25 pm

1 stop5h 40m

$362

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Wed 12/24

5:26 pm-10:22 pm

1 stop5h 56m

Chicago Midway

Tue 12/30

9:50 am-4:41 pm

1 stop5h 51m

$387

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Sat 12/20

5:26 pm-10:22 pm

1 stop5h 56m

Chicago Midway

Thu 1/8

6:45 am-1:25 pm

1 stop5h 40m

$407

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Sun 11/23

7:00 am-11:52 am

1 stop5h 52m

Chicago Midway

Thu 11/27

6:00 am-2:00 pm

1 stop7h 00m

$407

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Wed 11/12

7:00 am-11:52 am

1 stop5h 52m

Chicago Midway

Sun 11/16

10:47 am-4:19 pm

1 stop4h 32m

$467

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Fri 11/14

7:08 pm-11:40 pm

1 stop5h 32m

Chicago Midway

Tue 11/18

6:00 am-11:34 am

1 stop4h 34m

$487

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Mon 11/24

12:37 pm-11:40 pm

1 stop12h 03m

Chicago Midway

Thu 11/27

6:00 am-2:00 pm

1 stop7h 00m

$545

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Thu 11/27

11:35 am-4:39 pm

1 stop6h 04m

Chicago Midway

Fri 11/28

6:00 am-8:18 pm

1 stop13h 18m

$554

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Sun 11/23

5:35 am-9:52 am

1 stop5h 17m

Chicago Midway

Fri 11/28

6:00 am-10:18 pm

1 stop15h 18m

$554

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 18 results
1
2

Compare providers for flights from Tallahassee to Midway

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 Tallahassee to Midway in October.
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 Tallahassee-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Tallahassee-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Tallahassee-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Tallahassee-Chicago Midway Airport 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 Tallahassee-Chicago Midway Airport 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 Tallahassee to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Tallahassee 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 Tallahassee to Chicago Midway Airport

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

Currently, June is the cheapest month in which you can book a flight from Tallahassee to Chicago Midway Airport (average of $99). Flying from Tallahassee to Chicago Midway Airport in July is currently the most expensive (average of $443). 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.

What is the cheapest time of day to fly from TLH to MDW?

Find hourly flight availability from Tallahassee to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 30, 2025.

It’s typically best to fly out from Tallahassee to Chicago Midway Airport at noon. Doing so could potentially save you 33% on the flight price compared to flying in the morning, which is usually more expensive.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated October 30, 2025.
See what other customers who have flown with Delta from Tallahassee to Chicago Midway Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,998 reviews

Crew

8.5

Comfort

7.9

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Delta
7.9
Good
7,998 reviews
Delta
7.9
Good
7,998 reviews

Crew

8.5

Comfort

7.9

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.

Related info for your journey

Find useful and relevant information for your journey from Tallahassee to Midway. 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 from for flights from Tallahassee to Chicago Midway?

    For a flight from Tallahassee to Chicago Midway, you will be flying from Tallahassee. Tallahassee (TLH) is just 5.0 mi from the center of the city. Tallahassee is the only Tallahassee airport and it handles 0 outbound flights to Chicago Midway per day. 1 airline has flights to Chicago Midway from Tallahassee on a regular basis.

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

    There are many flights that can get you from Tallahassee to Chicago Midway Airport in 5h 19m. Fly via Delta to get the fastest option. The distance from Tallahassee to Chicago Midway Airport is about 809 mi.

  • What is the cheapest airline to fly from Tallahassee to Chicago Midway Airport round-trip?

    Currently priced at $426, Delta will fly you from Tallahassee to Chicago Midway Airport and back. In addition to Delta, many other airlines offer competitively priced options for your trip. Delta is 36% cheaper than the average price of flights available within the next 90 days to this destination.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Tallahassee to Midway 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 Tallahassee to Chicago Midway Airport?

    Currently, June is the cheapest month in which you can book a flight from Tallahassee to Chicago Midway Airport (average of $99). Flying from Tallahassee to Chicago Midway Airport in July is currently the most expensive (average of $443). 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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Top airline flying from Tallahassee to Midway

Discover the top airline that operate flights from Tallahassee to Midway. 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$426Average$606FlexibilityNo cancel feeOn-timeN/A

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