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Midway

$308+ 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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
TLH — MDW
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 January 29, 2026.

This Delta deal was found by Cheapflights users on 1/27. 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 2/215:30 am
TLH
-
MDW
1 stop5h 51m
Delta
Sat 2/286:00 am
MDW
-
TLH
1 stop5h 43m
Delta
Deal found 1/27$317
This Delta deal was found by Cheapflights users on 1/28. 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.
Tue 3/101:16 pm
TLH
-
MDW
1 stop5h 06m
Delta
Mon 3/166:00 am
MDW
-
TLH
1 stop5h 28m
Delta
Deal found 1/28$417
This Delta deal was found by Cheapflights users on 1/28. 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.
Mon 3/97:39 am
TLH
-
MDW
1 stop5h 23m
Delta
Mon 3/166:00 am
MDW
-
TLH
1 stop5h 28m
Delta
Deal found 1/28$427
This Delta deal was found by Cheapflights users on 1/27. 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 3/65:23 pm
TLH
-
MDW
1 stop6h 08m
Delta
Sun 3/86:00 am
MDW
-
TLH
1 stop5h 28m
Delta
Deal found 1/27$463
This Delta deal was found by Cheapflights users on 1/27. 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 5/205:10 pm
TLH
-
MDW
1 stop5h 35m
Delta
Wed 5/271:05 pm
MDW
-
TLH
1 stop4h 39m
Delta
Deal found 1/27$483
This Delta deal was found by Cheapflights users on 1/27. 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 2/105:30 am
TLH
-
MDW
1 stop5h 23m
Delta
Sat 2/146:00 am
MDW
-
TLH
1 stop5h 43m
Delta
Deal found 1/27$487
This Delta deal was found by Cheapflights users on 1/27. 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 2/147:23 am
TLH
-
MDW
1 stop3h 58m
Delta
Mon 2/166:00 am
MDW
-
TLH
1 stop5h 43m
Delta
Deal found 1/27$523
This Delta deal was found by Cheapflights users on 1/27. 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 2/205:23 pm
TLH
-
MDW
1 stop6h 08m
Delta
Sun 2/226:00 am
MDW
-
TLH
1 stop5h 43m
Delta
Deal found 1/27$541
This Delta deal was found by Cheapflights users on 1/27. 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 2/75:00 pm
TLH
-
MDW
1 stop6h 22m
Delta
Sat 2/214:13 pm
MDW
-
TLH
1 stop5h 07m
Delta
Deal found 1/27$583
This Delta deal was found by Cheapflights users on 1/28. 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 3/195:36 am
TLH
-
MDW
1 stop5h 20m
Delta
Mon 3/2310:45 am
MDW
-
TLH
1 stop6h 39m
Delta
Deal found 1/28$591
This Delta deal was found by Cheapflights users on 1/28. 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 4/25:36 am
TLH
-
MDW
1 stop5h 20m
Delta
Mon 4/612:47 pm
MDW
-
TLH
1 stop4h 37m
Delta
Deal found 1/28$597
This Delta deal was found by Cheapflights users on 1/27. 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 2/55:30 am
TLH
-
MDW
1 stop5h 23m
Delta
Sun 2/226:00 am
MDW
-
TLH
1 stop5h 43m
Delta
Deal found 1/27$631

Find 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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$317
(Delta)

One-way from

$308
(Delta)

Popular in

January

Cheapest in

September

Average price

$720
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. 21% potential increase in price ($142 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 29, 2026.
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

Sat 2/21

5:30 am-10:21 am

1 stop5h 51m

Chicago Midway

Sat 2/28

6:00 am-12:43 pm

1 stop5h 43m

$317

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Tue 3/10

7:39 am-12:02 pm

1 stop5h 23m

Chicago Midway

Sun 3/15

6:00 am-12:28 pm

1 stop5h 28m

$417

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Wed 3/11

5:36 am-9:56 am

1 stop5h 20m

Chicago Midway

Sun 3/15

6:00 am-12:28 pm

1 stop5h 28m

$417

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Wed 3/11

7:09 pm-10:31 pm

1 stop4h 22m

Chicago Midway

Mon 3/16

6:00 am-12:28 pm

1 stop5h 28m

$417

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Mon 3/9

7:09 pm-10:31 pm

1 stop4h 22m

Chicago Midway

Sun 3/15

6:00 am-12:28 pm

1 stop5h 28m

$427

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Mon 3/9

7:39 am-12:02 pm

1 stop5h 23m

Chicago Midway

Mon 3/16

6:00 am-12:28 pm

1 stop5h 28m

$427

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Fri 2/27

7:29 pm-10:31 pm

1 stop4h 02m

Chicago Midway

Fri 3/6

10:49 am-6:40 pm

1 stop6h 51m

$427

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Fri 3/6

5:23 pm-10:31 pm

1 stop6h 08m

Chicago Midway

Sun 3/8

6:00 am-12:28 pm

1 stop5h 28m

$463

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Wed 5/20

5:10 pm-9:45 pm

1 stop5h 35m

Chicago Midway

Wed 5/27

1:05 pm-6:44 pm

1 stop4h 39m

$483

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Fri 2/13

5:30 am-9:54 am

1 stop5h 24m

Chicago Midway

Tue 2/17

10:49 am-4:35 pm

1 stop4h 46m

$487

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 17 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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Tallahassee-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 $108). Flying from Tallahassee to Chicago Midway Airport in July is currently the most expensive (average of $502). 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 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 January 29, 2026.
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
8,128 reviews

Entertainment

7.8

Crew

8.5

Comfort

7.9

Overall

7.9

Boarding

8.1

Food

7.2

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
8,128 reviews
Delta
7.9
Good
8,128 reviews

Entertainment

7.8

Crew

8.5

Comfort

7.9

Overall

7.9

Boarding

8.1

Food

7.2

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 51m. 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 $257, 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.

  • 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 $108). Flying from Tallahassee to Chicago Midway Airport in July is currently the most expensive (average of $502). 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
Lansing
Merrillville
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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$257Average$536FlexibilityNo cancel feeOn-timeN/A

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