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$159+ 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 10/7. Fares are subject to change and may not be available on all flights or dates of travel.
TLH — MDW
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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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 September 17, 2025.

Round-trip from

$317
(Delta)

One-way from

$159
(Delta)

Popular in

January

Cheapest in

December

Average price

$525
From Tallahassee to Chicago Midway
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One-way flight from Tallahassee to Chicago Midway
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Highest demand for flights based on searches. 11% potential increase in price ($84 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($36 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 17, 2025.

This Delta deal was found by Cheapflights users on 9/17. 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 10/155:05 pmTLH - MDW
1 stop6h 09mDelta
Wed 10/226:00 amMDW - TLH
1 stop4h 30mDelta
Deal found 9/17$317
This Delta deal was found by Cheapflights users on 9/17. 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 12/57:08 pmTLH - MDW
1 stop5h 24mDelta
Mon 12/86:00 amMDW - TLH
1 stop4h 41mDelta
Deal found 9/17$407
This Delta deal was found by Cheapflights users on 9/16. 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 10/35:12 pmTLH - MDW
1 stop5h 24mDelta
Sun 10/126:00 amMDW - TLH
1 stop4h 30mDelta
Deal found 9/16$437
This Delta deal was found by Cheapflights users on 9/17. 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 10/25:40 amTLH - MDW
1 stop5h 00mDelta
Mon 10/612:48 pmMDW - TLH
1 stop6h 22mDelta
Deal found 9/17$467
This Delta deal was found by Cheapflights users on 9/16. 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 10/35:12 pmTLH - MDW
1 stop5h 24mDelta
Sat 10/114:23 pmMDW - TLH
1 stop5h 13mDelta
Deal found 9/16$473
This Delta deal was found by Cheapflights users on 9/16. 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 10/115:05 pmTLH - MDW
1 stop6h 09mDelta
Wed 10/156:00 amMDW - TLH
1 stop4h 30mDelta
Deal found 9/16$483
This Delta deal was found by Cheapflights users on 9/16. 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 10/115:05 pmTLH - MDW
1 stop6h 09mDelta
Mon 10/136:00 amMDW - TLH
1 stop9h 20mDelta
Deal found 9/16$491
This Delta deal was found by Cheapflights users on 9/16. 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 9/275:40 amTLH - MDW
1 stop5h 08mDelta
Tue 9/306:00 amMDW - TLH
1 stop5h 00mDelta
Deal found 9/16$542
This Delta deal was found by Cheapflights users on 9/17. 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 9/265:12 pmTLH - MDW
1 stop5h 24mDelta
Mon 9/2912:43 pmMDW - TLH
1 stop6h 28mDelta
Deal found 9/17$547
This Delta deal was found by Cheapflights users on 9/16. 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 10/411:50 amTLH - MDW
1 stop4h 36mDelta
Sat 10/116:00 amMDW - TLH
1 stop6h 52mDelta
Deal found 9/16$558
This Delta deal was found by Cheapflights users on 9/16. 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 9/175:40 amTLH - MDW
1 stop5h 00mDelta
Sat 9/2011:00 amMDW - TLH
1 stop6h 46mDelta
Deal found 9/16$647

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 September 17, 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 10/15

5:05 pm-10:14 pm

1 stop6h 09m

Chicago Midway

Wed 10/22

6:00 am-11:30 am

1 stop4h 30m

$317

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Fri 12/5

7:08 pm-11:32 pm

1 stop5h 24m

Chicago Midway

Mon 12/8

6:00 am-11:41 am

1 stop4h 41m

$407

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Fri 10/3

5:12 pm-9:36 pm

1 stop5h 24m

Chicago Midway

Sun 10/12

6:00 am-11:30 am

1 stop4h 30m

$437

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Sat 10/4

5:09 pm-9:10 pm

1 stop5h 01m

Chicago Midway

Sun 10/12

6:00 am-11:30 am

1 stop4h 30m

$437

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Tue 12/9

12:45 pm-4:36 pm

1 stop4h 51m

Chicago Midway

Sat 12/13

6:00 am-1:49 pm

1 stop6h 49m

$483

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Sat 10/11

5:05 pm-10:14 pm

1 stop6h 09m

Chicago Midway

Wed 10/15

6:00 am-11:30 am

1 stop4h 30m

$483

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Sat 10/11

5:05 pm-10:14 pm

1 stop6h 09m

Chicago Midway

Mon 10/13

6:00 am-4:20 pm

1 stop9h 20m

$491

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Sat 10/4

11:50 am-3:26 pm

1 stop4h 36m

Chicago Midway

Sat 10/11

6:00 am-1:52 pm

1 stop6h 52m

$558

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Tue 10/28

6:00 am-9:40 am

1 stop4h 40m

Chicago Midway

Thu 10/30

10:40 am-6:31 pm

1 stop6h 51m

$633

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Tue 10/7

6:00 am-11:53 am

1 stop6h 53m

$159

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 13 results
1
2

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, April is the cheapest month in which you can book a flight from Tallahassee to Chicago Midway Airport (average of $160). Flying from Tallahassee to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 September 17, 2025.

It’s typically best to fly out from Tallahassee to Chicago Midway Airport at noon. Doing so could potentially save you 19% on the flight price compared to flying in the morning, which is usually more expensive.

How much does it cost to fly round-trip from Tallahassee to Chicago Midway Airport?

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 September 17, 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
8.0
Very good
7,961 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Overall

8.0

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
8.0
Very good
7,961 reviews
Delta
8.0
Very good
7,961 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Overall

8.0

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 6h 09m. 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 34% 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, April is the cheapest month in which you can book a flight from Tallahassee to Chicago Midway Airport (average of $160). Flying from Tallahassee to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Benton Harbor
Porter
Chesterton

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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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$426Average$603FlexibilityNo cancel feeOn-timeN/A

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