HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Tallahassee

$250+ 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 12/24. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — TLH
oct. 19 — oct. 261
dom. 10/19
dom. 10/26
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Tallahassee with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 septiembre 19, 2025.

Round-trip from

$418
(Delta)

One-way from

$250
(Delta)

Popular in

December

Cheapest in

August

Average price

$492
From Chicago Midway to Tallahassee
Search Deals
One-way flight from Chicago Midway to Tallahassee
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($92 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

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 septiembre 19, 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.
jue. 11/276:00 amMDW - TLH
1 stop3h 47mDelta
dom. 11/307:08 pmTLH - MDW
1 stop5h 24mDelta
Deal found 9/17$418
This Delta deal was found by Cheapflights users on 9/18. 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.
lun. 12/295:00 pmMDW - TLH
1 stop6h 03mDelta
sáb. 1/36:00 amTLH - MDW
1 stop4h 09mDelta
Deal found 9/18$463
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.
sáb. 10/44:25 pmMDW - TLH
1 stop5h 11mDelta
lun. 10/65:05 pmTLH - MDW
1 stop6h 09mDelta
Deal found 9/17$467
This Delta deal was found by Cheapflights users on 9/18. 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.
sáb. 10/186:00 amMDW - TLH
1 stop6h 52mDelta
sáb. 10/256:00 amTLH - MDW
1 stop4h 40mDelta
Deal found 9/18$483
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/276:00 amMDW - TLH
1 stop4h 30mDelta
mar. 10/286:00 amTLH - MDW
1 stop4h 40mDelta
Deal found 9/17$493
This Delta deal was found by Cheapflights users on 9/18. 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.
vie. 10/314:23 pmMDW - TLH
1 stop5h 13mDelta
dom. 11/25:00 amTLH - MDW
1 stop4h 45mDelta
Deal found 9/18$579
This Delta deal was found by Cheapflights users on 9/18. 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.
vie. 11/1412:47 pmMDW - TLH
1 stop4h 31mDelta
dom. 11/165:35 amTLH - MDW
1 stop5h 17mDelta
Deal found 9/18$597
This Delta deal was found by Cheapflights users on 9/18. 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.
mié. 11/266:00 amMDW - TLH
1 stop7h 00mDelta
sáb. 11/295:35 amTLH - MDW
1 stop5h 17mDelta
Deal found 9/18$598
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.
jue. 10/26:00 amMDW - TLH
1 stop5h 00mDelta
lun. 10/67:16 pmTLH - MDW
1 stop3h 58mDelta
Deal found 9/17$627
This Delta deal was found by Cheapflights users on 9/18. 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.
sáb. 10/114:23 pmMDW - TLH
1 stop5h 13mDelta
dom. 10/127:16 pmTLH - MDW
1 stop3h 58mDelta
Deal found 9/18$633
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.
mié. 10/86:00 amMDW - TLH
1 stop4h 30mDelta
vie. 10/107:16 pmTLH - MDW
1 stop3h 58mDelta
Deal found 9/17$714

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 septiembre 19, 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

jue. 11/27

6:00 am-10:47 am

1 stop3h 47m

Tallahassee

dom. 11/30

7:08 pm-11:32 pm

1 stop5h 24m

$418

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

lun. 12/29

5:00 pm-12:03 am

1 stop6h 03m

Tallahassee

sáb. 1/3

6:00 am-9:09 am

1 stop4h 09m

$463

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

sáb. 10/18

6:00 am-1:52 pm

1 stop6h 52m

Tallahassee

sáb. 10/25

6:00 am-9:40 am

1 stop4h 40m

$483

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

lun. 10/27

6:00 am-11:30 am

1 stop4h 30m

Tallahassee

mar. 10/28

6:00 am-9:40 am

1 stop4h 40m

$493

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

vie. 10/31

4:23 pm-10:36 pm

1 stop5h 13m

Tallahassee

dom. 11/2

5:00 am-8:45 am

1 stop4h 45m

$579

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

vie. 11/14

12:47 pm-6:18 pm

1 stop4h 31m

Tallahassee

dom. 11/16

5:35 am-9:52 am

1 stop5h 17m

$597

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

mié. 11/26

5:34 pm-10:18 pm

1 stop3h 44m

Tallahassee

sáb. 11/29

5:35 am-9:52 am

1 stop5h 17m

$598

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

sáb. 10/11

4:23 pm-10:36 pm

1 stop5h 13m

Tallahassee

dom. 10/12

7:16 pm-10:14 pm

1 stop3h 58m

$633

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

mié. 10/22

6:00 am-11:30 am

1 stop4h 30m

Tallahassee

lun. 10/27

6:00 am-9:40 am

1 stop4h 40m

$763

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

sáb. 10/11

4:23 pm-10:36 pm

1 stop5h 13m

$290

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/17

Showing 1-10 of 16 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 septiembre 19, 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
7,964 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

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
7,964 reviews
Delta
8.0
Very good
7,964 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

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.

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

    Departing from Chicago Midway Airport to Tallahassee will take you 3h 47m. 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, 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to Tallahassee

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Orlando flights
O'Hare Intl to Miami flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Tampa flights
Midway to Orlando flights
O'Hare Intl to Fort Myers flights
Midway to Miami flights
O'Hare Intl to Sarasota flights
Midway to Tampa flights
O'Hare Intl to Jacksonville flights
O'Hare Intl to West Palm Beach flights
Midway to Fort Lauderdale flights
O'Hare Intl to Key West flights
Midway to Fort Myers flights
O'Hare Intl to Pensacola flights
Midway to West Palm Beach flights
Midway to Jacksonville flights
Midway to Sarasota flights
O'Hare Intl to Panama City flights
Midway to Key West flights
Rockford to Orlando Sanford Intl flights
Midway to Pensacola flights
O'Hare Intl to Daytona Beach flights
Midway to Panama City flights
O'Hare Intl to Tallahassee flights
O'Hare Intl to Melbourne flights
Rockford to St Petersburg flights
Midway to Daytona Beach flights
O'Hare Intl to Valparaiso flights
Midway to Melbourne flights
O'Hare Intl to Gainesville flights
Midway to Orlando Sanford Intl flights
Midway to Valparaiso flights
Rockford to Punta Gorda flights
O'Hare Intl to St Petersburg flights
Midway to Punta Gorda flights
Midway to Gainesville flights
O'Hare Intl to Punta Gorda flights
O'Hare Intl to Orlando Sanford Intl flights
Midway to Valdosta flights
O'Hare Intl to Valdosta flights
O'Hare Intl to Destin flights

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 septiembre 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$401Average$618FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.