HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$190+ 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 9/2. Fares are subject to change and may not be available on all flights or dates of travel.
TLH — MDW
ago. 18 — ago. 251
lun. 8/18
lun. 8/25
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Tallahassee to Midway 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 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 agosto 13, 2025.

Round-trip from

$338
(Delta)

One-way from

$190
(Delta)

Popular in

January

Cheapest in

December

Average price

$728
From Tallahassee to Chicago Midway
Search Deals
One-way flight from Tallahassee to Chicago Midway
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($30 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals

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 agosto 13, 2025.

This Delta deal was found by Cheapflights users on 8/10. 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. 10/45:40 amTLH - MDW
1 stop5h 08mDelta
sáb. 10/1110:35 amMDW - TLH
1 stop4h 45mDelta
Deal found 8/10$338
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.
mié. 8/275:10 pmTLH - MDW
1 stop5h 34mDelta
dom. 8/316:00 amMDW - TLH
1 stop5h 01mDelta
Deal found 8/12$372
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.
vie. 9/265:12 pmTLH - MDW
1 stop5h 24mDelta
dom. 9/286:00 amMDW - TLH
1 stop5h 00mDelta
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.
mié. 10/86:00 amTLH - MDW
2 stops13h 25mDelta
sáb. 10/1111:10 amMDW - TLH
2 stops10h 26mDelta
Deal found 8/12$421
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.
jue. 9/255:12 pmTLH - MDW
1 stop5h 24mDelta
dom. 9/286:00 amMDW - TLH
1 stop5h 00mDelta
Deal found 8/12$423
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.
vie. 9/265:12 pmTLH - MDW
1 stop5h 24mDelta
lun. 9/2912:43 pmMDW - TLH
1 stop6h 28mDelta
Deal found 8/11$498
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.
jue. 9/255:12 pmTLH - MDW
1 stop5h 24mDelta
lun. 9/2912:43 pmMDW - TLH
1 stop6h 28mDelta
Deal found 8/11$534
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.
jue. 10/910:03 amTLH - MDW
1 stop7h 06mDelta
sáb. 10/116:00 amMDW - TLH
1 stop9h 20mDelta
Deal found 8/12$588
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.
lun. 9/225:12 pmTLH - MDW
1 stop5h 24mDelta
vie. 9/2612:43 pmMDW - TLH
1 stop6h 28mDelta
Deal found 8/12$597

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 agosto 13, 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

sáb. 10/4

5:40 am-9:48 am

1 stop5h 08m

Chicago Midway

sáb. 10/11

10:35 am-4:20 pm

1 stop4h 45m

$338

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

mié. 8/27

5:10 pm-9:44 pm

1 stop5h 34m

Chicago Midway

dom. 8/31

6:00 am-12:01 pm

1 stop5h 01m

$372

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

vie. 9/26

5:12 pm-9:36 pm

1 stop5h 24m

Chicago Midway

dom. 9/28

6:00 am-12:00 pm

1 stop5h 00m

$387

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

mié. 10/8

6:00 am-6:25 pm

2 stops13h 25m

Chicago Midway

dom. 10/12

6:00 am-11:30 am

1 stop4h 30m

$410

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

mié. 10/8

6:00 am-6:25 pm

2 stops13h 25m

Chicago Midway

sáb. 10/11

11:10 am-10:36 pm

2 stops10h 26m

$421

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

jue. 9/25

5:12 pm-9:36 pm

1 stop5h 24m

Chicago Midway

dom. 9/28

6:00 am-12:00 pm

1 stop5h 00m

$423

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

vie. 9/26

5:12 pm-9:36 pm

1 stop5h 24m

Chicago Midway

lun. 9/29

12:43 pm-8:11 pm

1 stop6h 28m

$498

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

jue. 9/25

5:12 pm-9:36 pm

1 stop5h 24m

Chicago Midway

lun. 9/29

12:43 pm-8:11 pm

1 stop6h 28m

$534

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

jue. 9/11

5:40 am-9:40 am

1 stop5h 00m

Chicago Midway

dom. 9/14

6:00 am-12:00 pm

1 stop5h 00m

$534

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

jue. 10/9

10:03 am-4:09 pm

1 stop7h 06m

Chicago Midway

dom. 10/12

6:00 am-11:30 am

1 stop4h 30m

$557

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/11

Showing 1-10 of 12 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 agosto 13, 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.

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 agosto 13, 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
7,979 reviews

Comfort

7.9

Food

7.3

Entertainment

7.9

Crew

8.5

Boarding

8.2

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
7,979 reviews
Delta
8.0
Very good
7,979 reviews

Comfort

7.9

Food

7.3

Entertainment

7.9

Crew

8.5

Boarding

8.2

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.

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

    Currently priced at $338, 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 51% 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
Valparaiso
Chesterton

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 Tallahassee to Midway

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

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 agosto 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$426Average$603FlexibilityNo 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.