TLH - MDW

$308 Find Cheap Flights from Tallahassee to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Tallahassee to Midway departing on 3/17. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Tallahassee to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Tallahassee to Chicago, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$407
Delta
Sat 5/9Mon 5/11
TLH - MDW • 1 stop
Cheapest one-way
$308
Delta
Tue 3/17
TLH - MDW • 1 stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Tallahassee to Midway (TLH-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Tallahassee to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Tallahassee to Midway

Sat, May 9 - Mon, May 11
Delta Logo
5:35 am - 9:51 am
TLH
-
MDW
5h 16m
1 stop
Delta Logo
6:00 am - 12:04 pm
MDW
-
TLH
5h 04m
1 stop
$407Delta
Tue, Mar 10 - Mon, Mar 16
Delta Logo
1:16 pm - 5:22 pm
TLH
-
MDW
5h 06m
1 stop
Delta Logo
6:00 am - 12:28 pm
MDW
-
TLH
5h 28m
1 stop
$417Delta
Mon, Mar 9 - Mon, Mar 16
Delta Logo
7:39 am - 12:02 pm
TLH
-
MDW
5h 23m
1 stop
Delta Logo
6:00 am - 12:28 pm
MDW
-
TLH
5h 28m
1 stop
$427Delta
Fri, Mar 6 - Sun, Mar 8
Delta Logo
5:23 pm - 10:31 pm
TLH
-
MDW
6h 08m
1 stop
Delta Logo
6:00 am - 12:28 pm
MDW
-
TLH
5h 28m
1 stop
$463Delta
Fri, Feb 13 - Tue, Feb 17
Delta Logo
5:30 am - 9:54 am
TLH
-
MDW
5h 24m
1 stop
Delta Logo
10:49 am - 4:35 pm
MDW
-
TLH
4h 46m
1 stop
$487Delta
Fri, Feb 27 - Sun, Mar 1
Delta Logo
7:29 pm - 10:31 pm
TLH
-
MDW
4h 02m
1 stop
Delta Logo
6:00 am - 12:43 pm
MDW
-
TLH
5h 43m
1 stop
$511Delta
Thu, Mar 19 - Mon, Mar 23
Delta Logo
5:36 am - 9:56 am
TLH
-
MDW
5h 20m
1 stop
Delta Logo
10:45 am - 6:24 pm
MDW
-
TLH
6h 39m
1 stop
$591Delta
Thu, Apr 2 - Mon, Apr 6
Delta Logo
5:36 am - 9:56 am
TLH
-
MDW
5h 20m
1 stop
Delta Logo
12:47 pm - 6:24 pm
MDW
-
TLH
4h 37m
1 stop
$597Delta
Thu, Mar 12 - Mon, Mar 16
Delta Logo
5:36 am - 9:56 am
TLH
-
MDW
5h 20m
1 stop
Delta Logo
6:00 am - 12:28 pm
MDW
-
TLH
5h 28m
1 stop
$688Delta
Fri, Mar 13 - Mon, Mar 16
Delta Logo
7:09 pm - 10:31 pm
TLH
-
MDW
4h 22m
1 stop
Delta Logo
6:00 am - 12:28 pm
MDW
-
TLH
5h 28m
1 stop
$808Delta
Booking Insights

Good to know

Cheapest flight$308
Flight from Tallahassee to Chicago Midway Airport

When to book flights from Tallahassee to Midway

Are your dates flexible? Find out the best times to travel from Tallahassee to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Tallahassee to Chicago Midway Airport flights

  • What is the cheapest flight from Tallahassee to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Tallahassee to Chicago Midway Airport was $308 for a one-way ticket and $407 for a round-trip.

  • Do I need a passport to fly between Tallahassee and Chicago Midway Airport?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which aircraft models fly most regularly from Tallahassee to Chicago Midway Airport?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Tallahassee to Chicago Midway Airport?

    SkyTeam is the only airline alliance operating flights between Tallahassee and Chicago Midway Airport.

  • How does KAYAK find such low prices on flights from Tallahassee to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Tallahassee to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Tallahassee to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Tallahassee is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Tallahassee to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Tallahassee with another airline. Booking your flights between Tallahassee and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Tallahassee to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Tallahassee up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Tallahassee to Midway

 
See real verified KAYAK customer reviews for airlines flying from Tallahassee to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Tallahassee to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 8126 reviews
8.1Boarding
7.8Entertainment
8.5Crew
7.9Comfort
7.2Food
Airline reviews

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

10.0 ExcellentSteven, Jan 2026
FLL - CVG
Read more Delta reviews

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

No WiFi. Comfort plus should have alcohol provided, crew only offered water or tea. Who the heck wants tea?

I have diamond medallion status and usually we are in comfort plus . We were in main this time ( which was fine ) and my husband wanted wine . I have at least 10 vouchers for drinks that are good for this year and next! The attendant would not take the picture of the voucher as proof and never came back to check as She asked me to pull it up on delta Wi-Fi. Instead my husband just used his Amex to buy the wine . Disappointing!!!

Food is basically Sun Chips, cookies or Cheezits. I had an exit row seat so I had plenty of room. The crew was very nice and efficient. Pilot kept us informed. Pretty good flight.

The only thing nice I can say is the flight crew was really nice and apologetic about the situation. They shared as much information as they had and advised us on what we could do about missing connecting flights. The boarding process was so slow. The gate agent was working by herself and should have had someone working with her. It took almost an hour to board because she was trying to board a full flight of people and provide customer service to everyone who was flying standby and/or had questions. It was really chaotic. This didn't help the fact that we were delayed and folks were missing connections the longer it took.

The food is terrible. The staff is wonderful. Comfort is good.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

Everything you need to know for your flight from Tallahassee to Midway

Information on your arrival and departure airports

Tallahassee (TLH)
Midway (MDW)