TLH - MDW

$357 Find Cheap Flights from Tallahassee to Chicago Midway Airport

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Tallahassee to Midway departing on 4/18. 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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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$357
Delta
Sat 4/18Sat 4/25
TLH - MDW • 1 stop
Nonstop flights
Not available
There are currently no direct flights between Tallahassee and Midway. You'll need at least 1 connection.
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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, Apr 18 - Sat, Apr 25
Delta Logo
6:44 pm - 10:28 pm
TLH
-
MDW
4h 44m
1 stop
Delta Logo
6:00 am - 12:11 pm
MDW
-
TLH
5h 11m
1 stop
$357Delta
Wed, Apr 8 - Wed, Apr 15
Delta Logo
7:09 pm - 10:31 pm
TLH
-
MDW
4h 22m
1 stop
Delta Logo
6:00 am - 12:11 pm
MDW
-
TLH
5h 11m
1 stop
$402Delta
Fri, Apr 10 - Wed, Apr 15
Delta Logo
5:12 pm - 10:31 pm
TLH
-
MDW
6h 19m
1 stop
Delta Logo
10:41 am - 4:24 pm
MDW
-
TLH
4h 43m
1 stop
$422Delta
Thu, Jun 11 - Tue, Jun 16
Delta Logo
5:10 pm - 9:45 pm
TLH
-
MDW
5h 35m
1 stop
Delta Logo
6:00 am - 12:04 pm
MDW
-
TLH
5h 04m
1 stop
$437Delta
Fri, Apr 24 - Mon, Apr 27
Delta Logo
7:05 pm - 10:28 pm
TLH
-
MDW
4h 23m
1 stop
Delta Logo
6:00 am - 12:11 pm
MDW
-
TLH
5h 11m
1 stop
$447Delta
Wed, Jul 15 - Sat, Jul 18
Delta Logo
5:10 pm - 9:45 pm
TLH
-
MDW
5h 35m
1 stop
Delta Logo
6:00 am - 12:04 pm
MDW
-
TLH
5h 04m
1 stop
$457Delta
Fri, Apr 24 - Mon, Apr 27
Delta Logo
5:15 pm - 10:28 pm
TLH
-
MDW
6h 13m
1 stop
Delta Logo
6:00 am - 12:11 pm
MDW
-
TLH
5h 11m
1 stop
$467Delta
Wed, Apr 29 - Wed, Apr 29
Delta Logo
5:34 am - 9:56 am
TLH
-
MDW
5h 22m
1 stop
Delta Logo
5:21 pm - 10:32 pm
MDW
-
TLH
4h 11m
1 stop
$498Delta
Tue, Jun 16 - Sun, Jun 21
Delta Logo
5:10 pm - 9:45 pm
TLH
-
MDW
5h 35m
1 stop
Delta Logo
6:00 am - 12:04 pm
MDW
-
TLH
5h 04m
1 stop
$503Delta
Thu, Jun 11 - Mon, Jun 15
Delta Logo
5:10 pm - 9:45 pm
TLH
-
MDW
5h 35m
1 stop
Delta Logo
5:25 pm - 10:20 pm
MDW
-
TLH
3h 55m
1 stop
$513Delta
Booking Insights

Good to know

Cheapest flight$357
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 $357 for a round-trip ticket.

  • 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 8296 reviews
7.8Entertainment
7.2Food
8.1Boarding
7.9Comfort
8.5Crew
Airline reviews

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

10.0 ExcellentAnonymous, Mar 2026
TPA - ATL
Read more Delta reviews

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.

An awesome flight crew. FC seat cushion just doesn’t cut it for a 3+ hour flight.

Delta continues to set the benchmark for traveler-friendly service with minimal disruption and clear communication within the mainland US (coast to coast). I am consistently pleased to be a Delta customer, and this experience once again met my expectations. There was a brief delay departing from MIA due to a technical issue that required the aircraft to return to the gate. However, the situation was handled professionally and transparently. Fortunately, my planned layover allowed ample buffer time, so the adjustment caused no stress. Overall, another smooth and reassuring experience.

Totally worth the miles to upgrade to Delta Comfort. Plenty of legroom.

This was my first time flying Delta ever and I had a great experience!

Flight delay was frustrating, also you cannot checkin online without delta app, web browser check-in throw errors

The flight was great as well as the airline staff

Got on the plane and sat there for an hour before departure.

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

Information on your arrival and departure airports

Tallahassee (TLH)
Midway (MDW)