Cheap flights from Chicago Midway Airport to Tallahassee from $309

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Tallahassee departing on 1/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago Midway Airport to Tallahassee

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:45 am - 1:23 pmMDW-TLH
5h 38m1 stop
Delta Logo
7:21 am - 11:59 amTLH-MDW
5h 38m1 stop
$317Delta
Find Deal
Sat, Jan 17 - Wed, Jan 21
Delta Logo
6:45 am - 1:23 pmMDW-TLH
5h 38m1 stop
Delta Logo
5:00 pm - 10:22 pmTLH-MDW
6h 22m1 stop
$328Delta
Find Deal
Thu, Jan 15 - Tue, Jan 20
Delta Logo
6:45 am - 1:23 pmMDW-TLH
5h 38m1 stop
Delta Logo
5:30 am - 10:27 amTLH-MDW
5h 57m1 stop
$339Delta
Find Deal
Fri, Jan 16 - Sun, Jan 18
Delta Logo
10:53 am - 6:40 pmMDW-TLH
6h 47m1 stop
Delta Logo
5:23 pm - 10:42 pmTLH-MDW
6h 19m1 stop
$362Delta
Find Deal
Fri, Feb 13 - Sat, Feb 21
Delta Logo
10:49 am - 4:23 pmMDW-TLH
4h 34m1 stop
Delta Logo
12:53 pm - 4:53 pmTLH-MDW
5h 00m1 stop
$363Delta
Find Deal
Tue, Mar 10 - Tue, Mar 17
Delta Logo
6:30 am - 12:06 pmMDW-TLH
4h 36m1 stop
Delta Logo
5:08 pm - 10:29 pmTLH-MDW
6h 21m1 stop
$387Delta
Find Deal
Tue, Mar 10 - Tue, Mar 17
Delta Logo
11:21 am - 4:47 pmMDW-TLH
4h 26m1 stop
Delta Logo
7:21 am - 11:59 amTLH-MDW
5h 38m1 stop
$407Delta
Find Deal
Thu, Jan 15 - Mon, Jan 19
Delta Logo
3:25 pm - 8:49 pmMDW-TLH
4h 24m1 stop
Delta Logo
5:26 pm - 10:22 pmTLH-MDW
5h 56m1 stop
$433Delta
Find Deal
Thu, Dec 25 - Wed, Dec 31
Delta Logo
3:25 pm - 8:49 pmMDW-TLH
4h 24m1 stop
Delta Logo
5:26 pm - 10:22 pmTLH-MDW
5h 56m1 stop
$443Delta
Find Deal
Thu, Dec 25 - Mon, Dec 29
Delta Logo
9:29 am - 8:49 pmMDW-TLH
10h 20m2 stops
Delta Logo
6:00 am - 9:05 amTLH-MDW
4h 05m1 stop
$456Delta
Find Deal
Thu, Dec 25 - Tue, Dec 30

Delta flights from Chicago Midway Airport to Tallahassee

Our best Delta deals on Chicago Midway Airport to Tallahassee flight tickets
Delta
Jan 17
MDW6:45 amChicago Midway
5h 38m
1 stop
TLH1:23 pmTallahassee
Jan 21
TLH7:21 amTallahassee
5h 38m
1 stop
MDW11:59 amChicago Midway
Delta
Jan 15
MDW6:45 amChicago Midway
5h 38m
1 stop
TLH1:23 pmTallahassee
Jan 20
TLH5:00 pmTallahassee
6h 22m
1 stop
MDW10:22 pmChicago Midway
Delta
Jan 16
MDW6:45 amChicago Midway
5h 38m
1 stop
TLH1:23 pmTallahassee
Jan 18
TLH5:30 amTallahassee
5h 57m
1 stop
MDW10:27 amChicago Midway

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated December 1, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Tallahassee that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

Sat 1/17

6:45 am-1:23 pm

1 stop5h 38m

Tallahassee

Wed 1/21

7:21 am-11:59 am

1 stop5h 38m

$317

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

Thu 1/15

6:45 am-1:23 pm

1 stop5h 38m

Tallahassee

Tue 1/20

5:00 pm-10:22 pm

1 stop6h 22m

$328

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

Fri 1/16

6:45 am-1:23 pm

1 stop5h 38m

Tallahassee

Sun 1/18

5:30 am-10:27 am

1 stop5h 57m

$339

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

Fri 2/13

10:53 am-6:40 pm

1 stop6h 47m

Tallahassee

Sat 2/21

5:23 pm-10:42 pm

1 stop6h 19m

$362

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

Tue 3/10

10:49 am-4:23 pm

1 stop4h 34m

Tallahassee

Tue 3/17

12:53 pm-4:53 pm

1 stop5h 00m

$363

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

Tue 3/10

6:30 am-12:06 pm

1 stop4h 36m

Tallahassee

Tue 3/17

5:08 pm-10:29 pm

1 stop6h 21m

$387

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

Thu 1/15

11:21 am-4:47 pm

1 stop4h 26m

Tallahassee

Mon 1/19

7:21 am-11:59 am

1 stop5h 38m

$407

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

Thu 12/25

3:25 pm-8:49 pm

1 stop4h 24m

Tallahassee

Wed 12/31

5:26 pm-10:22 pm

1 stop5h 56m

$433

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

Thu 12/25

3:25 pm-8:49 pm

1 stop4h 24m

Tallahassee

Mon 12/29

5:26 pm-10:22 pm

1 stop5h 56m

$443

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

Thu 12/25

9:29 am-8:49 pm

2 stops10h 20m

Tallahassee

Tue 12/30

6:00 am-9:05 am

1 stop4h 05m

$456

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 18 resultsSorted by cheapest first
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See travel insights to Tallahassee from

How to get the cheapest flight ticket from Chicago Midway Airport to Tallahassee

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Tallahassee?

The cheapest day to depart from Chicago Midway Airport to Tallahassee is on a Saturday. Travelers who choose to depart for Tallahassee on a Saturday will often find tickets for as low as $497. On the other hand, Thursday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $655.

What is the cheapest time of day to depart on your flight to Tallahassee?

Our data shows that the cheapest Chicago Midway Airport to Tallahassee flights are usually those with departure times at noon. Our users have found flights to Tallahassee at noon for as low as $589. Try not to purchase tickets in the afternoon because they tend to be around $647. Of course, these prices can vary depending on the time of year and what airport you fly to.

When to book flights from Chicago Midway Airport to Tallahassee

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Tallahassee according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Tallahassee (MDW to TLH) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Tallahassee

Fastest flight time

4h 34m

Direct flights

None
The fastest flight from Chicago Midway Airport to Tallahassee takes 4h 34m
There are no direct flights from Chicago Midway Airport to Tallahassee. There are no popular flight routes from Chicago Midway Airport to Tallahassee.
  • How far is Chicago Midway to Tallahassee by plane?

    Tallahassee is 806.8 mi away from Chicago Midway. Typically, this will take 4h 24m by plane in normal conditions.

  • When did momondo last update prices for flights from Chicago Midway Airport to Tallahassee Airport?

    Prices for flights from Chicago Midway Airport to Tallahassee Airport refresh daily.

  • How old do you have to be to fly from Chicago Midway Airport to Tallahassee Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Tallahassee Airport.

  • What documentation or ID do you need to fly to Tallahassee Airport?

    The necessary travel and health documents for your Tallahassee Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Tallahassee?

Book flights to Tallahassee if you plan to visit one of these locations
St. George Island
Thomasville
Apalachicola
Midway

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Tallahassee?

It is quick and easy to find Chicago to Tallahassee flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Tallahassee that suits you.

Can I find flights from Chicago to Tallahassee with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Chicago to Tallahassee flights to just show those with flexible booking policies.

How can momondo help me find flights from Chicago to Tallahassee?

momondo helps you find the best flight between Chicago and Tallahassee by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Chicago to Tallahassee right now. Can momondo alert me if prices change?

Price alerts on flights to Tallahassee from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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1 adult
Wed 12/31
Wed 1/7

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