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Cheap flights from Tallahassee to Chicago from $308

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Tallahassee to Chicago departing on 5/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Tallahassee to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
5:36 am - 9:56 am
TLH
-
MDW
5h 20m
1 stop
Delta Logo
12:52 pm - 5:49 pm
MDW
-
TLH
3h 57m
1 stop
$362Delta
Sat, Apr 11 - Tue, Apr 14
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
$388Delta
Sat, Apr 25 - Sun, Apr 26
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
$433Delta
Thu, Apr 2 - Mon, Apr 6
Delta Logo
5:11 pm - 10:28 pm
TLH
-
MDW
6h 17m
1 stop
Delta Logo
6:00 am - 12:11 pm
MDW
-
TLH
5h 11m
1 stop
$438Delta
Wed, Apr 22 - Sun, Apr 26
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
$459Delta
Thu, Apr 2 - Sun, Apr 5
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
$483Delta
Fri, Apr 3 - Mon, Apr 6
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
$509Delta
Fri, Apr 3 - Sun, Apr 5
Delta Logo
10:15 am - 4:12 pm
TLH
-
MDW
6h 57m
1 stop
Delta Logo
6:23 am - 1:57 pm
MDW
-
TLH
6h 34m
1 stop
$615Delta
Tue, Jun 2 - Fri, Jun 5
Delta Logo
5:36 am - 9:56 am
TLH
-
MDW
5h 20m
1 stop
Delta Logo
10:45 am - 4:27 pm
MDW
-
TLH
4h 42m
1 stop
$663Delta
Fri, Apr 3 - Mon, Apr 6
Delta Logo
7:09 pm - 10:31 pm
TLH
-
MDW
4h 22m
1 stop
Delta Logo
12:47 pm - 8:44 pm
MDW
-
TLH
6h 57m
1 stop
$724Delta
Sun, Mar 15 - Wed, Mar 18

Delta flights from Tallahassee to Chicago Midway Airport

Our best Delta deals on Tallahassee to Chicago Midway Airport flight tickets
Delta
Apr 25
TLH6:44 pmTallahassee
4h 44m
1 stop
MDW10:28 pmChicago Midway
Apr 26
MDW6:00 amChicago Midway
5h 11m
1 stop
TLH12:11 pmTallahassee
$388
Delta
Apr 2
TLH7:09 pmTallahassee
4h 22m
1 stop
MDW10:31 pmChicago Midway
Apr 6
MDW6:00 amChicago Midway
5h 28m
1 stop
TLH12:28 pmTallahassee
$433
Delta
Apr 22
TLH5:11 pmTallahassee
6h 17m
1 stop
MDW10:28 pmChicago Midway
Apr 26
MDW6:00 amChicago Midway
5h 11m
1 stop
TLH12:11 pmTallahassee
$438

momondo Fare Finder

 
Customize your flight search to find flights from Tallahassee to Chicago Midway Airport 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 March 2, 2026.
Use the filters below to find and compare flights from Tallahassee to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Sat 4/11

5:36 am-9:56 am

1 stop5h 20m

Chicago Midway

Tue 4/14

12:52 pm-5:49 pm

1 stop3h 57m

$362

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Sat 4/25

6:44 pm-10:28 pm

1 stop4h 44m

Chicago Midway

Sun 4/26

6:00 am-12:11 pm

1 stop5h 11m

$388

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Thu 4/2

7:09 pm-10:31 pm

1 stop4h 22m

Chicago Midway

Mon 4/6

6:00 am-12:28 pm

1 stop5h 28m

$433

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Wed 4/22

5:11 pm-10:28 pm

1 stop6h 17m

Chicago Midway

Sun 4/26

6:00 am-12:11 pm

1 stop5h 11m

$438

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Thu 4/2

7:09 pm-10:31 pm

1 stop4h 22m

Chicago Midway

Sun 4/5

6:00 am-12:28 pm

1 stop5h 28m

$459

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Fri 4/3

5:36 am-9:56 am

1 stop5h 20m

Chicago Midway

Mon 4/6

6:00 am-12:28 pm

1 stop5h 28m

$483

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Fri 4/3

5:36 am-9:56 am

1 stop5h 20m

Chicago Midway

Sun 4/5

6:00 am-12:28 pm

1 stop5h 28m

$509

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Tue 6/2

10:15 am-4:12 pm

1 stop6h 57m

Chicago Midway

Fri 6/5

6:23 am-1:57 pm

1 stop6h 34m

$615

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Fri 4/3

5:36 am-9:56 am

1 stop5h 20m

Chicago Midway

Mon 4/6

10:45 am-4:27 pm

1 stop4h 42m

$663

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Sun 3/15

7:09 pm-10:31 pm

1 stop4h 22m

Chicago Midway

Wed 3/18

12:47 pm-8:44 pm

1 stop6h 57m

$724

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Tallahassee to Chicago Midway Airport

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 airline that flies from Tallahassee to Chicago Midway?

Delta is the most popular carrier operating from Tallahassee to Chicago Midway

When to book flights from Tallahassee to Chicago Midway Airport

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

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

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

Fastest flight time

4h 22m

Direct flights

None
The fastest flight from Tallahassee to Chicago Midway Airport takes 4h 22m
There are no direct flights from Tallahassee to Chicago Midway Airport. There are no popular flight routes from Tallahassee to Chicago Midway Airport.
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  • How far is Tallahassee to Chicago Midway by plane?

    The distance between Tallahassee and Chicago Midway is about 806.8 mi. Flights usually cover this in 4h 22m, depending on flying conditions and air traffic around both airports.

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

    Prices for flights from Tallahassee Airport to Chicago Midway Airport are updated daily.

  • How many operators does momondo search for flights from Tallahassee Airport to Chicago Midway Airport?

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Tallahassee Airport to Chicago Midway Airport.

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

    The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular airline from Tallahassee to Chicago Midway Airport?

Best airlines flying from Tallahassee to Chicago Midway Airport

Compare and see reviews for airlines that fly from Tallahassee to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $257Free CancellationRating
7.9
8,237 reviews
Search Delta flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

It is quick and easy to find Tallahassee to Chicago 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 Chicago that suits you.

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

Yes. momondo enables you to select and highlight flights to Chicago from Tallahassee with this policy.

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

Once you have performed a search for Tallahassee to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Price alerts on flights to Chicago from Tallahassee 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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