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Cheap flights from Tallahassee to Chicago from $168

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 10/22. 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
1 adult, Economy, 0 bags

Find the cheapest flights from Tallahassee to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
5:10 pm - 10:33 pmTLH  Tallahassee-MDW Chicago Midway
6h 23m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:15 pm - 11:04 pmMDW  Chicago Midway-TLH Tallahassee
4h 49m1 stop Atlanta Hartsfield-Jackson
$447Delta
Sat, Oct 24 - Wed, Oct 28
Delta Logo
7:16 pm - 10:33 pmTLH  Tallahassee-MDW Chicago Midway
4h 17m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:04 am - 11:09 amMDW  Chicago Midway-TLH Tallahassee
4h 05m1 stop Atlanta Hartsfield-Jackson
$457Delta
Fri, Nov 6 - Sun, Nov 8
Delta Logo
10:18 am - 3:17 pmTLH  Tallahassee-MDW Chicago Midway
5h 59m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:04 am - 11:09 amMDW  Chicago Midway-TLH Tallahassee
4h 05m1 stop Atlanta Hartsfield-Jackson
$457Delta
Thu, Nov 5 - Sun, Nov 8
Delta Logo
5:53 pm - 10:44 pmTLH  Tallahassee-MDW Chicago Midway
5h 51m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:05 am - 11:15 amMDW  Chicago Midway-TLH Tallahassee
4h 10m1 stop Atlanta Hartsfield-Jackson
$457Delta
Wed, Sep 9 - Wed, Sep 16
Delta Logo
7:16 pm - 10:33 pmTLH  Tallahassee-MDW Chicago Midway
4h 17m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:09 pm - 11:04 pmMDW  Chicago Midway-TLH Tallahassee
4h 55m1 stop Atlanta Hartsfield-Jackson
$457Delta
Fri, Nov 6 - Mon, Nov 9
Delta Logo
6:00 pm - 10:36 pmTLH  Tallahassee-MDW Chicago Midway
5h 36m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:05 am - 11:15 amMDW  Chicago Midway-TLH Tallahassee
4h 10m1 stop Atlanta Hartsfield-Jackson
$457Delta
Thu, Sep 3 - Wed, Sep 9
Delta Logo
5:53 pm - 10:44 pmTLH  Tallahassee-MDW Chicago Midway
5h 51m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:05 am - 11:15 amMDW  Chicago Midway-TLH Tallahassee
4h 10m1 stop Atlanta Hartsfield-Jackson
$457Delta
Fri, Oct 2 - Sun, Oct 4

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Delta flights from Tallahassee to Chicago Midway Airport

Our best Delta deals on Tallahassee to Chicago Midway Airport flight tickets
Delta
Sep 19
TLH5:53 pmTallahassee
5h 51m
1 stop
MDW10:44 pmChicago Midway
Sep 22
MDW6:05 amChicago Midway
4h 10m
1 stop
TLH11:15 amTallahassee
$447
Delta
Nov 6
TLH7:16 pmTallahassee
4h 17m
1 stop
MDW10:33 pmChicago Midway
Nov 8
MDW6:04 amChicago Midway
4h 05m
1 stop
TLH11:09 amTallahassee
$457
Delta
Sep 5
TLH5:45 pmTallahassee
5h 51m
1 stop
MDW10:36 pmChicago Midway
Sep 12
MDW4:30 pmChicago Midway
5h 18m
1 stop
TLH10:48 pmTallahassee
$467

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 August 12, 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

Cheapest round-trip

TallahasseeChicago

TLH Tallahassee - MDW Chicago Midway

TLHMDW

Tallahassee

Sat 10/24

5:10 pm-10:33 pm

1 stop6h 23m

Chicago Midway

Wed 10/28

5:15 pm-11:04 pm

1 stop4h 49m

$447
Quickest round-trip

TallahasseeChicago

TLH Tallahassee - MDW Chicago Midway

TLHMDW

Tallahassee

Fri 11/6

7:16 pm-10:33 pm

1 stop4h 17m

Chicago Midway

Sun 11/8

6:04 am-11:09 am

1 stop4h 05m

$457

TallahasseeChicago

TLH Tallahassee - MDW Chicago Midway

TLHMDW

Tallahassee

Thu 11/5

10:18 am-3:17 pm

1 stop5h 59m

Chicago Midway

Sun 11/8

6:04 am-11:09 am

1 stop4h 05m

$457

TallahasseeChicago

TLH Tallahassee - MDW Chicago Midway

TLHMDW

Tallahassee

Wed 9/9

5:53 pm-10:44 pm

1 stop5h 51m

Chicago Midway

Wed 9/16

6:05 am-11:15 am

1 stop4h 10m

$457

TallahasseeChicago

TLH Tallahassee - MDW Chicago Midway

TLHMDW

Tallahassee

Fri 11/6

7:16 pm-10:33 pm

1 stop4h 17m

Chicago Midway

Mon 11/9

5:09 pm-11:04 pm

1 stop4h 55m

$457

TallahasseeChicago

TLH Tallahassee - MDW Chicago Midway

TLHMDW

Tallahassee

Thu 9/3

6:00 pm-10:36 pm

1 stop5h 36m

Chicago Midway

Wed 9/9

6:05 am-11:15 am

1 stop4h 10m

$457

TallahasseeChicago

TLH Tallahassee - MDW Chicago Midway

TLHMDW

Tallahassee

Fri 10/2

5:53 pm-10:44 pm

1 stop5h 51m

Chicago Midway

Sun 10/4

6:05 am-11:15 am

1 stop4h 10m

$457
Cheapest one-way

TallahasseeChicago

TLH Tallahassee - MDW Chicago Midway

TLHMDW

Tallahassee

Thu 10/22

8:25 am-10:58 am

2 stops27h 33m

$168

TallahasseeChicago

TLH Tallahassee - MDW Chicago Midway

TLHMDW

Tallahassee

Tue 9/8

9:38 am-5:51 pm

3 stops33h 13m

$194

TallahasseeChicago

TLH Tallahassee - MDW Chicago Midway

TLHMDW

Tallahassee

Tue 9/8

9:38 am-5:51 pm

2 stops33h 13m

$200

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 17 resultsSorted by cheapest first
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See travel insights to Chicago from

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 35m

Direct flights

None
The fastest flight from Tallahassee to Chicago Midway Airport takes 4h 35m
There are no direct flights from Tallahassee to Chicago Midway Airport. There are no popular flight routes from Tallahassee to Chicago Midway Airport.
Search flight deals

Frequently asked questions about flying from Tallahassee to Chicago Midway Airport

  • 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 35m, 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 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.

Traveling to a place near Chicago?

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