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Cheap flights from Tallahassee to Chicago from $111

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 8/25. 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
5:41 pm - 10:17 pm
TLH
-
MDW
5h 36m
1 stop
Delta Logo
6:00 am - 11:24 am
MDW
-
TLH
4h 24m
1 stop
$437Delta
Sat, Jun 13 - Tue, Jun 16
American Airlines Logo
5:10 pm - 11:30 pm
TLH
-
ORD
7h 20m
1 stop
American Airlines Logo
5:59 am - 1:09 pm
ORD
-
TLH
6h 10m
1 stop
$437American Airlines
Sat, Jun 13 - Tue, Jun 16
American Airlines Logo
1:40 pm - 9:00 pm
TLH
-
ORD
8h 20m
1 stop
American Airlines Logo
5:59 am - 1:09 pm
ORD
-
TLH
6h 10m
1 stop
$444American Airlines
Sat, Jun 13 - Wed, Jun 17
Delta Logo
5:41 pm - 10:17 pm
TLH
-
MDW
5h 36m
1 stop
Delta Logo
11:05 am - 6:14 pm
MDW
-
TLH
6h 09m
1 stop
$447Delta
Sat, Jun 13 - Wed, Jun 17
Delta Logo
5:23 pm - 11:03 pm
TLH
-
ORD
6h 40m
1 stop
Delta Logo
8:08 am - 2:41 pm
ORD
-
TLH
5h 33m
1 stop
$447Delta
Sat, Jun 6 - Fri, Jun 12
American Airlines Logo
7:00 am - 11:34 am
TLH
-
ORD
5h 34m
1 stop
American Airlines Logo
4:45 pm - 11:38 pm
ORD
-
TLH
5h 53m
1 stop
$454American Airlines
Sat, Jun 6 - Fri, Jun 12
Delta Logo
5:23 pm - 9:09 pm
TLH
-
MDW
4h 46m
1 stop
Delta Logo
11:05 am - 4:47 pm
MDW
-
TLH
4h 42m
1 stop
$457Delta
Sat, Jun 6 - Fri, Jun 12
American Airlines Logo
7:48 pm - 11:58 pm
TLH
-
ORD
5h 10m
1 stop
American Airlines Logo
5:00 am - 1:09 pm
ORD
-
TLH
7h 09m
1 stop
$457American Airlines
Thu, Jun 4 - Thu, Jun 11
Delta Logo
7:01 pm - 10:17 pm
TLH
-
MDW
4h 16m
1 stop
Delta Logo
5:11 pm - 10:53 pm
MDW
-
TLH
4h 42m
1 stop
$483Delta
Thu, Jun 11 - Mon, Jun 15
Delta Logo
7:01 pm - 11:59 pm
TLH
-
ORD
5h 58m
1 stop
Delta Logo
5:30 am - 11:24 am
ORD
-
TLH
4h 54m
1 stop
$483Delta
Thu, Jun 11 - Mon, Jun 15

American Airlines flights from Tallahassee to Chicago

Our best American Airlines deals on Tallahassee to Chicago flight tickets
American Airlines
Jun 13
TLH1:40 pmTallahassee
8h 20m
1 stop
ORD9:00 pmChicago O'Hare Intl
Jun 17
ORD5:59 amChicago O'Hare Intl
6h 10m
1 stop
TLH1:09 pmTallahassee
$444
American Airlines
Jun 6
TLH7:00 amTallahassee
5h 34m
1 stop
ORD11:34 amChicago O'Hare Intl
Jun 12
ORD4:45 pmChicago O'Hare Intl
5h 53m
1 stop
TLH11:38 pmTallahassee
$454
American Airlines
Jun 4
TLH7:48 pmTallahassee
5h 10m
1 stop
ORD11:58 pmChicago O'Hare Intl
Jun 11
ORD5:00 amChicago O'Hare Intl
7h 09m
1 stop
TLH1:09 pmTallahassee
$457

Delta flights from Tallahassee to Chicago

Our best Delta deals on Tallahassee to Chicago flight tickets
Delta
Sep 3
TLH5:35 amTallahassee
3h 59m
1 stop
ORD8:34 amChicago O'Hare Intl
Sep 9
ORD7:10 amChicago O'Hare Intl
6h 32m
1 stop
TLH2:42 pmTallahassee
$437
Delta
Nov 5
TLH7:15 pmTallahassee
5h 35m
1 stop
ORD11:50 pmChicago O'Hare Intl
Nov 8
ORD5:30 amChicago O'Hare Intl
5h 35m
1 stop
TLH12:05 pmTallahassee
$447
Delta
Jun 6
TLH5:23 pmTallahassee
4h 46m
1 stop
MDW9:09 pmChicago Midway
Jun 12
MDW11:05 amChicago Midway
4h 42m
1 stop
TLH4:47 pmTallahassee
$457

momondo Fare Finder

 
Customize your flight search to find flights from Tallahassee to Chicago 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 May 11, 2026.
Use the filters below to find and compare flights from Tallahassee to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Sat 6/13

5:41 pm-10:17 pm

1 stop5h 36m

Chicago Midway

Tue 6/16

6:00 am-11:24 am

1 stop4h 24m

$437

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Sat 6/13

5:10 pm-11:30 pm

1 stop7h 20m

Chicago O'Hare Intl

Tue 6/16

5:59 am-1:09 pm

1 stop6h 10m

$437

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Sat 6/13

1:40 pm-9:00 pm

1 stop8h 20m

Chicago O'Hare Intl

Wed 6/17

5:59 am-1:09 pm

1 stop6h 10m

$444

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Sat 6/13

5:41 pm-10:17 pm

1 stop5h 36m

Chicago Midway

Wed 6/17

11:05 am-6:14 pm

1 stop6h 09m

$447

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Sat 6/6

5:23 pm-11:03 pm

1 stop6h 40m

Chicago O'Hare Intl

Fri 6/12

8:08 am-2:41 pm

1 stop5h 33m

$447

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Sat 6/6

7:00 am-11:34 am

1 stop5h 34m

Chicago O'Hare Intl

Fri 6/12

4:45 pm-11:38 pm

1 stop5h 53m

$454

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Sat 6/6

5:23 pm-9:09 pm

1 stop4h 46m

Chicago Midway

Fri 6/12

11:05 am-4:47 pm

1 stop4h 42m

$457

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Thu 6/4

7:48 pm-11:58 pm

1 stop5h 10m

Chicago O'Hare Intl

Thu 6/11

5:00 am-1:09 pm

1 stop7h 09m

$457
Quickest round-trip

TallahasseeChicago

TLH - MDW

TLHMDW

Tallahassee

Thu 6/11

7:01 pm-10:17 pm

1 stop4h 16m

Chicago Midway

Mon 6/15

5:11 pm-10:53 pm

1 stop4h 42m

$483

TallahasseeChicago

TLH - ORD

TLHORD

Tallahassee

Thu 6/11

7:01 pm-11:59 pm

1 stop5h 58m

Chicago O'Hare Intl

Mon 6/15

5:30 am-11:24 am

1 stop4h 54m

$483

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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

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 typical price of a round-trip flight between Tallahassee and Chicago?

What is the cheapest month to fly to Chicago?

The month of November is, on average, the cheapest month to fly to Chicago from Tallahassee, with most prices found around $66. If you’re not able to fly to Chicago in November, then December is your next best option. Flight prices from Tallahassee to Chicago during December average around $158.

When to book flights from Tallahassee to Chicago

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

Cheap Tallahassee to Chicago (TLH to CHI) flight deals and tips

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

Fastest flight time

3h 59m

Direct flights

None
The fastest flight from Tallahassee to Chicago takes 3h 59m
There are no direct flights from Tallahassee to Chicago. There are no popular flight routes from Tallahassee to Chicago.
Search flight deals

Frequently asked questions about flying from Tallahassee to Chicago

  • How far is Tallahassee to Chicago by plane?

    The straight-line distance from Tallahassee to Chicago is 811.3 mi. By plane, this route typically takes 3h 59m.

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

    Prices for flights from Tallahassee Airport to Chicago were last updated today.

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Tallahassee Airport to Chicago.

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

    The necessary travel and health documents for your Chicago 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.

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

Best airlines flying from Tallahassee to Chicago

Compare and see reviews for airlines that fly from Tallahassee to Chicago with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $158Free CancellationRating
7.9
8,451 reviews
Search Delta flights
American AirlinesPriceFrom $316Free CancellationRating
7.1
11,667 reviews
Search American Airlines flights

Traveling to a place near Chicago?

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

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Tallahassee.

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

Yes. All flights to Chicago from Tallahassee on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Tallahassee.

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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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport