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Tallahassee

$159+ Cheap flights from Chicago (CHI) to Tallahassee (TLH)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — TLH
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Chicago to Tallahassee

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Tallahassee (TLH). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 16, 2025.

Round-trip from

$317
(American Airlines)

One-way from

$159
(American Airlines)

Popular in

December

Cheapest in

August

Average price

$492
From Chicago (CHI) to Tallahassee
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One-way flight from Chicago (CHI) to Tallahassee
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Highest demand for flights based on searches. 15% potential increase in price ($92 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($25 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Chicago to Tallahassee

Cheapest flights from Chicago to Tallahassee
Explore the most affordable flight options available from Chicago to Tallahassee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/117:10 amORD - TLH
1 stop4h 57mAmerican Airlines
Sat 10/256:52 pmTLH - ORD
1 stop5h 50mAmerican Airlines
Deal found 9/14$317
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/84:23 pmMDW - TLH
1 stop5h 13mDelta
Mon 11/107:08 pmTLH - MDW
1 stop5h 24mDelta
Deal found 9/16$362
This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/228:06 amORD - TLH
1 stop6h 49mAmerican Airlines
Mon 10/277:33 pmTLH - ORD
1 stop5h 20mAmerican Airlines
Deal found 9/14$362
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/114:23 pmMDW - TLH
1 stop5h 13mDelta
Tue 10/145:05 pmTLH - MDW
1 stop6h 09mDelta
Deal found 9/14$398
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/115:20 amORD - TLH
1 stop4h 13mDelta
Mon 10/137:16 pmTLH - ORD
1 stop5h 42mDelta
Deal found 9/14$403
This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/241:51 pmORD - TLH
1 stop5h 19mAmerican Airlines
Mon 10/276:04 pmTLH - ORD
1 stop6h 49mAmerican Airlines
Deal found 9/14$407
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/185:20 amORD - TLH
1 stop4h 13mDelta
Sat 10/185:05 pmTLH - ORD
1 stop7h 53mDelta
Deal found 9/15$430
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/910:35 amMDW - TLH
1 stop8h 35mDelta
Tue 10/145:05 pmTLH - MDW
1 stop6h 09mDelta
Deal found 9/14$431
This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/96:00 amORD - TLH
1 stop8h 09mAmerican Airlines
Tue 10/144:34 pmTLH - ORD
1 stop5h 49mAmerican Airlines
Deal found 9/14$432
This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/119:10 amORD - TLH
1 stop4h 59mAmerican Airlines
Tue 10/149:56 amTLH - ORD
2 stops8h 56mAmerican Airlines
Deal found 9/14$433
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1110:35 amMDW - TLH
1 stop4h 45mDelta
Mon 10/137:16 pmTLH - MDW
1 stop3h 58mDelta
Deal found 9/14$443
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/265:34 pmMDW - TLH
1 stop3h 44mDelta
Sat 11/295:35 amTLH - MDW
1 stop5h 17mDelta
Deal found 9/15$453

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago 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, Cheapflights users made 2,558,603 searches. Data last updated September 16, 2025.
Use the filters below to find and compare flights from Chicago to Tallahassee that are best for you.

Fly from

Chicago

Fly to

Tallahassee

Route

Depart

Return

Price

ChicagoTallahassee

ORD - TLH

ORDTLH

Chicago O'Hare Intl

Wed 2/18

9:30 am-4:36 pm

1 stop6h 06m

Tallahassee

Sat 2/21

10:20 am-1:23 pm

1 stop4h 03m

$317

ChicagoTallahassee

ORD - TLH

ORDTLH

Chicago O'Hare Intl

Sat 10/11

1:14 pm-10:26 pm

1 stop8h 12m

Tallahassee

Tue 10/14

6:43 pm-10:54 pm

1 stop5h 11m

$317

ChicagoTallahassee

ORD - TLH

ORDTLH

Chicago O'Hare Intl

Wed 2/18

9:30 am-4:36 pm

1 stop6h 06m

Tallahassee

Wed 2/25

5:35 am-10:06 am

1 stop5h 31m

$317

ChicagoTallahassee

ORD - TLH

ORDTLH

Chicago O'Hare Intl

Tue 2/17

9:30 am-2:46 pm

1 stop4h 16m

Tallahassee

Fri 2/20

7:15 pm-11:54 pm

1 stop5h 39m

$317

ChicagoTallahassee

ORD - TLH

ORDTLH

Chicago O'Hare Intl

Thu 10/30

8:06 am-3:51 pm

1 stop6h 45m

Tallahassee

Sat 11/1

12:10 pm-4:05 pm

1 stop4h 55m

$362

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

Sat 11/8

4:23 pm-10:36 pm

1 stop5h 13m

Tallahassee

Mon 11/10

7:08 pm-11:32 pm

1 stop5h 24m

$362

ChicagoTallahassee

ORD - TLH

ORDTLH

Chicago O'Hare Intl

Thu 12/4

5:32 am-11:41 am

1 stop5h 09m

Tallahassee

Sat 12/6

5:07 pm-10:44 pm

1 stop6h 37m

$362

ChicagoTallahassee

ORD - TLH

ORDTLH

Chicago O'Hare Intl

Wed 2/18

7:10 am-2:46 pm

1 stop6h 36m

Tallahassee

Sun 2/22

7:15 pm-11:54 pm

1 stop5h 39m

$362

ChicagoTallahassee

ORD - TLH

ORDTLH

Chicago O'Hare Intl

Sat 11/8

1:26 pm-6:31 pm

1 stop4h 05m

Tallahassee

Mon 11/10

2:50 pm-6:47 pm

1 stop4h 57m

$362

ChicagoTallahassee

ORD - TLH

ORDTLH

Chicago O'Hare Intl

Mon 2/16

5:50 am-12:09 pm

1 stop5h 19m

Tallahassee

Sat 2/21

5:35 am-8:39 am

1 stop4h 04m

$362

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 38 results
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Best time to book a flight from Chicago to Tallahassee

Have a flexible travel schedule? Discover the best time to fly to Tallahassee from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Tallahassee

What is the cheapest month to book a flight from Chicago to Tallahassee?

Currently, August is the cheapest month in which you can book a flight from Chicago to Tallahassee (average of $404). Flying from Chicago to Tallahassee in December is currently the most expensive (average of $551). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Tallahassee

Get insights into the airlines that provide service to Tallahassee. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Tallahassee. Reviews last updated September 16, 2025.
Read reviews from past customers who have flown Delta and American Airlines from Chicago to Tallahassee. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,957 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Entertainment

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Delta
8.0
Very good
7,957 reviews
Delta
8.0
Very good
7,957 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Entertainment

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,957 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Entertainment

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Tallahassee. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Tallahassee from Chicago?

    Tallahassee (TLH) is the airport you will fly into if you book a flight from Chicago to Tallahassee. You should not have trouble finding flights to Tallahassee from Chicago; the airport handles an average of 0 inbound flights from Chicago per day. You should also have plenty of airline options to choose from since 2 airlines have flights to the Tallahassee airport from Chicago. It is only a 5.0 mi journey from Tallahassee (TLH) to Tallahassee’s city center.

  • How long is the flight from Chicago to Tallahassee?

    For as low as $317, Delta can have you in Tallahassee from Chicago in 4h 17m. Chicago and Tallahassee are separated by a distance of 824 mi.

  • What are the cheapest airlines flying from Chicago to Tallahassee round-trip?

    Currently priced at $296, Delta will fly you from Chicago to Tallahassee and back. In addition to Delta, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on American Airlines for as low as $356. Delta is currently priced 43% below the average price you’ll pay for this route.

  • Can I find deals for flights from Chicago to Tallahassee that include hotel bookings?

    Yes. In addition to deals on Chicago to Tallahassee flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Tallahassee?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Tallahassee.

  • Can I find deals for business class flights from Chicago to Tallahassee?

    Yes. Cheapflights offers flight deals from Chicago to Tallahassee by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Tallahassee?

    Currently, August is the cheapest month in which you can book a flight from Chicago to Tallahassee (average of $404). Flying from Chicago to Tallahassee in December is currently the most expensive (average of $551). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Tallahassee?

Book flights to Tallahassee if you plan to visit one of these locations
Thomasville
Midway

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Alternative routes for Chicago to Tallahassee

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Top 2 airlines flying from Chicago to Tallahassee

Discover the top 2 airlines that operate flights from Chicago to Tallahassee. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$296Average$607FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$356Average$531FlexibilityNo cancel feeOn-time71%

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