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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 4/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — TLH
Mar 14 — Mar 211
Sat 3/14
Sat 3/21
1 adult, Economy
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Cheap 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 February 12, 2026.

This Delta deal was found by Cheapflights users on 2/10. 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 5/164:30 pm
MDW
-
TLH
1 stop5h 22m
Delta
Tue 5/195:23 pm
TLH
-
MDW
1 stop4h 46m
Delta
Deal found 2/10$317
This American Airlines deal was found by Cheapflights users on 2/9. 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.
Tue 3/102:57 pm
ORD
-
TLH
1 stop8h 12m
American Airlines
Tue 3/176:10 am
TLH
-
ORD
1 stop6h 55m
American Airlines
Deal found 2/9$317
This Delta deal was found by Cheapflights users on 2/9. 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.
Tue 3/1012:47 pm
MDW
-
TLH
1 stop5h 45m
Delta
Tue 3/175:36 am
TLH
-
MDW
1 stop5h 20m
Delta
Deal found 2/9$327
This American Airlines deal was found by Cheapflights users on 2/10. 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 3/1110:28 am
ORD
-
TLH
1 stop4h 48m
American Airlines
Sun 3/157:55 pm
TLH
-
ORD
1 stop5h 21m
American Airlines
Deal found 2/10$362
This Delta deal was found by Cheapflights users on 2/10. 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.
Tue 3/319:40 am
ORD
-
TLH
1 stop5h 47m
Delta
Mon 4/67:09 pm
TLH
-
ORD
1 stop5h 45m
Delta
Deal found 2/10$367
This Delta deal was found by Cheapflights users on 2/10. 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 5/25:10 am
ORD
-
TLH
1 stop6h 01m
Delta
Mon 5/47:06 pm
TLH
-
ORD
1 stop5h 53m
Delta
Deal found 2/10$372
This American Airlines deal was found by Cheapflights users on 2/9. 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.
Tue 3/316:10 am
ORD
-
TLH
1 stop6h 26m
American Airlines
Mon 4/67:55 pm
TLH
-
ORD
1 stop5h 11m
American Airlines
Deal found 2/9$398
This Delta deal was found by Cheapflights users on 2/8. 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.
Tue 2/2412:45 pm
MDW
-
TLH
1 stop5h 49m
Delta
Tue 3/35:30 am
TLH
-
MDW
1 stop5h 24m
Delta
Deal found 2/8$402
This Delta deal was found by Cheapflights users on 2/8. 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.
Tue 2/2411:18 am
ORD
-
TLH
1 stop4h 17m
Delta
Tue 3/31:28 pm
TLH
-
ORD
1 stop6h 51m
Delta
Deal found 2/8$402
This Delta deal was found by Cheapflights users on 2/12. 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 3/127:10 am
ORD
-
TLH
1 stop6h 55m
Delta
Mon 3/167:09 pm
TLH
-
ORD
1 stop5h 45m
Delta
Deal found 2/12$407
This Delta deal was found by Cheapflights users on 2/11. 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.
Fri 4/310:45 am
MDW
-
TLH
1 stop4h 42m
Delta
Sun 4/55:36 am
TLH
-
MDW
1 stop5h 20m
Delta
Deal found 2/11$417
This American Airlines deal was found by Cheapflights users on 2/9. 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 3/127:12 am
ORD
-
TLH
1 stop6h 48m
American Airlines
Sun 3/157:55 pm
TLH
-
ORD
1 stop5h 21m
American Airlines
Deal found 2/9$443

Find 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 February 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$317
(Delta)

One-way from

$159
(American Airlines)

Popular in

July

Cheapest in

August

Average price

$447
Provider with most accurate pricing for Chicago (CHI)-Tallahassee flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Tallahassee flights.
Search Deals
From Chicago (CHI) to Tallahassee
Search Deals
One-way flight from Chicago (CHI) to Tallahassee
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($10 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 February 12, 2026.
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

MDW - TLH

MDWTLH

Chicago Midway

Sat 5/16

4:30 pm-10:52 pm

1 stop5h 22m

Tallahassee

Tue 5/19

5:23 pm-9:09 pm

1 stop4h 46m

$317

ChicagoTallahassee

ORD - TLH

ORDTLH

Chicago O'Hare Intl

Wed 3/11

1:39 pm-7:30 pm

1 stop4h 51m

Tallahassee

Wed 3/18

7:55 pm-12:06 am

1 stop5h 11m

$317

ChicagoTallahassee

ORD - TLH

ORDTLH

Chicago O'Hare Intl

Wed 3/11

11:10 am-4:27 pm

1 stop4h 17m

Tallahassee

Wed 3/18

5:36 am-8:30 am

1 stop3h 54m

$317

ChicagoTallahassee

ORD - TLH

ORDTLH

Chicago O'Hare Intl

Wed 3/18

4:04 pm-11:04 pm

1 stop6h 00m

Tallahassee

Mon 3/23

7:55 pm-12:06 am

1 stop5h 11m

$362

ChicagoTallahassee

ORD - TLH

ORDTLH

Chicago O'Hare Intl

Sat 5/2

5:10 am-12:11 pm

1 stop6h 01m

Tallahassee

Mon 5/4

7:06 pm-11:59 pm

1 stop5h 53m

$362

ChicagoTallahassee

ORD - TLH

ORDTLH

Chicago O'Hare Intl

Wed 3/11

1:39 pm-7:30 pm

1 stop4h 51m

Tallahassee

Sun 3/15

7:55 pm-12:16 am

1 stop5h 21m

$362

ChicagoTallahassee

ORD - TLH

ORDTLH

Chicago O'Hare Intl

Tue 3/31

9:40 am-4:27 pm

1 stop5h 47m

Tallahassee

Mon 4/6

7:09 pm-11:54 pm

1 stop5h 45m

$367

ChicagoTallahassee

ORD - TLH

ORDTLH

Chicago O'Hare Intl

Sat 4/18

7:14 am-12:11 pm

1 stop3h 57m

Tallahassee

Sun 4/19

3:46 pm-8:16 pm

1 stop5h 30m

$367

ChicagoTallahassee

ORD - TLH

ORDTLH

Chicago O'Hare Intl

Wed 4/1

11:10 am-4:27 pm

1 stop4h 17m

Tallahassee

Sun 4/5

5:36 am-8:30 am

1 stop3h 54m

$367

ChicagoTallahassee

MDW - TLH

MDWTLH

Chicago Midway

Tue 2/24

12:45 pm-7:34 pm

1 stop5h 49m

Tallahassee

Tue 3/3

5:30 am-9:54 am

1 stop5h 24m

$402

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/10

Showing 1-10 of 29 results
1
2
3

Compare providers for flights from Chicago to Tallahassee

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Tallahassee in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Tallahassee flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Tallahassee flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Tallahassee flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Tallahassee flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Tallahassee flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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, February is the cheapest month in which you can book a flight from Chicago to Tallahassee (average of $161). Flying from Chicago to Tallahassee in December is currently the most expensive (average of $254). 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.

How much does it cost to fly round-trip from Chicago to Tallahassee?

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 February 12, 2026.
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
7.9
Good
8,183 reviews

Comfort

7.9

Food

7.2

Entertainment

7.8

Crew

8.5

Boarding

8.1

Overall

7.9

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
7.9
Good
8,183 reviews
Delta
7.9
Good
8,183 reviews

Comfort

7.9

Food

7.2

Entertainment

7.8

Crew

8.5

Boarding

8.1

Overall

7.9

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
11,272 reviews
Delta
7.9
Good
8,183 reviews

Comfort

7.9

Food

7.2

Entertainment

7.8

Crew

8.5

Boarding

8.1

Overall

7.9

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 51m. Chicago and Tallahassee are separated by a distance of 824 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 38% 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, February is the cheapest month in which you can book a flight from Chicago to Tallahassee (average of $161). Flying from Chicago to Tallahassee in December is currently the most expensive (average of $254). 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

See prices for flight routes from nearby airports that may be better suited for you.
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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 February 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$296Average$596FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$356Average$531FlexibilityNo cancel feeOn-time71%

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