$152+ Cheap flights from Tallahassee (TLH) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
TLH — CHI
Oct 23 — Oct 301
Round-trip
1 adult, Economy
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Find cheap flights from Tallahassee to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Tallahassee to Chicago
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Cheapest flights from Tallahassee to ChicagoExplore the most affordable flight options available from Tallahassee to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 23, 2026.
Explore the most affordable flight options available from Tallahassee to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/228:30 am -
2 stops11h 01m
Mon 10/268:04 am -
1 stop25h 31m
Deal found 9/18![Multiple Airlines logo]()
$288
This Delta deal was found by Cheapflights users on 9/22. 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 11/116:00 am -
1 stop5h 24m
Sat 11/144:13 pm -
1 stop5h 49m
Deal found 9/22![Delta logo]()
$467
This American Airlines deal was found by Cheapflights users on 9/18. 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 12/252:19 pm -
1 stop8h 11m
Wed 12/3012:30 pm -
1 stop6h 25m
Deal found 9/18![American Airlines logo]()
$467
This Delta deal was found by Cheapflights users on 9/21. 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 12/117:03 pm -
1 stop4h 51m
Mon 12/1411:28 am -
1 stop5h 37m
Deal found 9/21![Delta logo]()
$477
This Delta deal was found by Cheapflights users on 9/22. 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 11/53:24 pm -
1 stop6h 14m
Sun 11/85:27 am -
1 stop4h 42m
Deal found 9/22![Delta logo]()
$477
This American Airlines deal was found by Cheapflights users on 9/18. 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 10/167:33 pm -
1 stop6h 05m
Sat 10/246:29 am -
1 stop5h 47m
Deal found 9/18![American Airlines logo]()
$487
This American Airlines deal was found by Cheapflights users on 9/19. 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 10/109:55 am -
1 stop6h 36m
Sat 10/174:45 pm -
1 stop4h 51m
Deal found 9/19![American Airlines logo]()
$497
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1610:15 am -
2 stops33h 16m
Sat 10/248:04 am -
1 stop22h 46m
Deal found 9/18![Multiple Airlines logo]()
$499
This Delta deal was found by Cheapflights users on 9/22. 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 11/57:00 pm -
1 stop4h 33m
Sun 11/86:04 am -
1 stop4h 05m
Deal found 9/22![Delta logo]()
$518
This Kiwi.com deal was found by Cheapflights users on 9/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:30 am -
2 stops11h 01m
Sun 10/188:04 am -
1 stop24h 31m
Deal found 9/22![Multiple Airlines logo]()
$524
This Delta deal was found by Cheapflights users on 9/20. 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 10/97:00 pm -
1 stop5h 57m
Sun 10/115:27 am -
1 stop4h 47m
Deal found 9/20![Delta logo]()
$527
This American Airlines deal was found by Cheapflights users on 9/19. 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 10/227:33 pm -
1 stop6h 05m
Sun 10/256:29 am -
1 stop7h 27m
Deal found 9/19![American Airlines logo]()
$529
Best flights from Tallahassee to ChicagoDiscover carefully curated flight deals from Tallahassee to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 23, 2026.
Discover carefully curated flight deals from Tallahassee to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 23, 2026.
This Delta deal was found by Cheapflights users on 9/21. 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 11/116:00 am -
1 stop5h 24m
Sat 11/144:13 pm -
1 stop5h 49m
Deal found 9/21![Delta logo]()
$467
This American Airlines deal was found by Cheapflights users on 9/22. 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 10/307:33 pm -
1 stop6h 05m
Sun 11/16:41 am -
1 stop5h 36m
Deal found 9/22![American Airlines logo]()
$477
This Delta deal was found by Cheapflights users on 9/22. 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 10/305:10 pm -
1 stop6h 23m
Tue 11/36:04 am -
1 stop4h 10m
Deal found 9/22![Delta logo]()
$467
This Delta deal was found by Cheapflights users on 9/22. 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 10/303:24 pm -
1 stop6h 14m
Tue 11/31:23 pm -
1 stop5h 22m
Deal found 9/22![Delta logo]()
$467
This Delta deal was found by Cheapflights users on 9/21. 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 11/116:00 am -
1 stop7h 20m
Sun 11/155:30 am -
1 stop4h 50m
Deal found 9/21![Delta logo]()
$467
This American Airlines deal was found by Cheapflights users on 9/20. 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 10/146:00 am -
1 stop6h 10m
Sun 10/188:05 am -
1 stop5h 51m
Deal found 9/20![American Airlines logo]()
$588
This Delta deal was found by Cheapflights users on 9/21. 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 12/117:03 pm -
1 stop4h 51m
Mon 12/1411:28 am -
1 stop5h 37m
Deal found 9/21![Delta logo]()
$477
This Delta deal was found by Cheapflights users on 9/18. 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 10/227:00 pm -
1 stop4h 33m
Mon 10/2612:49 pm -
1 stop4h 16m
Deal found 9/18![Delta logo]()
$477
This Delta deal was found by Cheapflights users on 9/20. 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 11/57:00 pm -
1 stop4h 33m
Sun 11/86:04 am -
1 stop4h 05m
Deal found 9/20![Delta logo]()
$477
This Delta deal was found by Cheapflights users on 9/22. 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 11/53:24 pm -
1 stop6h 14m
Sun 11/85:27 am -
1 stop4h 42m
Deal found 9/22![Delta logo]()
$477
This Delta deal was found by Cheapflights users on 9/19. 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 10/223:24 pm -
1 stop6h 14m
Sun 10/255:27 am -
1 stop4h 47m
Deal found 9/19![Delta logo]()
$477
This KAYAK deal was found by Cheapflights users on 9/22. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/278:15 am -
1 stop4h 39m
Fri 10/305:09 pm -
1 stop20h 30m
Deal found 9/22![Delta logo]()
$555
This Delta deal was found by Cheapflights users on 9/19. 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 10/225:10 pm -
1 stop6h 23m
Sun 10/2510:59 am -
1 stop6h 06m
Deal found 9/19![Delta logo]()
$672
This Delta deal was found by Cheapflights users on 9/18. 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 11/310:21 am -
1 stop5h 56m
Thu 11/511:38 am -
1 stop3h 47m
Deal found 9/18![Delta logo]()
$685
This Delta deal was found by Cheapflights users on 9/22. 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 11/106:00 am -
1 stop5h 24m
Wed 11/111:05 pm -
1 stop5h 41m
Deal found 9/22![Delta logo]()
$685
This Delta deal was found by Cheapflights users on 9/21. 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 10/105:10 pm -
1 stop6h 23m
Mon 10/125:09 pm -
1 stop4h 55m
Deal found 9/21![Delta logo]()
$705
This Delta deal was found by Cheapflights users on 9/19. 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.
Sun 10/48:38 am -
1 stop6h 51m
Thu 10/85:27 am -
1 stop4h 47m
Deal found 9/19![Delta logo]()
$805
This Delta deal was found by Cheapflights users on 9/18. 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 1/1310:20 am -
1 stop4h 00m
Mon 1/189:50 am -
2 stops7h 54m
Deal found 9/18![Delta logo]()
$835
This Delta deal was found by Cheapflights users on 9/20. 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 12/253:00 pm -
1 stop5h 59m
Wed 12/301:26 pm -
2 stops9h 26m
Deal found 9/20![Delta logo]()
$845
Last-minute flights from Tallahassee to ChicagoDiscover last-minute flight deals from Tallahassee to Chicago. Data last updated September 23, 2026 and is based on user searches.
Discover last-minute flight deals from Tallahassee to Chicago. Data last updated September 23, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/22. 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 10/75:10 pm -
1 stop6h 23m
Sun 10/116:04 am -
1 stop4h 10m
Deal found 9/22![Delta logo]()
$550
This Delta deal was found by Cheapflights users on 9/20. 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 10/97:00 pm -
1 stop5h 57m
Sun 10/115:27 am -
1 stop4h 47m
Deal found 9/20![Delta logo]()
$527
This American Airlines deal was found by Cheapflights users on 9/19. 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 10/109:55 am -
1 stop6h 36m
Sat 10/174:45 pm -
1 stop4h 51m
Deal found 9/19![American Airlines logo]()
$497
This Kiwi.com deal was found by Cheapflights users on 9/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:30 am -
2 stops11h 01m
Sun 10/188:04 am -
1 stop24h 31m
Deal found 9/22![Multiple Airlines logo]()
$524
This American Airlines deal was found by Cheapflights users on 9/18. 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 10/167:33 pm -
1 stop6h 05m
Sat 10/246:29 am -
1 stop5h 47m
Deal found 9/18![American Airlines logo]()
$487
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1610:15 am -
2 stops33h 16m
Sat 10/248:04 am -
1 stop22h 46m
Deal found 9/18![Multiple Airlines logo]()
$499
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/228:30 am -
2 stops11h 01m
Mon 10/268:04 am -
1 stop25h 31m
Deal found 9/18![Multiple Airlines logo]()
$288
This Delta deal was found by Cheapflights users on 9/18. 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 10/227:00 pm -
1 stop4h 33m
Mon 10/2612:49 pm -
1 stop4h 16m
Deal found 9/18![Delta logo]()
$477
This Delta deal was found by Cheapflights users on 9/20. 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 10/223:24 pm -
1 stop6h 14m
Sun 10/255:27 am -
1 stop4h 47m
Deal found 9/20![Delta logo]()
$477
This American Airlines deal was found by Cheapflights users on 9/19. 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 10/227:33 pm -
1 stop6h 05m
Sun 10/256:29 am -
1 stop7h 27m
Deal found 9/19![American Airlines logo]()
$529
This Delta deal was found by Cheapflights users on 9/22. 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 10/303:24 pm -
1 stop6h 14m
Tue 11/31:23 pm -
1 stop5h 22m
Deal found 9/22![Delta logo]()
$467
This Delta deal was found by Cheapflights users on 9/23. 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 10/3110:21 am -
1 stop5h 56m
Tue 11/36:04 am -
1 stop4h 10m
Deal found 9/23![Delta logo]()
$467
One-way flights from Tallahassee to ChicagoSearch for one-way flight options from Tallahassee to Chicago. Find affordable one-way fares based on user searches. Data last updated September 23, 2026.
Search for one-way flight options from Tallahassee to Chicago. Find affordable one-way fares based on user searches. Data last updated September 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/273:57 pm -
2 stops21h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Multiple Airlines logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 9/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/38:30 am -
2 stops13h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Multiple Airlines logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 9/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/228:30 am -
2 stops10h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Multiple Airlines logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 9/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/228:30 am -
2 stops11h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Multiple Airlines logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 9/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:30 am -
2 stops10h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Multiple Airlines logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/188:30 am -
3 stops54h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Multiple Airlines logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 9/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:30 am -
2 stops11h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Multiple Airlines logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/188:30 am -
3 stops55h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Multiple Airlines logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 9/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/31:12 pm -
1 stop24h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Multiple Airlines logo]()
$224
This Delta deal was found by Cheapflights users on 9/22. 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 10/225:10 pm -
1 stop6h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Delta logo]()
$343
This Delta deal was found by Cheapflights users on 9/21. 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 10/155:10 pm -
1 stop6h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Delta logo]()
$373
Find flight deals from Tallahassee to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Tallahassee (TLH) to Chicago (CHI). 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 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $288 (Kiwi.com) |
One-way from | $152 (Kiwi.com) |
Popular in | October |
Cheapest in | May |
Average price | $557 |
Cheapflights 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, Cheapflights users made 7,457,451 searches. Data last updated September 23, 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
Cheapest round-trip
TallahasseeChicago
TLH Tallahassee - ORD Chicago O'Hare Intl
TLHORD
Tallahassee
Sun 10/18
8:30 am-2:25 pm
3 stops54h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$179
TallahasseeChicago
TLH Tallahassee - ORD Chicago O'Hare Intl
TLHORD
Tallahassee
Thu 12/3
1:12 pm-12:50 pm
1 stop24h 38m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$224
TallahasseeChicago
TLH Tallahassee - ORD Chicago O'Hare Intl
TLHORD
Tallahassee
Thu 10/15
1:12 pm-3:30 pm
1 stop27h 18m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$286
TallahasseeChicago
TLH Tallahassee - MDW Chicago Midway
TLHMDW
Tallahassee
Thu 12/3
8:00 am-12:04 pm
1 stop5h 04m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$343
TallahasseeChicago
TLH Tallahassee - ORD Chicago O'Hare Intl
TLHORD
Tallahassee
Mon 11/23
6:10 am-11:06 am
1 stop5h 56m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$343
TallahasseeChicago
TLH Tallahassee - MDW Chicago Midway
TLHMDW
Tallahassee
Thu 10/22
5:10 pm-10:33 pm
1 stop6h 23m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$343
TallahasseeChicago
TLH Tallahassee - ORD Chicago O'Hare Intl
TLHORD
Tallahassee
Wed 11/25
7:45 pm-11:59 pm
1 stop5h 14m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$343
TallahasseeChicago
TLH Tallahassee - MDW Chicago Midway
TLHMDW
Tallahassee
Fri 11/27
5:09 pm-10:54 pm
1 stop6h 45m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$343
Quickest round-trip
TallahasseeChicago
TLH Tallahassee - ORD Chicago O'Hare Intl
TLHORD
Tallahassee
Tue 11/24
6:00 am-9:22 am
1 stop4h 22m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$343
TallahasseeChicago
TLH Tallahassee - MDW Chicago Midway
TLHMDW
Tallahassee
Thu 10/15
8:30 am-11:43 pm
3 stops16h 13m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$346
Showing 1-10 of 34 resultsSorted by cheapest first
Compare providers for flights from Tallahassee to Chicago
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 Tallahassee to Chicago in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Tallahassee-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Tallahassee-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Tallahassee-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Tallahassee-Chicago 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 Tallahassee-Chicago 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 Tallahassee to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Tallahassee with our price prediction graph.
TLH-CHI
TLH-ORD
TLH-MDW
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 Tallahassee to Chicago
TLH-CHI
TLH-ORD
TLH-MDW
What is the cheapest month to book a flight from Tallahassee to Chicago?
Currently, May is the cheapest month in which you can book a flight from Tallahassee to Chicago (average of $406). Flying from Tallahassee to Chicago in October is currently the most expensive (average of $683). 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 Tallahassee to Chicago?
Airfare is below average for this route at the moment.
Tallahassee to Chicago flights typically cost between $560 and $678 in October.The cheapest round-trip price found within the last 5 days was $288 on Multiple Airlines (Oct 22-Oct 26).
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated September 23, 2026.
See what other customers who have flown with Delta and American Airlines from Tallahassee to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Comfort
7.8
Overall
7.8
Food
7.2
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Boarding
8.1
Comfort
7.8
Overall
7.8
Food
7.2
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Boarding
8.1
Comfort
7.8
Overall
7.8
Food
7.2
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Related info for your journey
Find useful and relevant information for your journey from Tallahassee to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 23, 2026.
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Tallahassee and Chicago flights
Browse other Tallahassee and Chicago flight options. Last updated on September 23, 2026.
Other flights from Tallahassee
Browse through other flights departing from Tallahassee. Flights are based on user searches made on Cheapflights and were last updated on September 23, 2026.
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Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Tallahassee to Chicago
Discover the top 2 airlines that operate flights from Tallahassee to Chicago. 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 7,457,451 searches. Data last updated September 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$158 | Average$446 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$398 | Average$483 | FlexibilityNo cancel fee | On-time71% |