$151+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
TLH — CHI
Nov 22 — Nov 291
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 October 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 October 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/18. 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 11/128:20 am -
2 stops11h 25m
Sat 11/147:55 am -
1 stop22h 45m
Deal found 10/18![Multiple Airlines logo]()
$360
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/311:15 am -
2 stops32h 15m
Sat 11/77:55 am -
1 stop22h 45m
Deal found 10/19![Multiple Airlines logo]()
$381
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 11/269:15 am -
1 stop15h 19m
Wed 12/23:55 pm -
2 stops19h 37m
Deal found 10/22![Multiple Airlines logo]()
$385
This American Airlines deal was found by Cheapflights users on 10/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/252:19 pm -
1 stop6h 59m
Wed 12/304:40 pm -
1 stop6h 55m
Deal found 10/21![American Airlines logo]()
$487
This American Airlines deal was found by Cheapflights users on 10/22. 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.
Sun 11/226:21 pm -
1 stop7h 26m
Tue 12/16:41 am -
1 stop7h 18m
Deal found 10/22![American Airlines logo]()
$488
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/151:02 pm -
1 stop27h 35m
Fri 11/202:52 pm -
2 stops39h 48m
Deal found 10/21![Multiple Airlines logo]()
$491
This Delta deal was found by Cheapflights users on 10/19. 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 12/35:10 pm -
1 stop6h 44m
Thu 12/106:00 am -
1 stop4h 24m
Deal found 10/19![Delta logo]()
$497
This Delta deal was found by Cheapflights users on 10/21. 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 12/105:10 pm -
1 stop4h 43m
Thu 12/247:25 am -
1 stop3h 53m
Deal found 10/21![Delta logo]()
$497
This Delta deal was found by Cheapflights users on 10/17. 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 11/125:10 pm -
1 stop6h 44m
Mon 11/165:13 pm -
1 stop4h 49m
Deal found 10/17![Delta logo]()
$507
This American Airlines deal was found by Cheapflights users on 10/20. 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.
Sat 11/146:23 pm -
1 stop6h 33m
Fri 11/2011:44 am -
1 stop4h 28m
Deal found 10/20![American Airlines logo]()
$507
This Delta deal was found by Cheapflights users on 10/18. 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 11/118:06 am -
1 stop4h 53m
Sat 11/1411:27 am -
1 stop3h 57m
Deal found 10/18![Delta logo]()
$517
This Delta deal was found by Cheapflights users on 10/18. 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 11/116:00 am -
1 stop7h 20m
Sun 11/155:30 am -
1 stop4h 50m
Deal found 10/18![Delta logo]()
$517
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 October 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 October 23, 2026.
This American Airlines deal was found by Cheapflights users on 10/19. 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.
Fri 12/252:19 pm -
1 stop6h 59m
Wed 12/304:40 pm -
1 stop6h 55m
Deal found 10/19![American Airlines logo]()
$487
This Delta deal was found by Cheapflights users on 10/21. 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.
Sun 11/226:00 am -
1 stop4h 25m
Tue 12/110:36 am -
1 stop4h 49m
Deal found 10/21![Delta logo]()
$487
This Kiwi.com deal was found by Cheapflights users on 10/22. 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.
Wed 11/251:12 pm -
1 stop11h 22m
Sun 11/295:12 pm -
2 stops45h 05m
Deal found 10/22![Multiple Airlines logo]()
$724
This Delta deal was found by Cheapflights users on 10/17. 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 11/125:10 pm -
1 stop6h 44m
Mon 11/165:13 pm -
1 stop4h 49m
Deal found 10/17![Delta logo]()
$507
This Delta deal was found by Cheapflights users on 10/17. 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 11/156:00 am -
1 stop7h 20m
Sun 11/225:30 am -
1 stop4h 50m
Deal found 10/17![Delta logo]()
$507
This American Airlines deal was found by Cheapflights users on 10/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:23 pm -
1 stop6h 33m
Fri 11/2011:44 am -
1 stop4h 28m
Deal found 10/21![American Airlines logo]()
$577
This Delta deal was found by Cheapflights users on 10/18. 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.
Fri 11/63:24 pm -
1 stop6h 14m
Sat 11/78:05 am -
1 stop5h 34m
Deal found 10/18![Delta logo]()
$547
This Delta deal was found by Cheapflights users on 10/19. 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.
Fri 11/67:00 pm -
1 stop4h 33m
Sun 11/86:04 am -
1 stop4h 05m
Deal found 10/19![Delta logo]()
$577
This Delta deal was found by Cheapflights users on 10/20. 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 10/20![Delta logo]()
$577
This American Airlines deal was found by Cheapflights users on 10/22. 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.
Thu 11/268:00 am -
1 stop5h 26m
Sun 11/296:41 am -
1 stop5h 32m
Deal found 10/22![American Airlines logo]()
$804
This Delta deal was found by Cheapflights users on 10/19. 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 11/56:00 am -
1 stop4h 25m
Sun 11/85:27 am -
1 stop4h 42m
Deal found 10/19![Delta logo]()
$577
This American Airlines deal was found by Cheapflights users on 10/22. 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.
Wed 11/257:45 pm -
1 stop5h 14m
Sun 11/295:19 am -
1 stop6h 54m
Deal found 10/22![American Airlines logo]()
$804
This Delta deal was found by Cheapflights users on 10/19. 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.
Fri 11/63:24 pm -
1 stop4h 47m
Sun 11/85:27 am -
1 stop4h 42m
Deal found 10/19![Delta logo]()
$577
This Delta deal was found by Cheapflights users on 10/22. 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 12/98:00 am -
1 stop5h 04m
Tue 1/56:00 am -
1 stop5h 05m
Deal found 10/22![Delta logo]()
$598
This Delta deal was found by Cheapflights users on 10/22. 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.
Sat 11/145:09 pm -
1 stop6h 45m
Fri 11/201:05 pm -
1 stop6h 32m
Deal found 10/22![Delta logo]()
$618
This Delta deal was found by Cheapflights users on 10/18. 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.
Sun 11/156:00 am -
1 stop5h 24m
Fri 11/201:05 pm -
1 stop6h 32m
Deal found 10/18![Delta logo]()
$775
This Delta deal was found by Cheapflights users on 10/20. 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.
Tue 11/36:00 am -
1 stop5h 43m
Fri 11/64:19 pm -
1 stop5h 45m
Deal found 10/20![Delta logo]()
$825
This Delta deal was found by Cheapflights users on 10/18. 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.
Sat 3/205:35 am -
1 stop5h 17m
Tue 3/239:30 am -
2 stops8h 51m
Deal found 10/18![Delta logo]()
$1,010
This Delta deal was found by Cheapflights users on 10/17. 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 11/157:00 pm -
1 stop4h 54m
Sun 11/221:31 pm -
2 stops8h 31m
Deal found 10/17![Delta logo]()
$1,020
Last-minute flights from Tallahassee to ChicagoDiscover last-minute flight deals from Tallahassee to Chicago. Data last updated October 23, 2026 and is based on user searches.
Discover last-minute flight deals from Tallahassee to Chicago. Data last updated October 23, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/311:15 am -
2 stops32h 15m
Sat 11/77:55 am -
1 stop22h 45m
Deal found 10/19![Multiple Airlines logo]()
$381
This Delta deal was found by Cheapflights users on 10/18. 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 11/118:06 am -
1 stop4h 53m
Sat 11/1411:27 am -
1 stop3h 57m
Deal found 10/18![Delta logo]()
$517
This Delta deal was found by Cheapflights users on 10/18. 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 11/116:00 am -
1 stop7h 20m
Sun 11/155:30 am -
1 stop4h 50m
Deal found 10/18![Delta logo]()
$517
This Kiwi.com deal was found by Cheapflights users on 10/18. 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 11/128:20 am -
2 stops11h 25m
Sat 11/147:55 am -
1 stop22h 45m
Deal found 10/18![Multiple Airlines logo]()
$360
This Delta deal was found by Cheapflights users on 10/17. 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 11/125:10 pm -
1 stop6h 44m
Mon 11/165:13 pm -
1 stop4h 49m
Deal found 10/17![Delta logo]()
$507
This American Airlines deal was found by Cheapflights users on 10/20. 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.
Sat 11/146:23 pm -
1 stop6h 33m
Fri 11/2011:44 am -
1 stop4h 28m
Deal found 10/20![American Airlines logo]()
$507
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/151:02 pm -
1 stop27h 35m
Fri 11/202:52 pm -
2 stops39h 48m
Deal found 10/21![Multiple Airlines logo]()
$491
This American Airlines deal was found by Cheapflights users on 10/20. 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 11/184:32 pm -
1 stop6h 58m
Wed 11/254:40 pm -
1 stop6h 19m
Deal found 10/20![American Airlines logo]()
$497
This Delta deal was found by Cheapflights users on 10/22. 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 11/197:00 pm -
1 stop5h 54m
Thu 11/265:50 pm -
1 stop4h 12m
Deal found 10/22![Delta logo]()
$527
This Delta deal was found by Cheapflights users on 10/21. 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.
Sun 11/226:00 am -
1 stop4h 25m
Tue 12/110:36 am -
1 stop4h 49m
Deal found 10/21![Delta logo]()
$487
This American Airlines deal was found by Cheapflights users on 10/22. 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.
Sun 11/226:21 pm -
1 stop7h 26m
Tue 12/16:41 am -
1 stop7h 18m
Deal found 10/22![American Airlines logo]()
$488
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 11/269:15 am -
1 stop15h 19m
Wed 12/23:55 pm -
2 stops19h 37m
Deal found 10/22![Multiple Airlines logo]()
$385
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 October 23, 2026.
Search for one-way flight options from Tallahassee to Chicago. Find affordable one-way fares based on user searches. Data last updated October 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/17. 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 11/158:20 am -
2 stops34h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![Multiple Airlines logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 12/108:30 am -
2 stops8h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 12/108:30 am -
3 stops12h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 12/178:30 am -
3 stops39h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Multiple Airlines logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 10/18. 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.
Tue 3/162:02 pm -
1 stop27h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Multiple Airlines logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 10/18. 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.
Tue 11/311:15 am -
2 stops13h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Multiple Airlines logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/38:30 am -
2 stops28h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Multiple Airlines logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 10/18. 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.
Tue 11/311:15 am -
2 stops32h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Multiple Airlines logo]()
$223
This Delta deal was found by Cheapflights users on 10/21. 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 1/16:10 am -
1 stop17h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Delta logo]()
$290
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/38:30 am -
3 stops40h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Multiple Airlines logo]()
$298
This Kiwi.com deal was found by Cheapflights users on 10/18. 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 11/228:20 am -
2 stops30h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Multiple Airlines logo]()
$306
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
Sun 11/2911:19 pm -
2 stops39h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Multiple Airlines logo]()
$322
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 October 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $343 (Kiwi.com) |
One-way from | $151 (Kiwi.com) |
Popular in | October |
Cheapest in | May |
Average price | $690 |
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 October 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 - MDW Chicago Midway
TLHMDW
Tallahassee
Thu 12/10
8:30 am-4:06 pm
2 stops8h 36m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$153
TallahasseeChicago
TLH Tallahassee - ORD Chicago O'Hare Intl
TLHORD
Tallahassee
Thu 12/17
1:12 pm-4:59 pm
1 stop28h 47m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$209
TallahasseeChicago
TLH Tallahassee - ORD Chicago O'Hare Intl
TLHORD
Tallahassee
Sun 11/15
8:20 am-8:46 am
2 stops25h 26m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$219
TallahasseeChicago
TLH Tallahassee - MDW Chicago Midway
TLHMDW
Tallahassee
Sun 11/15
8:20 am-5:47 pm
3 stops34h 27m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$246
TallahasseeChicago
TLH Tallahassee - MDW Chicago Midway
TLHMDW
Tallahassee
Fri 1/1
6:10 am-10:22 pm
1 stop17h 12m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$290
TallahasseeChicago
TLH Tallahassee - MDW Chicago Midway
TLHMDW
Tallahassee
Tue 11/3
11:15 am-11:22 am
3 stops25h 07m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$304
TallahasseeChicago
TLH Tallahassee - ORD Chicago O'Hare Intl
TLHORD
Tallahassee
Sun 11/29
11:19 pm-1:51 pm
2 stops39h 32m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$322
TallahasseeChicago
TLH Tallahassee - ORD Chicago O'Hare Intl
TLHORD
Tallahassee
Fri 1/1
6:10 am-8:18 pm
2 stops15h 08m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$340
TallahasseeChicago
TLH Tallahassee - ORD Chicago O'Hare Intl
TLHORD
Tallahassee
Wed 12/16
4:37 pm-11:59 pm
1 stop8h 22m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$348
TallahasseeChicago
TLH Tallahassee - ORD Chicago O'Hare Intl
TLHORD
Tallahassee
Wed 12/9
2:56 pm-10:36 pm
1 stop8h 40m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$348
Showing 1-10 of 38 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 October.
| 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-MDW
TLH-ORD
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-MDW
TLH-ORD
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 $672). 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 $643 and $734 in November.The cheapest round-trip price found within the last 5 days was $343 on Multiple Airlines (Nov 12-Nov 16).
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 October 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.
Entertainment
7.8
Food
7.2
Overall
7.8
Crew
8.5
Comfort
7.8
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Entertainment
7.8
Food
7.2
Overall
7.8
Crew
8.5
Comfort
7.8
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Entertainment
7.8
Food
7.2
Overall
7.8
Crew
8.5
Comfort
7.8
Boarding
8.1
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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Chicago
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Tallahassee and Chicago flights
Browse other Tallahassee and Chicago flight options. Last updated on October 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 October 23, 2026.
Popular flight searches
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 October 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$158 | Average$446 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$316 | Average$466 | FlexibilityNo cancel fee | On-time71% |