$158+ Cheap flights from Tallahassee (TLH) to Chicago (CHI)
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 4/14. Fares are subject to change and may not be available on all flights or dates of travel.
TLH — CHI
Mar 24 — Mar 311
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
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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 February 22, 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 February 22, 2026.
This Delta deal was found by Cheapflights users on 2/20. 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.
Wed 5/132:41 pm
TLH
- ORD
1 stop6h 44m
Delta
Sat 5/167:05 am
ORD
- TLH
1 stop5h 51m
Delta
Deal found 2/20![Delta logo]()
$317
This Delta deal was found by Cheapflights users on 2/20. 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.
Wed 5/137:07 pm
TLH
- ORD
1 stop5h 52m
Delta
Sun 5/176:00 am
ORD
- TLH
1 stop6h 56m
Delta
Deal found 2/20![Delta logo]()
$362
This Delta deal was found by Cheapflights users on 2/19. 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.
Tue 7/73:40 pm
TLH
- ORD
1 stop5h 38m
Delta
Sun 7/126:00 am
ORD
- TLH
1 stop5h 04m
Delta
Deal found 2/19![Delta logo]()
$397
This Delta deal was found by Cheapflights users on 2/21. 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 4/115:36 am
TLH
- MDW
1 stop5h 20m
Delta
Mon 4/1312:52 pm
MDW
- TLH
1 stop4h 28m
Delta
Deal found 2/21![Delta logo]()
$407
This Delta deal was found by Cheapflights users on 2/19. 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 4/25:36 am
TLH
- ORD
1 stop3h 54m
Delta
Sun 4/57:10 am
ORD
- TLH
1 stop4h 18m
Delta
Deal found 2/19![Delta logo]()
$407
This American Airlines deal was found by Cheapflights users on 2/20. 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 3/1112:04 pm
TLH
- ORD
1 stop6h 53m
American Airlines
Sat 3/143:16 pm
ORD
- TLH
1 stop6h 09m
American Airlines
Deal found 2/20![American Airlines logo]()
$447
This Delta deal was found by Cheapflights users on 2/19. 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 3/55:30 am
TLH
- MDW
1 stop5h 24m
Delta
Mon 3/910:45 am
MDW
- TLH
1 stop4h 42m
Delta
Deal found 2/19![Delta logo]()
$487
This Delta deal was found by Cheapflights users on 2/19. 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 3/57:29 pm
TLH
- ORD
1 stop5h 27m
Delta
Sat 3/76:45 am
ORD
- TLH
1 stop7h 08m
Delta
Deal found 2/19![Delta logo]()
$487
This Delta deal was found by Cheapflights users on 2/20. 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.
Mon 3/305:12 pm
TLH
- ORD
1 stop4h 58m
Delta
Wed 4/111:10 am
ORD
- TLH
1 stop4h 17m
Delta
Deal found 2/20![Delta logo]()
$496
This Delta deal was found by Cheapflights users on 2/19. 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 4/25:36 am
TLH
- MDW
1 stop5h 20m
Delta
Sun 4/56:00 am
MDW
- TLH
1 stop5h 28m
Delta
Deal found 2/19![Delta logo]()
$523
This Delta deal was found by Cheapflights users on 2/21. 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 3/157:09 pm
TLH
- ORD
1 stop5h 45m
Delta
Wed 3/182:38 pm
ORD
- TLH
1 stop5h 06m
Delta
Deal found 2/21![Delta logo]()
$526
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Sun 3/157:55 pm
TLH
- ORD
1 stop5h 21m
American Airlines
Wed 3/183:16 pm
ORD
- TLH
1 stop6h 09m
American Airlines
Deal found 2/19![American Airlines logo]()
$531
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 February 22, 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 February 22, 2026.
This Delta deal was found by Cheapflights users on 2/22. 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 5/137:07 pm
TLH
- ORD
1 stop5h 52m
Delta
Sun 5/177:07 am
ORD
- TLH
1 stop5h 50m
Delta
Deal found 2/22![Delta logo]()
$362
This American Airlines deal was found by Cheapflights users on 2/19. 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 4/166:30 am
TLH
- ORD
1 stop4h 42m
American Airlines
Mon 4/205:00 am
ORD
- TLH
1 stop5h 42m
American Airlines
Deal found 2/19![American Airlines logo]()
$407
This Delta deal was found by Cheapflights users on 2/18. 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 3/265:36 am
TLH
- ORD
1 stop3h 54m
Delta
Wed 4/111:10 am
ORD
- TLH
1 stop6h 14m
Delta
Deal found 2/18![Delta logo]()
$362
This Delta deal was found by Cheapflights users on 2/19. 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.
Sat 7/117:30 am
TLH
- ORD
1 stop5h 39m
Delta
Wed 7/156:00 am
ORD
- TLH
1 stop5h 04m
Delta
Deal found 2/19![Delta logo]()
$397
This Delta deal was found by Cheapflights users on 2/19. 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.
Wed 7/157:15 pm
TLH
- ORD
1 stop5h 40m
Delta
Sat 7/186:00 am
ORD
- TLH
1 stop5h 04m
Delta
Deal found 2/19![Delta logo]()
$397
This Delta deal was found by Cheapflights users on 2/19. 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.
Wed 7/83:40 pm
TLH
- ORD
1 stop6h 36m
Delta
Sun 7/126:00 am
ORD
- TLH
1 stop5h 04m
Delta
Deal found 2/19![Delta logo]()
$397
This Delta deal was found by Cheapflights users on 2/19. 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.
Tue 7/73:40 pm
TLH
- ORD
1 stop5h 38m
Delta
Sun 7/126:00 am
ORD
- TLH
1 stop5h 04m
Delta
Deal found 2/19![Delta logo]()
$397
This Delta deal was found by Cheapflights users on 2/19. 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.
Sat 7/185:35 am
TLH
- ORD
1 stop3h 59m
Delta
Wed 7/226:00 am
ORD
- TLH
1 stop5h 04m
Delta
Deal found 2/19![Delta logo]()
$397
This Delta deal was found by Cheapflights users on 2/22. 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 4/25:36 am
TLH
- ORD
1 stop3h 54m
Delta
Sun 4/57:10 am
ORD
- TLH
1 stop6h 55m
Delta
Deal found 2/22![Delta logo]()
$407
This Delta deal was found by Cheapflights users on 2/19. 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 3/61:28 pm
TLH
- MDW
1 stop5h 17m
Delta
Mon 3/910:45 am
MDW
- TLH
1 stop6h 39m
Delta
Deal found 2/19![Delta logo]()
$487
This Delta deal was found by Cheapflights users on 2/20. 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.
Sat 3/75:23 pm
TLH
- MDW
1 stop6h 08m
Delta
Wed 3/1112:47 pm
MDW
- TLH
1 stop4h 37m
Delta
Deal found 2/20![Delta logo]()
$487
This Delta deal was found by Cheapflights users on 2/19. 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 3/53:41 pm
TLH
- ORD
1 stop6h 20m
Delta
Sun 3/85:30 am
ORD
- TLH
1 stop5h 58m
Delta
Deal found 2/19![Delta logo]()
$487
This Delta deal was found by Cheapflights users on 2/19. 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 3/57:29 pm
TLH
- ORD
1 stop5h 27m
Delta
Sat 3/76:45 am
ORD
- TLH
1 stop7h 08m
Delta
Deal found 2/19![Delta logo]()
$487
This Delta deal was found by Cheapflights users on 2/22. 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 4/25:36 am
TLH
- MDW
1 stop5h 20m
Delta
Sun 4/56:00 am
MDW
- TLH
1 stop5h 28m
Delta
Deal found 2/22![Delta logo]()
$523
This Delta deal was found by Cheapflights users on 2/18. 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 3/157:09 pm
TLH
- MDW
1 stop4h 22m
Delta
Wed 3/1810:45 am
MDW
- TLH
1 stop4h 42m
Delta
Deal found 2/18![Delta logo]()
$599
This Delta deal was found by Cheapflights users on 2/22. 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 6/310:15 am
TLH
- MDW
1 stop6h 57m
Delta
Fri 6/56:23 am
MDW
- TLH
1 stop6h 34m
Delta
Deal found 2/22![Delta logo]()
$615
This Delta deal was found by Cheapflights users on 2/19. 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 3/65:23 pm
TLH
- MDW
1 stop6h 08m
Delta
Sun 3/810:45 am
MDW
- TLH
1 stop6h 39m
Delta
Deal found 2/19![Delta logo]()
$633
This Delta deal was found by Cheapflights users on 2/19. 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 3/57:23 am
TLH
- MDW
1 stop5h 36m
Delta
Sun 3/89:35 am
MDW
- TLH
2 stops10h 09m
Delta
Deal found 2/19![Delta logo]()
$801
Last-minute flights from Tallahassee to ChicagoDiscover last-minute flight deals from Tallahassee to Chicago. Data last updated February 22, 2026 and is based on user searches.
Discover last-minute flight deals from Tallahassee to Chicago. Data last updated February 22, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 2/18. 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.
Thu 2/267:55 pm
TLH
- ORD
1 stop5h 21m
American Airlines
Sun 3/18:26 am
ORD
- TLH
1 stop8h 19m
American Airlines
Deal found 2/18![American Airlines logo]()
$587
This Delta deal was found by Cheapflights users on 2/21. 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 3/41:28 pm
TLH
- ORD
1 stop6h 51m
Delta
Sat 3/76:45 am
ORD
- TLH
1 stop7h 08m
Delta
Deal found 2/21![Delta logo]()
$537
This Delta deal was found by Cheapflights users on 2/19. 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 3/55:30 am
TLH
- MDW
1 stop5h 24m
Delta
Mon 3/910:45 am
MDW
- TLH
1 stop4h 42m
Delta
Deal found 2/19![Delta logo]()
$487
This Delta deal was found by Cheapflights users on 2/19. 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 3/57:29 pm
TLH
- ORD
1 stop5h 27m
Delta
Sat 3/76:45 am
ORD
- TLH
1 stop7h 08m
Delta
Deal found 2/19![Delta logo]()
$487
This Delta deal was found by Cheapflights users on 2/19. 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 3/55:30 am
TLH
- MDW
1 stop5h 24m
Delta
Sat 3/74:13 pm
MDW
- TLH
1 stop5h 07m
Delta
Deal found 2/19![Delta logo]()
$563
This American Airlines deal was found by Cheapflights users on 2/20. 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 3/1112:04 pm
TLH
- ORD
1 stop6h 53m
American Airlines
Sat 3/143:16 pm
ORD
- TLH
1 stop6h 09m
American Airlines
Deal found 2/20![American Airlines logo]()
$447
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Thu 3/126:10 am
TLH
- ORD
1 stop5h 44m
American Airlines
Sun 3/155:00 am
ORD
- TLH
1 stop5h 36m
American Airlines
Deal found 2/20![American Airlines logo]()
$594
This Delta deal was found by Cheapflights users on 2/21. 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 3/157:09 pm
TLH
- ORD
1 stop5h 45m
Delta
Wed 3/182:38 pm
ORD
- TLH
1 stop5h 06m
Delta
Deal found 2/21![Delta logo]()
$526
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Sun 3/157:55 pm
TLH
- ORD
1 stop5h 21m
American Airlines
Wed 3/183:16 pm
ORD
- TLH
1 stop6h 09m
American Airlines
Deal found 2/19![American Airlines logo]()
$531
This Delta deal was found by Cheapflights users on 2/19. 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 3/157:09 pm
TLH
- MDW
1 stop4h 22m
Delta
Wed 3/1810:45 am
MDW
- TLH
1 stop4h 42m
Delta
Deal found 2/19![Delta logo]()
$548
This American Airlines deal was found by Cheapflights users on 2/20. 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 3/256:27 am
TLH
- ORD
1 stop8h 07m
American Airlines
Sun 3/293:16 pm
ORD
- TLH
1 stop6h 09m
American Airlines
Deal found 2/20![American Airlines logo]()
$362
This Delta deal was found by Cheapflights users on 2/20. 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.
Mon 3/305:12 pm
TLH
- ORD
1 stop4h 58m
Delta
Wed 4/111:10 am
ORD
- TLH
1 stop4h 17m
Delta
Deal found 2/20![Delta logo]()
$496
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 February 22, 2026.
Search for one-way flight options from Tallahassee to Chicago. Find affordable one-way fares based on user searches. Data last updated February 22, 2026.
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Tue 4/147:06 pm
TLH
- ORD
1 stop5h 48m
American Airlines
Deal found 2/20![American Airlines logo]()
$158
This Delta deal was found by Cheapflights users on 2/20. 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 3/175:12 pm
TLH
- MDW
1 stop6h 19m
Delta
Deal found 2/20![Delta logo]()
$159
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Tue 3/176:10 am
TLH
- ORD
1 stop6h 55m
American Airlines
Deal found 2/20![American Airlines logo]()
$159
This Delta deal was found by Cheapflights users on 2/21. 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 4/55:36 am
TLH
- MDW
1 stop5h 20m
Delta
Deal found 2/21![Delta logo]()
$308
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Mon 3/306:00 am
TLH
- ORD
1 stop8h 04m
American Airlines
Deal found 2/20![American Airlines logo]()
$308
This Delta deal was found by Cheapflights users on 2/18. 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 4/45:36 am
TLH
- MDW
1 stop5h 20m
Delta
Deal found 2/18![Delta logo]()
$338
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Sun 3/157:55 pm
TLH
- ORD
1 stop5h 21m
American Airlines
Deal found 2/20![American Airlines logo]()
$338
This Delta deal was found by Cheapflights users on 2/20. 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.
Sun 3/157:09 pm
TLH
- MDW
1 stop4h 22m
Delta
Deal found 2/20![Delta logo]()
$390
This American Airlines deal was found by Cheapflights users on 2/20. 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 3/147:55 pm
TLH
- ORD
1 stop5h 03m
American Airlines
Deal found 2/20![American Airlines logo]()
$440
This American Airlines deal was found by Cheapflights users on 2/21. 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.
Sun 3/16:15 pm
TLH
- ORD
1 stop6h 21m
American Airlines
Deal found 2/21![American Airlines logo]()
$458
This American Airlines deal was found by Cheapflights users on 2/21. 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.
Tue 3/313:03 pm
TLH
- ORD
2 stops6h 07m
American Airlines
Deal found 2/21![American Airlines logo]()
$494
This American Airlines deal was found by Cheapflights users on 2/21. 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.
Sun 4/512:04 pm
TLH
- ORD
2 stops6h 59m
American Airlines
Deal found 2/21![American Airlines logo]()
$637
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 February 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $317 (Delta) |
One-way from | $158 (American Airlines) |
Popular in | January |
Cheapest in | September |
Average price | $437 |
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 2,558,603 searches. Data last updated February 22, 2026.
Use the filters below to find and compare flights from Tallahassee to Chicago that are best for you.
Fly from
Tallahassee
Fly to
Chicago
Route
Depart
Return
Price
TallahasseeChicago
TLH - ORD
TLHORD
Tallahassee
Wed 5/13
7:07 pm-11:59 pm
1 stop5h 52m
Chicago O'Hare Intl
Sun 5/17
7:07 am-1:57 pm
1 stop5h 50m
$362
TallahasseeChicago
TLH - ORD
TLHORD
Tallahassee
Thu 3/26
5:36 am-8:30 am
1 stop3h 54m
Chicago O'Hare Intl
Wed 4/1
11:10 am-6:24 pm
1 stop6h 14m
$362
TallahasseeChicago
TLH - ORD
TLHORD
Tallahassee
Sat 7/11
7:30 am-12:09 pm
1 stop5h 39m
Chicago O'Hare Intl
Wed 7/15
6:00 am-12:04 pm
1 stop5h 04m
$397
TallahasseeChicago
TLH - ORD
TLHORD
Tallahassee
Wed 7/15
7:15 pm-11:55 pm
1 stop5h 40m
Chicago O'Hare Intl
Sat 7/18
6:00 am-12:04 pm
1 stop5h 04m
$397
TallahasseeChicago
TLH - ORD
TLHORD
Tallahassee
Wed 7/8
3:40 pm-9:16 pm
1 stop6h 36m
Chicago O'Hare Intl
Sun 7/12
6:00 am-12:04 pm
1 stop5h 04m
$397
TallahasseeChicago
TLH - ORD
TLHORD
Tallahassee
Tue 7/7
3:40 pm-8:18 pm
1 stop5h 38m
Chicago O'Hare Intl
Sun 7/12
6:00 am-12:04 pm
1 stop5h 04m
$397
TallahasseeChicago
TLH - ORD
TLHORD
Tallahassee
Sat 7/18
5:35 am-8:34 am
1 stop3h 59m
Chicago O'Hare Intl
Wed 7/22
6:00 am-12:04 pm
1 stop5h 04m
$397
TallahasseeChicago
TLH - ORD
TLHORD
Tallahassee
Thu 4/16
6:30 am-10:12 am
1 stop4h 42m
Chicago O'Hare Intl
Mon 4/20
5:00 am-11:42 am
1 stop5h 42m
$407
TallahasseeChicago
TLH - ORD
TLHORD
Tallahassee
Thu 4/2
5:36 am-8:30 am
1 stop3h 54m
Chicago O'Hare Intl
Sun 4/5
7:10 am-3:05 pm
1 stop6h 55m
$407
TallahasseeChicago
TLH - MDW
TLHMDW
Tallahassee
Fri 3/6
1:28 pm-5:45 pm
1 stop5h 17m
Chicago Midway
Mon 3/9
10:45 am-6:24 pm
1 stop6h 39m
$487
Showing 1-10 of 29 results
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 February.
| 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, June is the cheapest month in which you can book a flight from Tallahassee to Chicago (average of $112). Flying from Tallahassee to Chicago in January is currently the most expensive (average of $253). 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 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 February 22, 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
Overall
7.9
Comfort
7.9
Crew
8.5
Food
7.2
Boarding
8.1
Reviews
1 / 20
6.0
Goodpilar,May 2025
RSW - ATL
Entertainment
7.8
Overall
7.9
Comfort
7.9
Crew
8.5
Food
7.2
Boarding
8.1
Reviews
1 / 20
6.0
Goodpilar,May 2025
RSW - ATL
Entertainment
7.8
Overall
7.9
Comfort
7.9
Crew
8.5
Food
7.2
Boarding
8.1
Reviews
1 / 20
6.0
Goodpilar,May 2025
RSW - 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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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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 February 22, 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 February 22, 2026.
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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 2,558,603 searches. Data last updated February 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$158 | Average$509 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$356 | Average$501 | FlexibilityNo cancel fee | On-time71% |