$207+ 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 7/14. Fares are subject to change and may not be available on all flights or dates of travel.
TLH — CHI
Touko 22 — Touko 291
Round-trip
1 adult, Economy
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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 huhtikuu 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 huhtikuu 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/17. 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.
ti 7/142:17 pm
TLH
- ORD
1 stop23h 08m
Multiple Airlines
ke 7/227:55 am
ORD
- TLH
1 stop22h 33m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 4/19. 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.
ti 7/212:17 pm
TLH
- ORD
1 stop23h 08m
Multiple Airlines
la 7/257:55 am
ORD
- TLH
1 stop22h 33m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 4/19. 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.
ti 7/212:17 pm
TLH
- ORD
1 stop23h 08m
Multiple Airlines
ma 7/275:26 pm
ORD
- TLH
1 stop14h 32m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 4/19. 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.
to 7/2312:47 pm
TLH
- ORD
1 stop11h 21m
Multiple Airlines
la 7/257:55 am
ORD
- TLH
1 stop22h 33m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 4/19. 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.
to 7/2312:47 pm
TLH
- ORD
1 stop11h 21m
Multiple Airlines
ma 7/275:26 pm
ORD
- TLH
1 stop14h 32m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 4/19. 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.
ti 7/212:17 pm
TLH
- ORD
1 stop23h 08m
Multiple Airlines
ke 7/297:55 am
ORD
- TLH
1 stop22h 33m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$276
This Kiwi.com deal was found by Cheapflights users on 4/19. 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.
to 7/2312:47 pm
TLH
- ORD
1 stop11h 21m
Multiple Airlines
ke 7/297:55 am
ORD
- TLH
1 stop22h 33m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$295
This Delta deal was found by Cheapflights users on 4/21. 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.
ke 5/205:23 pm
TLH
- MDW
1 stop4h 46m
Delta
ke 5/2712:53 pm
MDW
- TLH
1 stop4h 28m
Delta
Deal found 4/21![Delta logo]()
$392
This Delta deal was found by Cheapflights users on 4/17. 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.
la 5/165:23 pm
TLH
- MDW
1 stop4h 46m
Delta
la 5/2310:45 am
MDW
- TLH
1 stop4h 46m
Delta
Deal found 4/17![Delta logo]()
$402
This Delta deal was found by Cheapflights users on 4/19. 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.
ti 7/215:41 pm
TLH
- MDW
1 stop5h 34m
Delta
ke 7/2912:41 pm
MDW
- TLH
1 stop4h 35m
Delta
Deal found 4/19![Delta logo]()
$427
This Delta deal was found by Cheapflights users on 4/19. 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.
ti 7/216:30 am
TLH
- MDW
1 stop6h 26m
Delta
la 7/254:22 pm
MDW
- TLH
1 stop5h 32m
Delta
Deal found 4/19![Delta logo]()
$437
This Delta deal was found by Cheapflights users on 4/19. 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.
to 7/237:01 pm
TLH
- MDW
1 stop4h 14m
Delta
la 7/254:22 pm
MDW
- TLH
1 stop5h 32m
Delta
Deal found 4/19![Delta logo]()
$447
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 huhtikuu 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 huhtikuu 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/17. 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.
ti 7/142:17 pm
TLH
- ORD
1 stop23h 08m
Multiple Airlines
ke 7/227:55 am
ORD
- TLH
1 stop22h 33m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$207
This American Airlines deal was found by Cheapflights users on 4/21. 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.
ke 5/206:09 am
TLH
- ORD
1 stop8h 07m
American Airlines
ke 5/274:45 pm
ORD
- TLH
1 stop4h 51m
American Airlines
Deal found 4/21![American Airlines logo]()
$392
This Delta deal was found by Cheapflights users on 4/21. 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.
ke 5/205:23 pm
TLH
- ORD
1 stop5h 30m
Delta
su 5/248:10 am
ORD
- TLH
1 stop4h 47m
Delta
Deal found 4/21![Delta logo]()
$402
This American Airlines deal was found by Cheapflights users on 4/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ti 5/196:09 am
TLH
- ORD
1 stop5h 55m
American Airlines
to 5/285:10 am
ORD
- TLH
1 stop5h 10m
American Airlines
Deal found 4/17![American Airlines logo]()
$402
This Delta deal was found by Cheapflights users on 4/19. 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.
ke 7/227:01 pm
TLH
- MDW
1 stop4h 14m
Delta
ti 7/286:05 am
MDW
- TLH
1 stop4h 16m
Delta
Deal found 4/19![Delta logo]()
$427
This Delta deal was found by Cheapflights users on 4/19. 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.
ti 7/215:41 pm
TLH
- MDW
1 stop5h 34m
Delta
ke 7/2912:41 pm
MDW
- TLH
1 stop4h 35m
Delta
Deal found 4/19![Delta logo]()
$427
This American Airlines deal was found by Cheapflights users on 4/20. 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.
to 9/35:31 pm
TLH
- ORD
1 stop6h 29m
American Airlines
ke 9/95:00 am
ORD
- TLH
1 stop4h 54m
American Airlines
Deal found 4/20![American Airlines logo]()
$437
This Delta deal was found by Cheapflights users on 4/19. 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.
ti 7/215:41 pm
TLH
- ORD
1 stop7h 12m
Delta
ti 7/288:03 am
ORD
- TLH
1 stop5h 34m
Delta
Deal found 4/19![Delta logo]()
$427
This Delta deal was found by Cheapflights users on 4/19. 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.
ke 7/227:01 pm
TLH
- MDW
1 stop4h 14m
Delta
ma 7/276:05 am
MDW
- TLH
1 stop4h 16m
Delta
Deal found 4/19![Delta logo]()
$437
This Delta deal was found by Cheapflights users on 4/20. 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.
ma 5/256:15 am
TLH
- MDW
1 stop4h 45m
Delta
ti 6/96:05 am
MDW
- TLH
1 stop4h 19m
Delta
Deal found 4/20![Delta logo]()
$437
This Delta deal was found by Cheapflights users on 4/19. 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.
pe 7/243:23 pm
TLH
- ORD
1 stop6h 10m
Delta
ti 7/289:45 am
ORD
- TLH
1 stop6h 05m
Delta
Deal found 4/19![Delta logo]()
$437
This Delta deal was found by Cheapflights users on 4/20. 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.
ma 5/255:23 pm
TLH
- ORD
1 stop5h 30m
Delta
ti 6/95:30 am
ORD
- TLH
1 stop4h 54m
Delta
Deal found 4/20![Delta logo]()
$437
This Delta deal was found by Cheapflights users on 4/21. 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.
to 6/117:01 pm
TLH
- ORD
1 stop5h 58m
Delta
ma 6/155:30 am
ORD
- TLH
1 stop4h 54m
Delta
Deal found 4/21![Delta logo]()
$473
This Delta deal was found by Cheapflights users on 4/19. 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.
pe 7/243:23 pm
TLH
- ORD
1 stop6h 10m
Delta
su 7/265:15 am
ORD
- TLH
1 stop5h 06m
Delta
Deal found 4/19![Delta logo]()
$473
This Delta deal was found by Cheapflights users on 4/19. 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.
to 6/117:01 pm
TLH
- MDW
1 stop4h 16m
Delta
ma 6/156:05 am
MDW
- TLH
1 stop4h 19m
Delta
Deal found 4/19![Delta logo]()
$503
This Delta deal was found by Cheapflights users on 4/21. 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.
ke 5/65:15 pm
TLH
- MDW
1 stop6h 13m
Delta
su 5/106:23 am
MDW
- TLH
1 stop6h 34m
Delta
Deal found 4/21![Delta logo]()
$520
This Delta deal was found by Cheapflights users on 4/22. 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.
to 5/78:05 am
TLH
- MDW
1 stop4h 51m
Delta
ma 5/1110:59 am
MDW
- TLH
1 stop4h 32m
Delta
Deal found 4/22![Delta logo]()
$527
This Delta deal was found by Cheapflights users on 4/18. 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.
to 9/35:35 am
TLH
- MDW
1 stop5h 15m
Delta
ke 9/910:35 am
MDW
- TLH
1 stop5h 00m
Delta
Deal found 4/18![Delta logo]()
$529
This Delta deal was found by Cheapflights users on 4/19. 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.
la 7/257:00 am
TLH
- MDW
1 stop4h 04m
Delta
la 7/254:22 pm
MDW
- TLH
1 stop16h 03m
Delta
Deal found 4/19![Delta logo]()
$546
Last-minute flights from Tallahassee to ChicagoDiscover last-minute flight deals from Tallahassee to Chicago. Data last updated huhtikuu 22, 2026 and is based on user searches.
Discover last-minute flight deals from Tallahassee to Chicago. Data last updated huhtikuu 22, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 4/21. 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.
ke 4/297:05 pm
TLH
- MDW
1 stop4h 23m
Delta
pe 5/2910:59 am
MDW
- TLH
1 stop4h 32m
Delta
Deal found 4/21![Delta logo]()
$480
This Delta deal was found by Cheapflights users on 4/21. 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.
ke 4/293:46 pm
TLH
- ORD
1 stop5h 30m
Delta
pe 5/292:59 pm
ORD
- TLH
1 stop4h 44m
Delta
Deal found 4/21![Delta logo]()
$480
This Delta deal was found by Cheapflights users on 4/20. 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.
ti 5/56:44 pm
TLH
- MDW
1 stop4h 44m
Delta
la 5/96:23 am
MDW
- TLH
1 stop6h 34m
Delta
Deal found 4/20![Delta logo]()
$513
This American Airlines deal was found by Cheapflights users on 4/21. 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.
ti 5/56:42 pm
TLH
- ORD
1 stop6h 06m
American Airlines
la 5/95:20 pm
ORD
- TLH
1 stop5h 36m
American Airlines
Deal found 4/21![American Airlines logo]()
$513
This Delta deal was found by Cheapflights users on 4/21. 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.
ke 5/65:15 pm
TLH
- MDW
1 stop6h 13m
Delta
su 5/106:23 am
MDW
- TLH
1 stop6h 34m
Delta
Deal found 4/21![Delta logo]()
$520
This Delta deal was found by Cheapflights users on 4/17. 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.
la 5/165:23 pm
TLH
- MDW
1 stop4h 46m
Delta
la 5/2310:45 am
MDW
- TLH
1 stop4h 46m
Delta
Deal found 4/17![Delta logo]()
$402
This Delta deal was found by Cheapflights users on 4/21. 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.
ke 5/205:23 pm
TLH
- MDW
1 stop4h 46m
Delta
ke 5/2712:53 pm
MDW
- TLH
1 stop4h 28m
Delta
Deal found 4/21![Delta logo]()
$392
This American Airlines deal was found by Cheapflights users on 4/21. 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.
ke 5/206:09 am
TLH
- ORD
1 stop8h 07m
American Airlines
ke 5/274:45 pm
ORD
- TLH
1 stop4h 51m
American Airlines
Deal found 4/21![American Airlines logo]()
$392
This Delta deal was found by Cheapflights users on 4/21. 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.
ke 5/205:23 pm
TLH
- ORD
1 stop5h 30m
Delta
su 5/248:10 am
ORD
- TLH
1 stop4h 47m
Delta
Deal found 4/21![Delta logo]()
$402
This Delta deal was found by Cheapflights users on 4/19. 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.
pe 5/227:07 pm
TLH
- ORD
1 stop5h 52m
Delta
su 5/247:05 am
ORD
- TLH
1 stop5h 52m
Delta
Deal found 4/19![Delta logo]()
$503
This Delta deal was found by Cheapflights users on 4/18. 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.
la 5/235:23 pm
TLH
- MDW
1 stop4h 46m
Delta
ti 5/266:23 am
MDW
- TLH
1 stop6h 34m
Delta
Deal found 4/18![Delta logo]()
$437
This American Airlines deal was found by Cheapflights users on 4/18. 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.
la 5/233:27 pm
TLH
- ORD
1 stop7h 10m
American Airlines
ti 5/262:24 pm
ORD
- TLH
1 stop8h 35m
American Airlines
Deal found 4/18![American Airlines logo]()
$437
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 huhtikuu 22, 2026.
Search for one-way flight options from Tallahassee to Chicago. Find affordable one-way fares based on user searches. Data last updated huhtikuu 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/18. 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.
su 10/111:07 pm
TLH
- ORD
1 stop11h 51m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$298
This Delta deal was found by Cheapflights users on 4/17. 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.
ke 6/1712:11 pm
TLH
- MDW
1 stop5h 05m
Delta
Deal found 4/17![Delta logo]()
$328
This American Airlines deal was found by Cheapflights users on 4/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ke 6/176:00 am
TLH
- ORD
1 stop5h 47m
American Airlines
Deal found 4/17![American Airlines logo]()
$328
This Delta deal was found by Cheapflights users on 4/19. 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.
ti 5/512:58 pm
TLH
- MDW
1 stop4h 28m
Delta
Deal found 4/19![Delta logo]()
$388
This American Airlines deal was found by Cheapflights users on 4/19. 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.
ma 5/46:42 pm
TLH
- ORD
1 stop6h 06m
American Airlines
Deal found 4/19![American Airlines logo]()
$388
This Delta deal was found by Cheapflights users on 4/19. 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.
ma 5/45:15 pm
TLH
- MDW
1 stop6h 13m
Delta
Deal found 4/19![Delta logo]()
$460
This Delta deal was found by Cheapflights users on 4/19. 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.
la 5/27:04 am
TLH
- ORD
1 stop4h 05m
Delta
Deal found 4/19![Delta logo]()
$488
This Delta deal was found by Cheapflights users on 4/17. 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.
ke 6/1710:11 am
TLH
- ORD
2 stops9h 18m
Delta
Deal found 4/17![Delta logo]()
$738
This Delta deal was found by Cheapflights users on 4/21. 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.
ke 5/610:09 am
TLH
- ORD
2 stops11h 31m
Delta
Deal found 4/21![Delta logo]()
$756
This Delta deal was found by Cheapflights users on 4/19. 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.
ma 5/410:09 am
TLH
- ORD
2 stops11h 31m
Delta
Deal found 4/19![Delta logo]()
$848
This Qatar Airways deal was found by Cheapflights users on 4/20. 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 Qatar Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
to 6/119:32 am
TLH
- ORD
2 stops56h 18m
Qatar Airways
Deal found 4/20![Qatar Airways logo]()
$2,277
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 huhtikuu 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $207 (Kiwi.com) |
Popular in | January |
Cheapest in | September |
Average price | $555 |
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 huhtikuu 22, 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 - ORD
TLHORD
Tallahassee
ti 7/14
2:17 pm-12:25 pm
1 stop23h 08m
Chicago O'Hare Intl
ke 7/22
7:55 am-7:28 am
1 stop22h 33m
$207
TallahasseeChicago
TLH - ORD
TLHORD
Tallahassee
ke 5/20
6:09 am-1:16 pm
1 stop8h 07m
Chicago O'Hare Intl
ke 5/27
4:45 pm-10:36 pm
1 stop4h 51m
$392
TallahasseeChicago
TLH - ORD
TLHORD
Tallahassee
ke 5/20
5:23 pm-9:53 pm
1 stop5h 30m
Chicago O'Hare Intl
su 5/24
8:10 am-1:57 pm
1 stop4h 47m
$402
TallahasseeChicago
TLH - ORD
TLHORD
Tallahassee
ti 5/19
6:09 am-11:04 am
1 stop5h 55m
Chicago O'Hare Intl
to 5/28
5:10 am-11:20 am
1 stop5h 10m
$402
Quickest round-trip
TallahasseeChicago
TLH - MDW
TLHMDW
Tallahassee
ke 7/22
7:01 pm-10:15 pm
1 stop4h 14m
Chicago Midway
ti 7/28
6:05 am-11:21 am
1 stop4h 16m
$427
TallahasseeChicago
TLH - MDW
TLHMDW
Tallahassee
ti 7/21
5:41 pm-10:15 pm
1 stop5h 34m
Chicago Midway
ke 7/29
12:41 pm-6:16 pm
1 stop4h 35m
$427
TallahasseeChicago
TLH - ORD
TLHORD
Tallahassee
ti 7/21
5:41 pm-11:53 pm
1 stop7h 12m
Chicago O'Hare Intl
ti 7/28
8:03 am-2:37 pm
1 stop5h 34m
$427
TallahasseeChicago
TLH - ORD
TLHORD
Tallahassee
to 9/3
5:31 pm-11:00 pm
1 stop6h 29m
Chicago O'Hare Intl
ke 9/9
5:00 am-10:54 am
1 stop4h 54m
$437
TallahasseeChicago
TLH - MDW
TLHMDW
Tallahassee
ke 7/22
7:01 pm-10:15 pm
1 stop4h 14m
Chicago Midway
ma 7/27
6:05 am-11:21 am
1 stop4h 16m
$437
TallahasseeChicago
TLH - MDW
TLHMDW
Tallahassee
ma 5/25
6:15 am-10:00 am
1 stop4h 45m
Chicago Midway
ti 6/9
6:05 am-11:24 am
1 stop4h 19m
$437
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 April.
| 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, November is the cheapest month in which you can book a flight from Tallahassee to Chicago (average of $66). Flying from Tallahassee to Chicago in January is currently the most expensive (average of $487). 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?
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 huhtikuu 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.
Comfort
7.9
Crew
8.5
Entertainment
7.8
Boarding
8.1
Food
7.2
Overall
7.9
Reviews
1 / 20
6.0
Goodpilar,May 2025
RSW - ATL
Comfort
7.9
Crew
8.5
Entertainment
7.8
Boarding
8.1
Food
7.2
Overall
7.9
Reviews
1 / 20
6.0
Goodpilar,May 2025
RSW - ATL
Comfort
7.9
Crew
8.5
Entertainment
7.8
Boarding
8.1
Food
7.2
Overall
7.9
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 locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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Other flights to Chicago
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Tallahassee and Chicago flights
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Other flights from Tallahassee
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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 huhtikuu 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$158 | Average$446 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$341 | Average$486 | FlexibilityNo cancel fee | On-time71% |