$101+ 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 9/22. Fares are subject to change and may not be available on all flights or dates of travel.
TLH — CHI
Sep 23 — Sep 301
Round-trip
1 adult, Economy
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Find cheap flights from Tallahassee to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Tallahassee to Chicago
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Cheapest flights from Tallahassee to ChicagoExplore the most affordable flight options available from Tallahassee to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 24, 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 August 24, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/221:07 pm -
2 stops12h 19m
Mon 10/268:04 am -
1 stop25h 26m
Deal found 8/20![Multiple Airlines logo]()
$265
This Kiwi.com deal was found by Cheapflights users on 8/21. 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.
Thu 10/221:07 pm -
2 stops12h 19m
Sat 10/248:04 am -
1 stop22h 41m
Deal found 8/21![Multiple Airlines logo]()
$271
This Kiwi.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/210:10 am -
2 stops12h 29m
Mon 10/57:11 am -
1 stop26h 19m
Deal found 8/23![Multiple Airlines logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 8/19. 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.
Sun 11/18:25 am -
2 stops25h 52m
Sat 11/78:00 am -
1 stop22h 45m
Deal found 8/19![Multiple Airlines logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 8/19. 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.
Thu 9/248:25 am -
2 stops10h 58m
Mon 9/287:11 am -
1 stop26h 19m
Deal found 8/19![Multiple Airlines logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 8/21. 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.
Thu 9/178:25 am -
2 stops10h 58m
Mon 9/217:11 am -
1 stop26h 19m
Deal found 8/21![Multiple Airlines logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 9/201:07 pm -
1 stop26h 38m
Tue 9/297:25 am -
2 stops47h 20m
Deal found 8/20![Multiple Airlines logo]()
$376
This Kiwi.com deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/88:25 am -
2 stops11h 06m
Sun 10/118:04 am -
1 stop24h 26m
Deal found 8/22![Multiple Airlines logo]()
$385
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/39:05 am -
1 stop14h 39m
Tue 10/612:49 pm -
1 stop5h 56m
Deal found 8/24![Delta logo]()
$442
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/39:05 am -
1 stop7h 19m
Thu 10/810:59 am -
1 stop8h 40m
Deal found 8/24![Delta logo]()
$447
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/39:05 am -
1 stop14h 39m
Sun 10/46:05 am -
1 stop4h 10m
Deal found 8/24![Delta logo]()
$452
This Delta deal was found by Cheapflights users on 8/19. 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 11/57:00 pm -
1 stop4h 33m
Sun 11/86:04 am -
1 stop4h 05m
Deal found 8/19![Delta logo]()
$457
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 August 24, 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 August 24, 2026.
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/39:05 am -
1 stop8h 32m
Tue 10/61:23 pm -
1 stop5h 22m
Deal found 8/24![Delta logo]()
$442
This American Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/87:33 pm -
1 stop6h 05m
Sun 10/115:00 am -
1 stop7h 16m
Deal found 8/23![American Airlines logo]()
$509
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/39:05 am -
1 stop8h 32m
Mon 10/56:40 am -
1 stop11h 14m
Deal found 8/24![Delta logo]()
$447
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:00 pm -
1 stop4h 33m
Sun 10/256:04 am -
1 stop4h 10m
Deal found 8/23![Delta logo]()
$457
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/57:00 pm -
1 stop4h 33m
Sun 11/86:04 am -
1 stop4h 05m
Deal found 8/22![Delta logo]()
$457
This Delta deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:00 pm -
1 stop5h 57m
Sat 10/245:27 am -
1 stop4h 49m
Deal found 8/21![Delta logo]()
$457
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/223:24 pm -
1 stop6h 14m
Sun 10/255:27 am -
1 stop4h 47m
Deal found 8/23![Delta logo]()
$457
This Delta deal was found by Cheapflights users on 8/22. 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 9/55:45 pm -
1 stop5h 51m
Sat 9/124:30 pm -
1 stop5h 18m
Deal found 8/22![Delta logo]()
$469
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:00 am -
1 stop5h 10m
Wed 9/96:05 am -
1 stop4h 10m
Deal found 8/23![Delta logo]()
$492
This Delta deal was found by Cheapflights users on 8/19. 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 9/245:53 pm -
1 stop5h 51m
Mon 9/286:05 am -
1 stop4h 10m
Deal found 8/19![Delta logo]()
$498
This Delta deal was found by Cheapflights users on 8/20. 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 9/36:00 pm -
1 stop5h 36m
Wed 9/96:05 am -
1 stop4h 10m
Deal found 8/20![Delta logo]()
$530
This Delta deal was found by Cheapflights users on 8/21. 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 9/36:00 pm -
1 stop6h 57m
Wed 9/910:44 am -
1 stop5h 18m
Deal found 8/21![Delta logo]()
$581
This Delta deal was found by Cheapflights users on 8/20. 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 11/188:00 am -
1 stop5h 20m
Fri 11/203:49 pm -
1 stop6h 15m
Deal found 8/20![Delta logo]()
$665
This Delta deal was found by Cheapflights users on 8/19. 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 11/512:00 pm -
2 stops9h 30m
Sun 11/85:27 am -
1 stop4h 42m
Deal found 8/19![Delta logo]()
$951
This Delta deal was found by Cheapflights users on 8/20. 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 9/52:25 pm -
1 stop5h 34m
Sat 9/1211:17 am -
2 stops7h 17m
Deal found 8/20![Delta logo]()
$963
Last-minute flights from Tallahassee to ChicagoDiscover last-minute flight deals from Tallahassee to Chicago. Data last updated August 24, 2026 and is based on user searches.
Discover last-minute flight deals from Tallahassee to Chicago. Data last updated August 24, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 8/19. 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 9/36:00 pm -
1 stop5h 36m
Wed 9/96:05 am -
1 stop4h 10m
Deal found 8/19![Delta logo]()
$507
This Delta deal was found by Cheapflights users on 8/19. 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 9/55:45 pm -
1 stop5h 51m
Sat 9/124:30 pm -
1 stop5h 18m
Deal found 8/19![Delta logo]()
$469
This American Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:05 am -
1 stop5h 55m
Sat 9/1210:05 am -
1 stop8h 28m
Deal found 8/19![American Airlines logo]()
$469
This Kiwi.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/612:47 pm -
1 stop25h 03m
Wed 9/97:11 am -
1 stop23h 34m
Deal found 8/23![Multiple Airlines logo]()
$466
This Kiwi.com deal was found by Cheapflights users on 8/21. 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.
Thu 9/178:25 am -
2 stops10h 58m
Mon 9/217:11 am -
1 stop26h 19m
Deal found 8/21![Multiple Airlines logo]()
$357
This American Airlines deal was found by Cheapflights users on 8/21. 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 9/186:54 pm -
1 stop4h 37m
Mon 9/216:59 am -
1 stop5h 33m
Deal found 8/21![American Airlines logo]()
$467
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 9/201:07 pm -
1 stop26h 38m
Tue 9/297:25 am -
2 stops47h 20m
Deal found 8/20![Multiple Airlines logo]()
$376
This Delta deal was found by Cheapflights users on 8/20. 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 9/205:53 pm -
1 stop5h 51m
Tue 9/295:11 pm -
1 stop4h 37m
Deal found 8/20![Delta logo]()
$447
This Delta deal was found by Cheapflights users on 8/20. 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 9/207:59 pm -
1 stop5h 00m
Tue 9/295:30 am -
1 stop4h 45m
Deal found 8/20![Delta logo]()
$447
This Kiwi.com deal was found by Cheapflights users on 8/19. 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.
Thu 9/248:25 am -
2 stops10h 58m
Mon 9/287:11 am -
1 stop26h 19m
Deal found 8/19![Multiple Airlines logo]()
$333
This American Airlines deal was found by Cheapflights users on 8/20. 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 9/246:54 pm -
1 stop4h 37m
Sun 9/278:42 am -
1 stop6h 35m
Deal found 8/20![American Airlines logo]()
$457
This Delta deal was found by Cheapflights users on 8/19. 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 9/245:53 pm -
1 stop5h 51m
Mon 9/286:05 am -
1 stop4h 10m
Deal found 8/19![Delta logo]()
$498
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 August 24, 2026.
Search for one-way flight options from Tallahassee to Chicago. Find affordable one-way fares based on user searches. Data last updated August 24, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/223:52 pm -
1 stop24h 28m
Deal found 8/23![Multiple Airlines logo]()
$101
This Kiwi.com deal was found by Cheapflights users on 8/21. 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.
Thu 9/248:25 am -
2 stops55h 55m
Deal found 8/21![Multiple Airlines logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 8/19. 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.
Thu 9/248:25 am -
2 stops10h 21m
Deal found 8/19![Multiple Airlines logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/108:25 am -
2 stops10h 21m
Deal found 8/23![Multiple Airlines logo]()
$237
This Delta deal was found by Cheapflights users on 8/22. 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 9/236:10 am -
1 stop17h 34m
Deal found 8/22![Delta logo]()
$298
This Delta deal was found by Cheapflights users on 8/22. 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 9/233:32 pm -
1 stop9h 27m
Deal found 8/22![Delta logo]()
$298
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:10 am -
1 stop17h 34m
Deal found 8/22![Delta logo]()
$308
This Delta deal was found by Cheapflights users on 8/19. 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 9/245:53 pm -
1 stop5h 51m
Deal found 8/19![Delta logo]()
$333
This Delta deal was found by Cheapflights users on 8/21. 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 9/277:59 pm -
1 stop5h 00m
Deal found 8/21![Delta logo]()
$333
This Delta deal was found by Cheapflights users on 8/20. 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 9/145:53 pm -
1 stop5h 51m
Deal found 8/20![Delta logo]()
$363
This American Airlines deal was found by Cheapflights users on 8/20. 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 9/1411:32 am -
1 stop7h 35m
Deal found 8/20![American Airlines logo]()
$363
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1010:17 am -
1 stop6h 07m
Deal found 8/23![Delta logo]()
$393
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 August 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $265 (Kiwi.com) |
One-way from | $101 (Kiwi.com) |
Popular in | October |
Cheapest in | September |
Average price | $529 |
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 August 24, 2026.
Use the filters below to find and compare flights from Tallahassee to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
TallahasseeChicago
TLH Tallahassee - ORD Chicago O'Hare Intl
TLHORD
Tallahassee
Sat 10/3
9:05 am-4:37 pm
1 stop8h 32m
Chicago O'Hare Intl
Tue 10/6
1:23 pm-7:45 pm
1 stop5h 22m
$442
TallahasseeChicago
TLH Tallahassee - ORD Chicago O'Hare Intl
TLHORD
Tallahassee
Sat 10/3
9:05 am-4:37 pm
1 stop8h 32m
Chicago O'Hare Intl
Mon 10/5
6:40 am-6:54 pm
1 stop11h 14m
$447
TallahasseeChicago
TLH Tallahassee - MDW Chicago Midway
TLHMDW
Tallahassee
Thu 10/22
7:00 pm-10:33 pm
1 stop4h 33m
Chicago Midway
Sun 10/25
6:04 am-11:14 am
1 stop4h 10m
$457
Quickest round-trip
TallahasseeChicago
TLH Tallahassee - MDW Chicago Midway
TLHMDW
Tallahassee
Thu 11/5
7:00 pm-10:33 pm
1 stop4h 33m
Chicago Midway
Sun 11/8
6:04 am-11:09 am
1 stop4h 05m
$457
TallahasseeChicago
TLH Tallahassee - ORD Chicago O'Hare Intl
TLHORD
Tallahassee
Thu 10/22
7:00 pm-11:57 pm
1 stop5h 57m
Chicago O'Hare Intl
Sat 10/24
5:27 am-11:16 am
1 stop4h 49m
$457
TallahasseeChicago
TLH Tallahassee - ORD Chicago O'Hare Intl
TLHORD
Tallahassee
Thu 10/22
3:24 pm-8:38 pm
1 stop6h 14m
Chicago O'Hare Intl
Sun 10/25
5:27 am-11:14 am
1 stop4h 47m
$457
TallahasseeChicago
TLH Tallahassee - MDW Chicago Midway
TLHMDW
Tallahassee
Sat 9/5
5:45 pm-10:36 pm
1 stop5h 51m
Chicago Midway
Sat 9/12
4:30 pm-10:48 pm
1 stop5h 18m
$469
TallahasseeChicago
TLH Tallahassee - MDW Chicago Midway
TLHMDW
Tallahassee
Sun 9/6
6:00 am-10:10 am
1 stop5h 10m
Chicago Midway
Wed 9/9
6:05 am-11:15 am
1 stop4h 10m
$492
TallahasseeChicago
TLH Tallahassee - MDW Chicago Midway
TLHMDW
Tallahassee
Thu 9/24
5:53 pm-10:44 pm
1 stop5h 51m
Chicago Midway
Mon 9/28
6:05 am-11:15 am
1 stop4h 10m
$498
TallahasseeChicago
TLH Tallahassee - ORD Chicago O'Hare Intl
TLHORD
Tallahassee
Thu 10/8
7:33 pm-12:38 am
1 stop6h 05m
Chicago O'Hare Intl
Sun 10/11
5:00 am-1:16 pm
1 stop7h 16m
$509
Showing 1-10 of 32 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 August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Tallahassee-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Tallahassee-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Tallahassee-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Tallahassee-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Tallahassee-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Tallahassee to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Tallahassee with our price prediction graph.
TLH-CHI
TLH-ORD
TLH-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Tallahassee to Chicago
TLH-CHI
TLH-ORD
TLH-MDW
What is the cheapest month to book a flight from Tallahassee to Chicago?
Currently, May is the cheapest month in which you can book a flight from Tallahassee to Chicago (average of $406). Flying from Tallahassee to Chicago in October is currently the most expensive (average of $650). 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 $435 and $524 in October.The cheapest round-trip price found within the last 5 days was $265 on Multiple Airlines (Oct 22-Oct 26).
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated August 24, 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.
Crew
8.5
Food
7.2
Boarding
8.1
Entertainment
7.8
Overall
7.8
Comfort
7.8
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Crew
8.5
Food
7.2
Boarding
8.1
Entertainment
7.8
Overall
7.8
Comfort
7.8
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Crew
8.5
Food
7.2
Boarding
8.1
Entertainment
7.8
Overall
7.8
Comfort
7.8
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Related info for your journey
Find useful and relevant information for your journey from Tallahassee to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Chicago
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Tallahassee and Chicago flights
Browse other Tallahassee and Chicago flight options. Last updated on August 24, 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 August 24, 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 7,457,451 searches. Data last updated August 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$158 | Average$456 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$398 | Average$501 | FlexibilityNo cancel fee | On-time71% |