$240+ 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 5/2. Fares are subject to change and may not be available on all flights or dates of travel.
TLH — CHI
May 11 — May 181
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 April 11, 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 April 11, 2026.
This Delta deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” 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 5/96:15 am
TLH
- MDW
1 stop4h 44m
Delta
Sat 5/1610:45 am
MDW
- TLH
1 stop4h 46m
Delta
Deal found 4/10![Delta logo]()
$357
This American Airlines deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” 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 5/912:11 pm
TLH
- ORD
1 stop5h 10m
American Airlines
Sat 5/164:00 pm
ORD
- TLH
1 stop5h 21m
American Airlines
Deal found 4/10![American Airlines logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 8/2312:47 pm
TLH
- ORD
1 stop12h 47m
Multiple Airlines
Fri 8/289:46 pm
ORD
- TLH
2 stops32h 42m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$376
This Kiwi.com deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” 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 8/1312:47 pm
TLH
- ORD
1 stop11h 21m
Multiple Airlines
Sun 8/169:34 pm
ORD
- TLH
2 stops34h 24m
Multiple Airlines
Deal found 4/10![Multiple Airlines logo]()
$379
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/205:23 pm
TLH
- MDW
1 stop4h 46m
Delta
Tue 5/265:12 pm
MDW
- TLH
1 stop16h 53m
Delta
Deal found 4/9![Delta logo]()
$381
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/207:07 pm
TLH
- ORD
1 stop5h 52m
Delta
Tue 6/25:30 am
ORD
- TLH
1 stop7h 27m
Delta
Deal found 4/9![Delta logo]()
$381
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/195:23 pm
TLH
- ORD
1 stop6h 04m
Delta
Tue 5/265:30 am
ORD
- TLH
1 stop4h 35m
Delta
Deal found 4/9![Delta logo]()
$392
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/205:23 pm
TLH
- MDW
1 stop4h 46m
Delta
Thu 6/46:23 am
MDW
- TLH
1 stop10h 58m
Delta
Deal found 4/9![Delta logo]()
$393
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/205:23 pm
TLH
- ORD
1 stop5h 30m
Delta
Mon 6/17:45 pm
ORD
- TLH
1 stop14h 20m
Delta
Deal found 4/9![Delta logo]()
$393
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/205:23 pm
TLH
- MDW
1 stop4h 46m
Delta
Sun 5/316:23 am
MDW
- TLH
1 stop6h 34m
Delta
Deal found 4/9![Delta logo]()
$402
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/1911:51 am
TLH
- ORD
1 stop6h 05m
Delta
Sun 5/315:30 am
ORD
- TLH
1 stop4h 35m
Delta
Deal found 4/9![Delta logo]()
$402
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/187:07 pm
TLH
- MDW
1 stop15h 53m
Delta
Fri 5/296:23 am
MDW
- TLH
1 stop10h 58m
Delta
Deal found 4/9![Delta logo]()
$405
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 April 11, 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 April 11, 2026.
This Delta deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” 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 5/96:15 am
TLH
- MDW
1 stop4h 44m
Delta
Sat 5/1610:45 am
MDW
- TLH
1 stop4h 46m
Delta
Deal found 4/10![Delta logo]()
$357
This American Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/87:54 pm
TLH
- ORD
1 stop5h 00m
American Airlines
Mon 5/115:20 pm
ORD
- TLH
1 stop5h 36m
American Airlines
Deal found 4/6![American Airlines logo]()
$447
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/205:23 pm
TLH
- MDW
1 stop4h 46m
Delta
Mon 6/16:23 am
MDW
- TLH
1 stop6h 34m
Delta
Deal found 4/9![Delta logo]()
$402
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/187:07 pm
TLH
- MDW
1 stop15h 53m
Delta
Wed 5/275:12 pm
MDW
- TLH
1 stop15h 13m
Delta
Deal found 4/9![Delta logo]()
$405
This Delta deal was found by Cheapflights users on 4/11. Clicking the “Pick Dates” 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 5/248:29 am
TLH
- MDW
1 stop7h 57m
Delta
Sun 5/316:23 am
MDW
- TLH
1 stop6h 34m
Delta
Deal found 4/11![Delta logo]()
$426
This Delta deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” 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 6/107:01 pm
TLH
- MDW
1 stop4h 16m
Delta
Sat 6/136:05 am
MDW
- TLH
1 stop4h 19m
Delta
Deal found 4/10![Delta logo]()
$437
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/86:15 am
TLH
- MDW
1 stop4h 45m
Delta
Mon 5/1110:59 am
MDW
- TLH
1 stop4h 32m
Delta
Deal found 4/6![Delta logo]()
$447
This KAYAK deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:30 am
TLH
- ORD
1 stop7h 06m
American Airlines
Wed 4/2211:15 am
ORD
- TLH
1 stop4h 50m
American Airlines
Deal found 4/6![American Airlines logo]()
$666
This Delta deal was found by Cheapflights users on 4/11. Clicking the “Pick Dates” 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 5/235:23 pm
TLH
- MDW
1 stop4h 46m
Delta
Sun 5/316:23 am
MDW
- TLH
1 stop6h 34m
Delta
Deal found 4/11![Delta logo]()
$447
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 6/1312:11 pm
TLH
- ORD
1 stop5h 45m
Delta
Mon 6/155:30 am
ORD
- TLH
1 stop4h 54m
Delta
Deal found 4/9![Delta logo]()
$447
This Delta deal was found by Cheapflights users on 4/11. Clicking the “Pick Dates” 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 5/265:23 pm
TLH
- MDW
1 stop4h 46m
Delta
Tue 6/25:15 pm
MDW
- TLH
1 stop16h 50m
Delta
Deal found 4/11![Delta logo]()
$452
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 4/256:44 pm
TLH
- MDW
1 stop4h 44m
Delta
Tue 4/286:00 am
MDW
- TLH
1 stop5h 11m
Delta
Deal found 4/6![Delta logo]()
$455
This Delta deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 8/143:40 pm
TLH
- ORD
1 stop6h 40m
Delta
Mon 8/171:15 pm
ORD
- TLH
1 stop6h 34m
Delta
Deal found 4/7![Delta logo]()
$467
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 6/1312:11 pm
TLH
- MDW
1 stop4h 29m
Delta
Mon 6/156:05 am
MDW
- TLH
1 stop4h 19m
Delta
Deal found 4/6![Delta logo]()
$473
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 6/115:41 pm
TLH
- ORD
1 stop5h 32m
Delta
Mon 6/155:30 am
ORD
- TLH
1 stop4h 54m
Delta
Deal found 4/6![Delta logo]()
$473
This Delta deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 6/47:07 pm
TLH
- ORD
1 stop5h 52m
Delta
Mon 6/85:30 am
ORD
- TLH
1 stop4h 54m
Delta
Deal found 4/7![Delta logo]()
$559
Last-minute flights from Tallahassee to ChicagoDiscover last-minute flight deals from Tallahassee to Chicago. Data last updated April 11, 2026 and is based on user searches.
Discover last-minute flight deals from Tallahassee to Chicago. Data last updated April 11, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” 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 5/96:15 am
TLH
- MDW
1 stop4h 44m
Delta
Sat 5/1610:45 am
MDW
- TLH
1 stop4h 46m
Delta
Deal found 4/10![Delta logo]()
$357
This American Airlines deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” 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 5/912:11 pm
TLH
- ORD
1 stop5h 10m
American Airlines
Sat 5/164:00 pm
ORD
- TLH
1 stop5h 21m
American Airlines
Deal found 4/10![American Airlines logo]()
$357
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/187:07 pm
TLH
- MDW
1 stop15h 53m
Delta
Tue 5/265:12 pm
MDW
- TLH
1 stop16h 53m
Delta
Deal found 4/9![Delta logo]()
$405
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/195:23 pm
TLH
- ORD
1 stop6h 04m
Delta
Tue 5/265:30 am
ORD
- TLH
1 stop4h 35m
Delta
Deal found 4/9![Delta logo]()
$392
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/192:43 pm
TLH
- ORD
1 stop4h 58m
Delta
Fri 5/2911:26 am
ORD
- TLH
1 stop4h 05m
Delta
Deal found 4/9![Delta logo]()
$402
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/205:23 pm
TLH
- MDW
1 stop4h 46m
Delta
Wed 6/36:23 am
MDW
- TLH
1 stop9h 08m
Delta
Deal found 4/9![Delta logo]()
$381
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/207:07 pm
TLH
- ORD
1 stop5h 52m
Delta
Tue 6/25:30 am
ORD
- TLH
1 stop7h 27m
Delta
Deal found 4/9![Delta logo]()
$381
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/205:23 pm
TLH
- MDW
1 stop4h 46m
Delta
Thu 6/46:23 am
MDW
- TLH
1 stop10h 58m
Delta
Deal found 4/9![Delta logo]()
$393
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/202:43 pm
TLH
- ORD
1 stop4h 58m
Delta
Thu 5/285:30 am
ORD
- TLH
1 stop14h 13m
Delta
Deal found 4/9![Delta logo]()
$393
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/205:23 pm
TLH
- MDW
1 stop4h 46m
Delta
Mon 6/16:23 am
MDW
- TLH
1 stop6h 34m
Delta
Deal found 4/9![Delta logo]()
$402
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/235:23 pm
TLH
- ORD
1 stop16h 16m
Delta
Tue 6/25:30 am
ORD
- TLH
1 stop7h 27m
Delta
Deal found 4/9![Delta logo]()
$405
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/268:05 am
TLH
- MDW
1 stop4h 51m
Delta
Wed 6/310:59 am
MDW
- TLH
1 stop10h 43m
Delta
Deal found 4/9![Delta logo]()
$416
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 April 11, 2026.
Search for one-way flight options from Tallahassee to Chicago. Find affordable one-way fares based on user searches. Data last updated April 11, 2026.
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/25:34 am
TLH
- ORD
1 stop4h 03m
Delta
Deal found 4/6![Delta logo]()
$240
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/25:34 am
TLH
- MDW
1 stop5h 40m
Delta
Deal found 4/6![Delta logo]()
$290
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 6/117:01 pm
TLH
- MDW
1 stop4h 16m
Delta
Deal found 4/6![Delta logo]()
$328
This American Airlines deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” 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 5/211:37 pm
TLH
- ORD
1 stop7h 11m
American Airlines
Deal found 4/10![American Airlines logo]()
$328
This American Airlines deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/27:54 pm
TLH
- ORD
1 stop5h 00m
American Airlines
Deal found 4/9![American Airlines logo]()
$350
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/17:05 pm
TLH
- MDW
1 stop4h 23m
Delta
Deal found 4/6![Delta logo]()
$358
This American Airlines deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 5/15:33 pm
TLH
- ORD
1 stop7h 21m
American Airlines
Deal found 4/7![American Airlines logo]()
$358
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 4/307:05 pm
TLH
- MDW
1 stop4h 23m
Delta
Deal found 4/6![Delta logo]()
$368
This American Airlines deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 4/216:09 am
TLH
- ORD
1 stop5h 55m
American Airlines
Deal found 4/7![American Airlines logo]()
$388
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/35:34 am
TLH
- MDW
1 stop5h 22m
Delta
Deal found 4/6![Delta logo]()
$410
This Delta deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 5/35:34 am
TLH
- ORD
1 stop4h 03m
Delta
Deal found 4/7![Delta logo]()
$410
This American Airlines deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 5/37:54 pm
TLH
- ORD
1 stop5h 00m
American Airlines
Deal found 4/7![American Airlines logo]()
$678
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 April 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $357 (Delta) |
One-way from | $240 (Delta) |
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 April 11, 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 - MDW
TLHMDW
Tallahassee
Sat 5/9
6:15 am-9:59 am
1 stop4h 44m
Chicago Midway
Sat 5/16
10:45 am-4:31 pm
1 stop4h 46m
$357
TallahasseeChicago
TLH - MDW
TLHMDW
Tallahassee
Wed 5/20
5:23 pm-9:09 pm
1 stop4h 46m
Chicago Midway
Mon 6/1
6:23 am-1:57 pm
1 stop6h 34m
$402
TallahasseeChicago
TLH - MDW
TLHMDW
Tallahassee
Mon 5/18
7:07 pm-10:00 am
1 stop15h 53m
Chicago Midway
Wed 5/27
5:12 pm-9:25 am
1 stop15h 13m
$405
TallahasseeChicago
TLH - MDW
TLHMDW
Tallahassee
Sun 5/24
8:29 am-3:26 pm
1 stop7h 57m
Chicago Midway
Sun 5/31
6:23 am-1:57 pm
1 stop6h 34m
$426
Quickest round-trip
TallahasseeChicago
TLH - MDW
TLHMDW
Tallahassee
Wed 6/10
7:01 pm-10:17 pm
1 stop4h 16m
Chicago Midway
Sat 6/13
6:05 am-11:24 am
1 stop4h 19m
$437
TallahasseeChicago
TLH - ORD
TLHORD
Tallahassee
Fri 5/8
7:54 pm-11:54 pm
1 stop5h 00m
Chicago O'Hare Intl
Mon 5/11
5:20 pm-11:56 pm
1 stop5h 36m
$447
TallahasseeChicago
TLH - MDW
TLHMDW
Tallahassee
Fri 5/8
6:15 am-10:00 am
1 stop4h 45m
Chicago Midway
Mon 5/11
10:59 am-4:31 pm
1 stop4h 32m
$447
TallahasseeChicago
TLH - MDW
TLHMDW
Tallahassee
Sat 5/23
5:23 pm-9:09 pm
1 stop4h 46m
Chicago Midway
Sun 5/31
6:23 am-1:57 pm
1 stop6h 34m
$447
TallahasseeChicago
TLH - ORD
TLHORD
Tallahassee
Sat 6/13
12:11 pm-4:56 pm
1 stop5h 45m
Chicago O'Hare Intl
Mon 6/15
5:30 am-11:24 am
1 stop4h 54m
$447
TallahasseeChicago
TLH - MDW
TLHMDW
Tallahassee
Tue 5/26
5:23 pm-9:09 pm
1 stop4h 46m
Chicago Midway
Tue 6/2
5:15 pm-11:05 am
1 stop16h 50m
$452
Showing 1-10 of 31 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-MDW
TLH-ORD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Tallahassee to Chicago
TLH-CHI
TLH-MDW
TLH-ORD
What is the cheapest month to book a flight from Tallahassee to Chicago?
Currently, December is the cheapest month in which you can book a flight from Tallahassee to Chicago (average of $158). 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.
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 April 11, 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.
Food
7.2
Crew
8.5
Entertainment
7.8
Overall
7.9
Boarding
8.1
Comfort
7.9
Reviews
1 / 20
6.0
Goodpilar,May 2025
RSW - ATL
Food
7.2
Crew
8.5
Entertainment
7.8
Overall
7.9
Boarding
8.1
Comfort
7.9
Reviews
1 / 20
6.0
Goodpilar,May 2025
RSW - ATL
Food
7.2
Crew
8.5
Entertainment
7.8
Overall
7.9
Boarding
8.1
Comfort
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 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 April 11, 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 April 11, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Tallahassee to Chicago
Discover the top 2 airlines that operate flights from Tallahassee to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$158 | Average$509 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$341 | Average$486 | FlexibilityNo cancel fee | On-time71% |