$190+ 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 8/23. Fares are subject to change and may not be available on all flights or dates of travel.
TLH — CHI
Jun 25 — Jul 21
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 May 26, 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 May 26, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/28:08 am
TLH
- ORD
2 stops12h 42m
Multiple Airlines
Mon 7/68:05 am
ORD
- TLH
1 stop23h 53m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$346
This Delta deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 9/38:07 am
TLH
- MDW
1 stop4h 44m
Delta
Wed 9/910:35 am
MDW
- TLH
1 stop5h 00m
Delta
Deal found 5/26![Delta logo]()
$437
This Delta deal was found by Cheapflights users on 5/24. 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.
Thu 9/37:01 pm
TLH
- ORD
1 stop6h 01m
Delta
Wed 9/95:30 am
ORD
- TLH
1 stop3h 56m
Delta
Deal found 5/24![Delta logo]()
$437
This Delta deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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
TLH
- MDW
1 stop5h 51m
Delta
Sat 9/124:30 pm
MDW
- TLH
1 stop4h 51m
Delta
Deal found 5/26![Delta logo]()
$447
This Delta deal was found by Cheapflights users on 5/23. 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.
Sat 9/52:25 pm
TLH
- ORD
1 stop7h 25m
Delta
Sat 9/123:35 pm
ORD
- TLH
1 stop5h 46m
Delta
Deal found 5/23![Delta logo]()
$447
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:10 pm
TLH
- MDW
1 stop5h 35m
Delta
Sun 11/86:00 am
MDW
- TLH
1 stop5h 05m
Delta
Deal found 5/21![Delta logo]()
$483
This Delta deal was found by Cheapflights users on 5/21. 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 11/57:15 pm
TLH
- ORD
1 stop5h 35m
Delta
Sun 11/85:30 am
ORD
- TLH
1 stop5h 35m
Delta
Deal found 5/21![Delta logo]()
$483
This American Airlines deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” 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 6/117:00 am
TLH
- ORD
1 stop6h 57m
American Airlines
Mon 6/152:24 pm
ORD
- TLH
1 stop8h 35m
American Airlines
Deal found 5/25![American Airlines logo]()
$487
This American Airlines deal was found by Cheapflights users on 5/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/27:50 pm
TLH
- ORD
1 stop5h 11m
American Airlines
Sun 7/55:07 am
ORD
- TLH
1 stop5h 27m
American Airlines
Deal found 5/24![American Airlines logo]()
$499
This Delta deal was found by Cheapflights users on 5/22. 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 6/65:23 pm
TLH
- MDW
1 stop4h 46m
Delta
Wed 6/106:00 am
MDW
- TLH
1 stop4h 24m
Delta
Deal found 5/22![Delta logo]()
$513
This American Airlines deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/63:27 pm
TLH
- ORD
1 stop7h 06m
American Airlines
Wed 6/104:05 pm
ORD
- TLH
1 stop6h 54m
American Airlines
Deal found 5/22![American Airlines logo]()
$513
This Delta deal was found by Cheapflights users on 5/21. 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 6/47:07 pm
TLH
- ORD
1 stop5h 52m
Delta
Wed 6/105:30 am
ORD
- TLH
1 stop4h 54m
Delta
Deal found 5/21![Delta logo]()
$520
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 May 26, 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 May 26, 2026.
This Delta deal was found by Cheapflights users on 5/24. 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.
Thu 9/37:01 pm
TLH
- MDW
1 stop4h 35m
Delta
Wed 9/910:35 am
MDW
- TLH
1 stop5h 00m
Delta
Deal found 5/24![Delta logo]()
$437
This American Airlines deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 6/197:48 pm
TLH
- ORD
1 stop5h 10m
American Airlines
Sun 6/215:00 am
ORD
- TLH
1 stop7h 09m
American Airlines
Deal found 5/26![American Airlines logo]()
$632
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:00 pm
TLH
- MDW
1 stop5h 36m
Delta
Sat 8/296:05 am
MDW
- TLH
1 stop6h 22m
Delta
Deal found 5/21![Delta logo]()
$437
This Delta deal was found by Cheapflights users on 5/21. 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.
Tue 6/236:30 am
TLH
- MDW
1 stop4h 39m
Delta
Sat 6/274:25 pm
MDW
- TLH
1 stop5h 28m
Delta
Deal found 5/21![Delta logo]()
$437
This Delta deal was found by Cheapflights users on 5/23. 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.
Wed 7/86:30 am
TLH
- MDW
1 stop6h 26m
Delta
Sat 7/116:00 am
MDW
- TLH
1 stop6h 20m
Delta
Deal found 5/23![Delta logo]()
$437
This Delta deal was found by Cheapflights users on 5/22. 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 8/148:07 am
TLH
- MDW
1 stop4h 44m
Delta
Mon 8/1710:54 am
MDW
- TLH
1 stop5h 17m
Delta
Deal found 5/22![Delta logo]()
$447
This Delta deal was found by Cheapflights users on 5/22. 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 9/55:10 pm
TLH
- MDW
1 stop5h 36m
Delta
Sat 9/124:30 pm
MDW
- TLH
1 stop4h 51m
Delta
Deal found 5/22![Delta logo]()
$447
This Delta deal was found by Cheapflights users on 5/23. 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.
Fri 7/35:41 pm
TLH
- ORD
1 stop7h 18m
Delta
Mon 7/66:35 am
ORD
- TLH
1 stop7h 06m
Delta
Deal found 5/23![Delta logo]()
$447
This Delta deal was found by Cheapflights users on 5/23. 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.
Sat 9/52:25 pm
TLH
- ORD
1 stop7h 25m
Delta
Sat 9/123:35 pm
ORD
- TLH
1 stop5h 46m
Delta
Deal found 5/23![Delta logo]()
$447
This Delta deal was found by Cheapflights users on 5/21. 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 6/187:01 pm
TLH
- ORD
1 stop5h 58m
Delta
Mon 6/228:08 am
ORD
- TLH
1 stop5h 33m
Delta
Deal found 5/21![Delta logo]()
$543
This Delta deal was found by Cheapflights users on 5/21. 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 6/216:30 am
TLH
- ORD
1 stop4h 43m
Delta
Sun 6/213:39 pm
ORD
- TLH
1 stop6h 14m
Delta
Deal found 5/21![Delta logo]()
$917
This Delta deal was found by Cheapflights users on 5/22. 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 9/37:15 pm
TLH
- ORD
1 stop5h 42m
Delta
Wed 9/97:10 am
ORD
- TLH
2 stops8h 25m
Delta
Deal found 5/22![Delta logo]()
$1,080
This Delta deal was found by Cheapflights users on 5/21. 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 11/57:15 pm
TLH
- ORD
1 stop5h 35m
Delta
Sun 11/87:05 am
ORD
- TLH
2 stops8h 29m
Delta
Deal found 5/21![Delta logo]()
$1,080
This Delta deal was found by Cheapflights users on 5/22. 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 9/197:30 am
TLH
- ORD
2 stops10h 06m
Delta
Fri 9/251:15 pm
ORD
- TLH
1 stop6h 34m
Delta
Deal found 5/22![Delta logo]()
$1,080
Last-minute flights from Tallahassee to ChicagoDiscover last-minute flight deals from Tallahassee to Chicago. Data last updated May 26, 2026 and is based on user searches.
Discover last-minute flight deals from Tallahassee to Chicago. Data last updated May 26, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 5/23. 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 5/287:07 pm
TLH
- ORD
1 stop5h 52m
Delta
Thu 6/411:26 am
ORD
- TLH
1 stop4h 05m
Delta
Deal found 5/23![Delta logo]()
$540
This Delta deal was found by Cheapflights users on 5/21. 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 6/47:07 pm
TLH
- ORD
1 stop5h 52m
Delta
Wed 6/105:30 am
ORD
- TLH
1 stop4h 54m
Delta
Deal found 5/21![Delta logo]()
$520
This American Airlines deal was found by Cheapflights users on 5/21. 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 6/57:48 pm
TLH
- ORD
1 stop5h 10m
American Airlines
Mon 6/84:05 pm
ORD
- TLH
1 stop6h 54m
American Airlines
Deal found 5/21![American Airlines logo]()
$527
This Delta deal was found by Cheapflights users on 5/24. 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.
Fri 6/55:23 pm
TLH
- ORD
1 stop5h 30m
Delta
Wed 6/105:30 am
ORD
- TLH
1 stop4h 54m
Delta
Deal found 5/24![Delta logo]()
$571
This Delta deal was found by Cheapflights users on 5/22. 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 6/65:23 pm
TLH
- MDW
1 stop4h 46m
Delta
Wed 6/106:00 am
MDW
- TLH
1 stop4h 24m
Delta
Deal found 5/22![Delta logo]()
$513
This American Airlines deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/63:27 pm
TLH
- ORD
1 stop7h 06m
American Airlines
Wed 6/104:05 pm
ORD
- TLH
1 stop6h 54m
American Airlines
Deal found 5/22![American Airlines logo]()
$513
This American Airlines deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/117:00 am
TLH
- ORD
1 stop5h 34m
American Airlines
Mon 6/154:05 pm
ORD
- TLH
1 stop6h 54m
American Airlines
Deal found 5/22![American Airlines logo]()
$447
This Delta deal was found by Cheapflights users on 5/21. 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 6/187:01 pm
TLH
- ORD
1 stop5h 58m
Delta
Mon 6/228:08 am
ORD
- TLH
1 stop5h 33m
Delta
Deal found 5/21![Delta logo]()
$543
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/195:41 pm
TLH
- MDW
1 stop5h 36m
Delta
Mon 6/226:00 am
MDW
- TLH
1 stop4h 24m
Delta
Deal found 5/21![Delta logo]()
$447
This Delta deal was found by Cheapflights users on 5/21. 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.
Tue 6/236:30 am
TLH
- MDW
1 stop4h 39m
Delta
Sat 6/274:25 pm
MDW
- TLH
1 stop5h 28m
Delta
Deal found 5/21![Delta logo]()
$437
This Delta deal was found by Cheapflights users on 5/21. 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.
Tue 6/233:26 pm
TLH
- ORD
1 stop6h 06m
Delta
Sat 6/2711:23 am
ORD
- TLH
1 stop4h 24m
Delta
Deal found 5/21![Delta logo]()
$437
This American Airlines deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” 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 6/267:48 pm
TLH
- ORD
1 stop5h 10m
American Airlines
Sun 6/285:10 am
ORD
- TLH
1 stop5h 10m
American Airlines
Deal found 5/25![American Airlines logo]()
$499
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 May 26, 2026.
Search for one-way flight options from Tallahassee to Chicago. Find affordable one-way fares based on user searches. Data last updated May 26, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/24. 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 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 stop24h 38m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$190
This Delta deal was found by Cheapflights users on 5/22. 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.
Mon 7/67:01 pm
TLH
- MDW
1 stop16h 04m
Delta
Deal found 5/22![Delta logo]()
$313
This Delta deal was found by Cheapflights users on 5/22. 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.
Mon 7/65:41 pm
TLH
- ORD
1 stop19h 53m
Delta
Deal found 5/22![Delta logo]()
$313
This Delta deal was found by Cheapflights users on 5/24. 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.
Fri 7/35:41 pm
TLH
- MDW
1 stop5h 36m
Delta
Deal found 5/24![Delta logo]()
$328
This American Airlines deal was found by Cheapflights users on 5/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/39:32 am
TLH
- ORD
1 stop6h 24m
American Airlines
Deal found 5/24![American Airlines logo]()
$328
This American Airlines deal was found by Cheapflights users on 5/23. 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.
Tue 6/307:00 am
TLH
- ORD
1 stop6h 57m
American Airlines
Deal found 5/23![American Airlines logo]()
$478
This Delta deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:15 am
TLH
- MDW
1 stop4h 45m
Delta
Deal found 5/22![Delta logo]()
$488
This American Airlines deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/313:27 pm
TLH
- ORD
1 stop7h 10m
American Airlines
Deal found 5/21![American Airlines logo]()
$488
This American Airlines deal was found by Cheapflights users on 5/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/412:05 pm
TLH
- ORD
2 stops6h 28m
American Airlines
Deal found 5/24![American Airlines logo]()
$637
This Delta deal was found by Cheapflights users on 5/24. 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.
Fri 7/37:00 am
TLH
- ORD
2 stops10h 30m
Delta
Deal found 5/24![Delta logo]()
$817
This Delta deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” 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 7/106:30 am
TLH
- MDW
2 stops7h 08m
Delta
Deal found 5/25![Delta logo]()
$837
This Delta deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” 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 7/106:30 am
TLH
- ORD
2 stops10h 53m
Delta
Deal found 5/25![Delta logo]()
$837
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 May 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $346 (Kiwi.com) |
One-way from | $190 (Kiwi.com) |
Popular in | January |
Cheapest in | September |
Average price | $406 |
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 May 26, 2026.
Use the filters below to find and compare flights from Tallahassee to Chicago that are best for you.
Fly from
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Route
Depart
Return
Cheapest round-trip
Quickest round-trip
TallahasseeChicago
TLH - MDW
TLHMDW
Tallahassee
Thu 9/3
7:01 pm-10:36 pm
1 stop4h 35m
Chicago Midway
Wed 9/9
10:35 am-4:35 pm
1 stop5h 00m
$437
TallahasseeChicago
TLH - MDW
TLHMDW
Tallahassee
Wed 8/26
6:00 pm-10:36 pm
1 stop5h 36m
Chicago Midway
Sat 8/29
6:05 am-1:27 pm
1 stop6h 22m
$437
TallahasseeChicago
TLH - MDW
TLHMDW
Tallahassee
Tue 6/23
6:30 am-10:09 am
1 stop4h 39m
Chicago Midway
Sat 6/27
4:25 pm-10:53 pm
1 stop5h 28m
$437
TallahasseeChicago
TLH - MDW
TLHMDW
Tallahassee
Wed 7/8
6:30 am-11:56 am
1 stop6h 26m
Chicago Midway
Sat 7/11
6:00 am-1:20 pm
1 stop6h 20m
$437
TallahasseeChicago
TLH - MDW
TLHMDW
Tallahassee
Fri 8/14
8:07 am-11:51 am
1 stop4h 44m
Chicago Midway
Mon 8/17
10:54 am-5:11 pm
1 stop5h 17m
$447
TallahasseeChicago
TLH - MDW
TLHMDW
Tallahassee
Sat 9/5
5:10 pm-9:46 pm
1 stop5h 36m
Chicago Midway
Sat 9/12
4:30 pm-10:21 pm
1 stop4h 51m
$447
TallahasseeChicago
TLH - ORD
TLHORD
Tallahassee
Fri 7/3
5:41 pm-11:59 pm
1 stop7h 18m
Chicago O'Hare Intl
Mon 7/6
6:35 am-2:41 pm
1 stop7h 06m
$447
TallahasseeChicago
TLH - ORD
TLHORD
Tallahassee
Sat 9/5
2:25 pm-8:50 pm
1 stop7h 25m
Chicago O'Hare Intl
Sat 9/12
3:35 pm-10:21 pm
1 stop5h 46m
$447
TallahasseeChicago
TLH - ORD
TLHORD
Tallahassee
Thu 6/18
7:01 pm-11:59 pm
1 stop5h 58m
Chicago O'Hare Intl
Mon 6/22
8:08 am-2:41 pm
1 stop5h 33m
$543
TallahasseeChicago
TLH - ORD
TLHORD
Tallahassee
Fri 6/19
7:48 pm-11:58 pm
1 stop5h 10m
Chicago O'Hare Intl
Sun 6/21
5:00 am-1:09 pm
1 stop7h 09m
$632
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 May.
| 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, 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 May 26, 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.
Overall
7.9
Comfort
7.8
Crew
8.5
Entertainment
7.8
Boarding
8.1
Food
7.2
Reviews
1 / 20
6.0
Goodpilar,May 2025
RSW - ATL
Overall
7.9
Comfort
7.8
Crew
8.5
Entertainment
7.8
Boarding
8.1
Food
7.2
Reviews
1 / 20
6.0
Goodpilar,May 2025
RSW - ATL
Overall
7.9
Comfort
7.8
Crew
8.5
Entertainment
7.8
Boarding
8.1
Food
7.2
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
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on May 26, 2026.
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Tallahassee and Chicago flights
Browse other Tallahassee and Chicago flight options. Last updated on May 26, 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 May 26, 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 May 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$158 | Average$472 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$316 | Average$501 | FlexibilityNo cancel fee | On-time71% |