$419+ Cheap flights from Tuscany to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
FLR — CHI
Nov 9 — Nov 161
Round-trip
1 adult, Economy
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Cheapest flights from Tuscany to ChicagoExplore the most affordable flight options available from Tuscany to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 10, 2026.
Explore the most affordable flight options available from Tuscany to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 10, 2026.
This lol.travel deal was found by Cheapflights users on 10/7. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/166:25 am -
1 stop13h 45m
Fri 10/233:00 pm -
1 stop12h 35m
Deal found 10/7![ITA Airways logo]()
$546
This lol.travel deal was found by Cheapflights users on 10/9. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/247:15 pm -
1 stop27h 15m
Fri 1/18:10 pm -
1 stop32h 25m
Deal found 10/9![TAP AIR PORTUGAL logo]()
$697
This lol.travel deal was found by Cheapflights users on 10/6. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/247:15 pm -
1 stop27h 15m
Fri 1/88:10 pm -
1 stop39h 20m
Deal found 10/6![TAP AIR PORTUGAL logo]()
$706
This Iberia deal was found by Cheapflights users on 10/9. 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:50 am -
1 stop15h 05m
Mon 11/305:40 pm -
1 stop19h 05m
Deal found 10/9![Iberia logo]()
$725
This Gotogate deal was found by Cheapflights users on 10/6. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/269:50 am -
1 stop13h 25m
Mon 11/306:50 pm -
1 stop12h 00m
Deal found 10/6![SWISS logo]()
$754
This lol.travel deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2212:40 pm -
1 stop32h 05m
Sun 11/299:50 pm -
1 stop30h 40m
Deal found 10/8![British Airways logo]()
$764
This Mytrip deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:00 am -
2 stops19h 15m
Tue 10/207:25 pm -
3 stops32h 30m
Deal found 10/5![Multiple Airlines logo]()
$804
This Delta deal was found by Cheapflights users on 10/7. 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.
Wed 11/46:40 am -
2 stops17h 07m
Thu 11/1211:27 am -
2 stops14h 33m
Deal found 10/7![Delta logo]()
$829
This KLM deal was found by Cheapflights users on 10/6. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2010:05 am -
2 stops35h 47m
Fri 11/276:00 pm -
2 stops41h 55m
Deal found 10/6![KLM logo]()
$839
This Expedia deal was found by Cheapflights users on 10/9. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1511:45 am -
1 stop35h 25m
Mon 10/1910:24 am -
2 stops17h 31m
Deal found 10/9![Scandinavian Airlines logo]()
$872
This Mytrip deal was found by Cheapflights users on 10/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/237:40 pm -
3 stops28h 40m
Mon 11/301:55 pm -
3 stops19h 15m
Deal found 10/9![Multiple Airlines logo]()
$899
This lol.travel deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:40 am -
1 stop16h 15m
Tue 10/206:35 pm -
2 stops16h 20m
Deal found 10/5![Lufthansa logo]()
$904
Best flights from Tuscany to ChicagoDiscover carefully curated flight deals from Tuscany to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 10, 2026.
Discover carefully curated flight deals from Tuscany to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 10, 2026.
This Iberia deal was found by Cheapflights users on 10/9. 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:50 am -
1 stop15h 05m
Mon 11/305:40 pm -
1 stop19h 05m
Deal found 10/9![Iberia logo]()
$725
This Mytrip deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2212:25 pm -
3 stops35h 55m
Sun 11/296:30 pm -
3 stops21h 25m
Deal found 10/8![Multiple Airlines logo]()
$779
This United Airlines deal was found by Cheapflights users on 10/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/286:30 am -
1 stop13h 40m
Mon 2/14:05 pm -
2 stops14h 45m
Deal found 10/9![United Airlines logo]()
$798
This British Airways deal was found by Cheapflights users on 10/7. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/2812:35 pm -
1 stop13h 40m
Mon 2/18:40 pm -
1 stop31h 30m
Deal found 10/7![British Airways logo]()
$805
This Delta deal was found by Cheapflights users on 10/6. 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 11/146:40 am -
1 stop14h 45m
Wed 11/1810:30 am -
2 stops17h 55m
Deal found 10/6![Delta logo]()
$821
This KLM deal was found by Cheapflights users on 10/6. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2010:05 am -
2 stops35h 47m
Fri 11/276:00 pm -
2 stops41h 55m
Deal found 10/6![KLM logo]()
$839
This lol.travel deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:40 am -
1 stop16h 15m
Tue 10/206:35 pm -
2 stops16h 20m
Deal found 10/5![Lufthansa logo]()
$904
This Mytrip deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:00 am -
2 stops19h 15m
Tue 10/207:25 pm -
3 stops32h 30m
Deal found 10/5![Multiple Airlines logo]()
$804
This Delta deal was found by Cheapflights users on 10/7. 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.
Wed 11/46:40 am -
1 stop14h 45m
Thu 11/122:44 pm -
2 stops13h 51m
Deal found 10/7![Delta logo]()
$824
This United Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:40 am -
1 stop16h 15m
Wed 10/216:06 pm -
2 stops16h 49m
Deal found 10/8![United Airlines logo]()
$911
This Delta deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 11/76:40 am -
2 stops18h 20m
Tue 11/101:31 pm -
2 stops17h 54m
Deal found 10/5![Delta logo]()
$829
This Delta deal was found by Cheapflights users on 10/7. 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.
Wed 11/46:40 am -
2 stops17h 07m
Thu 11/1211:27 am -
2 stops14h 33m
Deal found 10/7![Delta logo]()
$829
This United Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:40 am -
1 stop16h 15m
Tue 10/206:00 am -
2 stops28h 55m
Deal found 10/5![United Airlines logo]()
$914
This Mytrip deal was found by Cheapflights users on 10/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/144:45 pm -
2 stops29h 45m
Wed 11/187:00 pm -
2 stops18h 55m
Deal found 10/6![Multiple Airlines logo]()
$950
This Delta deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 11/196:40 am -
2 stops18h 24m
Thu 11/2611:27 am -
2 stops14h 33m
Deal found 10/5![Delta logo]()
$829
This Mytrip deal was found by Cheapflights users on 10/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/710:40 pm -
3 stops25h 05m
Thu 4/157:25 pm -
2 stops14h 45m
Deal found 10/7![Multiple Airlines logo]()
$969
This Mytrip deal was found by Cheapflights users on 10/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/237:40 pm -
3 stops28h 40m
Mon 11/301:55 pm -
2 stops19h 15m
Deal found 10/9![Multiple Airlines logo]()
$1,011
This Delta deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 11/226:40 am -
2 stops16h 59m
Sun 11/291:31 pm -
2 stops17h 54m
Deal found 10/8![Delta logo]()
$945
This Delta deal was found by Cheapflights users on 10/9. 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 11/236:40 am -
2 stops16h 59m
Mon 11/3012:30 pm -
2 stops15h 55m
Deal found 10/9![Delta logo]()
$945
This Delta deal was found by Cheapflights users on 10/6. 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.
Wed 12/236:40 am -
2 stops17h 44m
Thu 1/71:00 pm -
2 stops18h 25m
Deal found 10/6![Delta logo]()
$1,050
This Delta deal was found by Cheapflights users on 10/9. 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.
Thu 12/246:50 am -
2 stops17h 54m
Fri 1/19:30 am -
2 stops19h 05m
Deal found 10/9![Delta logo]()
$1,056
This Delta deal was found by Cheapflights users on 10/6. 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 12/246:50 am -
2 stops17h 34m
Fri 1/810:35 am -
2 stops18h 05m
Deal found 10/6![Delta logo]()
$1,062
Last-minute flights from Tuscany to ChicagoDiscover last-minute flight deals from Tuscany to Chicago. Data last updated October 10, 2026 and is based on user searches.
Discover last-minute flight deals from Tuscany to Chicago. Data last updated October 10, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:00 am -
2 stops19h 15m
Tue 10/207:25 pm -
3 stops32h 30m
Deal found 10/5![Multiple Airlines logo]()
$804
This Expedia deal was found by Cheapflights users on 10/9. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1511:45 am -
1 stop35h 25m
Mon 10/1910:24 am -
2 stops17h 31m
Deal found 10/9![Scandinavian Airlines logo]()
$872
This lol.travel deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:40 am -
1 stop16h 15m
Tue 10/206:35 pm -
2 stops16h 20m
Deal found 10/5![Lufthansa logo]()
$904
This lol.travel deal was found by Cheapflights users on 10/7. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/166:25 am -
1 stop13h 45m
Fri 10/233:00 pm -
1 stop12h 35m
Deal found 10/7![ITA Airways logo]()
$546
This Delta deal was found by Cheapflights users on 10/7. 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.
Wed 11/46:40 am -
2 stops17h 07m
Thu 11/1211:27 am -
2 stops14h 33m
Deal found 10/7![Delta logo]()
$829
This KLM deal was found by Cheapflights users on 10/6. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2010:05 am -
2 stops35h 47m
Fri 11/276:00 pm -
2 stops41h 55m
Deal found 10/6![KLM logo]()
$839
This lol.travel deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2212:40 pm -
1 stop32h 05m
Sun 11/299:50 pm -
1 stop30h 40m
Deal found 10/8![British Airways logo]()
$764
This Mytrip deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2212:25 pm -
3 stops35h 55m
Sun 11/296:30 pm -
3 stops21h 25m
Deal found 10/8![Multiple Airlines logo]()
$779
This Iberia deal was found by Cheapflights users on 10/9. 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:50 am -
1 stop15h 05m
Mon 11/305:40 pm -
1 stop19h 05m
Deal found 10/9![Iberia logo]()
$725
This Mytrip deal was found by Cheapflights users on 10/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/237:40 pm -
3 stops28h 40m
Mon 11/301:55 pm -
3 stops19h 15m
Deal found 10/9![Multiple Airlines logo]()
$899
This Gotogate deal was found by Cheapflights users on 10/6. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/269:50 am -
1 stop13h 25m
Mon 11/306:50 pm -
1 stop12h 00m
Deal found 10/6![SWISS logo]()
$754
This lol.travel deal was found by Cheapflights users on 10/6. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/266:30 am -
2 stops15h 32m
Mon 11/3012:50 pm -
2 stops13h 50m
Deal found 10/6![Air Canada logo]()
$767
One-way flights from Tuscany to ChicagoSearch for one-way flight options from Tuscany to Chicago. Find affordable one-way fares based on user searches. Data last updated October 10, 2026.
Search for one-way flight options from Tuscany to Chicago. Find affordable one-way fares based on user searches. Data last updated October 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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.
Wed 12/94:25 pm -
3 stops54h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Multiple Airlines logo]()
$419
This Kiwi.com deal was found by Cheapflights users on 10/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/191:25 pm -
3 stops33h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Multiple Airlines logo]()
$426
This Kiwi.com deal was found by Cheapflights users on 10/7. 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.
Sat 3/2712:55 pm -
3 stops35h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Multiple Airlines logo]()
$463
This Kiwi.com deal was found by Cheapflights users on 10/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/286:10 pm -
3 stops30h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Multiple Airlines logo]()
$474
This Kiwi.com deal was found by Cheapflights users on 10/7. 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.
Tue 11/109:50 am -
2 stops36h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Multiple Airlines logo]()
$494
This Kiwi.com deal was found by Cheapflights users on 10/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/195:35 pm -
3 stops44h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Multiple Airlines logo]()
$510
This Kiwi.com deal was found by Cheapflights users on 10/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:50 am -
2 stops39h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Multiple Airlines logo]()
$513
This Kiwi.com deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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.
Mon 11/28:20 pm -
3 stops50h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Multiple Airlines logo]()
$522
This Expedia deal was found by Cheapflights users on 10/6. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/287:10 am -
1 stop18h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![British Airways logo]()
$523
This Finnair deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Finnair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/178:50 am -
1 stop16h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Multiple Airlines logo]()
$531
This Delta deal was found by Cheapflights users on 10/6. 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 3/2811:20 am -
2 stops16h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Delta logo]()
$538
This Delta deal was found by Cheapflights users on 10/6. 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 3/286:30 am -
2 stops19h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Delta logo]()
$538
Find flight deals from Tuscany to Chicago
Keep the following information in mind while searching for Tuscany to Chicago flight deals. Data was last updated October 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $697 (lol.travel) |
One-way from | $419 (Kiwi.com) |
Popular in | April |
Cheapest in | January |
Average price | $872 |
Cheapflights Fare Finder
Customize your flight search to find flights from Tuscany 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 October 10, 2026.
Use the filters below to find and compare flights from Tuscany to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PisaChicago
PSA Pisa Gal Galilei - ORD Chicago O'Hare Intl
PSAORD
Pisa Gal Galilei
Wed 12/9
4:25 pm-3:30 pm
3 stops54h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$419
FlorenceChicago
FLR Florence Peretola - ORD Chicago O'Hare Intl
FLRORD
Florence Peretola
Sat 3/27
12:55 pm-6:15 pm
3 stops35h 20m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$463
FlorenceChicago
FLR Florence Peretola - ORD Chicago O'Hare Intl
FLRORD
Florence Peretola
Wed 3/17
9:00 pm-7:20 pm
3 stops28h 20m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$473
FlorenceChicago
FLR Florence Peretola - ORD Chicago O'Hare Intl
FLRORD
Florence Peretola
Sun 3/28
11:20 am-8:37 pm
2 stops16h 17m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$538
FlorenceChicago
FLR Florence Peretola - MDW Chicago Midway
FLRMDW
Florence Peretola
Sun 3/28
6:30 am-6:37 pm
2 stops19h 07m
Chicago Midway
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$538
Quickest round-trip
FlorenceChicago
FLR Florence Peretola - MDW Chicago Midway
FLRMDW
Florence Peretola
Wed 3/17
6:40 am-4:50 pm
2 stops16h 10m
Chicago Midway
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$540
FlorenceChicago
FLR Florence Peretola - MDW Chicago Midway
FLRMDW
Florence Peretola
Tue 11/10
6:40 pm-5:47 pm
3 stops54h 07m
Chicago Midway
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$549
FlorenceChicago
FLR Florence Peretola - ORD Chicago O'Hare Intl
FLRORD
Florence Peretola
Fri 10/16
1:00 pm-9:15 pm
3 stops39h 15m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$580
FlorenceChicago
FLR Florence Peretola - ORD Chicago O'Hare Intl
FLRORD
Florence Peretola
Sun 11/8
6:40 pm-11:35 am
2 stops47h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$641
FlorenceChicago
FLR Florence Peretola - ORD Chicago O'Hare Intl
FLRORD
Florence Peretola
Sun 11/8
11:25 am-6:20 pm
2 stops37h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$654
Showing 1-10 of 43 resultsSorted by cheapest first
Best time to book a flight from Tuscany to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Tuscany with our price prediction graph.
PSA-ORD
FLR-ORD
FLR-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 Tuscany to Chicago
ITTO-CHI
PSA-ORD
FLR-ORD
FLR-MDW
What is the cheapest month to book a flight from Tuscany to Chicago?
Currently, January is the cheapest month in which you can book a flight from Tuscany to Chicago (average of $648). Flying from Tuscany to Chicago in April is currently the most expensive (average of $2,106). 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.
Related info for your journey
Find useful and relevant information for your journey from Tuscany 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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Alternative routes for Tuscany to Chicago
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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 October 10, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
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Tuscany and Chicago flights
Browse other Tuscany and Chicago flight options. Last updated on October 10, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Tuscany to Chicago
Discover the top airline that operate flights from Tuscany 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 October 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$755 | Average$807 | FlexibilityNo cancel fee | On-time71% |