$403+ Cheap flights from Tuscany 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 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
FLR — CHI
Sep 20 — Sep 271
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 August 21, 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 August 21, 2026.
This deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1211:25 am -
1 stop12h 55m
Tue 1/126:30 pm -
1 stop12h 30m
Deal found 8/16![Icelandair logo]()
$467
This Gotogate deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/153:45 pm -
1 stop33h 30m
Wed 12/26:30 pm -
1 stop12h 30m
Deal found 8/17![Icelandair logo]()
$529
This Gotogate deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/153:45 pm -
1 stop33h 30m
Sat 1/96:30 pm -
1 stop12h 30m
Deal found 8/17![Icelandair logo]()
$530
This oojo deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/143:45 pm -
1 stop12h 40m
Sun 10/187:25 pm -
1 stop12h 10m
Deal found 8/18![Icelandair logo]()
$542
This Mytrip deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/113:45 pm -
1 stop12h 40m
Thu 11/266:30 pm -
1 stop12h 30m
Deal found 8/17![Icelandair logo]()
$543
This Justfly.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/143:45 pm -
1 stop12h 40m
Sat 1/96:30 pm -
1 stop12h 30m
Deal found 8/17![Icelandair logo]()
$546
This Justfly.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/153:45 pm -
1 stop33h 30m
Fri 1/86:30 pm -
1 stop12h 30m
Deal found 8/17![Icelandair logo]()
$548
This Gotogate deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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.
Sat 9/53:45 pm -
1 stop12h 40m
Sun 9/207:25 pm -
1 stop12h 10m
Deal found 8/16![Icelandair logo]()
$550
This Gotogate deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/43:45 pm -
1 stop12h 40m
Sun 9/207:25 pm -
1 stop12h 10m
Deal found 8/18![Icelandair logo]()
$553
This FlightHub deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/23:45 pm -
1 stop12h 40m
Fri 11/276:30 pm -
1 stop12h 30m
Deal found 8/17![Icelandair logo]()
$554
This lol.travel deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:25 am -
1 stop13h 45m
Tue 9/223:00 pm -
1 stop12h 35m
Deal found 8/19![ITA Airways logo]()
$571
This CheapTickets.ch deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapTickets.ch is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:50 pm -
1 stop28h 10m
Thu 10/86:00 pm -
1 stop17h 00m
Deal found 8/17![TAP AIR PORTUGAL logo]()
$603
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 August 21, 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 August 21, 2026.
This Delta deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/76:30 am -
1 stop15h 00m
Tue 9/225:10 pm -
1 stop18h 55m
Deal found 8/19![Delta logo]()
$669
This British Airways deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/510:00 am -
Nonstop10h 30m
Sun 9/209:15 pm -
1 stop30h 50m
Deal found 8/21![British Airways logo]()
$679
This Mytrip deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/36:00 am -
2 stops19h 15m
Mon 9/77:25 pm -
2 stops19h 05m
Deal found 8/19![Multiple Airlines logo]()
$682
This KLM deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/239:00 am -
1 stop16h 33m
Sat 10/105:31 pm -
1 stop12h 09m
Deal found 8/17![KLM logo]()
$705
This Icelandair deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Icelandair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/183:45 pm -
1 stop12h 40m
Fri 12/46:30 pm -
1 stop12h 30m
Deal found 8/17![Icelandair logo]()
$706
This Turkish Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/67:45 pm -
1 stop21h 15m
Fri 2/128:15 pm -
1 stop34h 35m
Deal found 8/18![Turkish Airlines logo]()
$711
This American Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/249:20 pm -
1 stop22h 05m
Mon 9/2810:25 pm -
1 stop14h 10m
Deal found 8/17![American Airlines logo]()
$778
This Scandinavian Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:55 pm -
2 stops33h 37m
Wed 10/77:15 pm -
2 stops30h 55m
Deal found 8/16![Scandinavian Airlines logo]()
$788
This lol.travel deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:30 am -
2 stops15h 22m
Tue 9/2211:05 am -
2 stops15h 35m
Deal found 8/17![Air Canada logo]()
$820
This United Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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.
Mon 9/216:50 am -
1 stop13h 05m
Wed 9/303:50 pm -
Nonstop9h 05m
Deal found 8/16![United Airlines logo]()
$828
This Air France deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:50 am -
2 stops17h 10m
Mon 3/155:59 pm -
2 stops14h 26m
Deal found 8/18![Air France logo]()
$983
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1512:45 pm -
2 stops18h 12m
Fri 12/46:25 pm -
1 stop17h 00m
Deal found 8/17![Delta logo]()
$675
This British Airways deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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.
Tue 9/112:15 pm -
1 stop14h 31m
Sat 9/54:53 pm -
1 stop34h 27m
Deal found 8/16![British Airways logo]()
$685
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:30 am -
2 stops19h 29m
Sun 9/205:10 pm -
1 stop11h 15m
Deal found 8/18![Delta logo]()
$675
This British Airways deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/249:20 pm -
2 stops26h 26m
Mon 9/287:05 pm -
1 stop33h 05m
Deal found 8/18![British Airways logo]()
$710
This Mytrip deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:00 am -
3 stops19h 15m
Wed 12/26:30 pm -
2 stops15h 15m
Deal found 8/17![Multiple Airlines logo]()
$782
This Delta deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:30 am -
2 stops18h 49m
Sun 10/1110:59 am -
1 stop16h 51m
Deal found 8/19![Delta logo]()
$678
This United Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 10/296:30 am -
1 stop13h 40m
Tue 3/99:20 am -
2 stops21h 30m
Deal found 8/16![United Airlines logo]()
$828
This KLM deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/510:15 pm -
2 stops22h 21m
Sat 9/126:00 pm -
2 stops20h 05m
Deal found 8/20![KLM logo]()
$843
This British Airways deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 11/1212:35 pm -
1 stop13h 10m
Sun 11/159:50 pm -
1 stop30h 40m
Deal found 8/16![British Airways logo]()
$711
This Mytrip deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/49:45 am -
2 stops18h 40m
Sun 9/207:25 pm -
2 stops19h 00m
Deal found 8/18![Multiple Airlines logo]()
$816
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:10 am -
2 stops17h 50m
Sat 11/711:33 am -
2 stops14h 47m
Deal found 8/20![Delta logo]()
$678
This United Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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.
Mon 11/26:30 am -
1 stop20h 35m
Wed 3/104:20 pm -
1 stop14h 20m
Deal found 8/16![United Airlines logo]()
$830
This Expedia deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/510:15 pm -
2 stops24h 29m
Sat 9/124:30 pm -
2 stops21h 35m
Deal found 8/20![KLM logo]()
$843
This British Airways deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:05 am -
1 stop13h 45m
Mon 9/214:01 pm -
2 stops23h 19m
Deal found 8/19![British Airways logo]()
$714
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/216:30 am -
2 stops19h 03m
Wed 9/307:01 pm -
2 stops14h 24m
Deal found 8/18![Delta logo]()
$680
This Mytrip deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:00 am -
3 stops19h 15m
Fri 12/46:30 pm -
3 stops19h 45m
Deal found 8/17![Multiple Airlines logo]()
$828
This United Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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.
Mon 11/26:30 am -
1 stop13h 40m
Thu 3/118:55 am -
2 stops21h 45m
Deal found 8/16![United Airlines logo]()
$833
This British Airways deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/212:20 pm -
2 stops34h 17m
Sun 2/71:31 pm -
2 stops14h 19m
Deal found 8/18![British Airways logo]()
$718
This Delta deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:30 am -
1 stop15h 00m
Wed 9/1610:25 am -
2 stops16h 10m
Deal found 8/21![Delta logo]()
$681
Last-minute flights from Tuscany to ChicagoDiscover last-minute flight deals from Tuscany to Chicago. Data last updated August 21, 2026 and is based on user searches.
Discover last-minute flight deals from Tuscany to Chicago. Data last updated August 21, 2026 and is based on user searches.
This Flightnetwork deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/263:45 pm -
1 stop33h 30m
Sat 10/317:30 pm -
1 stop12h 30m
Deal found 8/17![Icelandair logo]()
$546
This oojo deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/263:45 pm -
1 stop12h 40m
Sat 9/127:25 pm -
1 stop12h 00m
Deal found 8/17![Icelandair logo]()
$557
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:30 am -
2 stops18h 31m
Tue 9/85:37 pm -
2 stops13h 48m
Deal found 8/18![Delta logo]()
$675
This oojo deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/313:45 pm -
1 stop12h 40m
Wed 9/1610:25 pm -
1 stop33h 10m
Deal found 8/19![Icelandair logo]()
$559
This FlightHub deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/23:45 pm -
1 stop12h 40m
Fri 11/276:30 pm -
1 stop12h 30m
Deal found 8/17![Icelandair logo]()
$554
This Gotogate deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/43:45 pm -
1 stop12h 40m
Sun 9/207:25 pm -
1 stop12h 10m
Deal found 8/18![Icelandair logo]()
$553
This Gotogate deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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.
Sat 9/53:45 pm -
1 stop12h 40m
Sun 9/207:25 pm -
1 stop12h 10m
Deal found 8/16![Icelandair logo]()
$550
This Mytrip deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/113:45 pm -
1 stop12h 40m
Thu 11/266:30 pm -
1 stop12h 30m
Deal found 8/17![Icelandair logo]()
$543
This Mytrip deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/113:45 pm -
1 stop12h 40m
Sun 9/137:25 pm -
1 stop12h 10m
Deal found 8/17![Icelandair logo]()
$555
This lol.travel deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:25 am -
1 stop13h 45m
Tue 9/223:00 pm -
1 stop12h 35m
Deal found 8/19![ITA Airways logo]()
$571
This lol.travel deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:55 pm -
1 stop27h 15m
Tue 9/227:15 pm -
1 stop16h 50m
Deal found 8/17![Scandinavian Airlines logo]()
$675
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:30 am -
2 stops18h 49m
Tue 10/2012:49 pm -
2 stops15h 11m
Deal found 8/17![Delta logo]()
$678
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 August 21, 2026.
Search for one-way flight options from Tuscany to Chicago. Find affordable one-way fares based on user searches. Data last updated August 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 10/132:00 pm -
3 stops58h 50m
Deal found 8/16![Multiple Airlines logo]()
$403
This Kiwi.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/205:40 pm -
3 stops55h 10m
Deal found 8/18![Multiple Airlines logo]()
$406
This Expedia deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/16:50 am -
1 stop15h 05m
Deal found 8/17![Iberia logo]()
$408
This Kiwi.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1610:00 am -
3 stops38h 50m
Deal found 8/18![Multiple Airlines logo]()
$421
This Kiwi.com deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:00 am -
3 stops41h 50m
Deal found 8/16![Multiple Airlines logo]()
$430
This Kiwi.com deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 10/1210:00 am -
3 stops38h 50m
Deal found 8/16![Multiple Airlines logo]()
$438
This Kiwi.com deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 10/147:45 pm -
3 stops29h 05m
Deal found 8/16![Multiple Airlines logo]()
$449
This Kiwi.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/95:55 pm -
3 stops54h 55m
Deal found 8/18![Multiple Airlines logo]()
$450
This deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:05 am -
1 stop15h 50m
Deal found 8/20![British Airways logo]()
$465
This Kiwi.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:25 am -
3 stops42h 25m
Deal found 8/18![Multiple Airlines logo]()
$467
This Kiwi.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/174:40 pm -
3 stops29h 15m
Deal found 8/18![Multiple Airlines logo]()
$493
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/36:00 am -
3 stops41h 00m
Deal found 8/19![Multiple Airlines logo]()
$493
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 August 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $467 |
One-way from | $403 (Kiwi.com) |
Popular in | April |
Cheapest in | January |
Average price | $963 |
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 August 21, 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
RomeChicago
FCO Rome Fiumicino - ORD Chicago O'Hare Intl
FCOORD
Rome Fiumicino
Mon 9/7
6:30 am-2:30 pm
1 stop15h 00m
Chicago O'Hare Intl
Tue 9/22
5:10 pm-7:05 pm
1 stop18h 55m
$669
RomeChicago
FCO Rome Fiumicino - ORD Chicago O'Hare Intl
FCOORD
Rome Fiumicino
Thu 10/15
12:45 pm-11:57 pm
2 stops18h 12m
Chicago O'Hare Intl
Fri 12/4
6:25 pm-6:25 pm
1 stop17h 00m
$675
RomeChicago
FCO Rome Fiumicino - ORD Chicago O'Hare Intl
FCOORD
Rome Fiumicino
Sat 9/5
6:30 am-6:59 pm
2 stops19h 29m
Chicago O'Hare Intl
Sun 9/20
5:10 pm-11:25 am
1 stop11h 15m
$675
RomeChicago
FCO Rome Fiumicino - MDW Chicago Midway
FCOMDW
Rome Fiumicino
Tue 9/15
6:30 am-6:19 pm
2 stops18h 49m
Chicago Midway
Sun 10/11
10:59 am-10:50 am
1 stop16h 51m
$678
RomeChicago
FCO Rome Fiumicino - MDW Chicago Midway
FCOMDW
Rome Fiumicino
Sat 10/31
6:10 am-6:00 pm
2 stops17h 50m
Chicago Midway
Sat 11/7
11:33 am-9:20 am
2 stops14h 47m
$678
RomeChicago
FCO Rome Fiumicino - ORD Chicago O'Hare Intl
FCOORD
Rome Fiumicino
Sat 9/5
10:00 am-1:30 pm
Nonstop10h 30m
Chicago O'Hare Intl
Sun 9/20
9:15 pm-11:05 am
1 stop30h 50m
$679
RomeChicago
FCO Rome Fiumicino - MDW Chicago Midway
FCOMDW
Rome Fiumicino
Mon 9/21
6:30 am-6:33 pm
2 stops19h 03m
Chicago Midway
Wed 9/30
7:01 pm-4:25 pm
2 stops14h 24m
$680
RomeChicago
FCO Rome Fiumicino - ORD Chicago O'Hare Intl
FCOORD
Rome Fiumicino
Mon 8/31
6:30 am-2:30 pm
1 stop15h 00m
Chicago O'Hare Intl
Wed 9/16
10:25 am-9:35 am
2 stops16h 10m
$681
PisaChicago
PSA Pisa Gal Galilei - ORD Chicago O'Hare Intl
PSAORD
Pisa Gal Galilei
Thu 9/3
6:00 am-6:15 pm
2 stops19h 15m
Chicago O'Hare Intl
Mon 9/7
7:25 pm-9:30 pm
2 stops19h 05m
$682
RomeChicago
FCO Rome Fiumicino - ORD Chicago O'Hare Intl
FCOORD
Rome Fiumicino
Tue 9/1
12:15 pm-7:46 pm
1 stop14h 31m
Chicago O'Hare Intl
Sat 9/5
4:53 pm-10:20 am
1 stop34h 27m
$685
Showing 1-10 of 60 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.
CIA-ORD
FCO-ORD
FLR-ORD
PSA-ORD
FCO-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
CIA-ORD
FCO-ORD
FLR-ORD
PSA-ORD
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.
How much does it cost to fly round-trip from Tuscany to Chicago?
Airfare is below average for this route at the moment.
Tuscany to Chicago flights typically cost between $722 and $1,018 in September.The cheapest round-trip price found within the last 5 days was $571 on ITA Airways (Sep 17-Sep 22).
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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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 August 21, 2026.
Complete your trip
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Tuscany and Chicago flights
Browse other Tuscany and Chicago flight options. Last updated on August 21, 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 August 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$755 | Average$807 | FlexibilityNo cancel fee | On-time71% |