$383+ 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
Aug 2 — Aug 91
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 July 3, 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 July 3, 2026.
This lol.travel deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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 8/236:25 am
FLR
- ORD
1 stop13h 45m
ITA Airways
Sun 8/303:00 pm
ORD
- FLR
1 stop16h 45m
ITA Airways
Deal found 7/2![ITA Airways logo]()
$627
This lol.travel deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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.
Sat 8/223:30 pm
FLR
- ORD
1 stop28h 40m
ITA Airways
Sun 8/303:00 pm
ORD
- FLR
1 stop16h 45m
ITA Airways
Deal found 6/30![ITA Airways logo]()
$630
This lol.travel deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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.
Sat 8/296:25 am
FLR
- ORD
1 stop13h 45m
ITA Airways
Wed 9/23:00 pm
ORD
- FLR
1 stop16h 45m
ITA Airways
Deal found 6/28![ITA Airways logo]()
$631
This Booking.com deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/111:45 am
PSA
- ORD
1 stop35h 25m
Scandinavian Airlines
Fri 10/308:15 pm
ORD
- PSA
1 stop16h 55m
Scandinavian Airlines
Deal found 6/28![Scandinavian Airlines logo]()
$646
This Booking.com deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/317:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Wed 10/288:15 pm
ORD
- FLR
2 stops40h 00m
Scandinavian Airlines
Deal found 7/1![Scandinavian Airlines logo]()
$651
This Booking.com deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Wed 10/288:15 pm
ORD
- FLR
2 stops40h 00m
Scandinavian Airlines
Deal found 6/30![Scandinavian Airlines logo]()
$652
This lol.travel deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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 8/239:20 am
FCO
- ORD
Nonstop10h 50m
ITA Airways
Tue 9/83:00 pm
ORD
- FCO
Nonstop9h 25m
ITA Airways
Deal found 7/2![ITA Airways logo]()
$658
This Gotogate deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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.
Mon 8/317:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Fri 10/308:15 pm
ORD
- FLR
2 stops19h 00m
Scandinavian Airlines
Deal found 7/1![Scandinavian Airlines logo]()
$658
This Justfly.com deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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 12/1611:25 am
FCO
- ORD
1 stop12h 55m
Icelandair
Tue 3/167:30 pm
ORD
- FCO
1 stop12h 30m
Icelandair
Deal found 6/28![Icelandair logo]()
$661
This Trip.com deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/17:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Fri 10/308:15 pm
ORD
- FLR
2 stops19h 00m
Scandinavian Airlines
Deal found 6/30![Scandinavian Airlines logo]()
$661
This Kiwi.com deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” 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 7/223:45 pm
FCO
- ORD
1 stop12h 40m
Icelandair
Tue 9/17:25 pm
ORD
- FCO
1 stop12h 10m
Icelandair
Deal found 6/29![Icelandair logo]()
$662
This Mytrip deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/238:45 pm
FCO
- ORD
3 stops31h 40m
Multiple Airlines
Tue 9/87:25 pm
ORD
- FCO
2 stops18h 40m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$663
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 July 3, 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 July 3, 2026.
This British Airways deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 9/2210:00 am
FCO
- ORD
1 stop13h 46m
British Airways
Thu 10/89:15 pm
ORD
- FCO
1 stop12h 40m
British Airways
Deal found 7/1![British Airways logo]()
$664
This Scandinavian Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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.
Tue 9/157:25 pm
FCO
- ORD
1 stop27h 45m
Scandinavian Airlines
Thu 10/17:15 pm
ORD
- FCO
1 stop16h 20m
Scandinavian Airlines
Deal found 7/2![Scandinavian Airlines logo]()
$687
This American Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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 10/1612:50 pm
PSA
- ORD
2 stops16h 15m
American Airlines
Tue 10/206:40 pm
ORD
- PSA
2 stops17h 15m
American Airlines
Deal found 7/2![American Airlines logo]()
$765
This Delta deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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 7/236:30 am
FCO
- ORD
2 stops18h 59m
Delta
Wed 8/55:20 pm
ORD
- FCO
2 stops14h 05m
Delta
Deal found 6/28![Delta logo]()
$769
This KLM deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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 8/191:10 pm
FCO
- MDW
1 stop16h 26m
KLM
Sun 8/2310:54 am
MDW
- FCO
1 stop13h 41m
KLM
Deal found 6/30![KLM logo]()
$781
This Mytrip deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/218:50 am
CIA
- ORD
3 stops40h 25m
Multiple Airlines
Sun 9/67:25 pm
ORD
- CIA
2 stops18h 40m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$800
This United Airlines deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” 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.
Sat 8/226:30 am
FLR
- ORD
2 stops32h 00m
United Airlines
Sun 8/3010:25 am
ORD
- FLR
2 stops17h 35m
United Airlines
Deal found 6/29![United Airlines logo]()
$813
This Scandinavian Airlines deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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.
Fri 10/1611:45 am
PSA
- ORD
1 stop35h 25m
Scandinavian Airlines
Tue 10/207:15 pm
ORD
- PSA
1 stop32h 40m
Scandinavian Airlines
Deal found 6/28![Scandinavian Airlines logo]()
$732
This British Airways deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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.
Wed 8/267:50 pm
PSA
- ORD
1 stop25h 00m
British Airways
Sat 9/54:29 pm
ORD
- PSA
2 stops18h 36m
British Airways
Deal found 6/28![British Airways logo]()
$738
This Delta deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” 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 7/236:30 am
FCO
- ORD
1 stop14h 45m
Delta
Sun 7/2610:28 am
ORD
- FCO
2 stops16h 07m
Delta
Deal found 6/29![Delta logo]()
$769
This Scandinavian Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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.
Mon 8/318:10 pm
FCO
- ORD
2 stops27h 00m
Scandinavian Airlines
Wed 10/217:15 pm
ORD
- FCO
1 stop16h 20m
Scandinavian Airlines
Deal found 7/2![Scandinavian Airlines logo]()
$738
This Mytrip deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/236:20 am
CIA
- ORD
3 stops46h 00m
Multiple Airlines
Mon 8/317:25 pm
ORD
- CIA
3 stops19h 05m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$817
This British Airways deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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 7/1410:00 am
FCO
- ORD
Nonstop10h 40m
British Airways
Thu 7/237:05 pm
ORD
- FCO
1 stop20h 40m
British Airways
Deal found 6/28![British Airways logo]()
$744
This KLM deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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 8/263:40 pm
PSA
- ORD
1 stop29h 35m
KLM
Sat 9/55:18 pm
ORD
- PSA
2 stops20h 47m
KLM
Deal found 7/2![KLM logo]()
$839
This Delta deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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 8/1912:45 pm
FCO
- ORD
2 stops16h 59m
Delta
Sun 8/235:10 pm
ORD
- FCO
1 stop11h 15m
Delta
Deal found 6/30![Delta logo]()
$770
This British Airways deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” 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 7/1612:15 pm
FCO
- ORD
1 stop14h 11m
British Airways
Fri 7/247:05 pm
ORD
- FCO
1 stop13h 25m
British Airways
Deal found 6/29![British Airways logo]()
$749
This Mytrip deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” 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 7/1610:10 am
CIA
- ORD
3 stops36h 00m
Multiple Airlines
Fri 7/248:10 pm
ORD
- CIA
2 stops18h 00m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$825
This Scandinavian Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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 9/169:40 am
FCO
- ORD
1 stop13h 30m
Scandinavian Airlines
Fri 10/27:15 pm
ORD
- FCO
2 stops38h 25m
Scandinavian Airlines
Deal found 6/30![Scandinavian Airlines logo]()
$751
This KLM deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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 8/263:40 pm
PSA
- MDW
2 stops31h 35m
KLM
Sat 9/55:45 pm
MDW
- PSA
2 stops20h 20m
KLM
Deal found 7/2![KLM logo]()
$844
This Delta deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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 8/126:30 am
FCO
- MDW
2 stops18h 31m
Delta
Wed 8/1912:46 pm
MDW
- FCO
1 stop15h 04m
Delta
Deal found 6/28![Delta logo]()
$772
This American Airlines deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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.
Wed 7/157:05 am
FLR
- ORD
2 stops19h 21m
American Airlines
Mon 7/2712:50 pm
ORD
- FLR
2 stops15h 40m
American Airlines
Deal found 6/28![American Airlines logo]()
$994
This British Airways deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 7/2512:15 pm
FCO
- ORD
1 stop14h 14m
British Airways
Sat 8/19:15 pm
ORD
- FCO
1 stop13h 05m
British Airways
Deal found 6/27![British Airways logo]()
$749
This Mytrip deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 9/206:00 am
CIA
- ORD
3 stops46h 20m
Multiple Airlines
Wed 9/307:25 pm
ORD
- CIA
2 stops17h 55m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$826
This Delta deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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 8/196:30 am
FCO
- MDW
2 stops18h 31m
Delta
Sun 8/231:25 pm
MDW
- FCO
1 stop14h 35m
Delta
Deal found 6/30![Delta logo]()
$773
This Trip.com deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/13:00 pm
PSA
- MDW
2 stops32h 59m
KLM
Fri 10/305:15 pm
MDW
- PSA
2 stops43h 40m
KLM
Deal found 6/28![KLM logo]()
$853
This Expedia deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 10/19:20 pm
PSA
- ORD
1 stop25h 35m
British Airways
Thu 10/157:05 pm
ORD
- PSA
1 stop17h 30m
British Airways
Deal found 7/3![British Airways logo]()
$762
This Mytrip deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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 8/236:20 am
CIA
- ORD
3 stops46h 00m
Multiple Airlines
Sun 9/67:25 pm
ORD
- CIA
2 stops18h 40m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$848
This Delta deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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 7/3110:10 am
FCO
- MDW
2 stops19h 05m
Delta
Sun 8/1610:54 am
MDW
- FCO
1 stop16h 56m
Delta
Deal found 6/28![Delta logo]()
$779
This KLM deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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.
Tue 8/184:55 pm
PSA
- MDW
2 stops30h 20m
KLM
Sat 8/296:42 pm
MDW
- PSA
2 stops19h 23m
KLM
Deal found 6/30![KLM logo]()
$926
This Mytrip deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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 8/206:25 am
CIA
- ORD
3 stops45h 55m
Multiple Airlines
Tue 8/257:25 pm
ORD
- CIA
2 stops14h 15m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$856
Last-minute flights from Tuscany to ChicagoDiscover last-minute flight deals from Tuscany to Chicago. Data last updated July 3, 2026 and is based on user searches.
Discover last-minute flight deals from Tuscany to Chicago. Data last updated July 3, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” 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 7/223:45 pm
FCO
- ORD
1 stop12h 40m
Icelandair
Tue 9/17:25 pm
ORD
- FCO
1 stop12h 10m
Icelandair
Deal found 6/29![Icelandair logo]()
$662
This Icelandair deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” 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.
Wed 7/223:45 pm
FCO
- ORD
1 stop12h 40m
Icelandair
Mon 8/3110:25 pm
ORD
- FCO
1 stop33h 10m
Icelandair
Deal found 6/29![Icelandair logo]()
$668
This lol.travel deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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.
Wed 8/59:20 am
FCO
- ORD
Nonstop10h 50m
ITA Airways
Wed 8/123:00 pm
ORD
- FCO
Nonstop9h 25m
ITA Airways
Deal found 6/28![ITA Airways logo]()
$675
This lol.travel deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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.
Sat 8/223:30 pm
FLR
- ORD
1 stop28h 40m
ITA Airways
Sun 8/303:00 pm
ORD
- FLR
1 stop16h 45m
ITA Airways
Deal found 6/30![ITA Airways logo]()
$630
This lol.travel deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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 8/236:25 am
FLR
- ORD
1 stop13h 45m
ITA Airways
Sun 8/303:00 pm
ORD
- FLR
1 stop16h 45m
ITA Airways
Deal found 7/2![ITA Airways logo]()
$627
This lol.travel deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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 8/239:20 am
FCO
- ORD
Nonstop10h 50m
ITA Airways
Tue 9/83:00 pm
ORD
- FCO
Nonstop9h 25m
ITA Airways
Deal found 7/2![ITA Airways logo]()
$658
This Mytrip deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/238:45 pm
FCO
- ORD
3 stops31h 40m
Multiple Airlines
Tue 9/87:25 pm
ORD
- FCO
2 stops18h 40m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$663
This Iberia deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” 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.
Wed 8/2610:00 am
FCO
- ORD
Nonstop10h 30m
Iberia
Sat 9/124:55 pm
ORD
- FCO
Nonstop9h 15m
Iberia
Deal found 6/29![Iberia logo]()
$666
This lol.travel deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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.
Sat 8/296:25 am
FLR
- ORD
1 stop13h 45m
ITA Airways
Wed 9/23:00 pm
ORD
- FLR
1 stop16h 45m
ITA Airways
Deal found 6/28![ITA Airways logo]()
$631
This Booking.com deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/317:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Wed 10/288:15 pm
ORD
- FLR
2 stops40h 00m
Scandinavian Airlines
Deal found 7/1![Scandinavian Airlines logo]()
$651
This Gotogate deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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.
Mon 8/317:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Fri 10/308:15 pm
ORD
- FLR
2 stops19h 00m
Scandinavian Airlines
Deal found 7/1![Scandinavian Airlines logo]()
$658
This Scandinavian Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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.
Mon 8/317:25 pm
FCO
- ORD
1 stop27h 45m
Scandinavian Airlines
Wed 10/217:15 pm
ORD
- FCO
1 stop16h 20m
Scandinavian Airlines
Deal found 7/2![Scandinavian Airlines logo]()
$670
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 July 3, 2026.
Search for one-way flight options from Tuscany to Chicago. Find affordable one-way fares based on user searches. Data last updated July 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 10/1312:25 pm
FLR
- ORD
3 stops36h 25m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$383
This Kiwi.com deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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 10/146:25 am
FLR
- ORD
3 stops42h 25m
Multiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$387
This Kiwi.com deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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 9/166:10 am
PSA
- ORD
3 stops42h 40m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$388
This Orbitz deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:45 am
FLR
- ORD
1 stop14h 40m
Iberia
Deal found 6/28![Iberia logo]()
$403
This Iberia deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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.
Tue 9/16:45 am
FLR
- ORD
1 stop14h 40m
Iberia
Deal found 6/30![Iberia logo]()
$405
This Kiwi.com deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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 10/116:25 am
FLR
- ORD
3 stops42h 25m
Multiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$406
This Iberia deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 12/146:50 am
FLR
- ORD
2 stops20h 22m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$411
This Orbitz deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1310:00 pm
FLR
- ORD
2 stops27h 15m
Iberia
Deal found 7/2![Iberia logo]()
$424
This Kiwi.com deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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 9/189:55 pm
FLR
- ORD
3 stops50h 55m
Multiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$444
This Kiwi.com deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 10/219:00 am
FLR
- ORD
3 stops40h 15m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$446
This Kiwi.com deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 10/126:55 am
FLR
- ORD
3 stops41h 55m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$449
This Kiwi.com deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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 11/710:50 am
CIA
- ORD
3 stops40h 30m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$461
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 July 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $627 (lol.travel) |
One-way from | $383 (Kiwi.com) |
Popular in | April |
Cheapest in | October |
Average price | $805 |
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 2,558,603 searches. Data last updated July 3, 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
Quickest round-trip
RomeChicago
FCO - ORD
FCOORD
Rome Fiumicino
Tue 9/22
10:00 am-4:46 pm
1 stop13h 46m
Chicago O'Hare Intl
Thu 10/8
9:15 pm-4:55 pm
1 stop12h 40m
$664
RomeChicago
FCO - ORD
FCOORD
Rome Fiumicino
Tue 9/15
7:25 pm-4:10 pm
1 stop27h 45m
Chicago O'Hare Intl
Thu 10/1
7:15 pm-6:35 pm
1 stop16h 20m
$687
PisaChicago
PSA - ORD
PSAORD
Pisa Gal Galilei
Fri 10/16
11:45 am-4:10 pm
1 stop35h 25m
Chicago O'Hare Intl
Tue 10/20
7:15 pm-10:55 am
1 stop32h 40m
$732
PisaChicago
PSA - ORD
PSAORD
Pisa Gal Galilei
Wed 8/26
7:50 pm-1:50 pm
1 stop25h 00m
Chicago O'Hare Intl
Sat 9/5
4:29 pm-6:05 pm
2 stops18h 36m
$738
RomeChicago
FCO - ORD
FCOORD
Rome Fiumicino
Mon 8/31
8:10 pm-4:10 pm
2 stops27h 00m
Chicago O'Hare Intl
Wed 10/21
7:15 pm-6:35 pm
1 stop16h 20m
$738
RomeChicago
FCO - ORD
FCOORD
Rome Fiumicino
Tue 7/14
10:00 am-1:40 pm
Nonstop10h 40m
Chicago O'Hare Intl
Thu 7/23
7:05 pm-10:45 pm
1 stop20h 40m
$744
RomeChicago
FCO - ORD
FCOORD
Rome Fiumicino
Thu 7/16
12:15 pm-7:26 pm
1 stop14h 11m
Chicago O'Hare Intl
Fri 7/24
7:05 pm-3:30 pm
1 stop13h 25m
$749
RomeChicago
FCO - ORD
FCOORD
Rome Fiumicino
Sat 7/25
12:15 pm-7:29 pm
1 stop14h 14m
Chicago O'Hare Intl
Sat 8/1
9:15 pm-5:20 pm
1 stop13h 05m
$749
RomeChicago
FCO - ORD
FCOORD
Rome Fiumicino
Wed 9/16
9:40 am-4:10 pm
1 stop13h 30m
Chicago O'Hare Intl
Fri 10/2
7:15 pm-4:40 pm
2 stops38h 25m
$751
PisaChicago
PSA - ORD
PSAORD
Pisa Gal Galilei
Thu 10/1
9:20 pm-3:55 pm
1 stop25h 35m
Chicago O'Hare Intl
Thu 10/15
7:05 pm-7:35 pm
1 stop17h 30m
$762
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.
FLR-ORD
FCO-ORD
PSA-ORD
CIA-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
FLR-ORD
FCO-ORD
PSA-ORD
CIA-ORD
What is the cheapest month to book a flight from Tuscany to Chicago?
Currently, February is the cheapest month in which you can book a flight from Tuscany to Chicago (average of $559). Flying from Tuscany to Chicago in April is currently the most expensive (average of $907). 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?
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
Hammond
Lansing
Merrillville
Valparaiso
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
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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 July 3, 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 July 3, 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 2,558,603 searches. Data last updated July 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$755 | Average$807 | FlexibilityNo cancel fee | On-time71% |