$285+ Cheap flights from Chicago (CHI) to Tuscany
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — FLR
Jul 31 — Aug 71
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Tuscany with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Chicago to TuscanyExplore the most affordable flight options available from Chicago to Tuscany. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 1, 2026.
Explore the most affordable flight options available from Chicago to Tuscany. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 1, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/26:00 pm
ORD
- FLR
2 stops42h 05m
Scandinavian Airlines
Wed 10/147:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/26![Scandinavian Airlines logo]()
$551
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.
Mon 10/57:15 pm
ORD
- FLR
1 stop16h 50m
Scandinavian Airlines
Tue 10/137:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/28![Scandinavian Airlines logo]()
$559
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:15 pm
ORD
- FLR
1 stop16h 50m
Scandinavian Airlines
Tue 10/137:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/28![Scandinavian Airlines logo]()
$569
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.
Wed 10/77:15 pm
ORD
- FLR
1 stop16h 50m
Scandinavian Airlines
Fri 10/167:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/28![Scandinavian Airlines logo]()
$574
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/57:15 pm
ORD
- FLR
1 stop16h 50m
Scandinavian Airlines
Fri 10/167:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/28![Scandinavian Airlines logo]()
$584
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/237:15 pm
ORD
- PSA
1 stop32h 40m
Scandinavian Airlines
Thu 8/2711:45 am
PSA
- ORD
1 stop35h 25m
Scandinavian Airlines
Deal found 6/28![Scandinavian Airlines logo]()
$596
This FlightHub deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/77:15 pm
ORD
- FLR
1 stop16h 50m
Scandinavian Airlines
Tue 10/207:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/26![Scandinavian Airlines logo]()
$596
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/67:15 pm
ORD
- FLR
1 stop16h 50m
Scandinavian Airlines
Tue 9/157:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/30![Scandinavian Airlines logo]()
$600
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:15 pm
ORD
- FLR
1 stop16h 50m
Scandinavian Airlines
Thu 9/107:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/30![Scandinavian Airlines logo]()
$601
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.
Wed 10/77:15 pm
ORD
- FLR
1 stop16h 50m
Scandinavian Airlines
Tue 10/137:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/28![Scandinavian Airlines logo]()
$603
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.
Sun 8/237:15 pm
ORD
- FLR
1 stop16h 50m
Scandinavian Airlines
Mon 9/77:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/30![Scandinavian Airlines logo]()
$609
This oojo deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/77:15 pm
ORD
- FLR
1 stop16h 50m
Scandinavian Airlines
Wed 10/147:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/26![Scandinavian Airlines logo]()
$611
Best flights from Chicago to TuscanyDiscover carefully curated flight deals from Chicago to Tuscany that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 1, 2026.
Discover carefully curated flight deals from Chicago to Tuscany that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 1, 2026.
This Scandinavian Airlines 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/237:15 pm
ORD
- PSA
1 stop32h 40m
Scandinavian Airlines
Thu 8/2711:45 am
PSA
- ORD
2 stops41h 59m
Scandinavian Airlines
Deal found 6/27![Scandinavian Airlines logo]()
$720
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.
Tue 8/187:25 pm
ORD
- CIA
2 stops18h 45m
Multiple Airlines
Tue 9/81:20 pm
CIA
- ORD
3 stops35h 55m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$767
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.
Thu 8/610:54 am
MDW
- FCO
1 stop13h 41m
Delta
Wed 8/196:30 am
FCO
- MDW
2 stops18h 31m
Delta
Deal found 6/30![Delta logo]()
$776
This ITA 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/293:00 pm
ORD
- FCO
Nonstop9h 25m
ITA Airways
Sun 8/29:20 am
FCO
- ORD
Nonstop10h 50m
ITA Airways
Deal found 6/28![ITA Airways logo]()
$812
This KLM 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/191:25 pm
MDW
- PSA
2 stops17h 45m
KLM
Wed 8/263:40 pm
PSA
- MDW
2 stops31h 35m
KLM
Deal found 6/28![KLM logo]()
$813
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/116:00 pm
ORD
- FLR
1 stop11h 40m
United Airlines
Tue 8/189:50 am
FLR
- ORD
1 stop33h 45m
United Airlines
Deal found 6/30![United Airlines logo]()
$814
This British Airways 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/209:15 pm
ORD
- PSA
1 stop15h 45m
British Airways
Sat 11/2111:00 am
PSA
- ORD
1 stop14h 45m
British Airways
Deal found 6/30![British Airways logo]()
$941
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/214:05 pm
ORD
- PSA
1 stop18h 55m
Lufthansa
Fri 10/210:35 am
PSA
- ORD
1 stop16h 20m
Lufthansa
Deal found 6/29![Lufthansa logo]()
$947
This Delta deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/249:24 am
MDW
- FCO
1 stop18h 36m
Delta
Sat 12/121:30 pm
FCO
- MDW
1 stop15h 40m
Delta
Deal found 6/26![Delta logo]()
$777
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.
Wed 8/1211:05 am
ORD
- CIA
3 stops25h 45m
Multiple Airlines
Wed 8/2610:40 am
CIA
- ORD
2 stops16h 15m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$799
This Scandinavian 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:35 am
ORD
- PSA
2 stops20h 20m
Scandinavian Airlines
Fri 10/211:45 am
PSA
- ORD
2 stops39h 14m
Scandinavian Airlines
Deal found 6/29![Scandinavian Airlines logo]()
$804
This KLM 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/116:42 pm
MDW
- PSA
2 stops13h 53m
KLM
Tue 8/184:55 pm
PSA
- MDW
2 stops30h 20m
KLM
Deal found 6/29![KLM logo]()
$813
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/83:45 pm
ORD
- FCO
Nonstop9h 10m
United Airlines
Wed 7/158:00 am
FCO
- ORD
1 stop13h 00m
United Airlines
Deal found 6/30![United Airlines logo]()
$832
This ITA 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/13:00 pm
ORD
- FCO
Nonstop9h 25m
ITA Airways
Sat 8/159:20 am
FCO
- ORD
Nonstop10h 50m
ITA Airways
Deal found 6/29![ITA Airways logo]()
$855
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.
Tue 9/17:15 pm
ORD
- CIA
2 stops18h 55m
Multiple Airlines
Tue 9/86:05 am
CIA
- ORD
2 stops17h 05m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$804
This Scandinavian Airlines deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2110:30 am
ORD
- FLR
2 stops25h 35m
Scandinavian Airlines
Mon 9/287:55 pm
FLR
- ORD
2 stops33h 37m
Scandinavian Airlines
Deal found 6/26![Scandinavian Airlines logo]()
$820
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.
Mon 7/208:45 am
ORD
- FCO
1 stop17h 30m
United Airlines
Thu 7/309:45 am
FCO
- ORD
Nonstop10h 30m
United Airlines
Deal found 6/29![United Airlines logo]()
$835
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 7/810:28 am
ORD
- FCO
2 stops16h 07m
Delta
Wed 7/156:30 am
FCO
- ORD
1 stop15h 00m
Delta
Deal found 6/30![Delta logo]()
$844
This British Airways 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/227:05 pm
ORD
- PSA
1 stop33h 15m
British Airways
Sat 11/1411:00 am
PSA
- ORD
1 stop33h 50m
British Airways
Deal found 6/30![British Airways logo]()
$941
This ITA 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/13:00 pm
ORD
- FCO
Nonstop9h 25m
ITA Airways
Sat 9/129:20 am
FCO
- ORD
Nonstop10h 50m
ITA Airways
Deal found 6/29![ITA Airways logo]()
$879
This KLM deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/107:30 pm
ORD
- PSA
2 stops13h 35m
KLM
Mon 8/173:40 pm
PSA
- ORD
1 stop29h 35m
KLM
Deal found 6/26![KLM logo]()
$889
This Air France deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:30 pm
MDW
- FLR
2 stops12h 55m
Multiple Airlines
Tue 11/246:30 am
FLR
- MDW
2 stops16h 55m
Multiple Airlines
Deal found 6/26![Multiple Airlines logo]()
$830
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/213:35 pm
ORD
- FLR
1 stop14h 05m
United Airlines
Mon 8/2410:45 am
FLR
- ORD
1 stop32h 50m
United Airlines
Deal found 6/28![United Airlines logo]()
$854
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.
Fri 8/141:59 pm
ORD
- FLR
2 stops17h 26m
Delta
Fri 8/216:30 am
FLR
- ORD
1 stop14h 45m
Delta
Deal found 6/30![Delta logo]()
$854
This British Airways 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/189:15 pm
ORD
- PSA
1 stop15h 05m
British Airways
Tue 11/1710:20 am
PSA
- ORD
1 stop15h 25m
British Airways
Deal found 6/30![British Airways logo]()
$951
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.
Mon 9/211:19 pm
MDW
- PSA
2 stops17h 56m
KLM
Mon 11/167:40 pm
PSA
- MDW
2 stops28h 10m
KLM
Deal found 6/30![KLM logo]()
$891
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/81:25 pm
MDW
- FLR
2 stops15h 45m
Delta
Fri 8/216:30 am
FLR
- MDW
2 stops19h 03m
Delta
Deal found 7/1![Delta logo]()
$864
This British Airways 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/267:05 pm
ORD
- PSA
1 stop33h 30m
British Airways
Tue 11/1710:20 am
PSA
- ORD
1 stop34h 30m
British Airways
Deal found 6/30![British Airways logo]()
$951
This Condor 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 Condor is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/38:15 am
MDW
- FCO
2 stops30h 30m
Multiple Airlines
Thu 9/108:10 am
FCO
- MDW
2 stops20h 50m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$867
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/133:45 pm
ORD
- FCO
Nonstop9h 10m
United Airlines
Tue 8/186:50 am
FCO
- ORD
1 stop15h 05m
United Airlines
Deal found 6/28![United Airlines logo]()
$868
Last-minute flights from Chicago to TuscanyDiscover last-minute flight deals from Chicago to Tuscany. Data last updated July 1, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Tuscany. Data last updated July 1, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/307:25 pm
ORD
- FCO
1 stop12h 10m
Icelandair
Tue 7/73:45 pm
FCO
- ORD
1 stop12h 40m
Icelandair
Deal found 6/26![Icelandair logo]()
$777
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/77:25 pm
ORD
- FCO
1 stop12h 10m
Icelandair
Tue 7/143:45 pm
FCO
- ORD
1 stop12h 40m
Icelandair
Deal found 6/30![Icelandair logo]()
$776
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/73:00 pm
ORD
- FLR
1 stop20h 15m
ITA Airways
Wed 7/157:00 pm
FLR
- ORD
1 stop25h 10m
ITA Airways
Deal found 6/27![ITA Airways logo]()
$781
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/1410:56 am
ORD
- FCO
2 stops15h 54m
Multiple Airlines
Wed 8/198:10 am
FCO
- ORD
2 stops18h 17m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$774
This ITA Airways 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/153:00 pm
ORD
- FCO
Nonstop9h 25m
ITA Airways
Wed 7/229:20 am
FCO
- ORD
Nonstop10h 50m
ITA Airways
Deal found 6/30![ITA Airways logo]()
$778
This Gotogate deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/153:45 pm
ORD
- FCO
1 stop11h 35m
Multiple Airlines
Mon 8/3111:30 am
FCO
- ORD
1 stop15h 35m
Multiple Airlines
Deal found 6/26![Multiple Airlines logo]()
$781
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/176:00 pm
ORD
- FCO
1 stop15h 40m
TAP AIR PORTUGAL
Tue 8/48:00 pm
FCO
- ORD
1 stop27h 00m
TAP AIR PORTUGAL
Deal found 6/29![TAP AIR PORTUGAL logo]()
$775
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/176:00 pm
ORD
- FCO
1 stop33h 20m
TAP AIR PORTUGAL
Wed 7/298:00 pm
FCO
- ORD
1 stop23h 40m
TAP AIR PORTUGAL
Deal found 6/30![TAP AIR PORTUGAL logo]()
$780
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 7/226:00 pm
ORD
- FCO
1 stop23h 15m
TAP AIR PORTUGAL
Wed 8/58:00 pm
FCO
- ORD
1 stop23h 40m
TAP AIR PORTUGAL
Deal found 6/30![TAP AIR PORTUGAL logo]()
$772
This ITA 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/263:00 pm
ORD
- FCO
Nonstop9h 25m
ITA Airways
Thu 8/139:20 am
FCO
- ORD
Nonstop10h 50m
ITA Airways
Deal found 6/29![ITA Airways logo]()
$782
This ITA 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/273:00 pm
ORD
- FCO
Nonstop9h 25m
ITA Airways
Tue 8/119:20 am
FCO
- ORD
Nonstop10h 50m
ITA Airways
Deal found 6/29![ITA Airways logo]()
$770
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.
Wed 7/297:25 pm
ORD
- FCO
1 stop12h 00m
Multiple Airlines
Tue 8/189:25 pm
FCO
- ORD
3 stops29h 27m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$769
One-way flights from Chicago to TuscanySearch for one-way flight options from Chicago to Tuscany. Find affordable one-way fares based on user searches. Data last updated July 1, 2026.
Search for one-way flight options from Chicago to Tuscany. Find affordable one-way fares based on user searches. Data last updated July 1, 2026.
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.
Sun 8/307:25 pm
ORD
- FLR
3 stops44h 40m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$285
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.
Thu 10/154:49 pm
ORD
- FLR
2 stops47h 16m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$320
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.
Sun 9/2010:25 pm
ORD
- FLR
3 stops41h 30m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$346
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.
Mon 11/26:30 pm
ORD
- FLR
3 stops45h 00m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$348
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/207:05 pm
ORD
- FLR
1 stop20h 15m
British Airways
Deal found 7/1![British Airways logo]()
$349
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1410:25 pm
ORD
- FLR
2 stops29h 40m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$351
This Trip.com deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/277:25 pm
ORD
- FLR
2 stops15h 50m
Multiple Airlines
Deal found 6/26![Multiple Airlines logo]()
$352
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 7/297:25 pm
ORD
- FLR
3 stops44h 05m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$355
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/257:50 pm
ORD
- FLR
1 stop12h 00m
SWISS
Deal found 6/30![SWISS logo]()
$356
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/201:31 pm
ORD
- FLR
2 stops15h 04m
American Airlines
Deal found 7/1![American Airlines logo]()
$357
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 8/510:25 pm
ORD
- FLR
2 stops33h 15m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$361
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/201:28 pm
MDW
- FLR
2 stops15h 42m
Delta
Deal found 7/1![Delta logo]()
$364
Find flight deals from Chicago to Tuscany
Keep the following information in mind while searching for Chicago to Tuscany flight deals. Data was last updated July 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $551 (Kiwi.com) |
One-way from | $285 (Kiwi.com) |
Popular in | June |
Cheapest in | November |
Average price | $1,292 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Tuscany 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 1, 2026.
Use the filters below to find and compare flights from Chicago to Tuscany that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoPisa
ORD - PSA
ORDPSA
Chicago O'Hare Intl
Sun 8/23
7:15 pm-10:55 am
1 stop32h 40m
Pisa Gal Galilei
Thu 8/27
11:45 am-10:44 pm
2 stops41h 59m
$720
ChicagoRome
ORD - CIA
ORDCIA
Chicago O'Hare Intl
Tue 8/18
7:25 pm-9:10 pm
2 stops18h 45m
Rome Ciampino
Tue 9/8
1:20 pm-6:15 pm
3 stops35h 55m
$767
ChicagoRome
MDW - FCO
MDWFCO
Chicago Midway
Thu 8/6
10:54 am-7:35 am
1 stop13h 41m
Rome Fiumicino
Wed 8/19
6:30 am-6:01 pm
2 stops18h 31m
$776
ChicagoRome
MDW - FCO
MDWFCO
Chicago Midway
Mon 8/24
9:24 am-11:00 am
1 stop18h 36m
Rome Fiumicino
Sat 12/12
1:30 pm-10:10 pm
1 stop15h 40m
$777
ChicagoRome
ORD - CIA
ORDCIA
Chicago O'Hare Intl
Wed 8/12
11:05 am-7:50 pm
3 stops25h 45m
Rome Ciampino
Wed 8/26
10:40 am-7:55 pm
2 stops16h 15m
$799
ChicagoPisa
ORD - PSA
ORDPSA
Chicago O'Hare Intl
Mon 9/21
7:35 am-10:55 am
2 stops20h 20m
Pisa Gal Galilei
Fri 10/2
11:45 am-7:59 pm
2 stops39h 14m
$804
ChicagoRome
ORD - CIA
ORDCIA
Chicago O'Hare Intl
Tue 9/1
7:15 pm-9:10 pm
2 stops18h 55m
Rome Ciampino
Tue 9/8
6:05 am-4:10 pm
2 stops17h 05m
$804
Quickest round-trip
ChicagoRome
ORD - FCO
ORDFCO
Chicago O'Hare Intl
Wed 7/29
3:00 pm-7:25 am
Nonstop9h 25m
Rome Fiumicino
Sun 8/2
9:20 am-1:10 pm
Nonstop10h 50m
$812
ChicagoPisa
MDW - PSA
MDWPSA
Chicago Midway
Wed 8/19
1:25 pm-2:10 pm
2 stops17h 45m
Pisa Gal Galilei
Wed 8/26
3:40 pm-4:15 pm
2 stops31h 35m
$813
ChicagoPisa
MDW - PSA
MDWPSA
Chicago Midway
Tue 8/11
6:42 pm-3:35 pm
2 stops13h 53m
Pisa Gal Galilei
Tue 8/18
4:55 pm-4:15 pm
2 stops30h 20m
$813
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Chicago to Tuscany
Have a flexible travel schedule? Discover the best time to fly to Tuscany from Chicago with our price prediction graph.
ORD-PSA
ORD-CIA
MDW-FCO
ORD-FCO
MDW-PSA
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 Chicago to Tuscany
CHI-ITTO
ORD-PSA
ORD-CIA
MDW-FCO
ORD-FCO
What is the cheapest month to book a flight from Chicago to Tuscany?
Currently, October is the cheapest month in which you can book a flight from Chicago to Tuscany (average of $435). Flying from Chicago to Tuscany in June is currently the most expensive (average of $1,041). 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 Chicago to Tuscany?
How far ahead should I book a flight from Chicago to Tuscany?
To ensure you get the cheapest price possible for a flight from Chicago to Tuscany, you should look to book at least 47 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Reviews of airlines servicing Tuscany
Get insights into the airlines that provide service to Tuscany. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Tuscany. Reviews last updated July 1, 2026.
See what other customers who have flown with SWISS,Scandinavian Airlines, andUnited Airlines from Chicago to Tuscany have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
6.8
Boarding
7.7
Comfort
7.4
Overall
7.5
Crew
8.3
Food
7.1
Reviews
1 / 20
6.0
GoodCFJ,Mar 2026
ZRH - VCE
Entertainment
6.8
Boarding
7.7
Comfort
7.4
Overall
7.5
Crew
8.3
Food
7.1
Reviews
1 / 20
6.0
GoodCFJ,Mar 2026
ZRH - VCE
Entertainment
6.8
Boarding
7.7
Comfort
7.4
Overall
7.5
Crew
8.3
Food
7.1
Reviews
1 / 20
6.0
GoodCFJ,Mar 2026
ZRH - VCE
Entertainment
6.8
Boarding
7.7
Comfort
7.4
Overall
7.5
Crew
8.3
Food
7.1
Reviews
1 / 20
6.0
GoodCFJ,Mar 2026
ZRH - VCE
Entertainment
6.8
Boarding
7.7
Comfort
7.4
Overall
7.5
Crew
8.3
Food
7.1
Reviews
1 / 20
6.0
GoodCFJ,Mar 2026
ZRH - VCE
Entertainment
6.8
Boarding
7.7
Comfort
7.4
Overall
7.5
Crew
8.3
Food
7.1
Reviews
1 / 20
6.0
GoodCFJ,Mar 2026
ZRH - VCE
Related info for your journey
Find useful and relevant information for your journey from Chicago to Tuscany. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Tuscany
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Complete your trip
Complete your trip to Tuscany by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Tuscany by cabin class
Find flights from Chicago to Tuscany, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Tuscany flights
Browse other Chicago and Tuscany flight options. Last updated on July 1, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 10 airlines flying from Chicago to Tuscany
Discover the top 10 airlines that operate flights from Chicago to Tuscany. 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 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$443 | Average$662 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$458 | Average$1,031 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$588 | Average$923 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$602 | Average$1,023 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$619 | Average$1,183 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$630 | Average$931 | FlexibilityNo cancel fee | On-time76% | |
| Cheapest$644 | Average$993 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$690 | Average$1,138 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$758 | Average$963 | FlexibilityNo cancel fee | On-time81% | |
| Cheapest$860 | Average$1,306 | FlexibilityNo cancel fee | On-timeN/A |