$376+ 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 9/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — FLR
Jun 14 — Jun 211
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Tuscany with Cheapflights
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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 May 15, 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 May 15, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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
Thu 10/157:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 5/14![Scandinavian Airlines logo]()
$617
This oojo deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 9/187:15 pm
ORD
- FLR
1 stop32h 50m
Scandinavian Airlines
Fri 10/97:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 5/14![Scandinavian Airlines logo]()
$639
This Gotogate deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 10/16:00 pm
ORD
- FLR
1 stop17h 00m
TAP AIR PORTUGAL
Thu 10/156:50 pm
FLR
- ORD
1 stop28h 10m
TAP AIR PORTUGAL
Deal found 5/14![TAP AIR PORTUGAL logo]()
$682
This oojo deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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 10/76:00 pm
ORD
- FLR
1 stop33h 50m
TAP AIR PORTUGAL
Wed 10/1412:05 pm
FLR
- ORD
1 stop31h 35m
TAP AIR PORTUGAL
Deal found 5/15![TAP AIR PORTUGAL logo]()
$687
This FlightHub deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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.
Thu 10/226:00 pm
ORD
- FLR
1 stop34h 00m
TAP AIR PORTUGAL
Thu 11/57:15 pm
FLR
- ORD
1 stop27h 15m
TAP AIR PORTUGAL
Deal found 5/14![TAP AIR PORTUGAL logo]()
$696
This FlightHub deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 10/236:00 pm
ORD
- FLR
1 stop17h 00m
TAP AIR PORTUGAL
Sat 11/712:20 pm
FLR
- ORD
1 stop34h 10m
TAP AIR PORTUGAL
Deal found 5/14![TAP AIR PORTUGAL logo]()
$699
This FlightHub deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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.
Thu 10/16:00 pm
ORD
- FLR
1 stop17h 00m
TAP AIR PORTUGAL
Tue 10/1311:50 am
FLR
- ORD
1 stop35h 10m
TAP AIR PORTUGAL
Deal found 5/14![TAP AIR PORTUGAL logo]()
$704
This oojo deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 10/97:15 pm
ORD
- FLR
1 stop16h 25m
Scandinavian Airlines
Mon 10/127:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 5/13![Scandinavian Airlines logo]()
$710
This CheapOair deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/71:30 pm
ORD
- FLR
2 stops22h 35m
Scandinavian Airlines
Wed 10/147:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 5/15![Scandinavian Airlines logo]()
$721
This Kiwi.com deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 8/167:15 pm
ORD
- FLR
1 stop16h 50m
Scandinavian Airlines
Tue 9/157:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 5/14![Scandinavian Airlines logo]()
$725
This oojo deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 12/25:10 pm
ORD
- PSA
1 stop11h 25m
British Airways
Tue 12/810:20 am
PSA
- ORD
1 stop34h 30m
British Airways
Deal found 5/10![British Airways logo]()
$754
This British Airways deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/89:45 pm
ORD
- PSA
1 stop28h 45m
British Airways
Thu 11/1912:30 pm
PSA
- ORD
1 stop13h 15m
British Airways
Deal found 5/9![British Airways logo]()
$759
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 May 15, 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 May 15, 2026.
This Scandinavian Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/167:15 pm
ORD
- PSA
1 stop32h 40m
Scandinavian Airlines
Tue 9/1511:45 am
PSA
- ORD
2 stops52h 43m
Scandinavian Airlines
Deal found 5/9![Scandinavian Airlines logo]()
$766
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 8/1010:54 am
MDW
- FLR
2 stops15h 01m
Delta
Fri 8/216:30 am
FLR
- MDW
2 stops19h 03m
Delta
Deal found 5/14![Delta logo]()
$816
This Mytrip deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/89:50 pm
ORD
- CIA
2 stops16h 30m
Multiple Airlines
Mon 11/169:05 pm
CIA
- ORD
3 stops27h 15m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$861
This Cheapflightsfares deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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.
Sun 8/163:35 pm
ORD
- FLR
1 stop14h 05m
Lufthansa
Tue 9/158:15 am
FLR
- ORD
2 stops19h 06m
Lufthansa
Deal found 5/15![Lufthansa logo]()
$878
This KLM deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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.
Sun 8/21:49 pm
MDW
- PSA
2 stops18h 01m
KLM
Mon 8/103:40 pm
PSA
- MDW
2 stops31h 35m
KLM
Deal found 5/14![KLM logo]()
$902
This United Airlines deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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.
Sun 8/210:30 pm
ORD
- PSA
1 stop12h 25m
United Airlines
Mon 8/1010:20 am
PSA
- ORD
1 stop31h 40m
United Airlines
Deal found 5/14![United Airlines logo]()
$920
This Turkish Airlines deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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.
Fri 9/2511:25 am
ORD
- FLR
2 stops28h 15m
Turkish Airlines
Sun 10/46:25 am
FLR
- ORD
2 stops34h 15m
Turkish Airlines
Deal found 5/14![Turkish Airlines logo]()
$1,062
This Delta deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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 8/82:27 pm
ORD
- FLR
2 stops16h 58m
Delta
Fri 8/216:30 am
FLR
- ORD
1 stop14h 45m
Delta
Deal found 5/15![Delta logo]()
$857
This Scandinavian Airlines deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 10/117:15 pm
ORD
- FCO
2 stops17h 05m
Scandinavian Airlines
Sun 10/189:30 am
FCO
- ORD
1 stop13h 40m
Scandinavian Airlines
Deal found 5/11![Scandinavian Airlines logo]()
$884
This Mytrip deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 9/29:00 pm
ORD
- CIA
2 stops16h 20m
Multiple Airlines
Thu 9/246:05 am
CIA
- ORD
3 stops43h 10m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$891
This United Airlines deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 6/168:45 am
ORD
- FCO
1 stop17h 30m
United Airlines
Fri 6/269:45 am
FCO
- ORD
Nonstop10h 30m
United Airlines
Deal found 5/14![United Airlines logo]()
$927
This KLM deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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.
Thu 8/610:54 am
MDW
- FCO
1 stop13h 41m
KLM
Sun 8/169:00 am
FCO
- MDW
1 stop16h 33m
KLM
Deal found 5/14![KLM logo]()
$968
This Scandinavian Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:00 am
ORD
- PSA
2 stops30h 10m
Scandinavian Airlines
Fri 9/1811:45 am
PSA
- ORD
2 stops41h 21m
Scandinavian Airlines
Deal found 5/9![Scandinavian Airlines logo]()
$884
This Mytrip deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 5/289:55 am
ORD
- CIA
3 stops28h 50m
Multiple Airlines
Thu 6/186:05 am
CIA
- ORD
3 stops40h 55m
Multiple Airlines
Deal found 5/14![Multiple Airlines logo]()
$894
This United Airlines deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 6/293:45 pm
ORD
- FCO
Nonstop9h 10m
United Airlines
Mon 7/1310:50 am
FCO
- ORD
1 stop34h 10m
United Airlines
Deal found 5/14![United Airlines logo]()
$934
This Delta deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/21:22 pm
MDW
- FCO
1 stop14h 38m
Delta
Fri 6/121:10 pm
FCO
- MDW
1 stop16h 07m
Delta
Deal found 5/10![Delta logo]()
$938
This Turkish Airlines deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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.
Wed 9/98:10 pm
ORD
- FLR
2 stops39h 05m
Turkish Airlines
Sun 9/2011:25 am
FLR
- ORD
2 stops29h 15m
Turkish Airlines
Deal found 5/13![Turkish Airlines logo]()
$1,063
This KLM deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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.
Sun 8/21:18 pm
MDW
- PSA
2 stops18h 32m
KLM
Sun 8/99:45 pm
PSA
- MDW
2 stops25h 30m
KLM
Deal found 5/14![KLM logo]()
$972
This Mytrip deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 10/1511:05 am
ORD
- CIA
3 stops26h 25m
Multiple Airlines
Wed 10/218:35 pm
CIA
- ORD
3 stops28h 40m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$918
This Delta deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/31:22 pm
MDW
- FCO
2 stops13h 43m
Delta
Thu 6/256:30 am
FCO
- MDW
2 stops18h 48m
Delta
Deal found 5/11![Delta logo]()
$943
This United Airlines deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 11/43:40 pm
ORD
- FCO
Nonstop9h 05m
United Airlines
Wed 11/111:30 pm
FCO
- ORD
1 stop13h 35m
United Airlines
Deal found 5/10![United Airlines logo]()
$957
This Scandinavian Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/287:30 am
ORD
- FCO
2 stops20h 35m
Scandinavian Airlines
Fri 9/119:40 am
FCO
- ORD
1 stop13h 30m
Scandinavian Airlines
Deal found 5/9![Scandinavian Airlines logo]()
$996
This Mytrip deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 9/211:05 am
ORD
- CIA
3 stops25h 45m
Multiple Airlines
Thu 9/108:15 pm
CIA
- ORD
2 stops23h 20m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$921
This KLM deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 8/11:18 pm
MDW
- PSA
2 stops17h 57m
KLM
Sun 8/99:45 pm
PSA
- MDW
2 stops25h 30m
KLM
Deal found 5/14![KLM logo]()
$1,022
This Delta deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:58 pm
MDW
- FCO
2 stops14h 27m
Delta
Thu 6/189:45 am
FCO
- MDW
1 stop19h 32m
Delta
Deal found 5/12![Delta logo]()
$947
This United Airlines deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 10/151:12 pm
ORD
- FCO
1 stop12h 03m
United Airlines
Sun 10/259:45 am
FCO
- ORD
Nonstop10h 25m
United Airlines
Deal found 5/14![United Airlines logo]()
$958
This Scandinavian Airlines deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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.
Thu 9/247:00 am
ORD
- FCO
2 stops28h 35m
Scandinavian Airlines
Sat 10/2410:15 pm
FCO
- ORD
2 stops26h 30m
Scandinavian Airlines
Deal found 5/14![Scandinavian Airlines logo]()
$1,003
This Kiwi.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 9/25:10 pm
ORD
- CIA
1 stop19h 40m
Multiple Airlines
Mon 9/147:10 pm
CIA
- ORD
2 stops27h 00m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$927
This KLM deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 8/11:18 pm
MDW
- FCO
1 stop14h 42m
KLM
Sun 8/99:00 am
FCO
- MDW
1 stop16h 33m
KLM
Deal found 5/14![KLM logo]()
$1,046
This United Airlines deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 9/18:45 am
ORD
- PSA
2 stops26h 10m
United Airlines
Wed 9/910:45 am
PSA
- ORD
1 stop16h 10m
United Airlines
Deal found 5/13![United Airlines logo]()
$973
Last-minute flights from Chicago to TuscanyDiscover last-minute flight deals from Chicago to Tuscany. Data last updated May 15, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Tuscany. Data last updated May 15, 2026 and is based on user searches.
This Air Serbia deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Serbia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/134:40 pm
ORD
- FCO
1 stop32h 15m
Air Serbia
Tue 5/199:25 am
FCO
- ORD
1 stop36h 05m
Air Serbia
Deal found 5/9![Air Serbia logo]()
$831
This oojo deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 5/166:05 pm
ORD
- FCO
1 stop23h 10m
TAP AIR PORTUGAL
Thu 5/218:00 pm
FCO
- ORD
1 stop27h 00m
TAP AIR PORTUGAL
Deal found 5/11![TAP AIR PORTUGAL logo]()
$832
This Mytrip deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 5/279:55 am
ORD
- FCO
2 stops30h 25m
Multiple Airlines
Sat 6/136:15 am
FCO
- ORD
2 stops22h 00m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$834
This Kiwi.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 5/2710:30 am
MDW
- FCO
2 stops29h 50m
Multiple Airlines
Wed 6/32:15 pm
FCO
- MDW
1 stop26h 20m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$856
This Mytrip deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 5/319:55 am
ORD
- FCO
2 stops22h 55m
Multiple Airlines
Tue 6/911:00 am
FCO
- ORD
2 stops18h 05m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$827
This Mytrip deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 6/39:55 am
ORD
- FCO
2 stops30h 25m
Multiple Airlines
Wed 6/1712:15 pm
FCO
- ORD
3 stops31h 55m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$829
This Mytrip deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 6/39:55 am
ORD
- FCO
2 stops30h 25m
Multiple Airlines
Wed 6/107:10 pm
FCO
- ORD
2 stops24h 55m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$835
This Kiwi.com deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 6/310:15 am
MDW
- FCO
2 stops30h 05m
Multiple Airlines
Wed 6/102:15 pm
FCO
- MDW
1 stop26h 20m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$841
This Mytrip deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 6/410:43 am
ORD
- CIA
3 stops28h 02m
Multiple Airlines
Tue 6/169:05 pm
CIA
- ORD
3 stops46h 35m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$867
This Mytrip deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 6/149:55 am
ORD
- CIA
2 stops26h 30m
Multiple Airlines
Wed 6/246:55 am
CIA
- ORD
3 stops35h 55m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$861
This Mytrip deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 6/169:55 am
ORD
- FCO
2 stops28h 55m
Multiple Airlines
Tue 6/238:10 am
FCO
- ORD
2 stops20h 55m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$845
This Mytrip deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/271:55 pm
ORD
- FCO
2 stops36h 20m
Air Canada
Wed 8/2611:30 am
FCO
- ORD
1 stop30h 51m
Air Canada
Deal found 5/11![Air Canada logo]()
$840
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 May 15, 2026.
Search for one-way flight options from Chicago to Tuscany. Find affordable one-way fares based on user searches. Data last updated May 15, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 9/2710:25 pm
ORD
- FLR
3 stops30h 25m
Multiple Airlines
Deal found 5/14![Multiple Airlines logo]()
$376
This Air Serbia deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 Serbia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/264:40 pm
ORD
- FLR
1 stop33h 00m
Air Serbia
Deal found 5/12![Air Serbia logo]()
$400
This American Airlines deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 8/147:05 pm
ORD
- FLR
1 stop20h 15m
American Airlines
Deal found 5/13![American Airlines logo]()
$401
This Kiwi.com deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 10/49:30 pm
ORD
- FLR
3 stops27h 55m
Multiple Airlines
Deal found 5/14![Multiple Airlines logo]()
$407
This Mytrip deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 9/117:25 pm
ORD
- FLR
2 stops20h 30m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$409
This Cheapflightsfares deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 8/259:15 pm
ORD
- FLR
1 stop18h 05m
British Airways
Deal found 5/13![British Airways logo]()
$413
This American Airlines deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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.
Mon 9/219:00 pm
ORD
- FLR
1 stop18h 20m
American Airlines
Deal found 5/11![American Airlines logo]()
$420
This American Airlines deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 8/2512:41 pm
ORD
- FLR
2 stops15h 54m
American Airlines
Deal found 5/13![American Airlines logo]()
$424
This Kiwi.com deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 7/510:25 pm
ORD
- FLR
3 stops27h 00m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$425
This Kiwi.com deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 9/107:25 pm
ORD
- FLR
3 stops44h 40m
Multiple Airlines
Deal found 5/14![Multiple Airlines logo]()
$433
This Kiwi.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/1310:15 am
MDW
- FLR
3 stops53h 50m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$437
This Kiwi.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/123:20 pm
MDW
- FLR
3 stops24h 45m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$446
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 May 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $617 (Kiwi.com) |
One-way from | $376 (Kiwi.com) |
Popular in | June |
Cheapest in | November |
Average price | $1,102 |
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 May 15, 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 8/16
7:15 pm-10:55 am
1 stop32h 40m
Pisa Gal Galilei
Tue 9/15
11:45 am-9:28 am
2 stops52h 43m
$766
ChicagoFlorence
MDW - FLR
MDWFLR
Chicago Midway
Mon 8/10
10:54 am-8:55 am
2 stops15h 01m
Florence Peretola
Fri 8/21
6:30 am-6:33 pm
2 stops19h 03m
$816
ChicagoFlorence
ORD - FLR
ORDFLR
Chicago O'Hare Intl
Sat 8/8
2:27 pm-2:25 pm
2 stops16h 58m
Florence Peretola
Fri 8/21
6:30 am-2:15 pm
1 stop14h 45m
$857
ChicagoRome
ORD - CIA
ORDCIA
Chicago O'Hare Intl
Sun 11/8
9:50 pm-9:20 pm
2 stops16h 30m
Rome Ciampino
Mon 11/16
9:05 pm-5:20 pm
3 stops27h 15m
$861
ChicagoFlorence
ORD - FLR
ORDFLR
Chicago O'Hare Intl
Sun 8/16
3:35 pm-12:40 pm
1 stop14h 05m
Florence Peretola
Tue 9/15
8:15 am-8:21 pm
2 stops19h 06m
$878
ChicagoRome
ORD - FCO
ORDFCO
Chicago O'Hare Intl
Sun 10/11
7:15 pm-7:20 pm
2 stops17h 05m
Rome Fiumicino
Sun 10/18
9:30 am-4:10 pm
1 stop13h 40m
$884
ChicagoPisa
ORD - PSA
ORDPSA
Chicago O'Hare Intl
Sat 8/22
6:00 am-7:10 pm
2 stops30h 10m
Pisa Gal Galilei
Fri 9/18
11:45 am-10:06 pm
2 stops41h 21m
$884
ChicagoRome
ORD - CIA
ORDCIA
Chicago O'Hare Intl
Wed 9/2
9:00 pm-8:20 pm
2 stops16h 20m
Rome Ciampino
Thu 9/24
6:05 am-6:15 pm
3 stops43h 10m
$891
ChicagoRome
ORD - CIA
ORDCIA
Chicago O'Hare Intl
Thu 5/28
9:55 am-9:45 pm
3 stops28h 50m
Rome Ciampino
Thu 6/18
6:05 am-4:00 pm
3 stops40h 55m
$894
ChicagoPisa
MDW - PSA
MDWPSA
Chicago Midway
Sun 8/2
1:49 pm-2:50 pm
2 stops18h 01m
Pisa Gal Galilei
Mon 8/10
3:40 pm-4:15 pm
2 stops31h 35m
$902
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-FLR
MDW-FLR
ORD-PSA
ORD-CIA
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-FLR
MDW-FLR
ORD-PSA
ORD-CIA
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 46 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.
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 August is currently the most expensive (average of $583). 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?
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 May 15, 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
Crew
8.3
Food
7.1
Overall
7.5
Boarding
7.7
Comfort
7.4
Reviews
1 / 20
6.0
GoodCFJ,Mar 2026
ZRH - VCE
Entertainment
6.8
Crew
8.3
Food
7.1
Overall
7.5
Boarding
7.7
Comfort
7.4
Reviews
1 / 20
6.0
GoodCFJ,Mar 2026
ZRH - VCE
Entertainment
6.8
Crew
8.3
Food
7.1
Overall
7.5
Boarding
7.7
Comfort
7.4
Reviews
1 / 20
6.0
GoodCFJ,Mar 2026
ZRH - VCE
Entertainment
6.8
Crew
8.3
Food
7.1
Overall
7.5
Boarding
7.7
Comfort
7.4
Reviews
1 / 20
6.0
GoodCFJ,Mar 2026
ZRH - VCE
Entertainment
6.8
Crew
8.3
Food
7.1
Overall
7.5
Boarding
7.7
Comfort
7.4
Reviews
1 / 20
6.0
GoodCFJ,Mar 2026
ZRH - VCE
Entertainment
6.8
Crew
8.3
Food
7.1
Overall
7.5
Boarding
7.7
Comfort
7.4
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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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 May 15, 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 May 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$443 | Average$665 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$458 | Average$832 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$491 | Average$779 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$586 | Average$1,259 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$588 | Average$965 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$630 | Average$1,106 | FlexibilityNo cancel fee | On-time76% | |
| Cheapest$687 | Average$1,036 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$690 | Average$1,136 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$758 | Average$940 | FlexibilityNo cancel fee | On-time81% | |
| Cheapest$860 | Average$1,253 | FlexibilityNo cancel fee | On-timeN/A |