$333+ 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 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — FLR
Jul 9 — Jul 161
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 June 9, 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 June 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/47:15 pm
ORD
- FLR
1 stop16h 50m
Scandinavian Airlines
Fri 10/167:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/8![Scandinavian Airlines logo]()
$587
This Kiwi.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 10/47:15 pm
ORD
- FLR
1 stop16h 50m
Scandinavian Airlines
Tue 10/137:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/4![Scandinavian Airlines logo]()
$591
This FlightHub deal was found by Cheapflights users on 6/9. 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 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
Wed 10/147:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/9![Scandinavian Airlines logo]()
$613
This FlightHub deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub 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
Fri 10/167:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/8![Scandinavian Airlines logo]()
$614
This FlightHub deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/267:15 pm
ORD
- FLR
2 stops30h 55m
Scandinavian Airlines
Fri 10/97:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/8![Scandinavian Airlines logo]()
$615
This FlightHub deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 9/187:15 pm
ORD
- FLR
2 stops54h 55m
Scandinavian Airlines
Fri 10/97:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/4![Scandinavian Airlines logo]()
$616
This Kiwi.com deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:15 pm
ORD
- FLR
1 stop16h 50m
Scandinavian Airlines
Wed 10/147:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/8![Scandinavian Airlines logo]()
$619
This Kiwi.com deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:15 pm
ORD
- FLR
1 stop16h 50m
Scandinavian Airlines
Tue 10/67:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/8![Scandinavian Airlines logo]()
$620
This Scandinavian Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/297:15 pm
ORD
- FLR
1 stop16h 50m
Scandinavian Airlines
Fri 10/167:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/8![Scandinavian Airlines logo]()
$636
This Justfly.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
Fri 10/27:15 pm
ORD
- FLR
1 stop16h 25m
Scandinavian Airlines
Mon 10/127:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/4![Scandinavian Airlines logo]()
$644
This American Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/27:05 pm
ORD
- PSA
1 stop17h 55m
American Airlines
Tue 8/186:30 pm
PSA
- ORD
1 stop28h 25m
American Airlines
Deal found 6/8![American Airlines logo]()
$751
This oojo deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 10/237:00 am
ORD
- PSA
2 stops29h 10m
Scandinavian Airlines
Sat 10/318:00 pm
PSA
- ORD
1 stop27h 45m
Scandinavian Airlines
Deal found 6/4![Scandinavian Airlines logo]()
$777
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 June 9, 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 June 9, 2026.
This Scandinavian Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 9/197:15 pm
ORD
- FLR
1 stop16h 50m
Scandinavian Airlines
Fri 10/97:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/4![Scandinavian Airlines logo]()
$667
This British Airways deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:00 pm
ORD
- FLR
1 stop22h 20m
British Airways
Wed 11/412:10 pm
FLR
- ORD
1 stop32h 40m
British Airways
Deal found 6/6![British Airways logo]()
$792
This KLM deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Tue 8/184:55 pm
PSA
- MDW
2 stops30h 20m
KLM
Deal found 6/8![KLM logo]()
$800
This British Airways deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/221:43 pm
ORD
- FLR
2 stops14h 47m
Multiple Airlines
Thu 11/53:20 pm
FLR
- ORD
2 stops26h 31m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$839
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/84:30 pm
ORD
- FLR
2 stops14h 55m
Delta
Fri 8/216:30 am
FLR
- ORD
1 stop14h 45m
Delta
Deal found 6/9![Delta logo]()
$856
This Air Serbia deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Serbia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/94:40 pm
ORD
- FLR
1 stop33h 00m
Air Serbia
Sun 9/208:40 pm
FLR
- ORD
1 stop24h 50m
Air Serbia
Deal found 6/7![Air Serbia logo]()
$864
This ITA Airways deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/223:00 pm
ORD
- FCO
Nonstop9h 25m
ITA Airways
Thu 7/309:20 am
FCO
- ORD
Nonstop10h 50m
ITA Airways
Deal found 6/6![ITA Airways logo]()
$883
This United Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/303:45 pm
ORD
- FCO
Nonstop9h 10m
United Airlines
Wed 8/129:45 am
FCO
- ORD
Nonstop10h 30m
United Airlines
Deal found 6/6![United Airlines logo]()
$883
This Cheapflightsfares deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2110:30 pm
ORD
- PSA
1 stop12h 30m
Lufthansa
Fri 10/210:35 am
PSA
- ORD
1 stop16h 20m
Lufthansa
Deal found 6/5![Lufthansa logo]()
$949
This Scandinavian Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 9/297:30 am
ORD
- FLR
2 stops28h 35m
Scandinavian Airlines
Tue 10/137:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/4![Scandinavian Airlines logo]()
$691
This Scandinavian Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 9/237:15 pm
ORD
- FLR
1 stop16h 50m
Scandinavian Airlines
Fri 10/97:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/4![Scandinavian Airlines logo]()
$707
This British Airways deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/151:43 pm
ORD
- PSA
2 stops15h 17m
British Airways
Thu 11/1212:30 pm
PSA
- ORD
2 stops26h 48m
British Airways
Deal found 6/5![British Airways logo]()
$823
This British Airways deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/211:43 pm
ORD
- FLR
2 stops14h 52m
Multiple Airlines
Wed 11/412:10 pm
FLR
- ORD
2 stops26h 05m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$850
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/81:27 pm
MDW
- FCO
1 stop14h 33m
Delta
Sat 8/226:30 am
FCO
- MDW
2 stops18h 31m
Delta
Deal found 6/8![Delta logo]()
$857
This KLM deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1510:56 am
MDW
- FCO
1 stop13h 39m
KLM
Sat 8/221:10 pm
FCO
- MDW
1 stop16h 26m
KLM
Deal found 6/5![KLM logo]()
$857
This Scandinavian Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:35 pm
ORD
- FLR
2 stops32h 30m
Scandinavian Airlines
Thu 10/87:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/5![Scandinavian Airlines logo]()
$733
This ITA Airways deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/293:00 pm
ORD
- FCO
Nonstop9h 25m
ITA Airways
Thu 7/99:20 am
FCO
- ORD
Nonstop10h 50m
ITA Airways
Deal found 6/8![ITA Airways logo]()
$901
This United Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/711:05 am
ORD
- PSA
2 stops23h 50m
United Airlines
Tue 7/1410:35 am
PSA
- ORD
1 stop16h 20m
United Airlines
Deal found 6/9![United Airlines logo]()
$901
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 8/156:05 am
MDW
- FCO
1 stop18h 30m
Delta
Sat 8/221:10 pm
FCO
- MDW
1 stop16h 26m
Delta
Deal found 6/4![Delta logo]()
$858
This Condor deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Condor is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/178:15 am
MDW
- FCO
2 stops30h 35m
Multiple Airlines
Mon 8/248:10 am
FCO
- MDW
2 stops20h 50m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$886
This Scandinavian Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:15 pm
ORD
- FLR
1 stop33h 15m
Scandinavian Airlines
Fri 10/27:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/5![Scandinavian Airlines logo]()
$736
This KLM deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/261:18 pm
MDW
- PSA
2 stops18h 32m
KLM
Mon 8/103:40 pm
PSA
- MDW
2 stops31h 35m
KLM
Deal found 6/6![KLM logo]()
$891
This British Airways deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/35:00 pm
ORD
- FCO
Nonstop9h 10m
British Airways
Sun 8/1610:00 am
FCO
- ORD
Nonstop10h 40m
British Airways
Deal found 6/6![British Airways logo]()
$903
This United Airlines deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/266:30 pm
ORD
- PSA
1 stop16h 25m
United Airlines
Mon 8/1010:20 am
PSA
- ORD
1 stop33h 35m
United Airlines
Deal found 6/7![United Airlines logo]()
$913
This ITA Airways deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/193:00 pm
ORD
- FCO
Nonstop9h 25m
ITA Airways
Wed 7/299:20 am
FCO
- ORD
Nonstop10h 50m
ITA Airways
Deal found 6/8![ITA Airways logo]()
$929
This Delta deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/121:27 pm
MDW
- FLR
2 stops15h 43m
Delta
Mon 8/246:30 am
FLR
- MDW
2 stops18h 31m
Delta
Deal found 6/6![Delta logo]()
$866
This Orbitz deal was found by Cheapflights users on 6/9. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/78:45 am
ORD
- PSA
2 stops18h 20m
Multiple Airlines
Tue 7/1410:35 am
PSA
- ORD
2 stops16h 30m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$905
This British Airways deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/224:55 pm
ORD
- FCO
Nonstop9h 15m
British Airways
Thu 7/910:00 am
FCO
- ORD
Nonstop10h 40m
British Airways
Deal found 6/7![British Airways logo]()
$923
This United Airlines deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/163:45 pm
ORD
- FCO
Nonstop9h 10m
United Airlines
Tue 7/289:45 am
FCO
- ORD
Nonstop10h 30m
United Airlines
Deal found 6/7![United Airlines logo]()
$923
This ITA Airways deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/53:00 pm
ORD
- FCO
Nonstop9h 25m
ITA Airways
Sun 8/99:20 am
FCO
- ORD
Nonstop10h 50m
ITA Airways
Deal found 6/5![ITA Airways logo]()
$933
Last-minute flights from Chicago to TuscanyDiscover last-minute flight deals from Chicago to Tuscany. Data last updated June 9, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Tuscany. Data last updated June 9, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/65:00 pm
ORD
- FCO
Nonstop9h 10m
Iberia
Wed 7/1510:00 am
FCO
- ORD
Nonstop10h 40m
Iberia
Deal found 6/8![Iberia logo]()
$832
This British Airways deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/67:05 pm
ORD
- FCO
1 stop13h 05m
British Airways
Wed 7/221:30 pm
FCO
- ORD
1 stop15h 30m
British Airways
Deal found 6/7![British Airways logo]()
$835
This oojo deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/87:05 pm
ORD
- FCO
1 stop17h 15m
British Airways
Wed 7/2210:00 am
FCO
- ORD
Nonstop10h 40m
British Airways
Deal found 6/8![British Airways logo]()
$826
This American Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/810:30 pm
ORD
- FCO
1 stop13h 50m
American Airlines
Wed 7/1510:00 am
FCO
- ORD
Nonstop10h 40m
American Airlines
Deal found 6/8![American Airlines logo]()
$829
This Cheapflightsfares deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/129:15 pm
ORD
- FCO
1 stop12h 50m
Multiple Airlines
Wed 7/226:45 am
FCO
- ORD
1 stop15h 15m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$828
This lol.travel deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
Mon 7/209:40 pm
ORD
- FLR
1 stop15h 35m
Lufthansa
Tue 8/41:40 pm
FLR
- ORD
1 stop13h 15m
Lufthansa
Deal found 6/4![Lufthansa logo]()
$823
This United Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/203:45 pm
ORD
- FCO
Nonstop9h 10m
United Airlines
Tue 7/289:45 am
FCO
- ORD
Nonstop10h 30m
United Airlines
Deal found 6/8![United Airlines logo]()
$833
This United Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/203:45 pm
ORD
- FCO
Nonstop9h 10m
United Airlines
Thu 7/307:10 am
FCO
- ORD
1 stop12h 45m
United Airlines
Deal found 6/8![United Airlines logo]()
$834
This Air France deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/211:18 pm
MDW
- FCO
1 stop14h 42m
Air France
Tue 7/289:00 am
FCO
- MDW
1 stop16h 25m
Air France
Deal found 6/6![Air France logo]()
$836
This United Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/218:45 am
ORD
- FCO
1 stop17h 30m
United Airlines
Fri 8/710:00 am
FCO
- ORD
1 stop16h 55m
United Airlines
Deal found 6/8![United Airlines logo]()
$837
This United Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2211:05 am
ORD
- FCO
1 stop15h 10m
United Airlines
Tue 8/48:00 am
FCO
- ORD
1 stop17h 15m
United Airlines
Deal found 6/8![United Airlines logo]()
$836
This Kiwi.com deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/263:35 pm
ORD
- FCO
1 stop11h 25m
Lufthansa
Fri 8/71:20 pm
FCO
- ORD
1 stop13h 35m
Lufthansa
Deal found 6/8![Lufthansa logo]()
$831
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 June 9, 2026.
Search for one-way flight options from Chicago to Tuscany. Find affordable one-way fares based on user searches. Data last updated June 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3010:25 pm
ORD
- PSA
2 stops31h 05m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/217:25 pm
ORD
- FLR
3 stops31h 20m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$340
This oojo deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/184:06 pm
ORD
- FLR
2 stops14h 59m
British Airways
Deal found 6/7![British Airways logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:25 pm
ORD
- PSA
2 stops37h 00m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$348
This Cheapflightsfares deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/205:00 pm
ORD
- FLR
1 stop11h 35m
British Airways
Deal found 6/8![British Airways logo]()
$349
This American Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/145:55 pm
ORD
- FLR
1 stop21h 25m
American Airlines
Deal found 6/6![American Airlines logo]()
$352
This American Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/201:43 pm
ORD
- FLR
2 stops14h 52m
American Airlines
Deal found 6/8![American Airlines logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/117:25 pm
ORD
- PSA
2 stops16h 55m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$359
This Iberia deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:35 pm
ORD
- FLR
2 stops18h 00m
Iberia
Deal found 6/6![Iberia logo]()
$368
This FlightHub deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/128:25 pm
ORD
- FLR
2 stops32h 10m
British Airways
Deal found 6/5![British Airways logo]()
$372
This Iberia deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
Sun 10/255:05 pm
ORD
- FLR
2 stops17h 45m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$373
This Kiwi.com deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/57:25 pm
ORD
- FLR
2 stops20h 30m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$374
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 June 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $587 (Kiwi.com) |
One-way from | $333 (Kiwi.com) |
Popular in | June |
Cheapest in | November |
Average price | $1,359 |
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 June 9, 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
ChicagoFlorence
ORD - FLR
ORDFLR
Chicago O'Hare Intl
Sat 9/19
7:15 pm-7:05 pm
1 stop16h 50m
Florence Peretola
Fri 10/9
7:55 pm-4:10 pm
1 stop27h 15m
$667
ChicagoFlorence
ORD - FLR
ORDFLR
Chicago O'Hare Intl
Tue 9/29
7:30 am-7:05 pm
2 stops28h 35m
Florence Peretola
Tue 10/13
7:55 pm-4:10 pm
1 stop27h 15m
$691
ChicagoFlorence
ORD - FLR
ORDFLR
Chicago O'Hare Intl
Wed 9/23
7:15 pm-7:05 pm
1 stop16h 50m
Florence Peretola
Fri 10/9
7:55 pm-4:10 pm
1 stop27h 15m
$707
ChicagoFlorence
ORD - FLR
ORDFLR
Chicago O'Hare Intl
Fri 9/25
7:35 pm-11:05 am
2 stops32h 30m
Florence Peretola
Thu 10/8
7:55 pm-4:10 pm
1 stop27h 15m
$733
ChicagoFlorence
ORD - FLR
ORDFLR
Chicago O'Hare Intl
Wed 9/23
7:15 pm-11:30 am
1 stop33h 15m
Florence Peretola
Fri 10/2
7:55 pm-4:10 pm
1 stop27h 15m
$736
ChicagoFlorence
ORD - FLR
ORDFLR
Chicago O'Hare Intl
Wed 10/21
5:00 pm-10:20 pm
1 stop22h 20m
Florence Peretola
Wed 11/4
12:10 pm-1:50 pm
1 stop32h 40m
$792
ChicagoPisa
MDW - PSA
MDWPSA
Chicago Midway
Sun 8/2
1:18 pm-2:50 pm
2 stops18h 32m
Pisa Gal Galilei
Tue 8/18
4:55 pm-4:15 pm
2 stops30h 20m
$800
ChicagoPisa
ORD - PSA
ORDPSA
Chicago O'Hare Intl
Thu 10/15
1:43 pm-12:00 pm
2 stops15h 17m
Pisa Gal Galilei
Thu 11/12
12:30 pm-8:18 am
2 stops26h 48m
$823
ChicagoFlorence
ORD - FLR
ORDFLR
Chicago O'Hare Intl
Thu 10/22
1:43 pm-11:30 am
2 stops14h 47m
Florence Peretola
Thu 11/5
3:20 pm-10:51 am
2 stops26h 31m
$839
ChicagoFlorence
ORD - FLR
ORDFLR
Chicago O'Hare Intl
Wed 10/21
1:43 pm-11:35 am
2 stops14h 52m
Florence Peretola
Wed 11/4
12:10 pm-7:15 am
2 stops26h 05m
$850
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
ORD-PSA
MDW-FLR
MDW-PSA
ORD-FCO
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
ORD-PSA
MDW-FLR
MDW-PSA
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 $661). 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 45 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 June 9, 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
Food
7.1
Overall
7.5
Boarding
7.7
Comfort
7.4
Crew
8.3
Reviews
1 / 20
6.0
GoodCFJ,Mar 2026
ZRH - VCE
Entertainment
6.8
Food
7.1
Overall
7.5
Boarding
7.7
Comfort
7.4
Crew
8.3
Reviews
1 / 20
6.0
GoodCFJ,Mar 2026
ZRH - VCE
Entertainment
6.8
Food
7.1
Overall
7.5
Boarding
7.7
Comfort
7.4
Crew
8.3
Reviews
1 / 20
6.0
GoodCFJ,Mar 2026
ZRH - VCE
Entertainment
6.8
Food
7.1
Overall
7.5
Boarding
7.7
Comfort
7.4
Crew
8.3
Reviews
1 / 20
6.0
GoodCFJ,Mar 2026
ZRH - VCE
Entertainment
6.8
Food
7.1
Overall
7.5
Boarding
7.7
Comfort
7.4
Crew
8.3
Reviews
1 / 20
6.0
GoodCFJ,Mar 2026
ZRH - VCE
Entertainment
6.8
Food
7.1
Overall
7.5
Boarding
7.7
Comfort
7.4
Crew
8.3
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 June 9, 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 June 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$443 | Average$665 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$458 | Average$884 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$491 | Average$850 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$588 | Average$965 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$602 | Average$1,080 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$630 | Average$1,059 | FlexibilityNo cancel fee | On-time76% | |
| Cheapest$687 | Average$1,036 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$690 | Average$1,133 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$758 | Average$940 | FlexibilityNo cancel fee | On-time81% | |
| Cheapest$809 | Average$1,300 | FlexibilityNo cancel fee | On-timeN/A |