$213+ 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 4/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — FLR
Mar 5 — Mar 121
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 February 3, 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 February 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Sat 4/187:15 pm
ORD
- FLR
1 stop16h 50m
Scandinavian Airlines
Fri 4/247:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 2/1![Scandinavian Airlines logo]()
$420
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Fri 4/177:15 pm
ORD
- FLR
1 stop32h 20m
Scandinavian Airlines
Fri 4/247:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 2/1![Scandinavian Airlines logo]()
$429
This oojo deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/137:15 pm
ORD
- FLR
1 stop16h 50m
Scandinavian Airlines
Fri 4/247:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 2/2![Scandinavian Airlines logo]()
$438
This Mytrip deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/307:15 pm
ORD
- FLR
1 stop16h 50m
Scandinavian Airlines
Tue 4/147:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 2/2![Scandinavian Airlines logo]()
$452
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Fri 4/37:15 pm
ORD
- FLR
2 stops39h 05m
Scandinavian Airlines
Fri 4/1712:20 pm
FLR
- ORD
1 stop34h 50m
Scandinavian Airlines
Deal found 2/1![Scandinavian Airlines logo]()
$461
This oojo deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/107:15 pm
ORD
- FLR
1 stop32h 20m
Scandinavian Airlines
Fri 4/247:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 2/3![Scandinavian Airlines logo]()
$467
This oojo deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/227:15 pm
ORD
- FLR
1 stop16h 50m
Scandinavian Airlines
Thu 4/3012:20 pm
FLR
- ORD
1 stop34h 50m
Scandinavian Airlines
Deal found 2/2![Scandinavian Airlines logo]()
$478
This Rumbo deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Rumbo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/227:10 pm
ORD
- FCO
1 stop32h 55m
Scandinavian Airlines
Tue 3/1011:55 am
FCO
- ORD
1 stop35h 50m
Scandinavian Airlines
Deal found 2/2![Scandinavian Airlines logo]()
$496
This Mytrip deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/28:16 pm
ORD
- FLR
3 stops34h 44m
Multiple Airlines
Mon 3/97:00 pm
FLR
- ORD
2 stops35h 40m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$496
This Flightnetwork deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2212:50 pm
ORD
- FCO
1 stop13h 35m
Air Canada
Tue 3/109:35 am
FCO
- ORD
2 stops16h 10m
Air Canada
Deal found 2/2![Air Canada logo]()
$497
This FlightHub deal was found by Cheapflights users on 2/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/207:15 pm
ORD
- FCO
1 stop16h 20m
Scandinavian Airlines
Wed 5/611:10 am
FCO
- ORD
2 stops60h 00m
Scandinavian Airlines
Deal found 2/1![Scandinavian Airlines logo]()
$498
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/229:50 pm
ORD
- FCO
1 stop13h 25m
Multiple Airlines
Tue 3/109:35 am
FCO
- ORD
1 stop13h 45m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$499
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 February 3, 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 February 3, 2026.
This oojo deal was found by Cheapflights users on 2/1. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/107:15 pm
ORD
- FLR
1 stop32h 20m
Scandinavian Airlines
Fri 4/247:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 2/1![Scandinavian Airlines logo]()
$468
This oojo deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:15 pm
ORD
- FLR
1 stop16h 35m
TAP AIR PORTUGAL
Sat 5/166:45 pm
FLR
- ORD
1 stop28h 15m
TAP AIR PORTUGAL
Deal found 2/3![TAP AIR PORTUGAL logo]()
$496
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/33:45 pm
ORD
- FCO
Nonstop9h 00m
United Airlines
Wed 3/111:30 pm
FCO
- ORD
1 stop13h 35m
United Airlines
Deal found 2/2![United Airlines logo]()
$523
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/910:45 am
MDW
- FCO
1 stop16h 45m
Delta
Tue 3/179:05 am
FCO
- MDW
1 stop14h 49m
Delta
Deal found 2/2![Delta logo]()
$539
This Finnair deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Finnair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/174:55 pm
ORD
- FCO
Nonstop9h 15m
Finnair
Wed 4/2210:00 am
FCO
- ORD
Nonstop10h 40m
Finnair
Deal found 2/2![Finnair logo]()
$586
This KLM deal was found by Cheapflights users on 2/1. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/1710:49 am
MDW
- FCO
1 stop16h 41m
KLM
Mon 3/309:00 am
FCO
- MDW
1 stop15h 54m
KLM
Deal found 2/1![KLM logo]()
$589
This oojo deal was found by Cheapflights users on 2/1. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/287:25 pm
ORD
- PSA
2 stops55h 05m
British Airways
Sat 3/711:00 am
PSA
- ORD
1 stop33h 50m
British Airways
Deal found 2/1![British Airways logo]()
$597
This American Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/196:25 pm
ORD
- PSA
2 stops33h 45m
American Airlines
Thu 3/2612:30 pm
PSA
- ORD
2 stops26h 33m
American Airlines
Deal found 2/2![American Airlines logo]()
$604
This Mytrip deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/78:40 am
ORD
- CIA
3 stops30h 10m
Multiple Airlines
Mon 4/135:55 pm
CIA
- ORD
2 stops26h 00m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$605
This oojo deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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 4/227:15 pm
ORD
- FLR
1 stop33h 15m
Scandinavian Airlines
Thu 4/307:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 1/31![Scandinavian Airlines logo]()
$478
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/23:45 pm
ORD
- FCO
Nonstop9h 00m
United Airlines
Thu 3/267:05 am
FCO
- ORD
1 stop13h 20m
United Airlines
Deal found 2/2![United Airlines logo]()
$523
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/91:10 pm
MDW
- FCO
2 stops13h 35m
Delta
Wed 3/188:20 am
FCO
- MDW
2 stops20h 11m
Delta
Deal found 2/2![Delta logo]()
$543
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/233:45 pm
ORD
- FCO
Nonstop9h 00m
United Airlines
Tue 3/39:45 am
FCO
- ORD
Nonstop10h 25m
United Airlines
Deal found 2/2![United Airlines logo]()
$524
This Scandinavian Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/710:40 am
ORD
- FLR
2 stops17h 50m
Scandinavian Airlines
Tue 4/147:55 pm
FLR
- ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 2/2![Scandinavian Airlines logo]()
$535
This Delta deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/186:40 pm
MDW
- FCO
2 stops15h 45m
Delta
Tue 3/36:10 am
FCO
- MDW
2 stops19h 30m
Delta
Deal found 2/3![Delta logo]()
$544
This Mytrip deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/122:20 pm
ORD
- CIA
2 stops23h 50m
Multiple Airlines
Sun 4/196:35 pm
CIA
- ORD
2 stops32h 20m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$624
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/33:45 pm
ORD
- FCO
Nonstop9h 00m
United Airlines
Tue 3/3111:30 am
FCO
- ORD
1 stop14h 17m
United Airlines
Deal found 2/2![United Airlines logo]()
$528
This Delta deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/101:10 pm
MDW
- FCO
2 stops16h 45m
Delta
Wed 4/221:10 pm
FCO
- MDW
1 stop16h 18m
Delta
Deal found 2/3![Delta logo]()
$549
This KAYAK deal was found by Cheapflights users on 2/1. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/227:15 pm
ORD
- FLR
2 stops30h 55m
Scandinavian Airlines
Wed 4/297:55 pm
FLR
- ORD
2 stops52h 46m
Scandinavian Airlines
Deal found 2/1![Scandinavian Airlines logo]()
$554
This Cheapflightsfares deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/155:00 pm
ORD
- PSA
1 stop11h 20m
British Airways
Tue 4/2812:35 pm
PSA
- ORD
1 stop12h 40m
British Airways
Deal found 2/2![British Airways logo]()
$683
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/19:50 pm
ORD
- FCO
1 stop13h 25m
United Airlines
Tue 3/319:45 am
FCO
- ORD
Nonstop10h 20m
United Airlines
Deal found 2/2![United Airlines logo]()
$532
This Mytrip deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/33:55 pm
ORD
- CIA
3 stops16h 35m
Multiple Airlines
Mon 3/94:45 pm
CIA
- ORD
2 stops27h 25m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$644
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/251:26 pm
MDW
- FCO
2 stops15h 29m
Delta
Tue 3/312:40 pm
FCO
- MDW
1 stop16h 53m
Delta
Deal found 2/2![Delta logo]()
$549
This KLM deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/201:23 pm
MDW
- FCO
1 stop14h 37m
KLM
Thu 4/309:00 am
FCO
- MDW
1 stop15h 58m
KLM
Deal found 2/2![KLM logo]()
$739
This oojo deal was found by Cheapflights users on 2/1. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/172:05 pm
ORD
- PSA
2 stops18h 45m
British Airways
Thu 4/2312:15 pm
PSA
- ORD
1 stop13h 00m
British Airways
Deal found 2/1![British Airways logo]()
$691
This United Airlines deal was found by Cheapflights users on 2/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/182:00 pm
ORD
- FCO
1 stop14h 05m
United Airlines
Tue 3/39:45 am
FCO
- ORD
Nonstop10h 25m
United Airlines
Deal found 2/1![United Airlines logo]()
$533
This Scandinavian Airlines deal was found by Cheapflights users on 2/1. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/196:04 am
ORD
- FLR
2 stops30h 01m
Scandinavian Airlines
Thu 4/2312:20 pm
FLR
- ORD
1 stop34h 50m
Scandinavian Airlines
Deal found 2/1![Scandinavian Airlines logo]()
$595
This Mytrip deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/1610:55 pm
ORD
- CIA
2 stops16h 45m
Multiple Airlines
Wed 4/110:05 am
CIA
- ORD
2 stops16h 45m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$655
This Delta deal was found by Cheapflights users on 2/1. 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.
Wed 4/159:31 am
MDW
- FCO
1 stop17h 44m
Delta
Thu 4/236:30 am
FCO
- MDW
2 stops18h 28m
Delta
Deal found 2/1![Delta logo]()
$574
This United Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/146:20 pm
ORD
- FCO
1 stop31h 10m
United Airlines
Tue 2/249:45 am
FCO
- ORD
Nonstop10h 25m
United Airlines
Deal found 1/31![United Airlines logo]()
$540
Last-minute flights from Chicago to TuscanyDiscover last-minute flight deals from Chicago to Tuscany. Data last updated February 3, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Tuscany. Data last updated February 3, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/68:15 pm
ORD
- FCO
1 stop12h 35m
TAP AIR PORTUGAL
Sun 2/85:45 am
FCO
- ORD
1 stop16h 00m
TAP AIR PORTUGAL
Deal found 2/2![TAP AIR PORTUGAL logo]()
$504
This Rumbo deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Rumbo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/227:10 pm
ORD
- FCO
1 stop32h 55m
Scandinavian Airlines
Tue 3/1011:55 am
FCO
- ORD
1 stop35h 50m
Scandinavian Airlines
Deal found 2/2![Scandinavian Airlines logo]()
$496
This Flightnetwork deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2212:50 pm
ORD
- FCO
1 stop13h 35m
Air Canada
Tue 3/109:35 am
FCO
- ORD
2 stops16h 10m
Air Canada
Deal found 2/2![Air Canada logo]()
$497
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/229:50 pm
ORD
- FCO
1 stop13h 25m
Multiple Airlines
Tue 3/109:35 am
FCO
- ORD
1 stop13h 45m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$499
This KLM deal was found by Cheapflights users on 2/1. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2212:45 pm
MDW
- FCO
1 stop14h 45m
KLM
Tue 3/109:05 am
FCO
- MDW
1 stop14h 49m
KLM
Deal found 2/1![KLM logo]()
$525
This Delta deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2210:49 am
MDW
- FCO
1 stop16h 41m
Delta
Tue 3/109:05 am
FCO
- MDW
1 stop14h 49m
Delta
Deal found 2/3![Delta logo]()
$530
This Air France deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2212:45 pm
MDW
- FCO
1 stop14h 45m
Air France
Tue 3/109:05 am
FCO
- MDW
1 stop14h 49m
Air France
Deal found 2/2![Air France logo]()
$533
This Iberia deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/236:30 pm
ORD
- FCO
1 stop13h 25m
Multiple Airlines
Tue 3/37:30 am
FCO
- ORD
1 stop14h 25m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$506
This oojo deal was found by Cheapflights users on 2/1. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/19:45 pm
ORD
- FCO
1 stop17h 10m
British Airways
Wed 3/111:10 pm
FCO
- ORD
1 stop14h 08m
British Airways
Deal found 2/1![British Airways logo]()
$503
This oojo deal was found by Cheapflights users on 2/1. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/38:45 pm
ORD
- FCO
2 stops38h 35m
British Airways
Wed 3/111:10 pm
FCO
- ORD
1 stop14h 08m
British Airways
Deal found 2/1![British Airways logo]()
$501
This oojo deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:48 pm
ORD
- FCO
2 stops40h 32m
British Airways
Tue 3/1011:35 am
FCO
- ORD
1 stop18h 01m
British Airways
Deal found 2/2![British Airways logo]()
$508
This oojo deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/43:39 pm
ORD
- FCO
2 stops19h 41m
British Airways
Tue 3/1011:35 am
FCO
- ORD
1 stop18h 01m
British Airways
Deal found 2/2![British Airways logo]()
$502
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 February 3, 2026.
Search for one-way flight options from Chicago to Tuscany. Find affordable one-way fares based on user searches. Data last updated February 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:31 am
ORD
- FCO
2 stops29h 54m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/196:31 am
ORD
- FCO
2 stops42h 49m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Fri 4/246:31 am
ORD
- FCO
2 stops35h 54m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/146:31 am
ORD
- FCO
2 stops27h 39m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:31 am
ORD
- FCO
2 stops34h 09m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/196:31 am
ORD
- FLR
2 stops42h 54m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/36:31 am
ORD
- FCO
2 stops46h 24m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 4/296:31 am
ORD
- FCO
3 stops59h 24m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/276:31 am
ORD
- FCO
2 stops27h 39m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$261
This Mytrip deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/197:25 pm
ORD
- CIA
2 stops18h 45m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$261
This Mytrip deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:30 pm
ORD
- CIA
2 stops18h 30m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$264
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/281:35 pm
ORD
- FCO
1 stop17h 55m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$267
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 February 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $420 (Kiwi.com) |
One-way from | $213 (Kiwi.com) |
Popular in | June |
Cheapest in | November |
Average price | $897 |
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 February 3, 2026.
Use the filters below to find and compare flights from Chicago to Tuscany that are best for you.
Fly from
Chicago
Fly to
Tuscany
Route
Depart
Return
Price
ChicagoFlorence
ORD - FLR
ORDFLR
Chicago O'Hare Intl
Fri 4/10
7:15 pm-10:35 am
1 stop32h 20m
Florence Peretola
Fri 4/24
7:55 pm-4:10 pm
1 stop27h 15m
$468
ChicagoFlorence
ORD - FLR
ORDFLR
Chicago O'Hare Intl
Wed 4/22
7:15 pm-11:30 am
1 stop33h 15m
Florence Peretola
Thu 4/30
7:55 pm-4:10 pm
1 stop27h 15m
$478
ChicagoFlorence
ORD - FLR
ORDFLR
Chicago O'Hare Intl
Sat 5/2
6:15 pm-5:50 pm
1 stop16h 35m
Florence Peretola
Sat 5/16
6:45 pm-4:00 pm
1 stop28h 15m
$496
ChicagoRome
ORD - FCO
ORDFCO
Chicago O'Hare Intl
Tue 3/3
3:45 pm-7:45 am
Nonstop9h 00m
Rome Fiumicino
Wed 3/11
1:30 pm-9:05 pm
1 stop13h 35m
$523
ChicagoRome
ORD - FCO
ORDFCO
Chicago O'Hare Intl
Mon 3/2
3:45 pm-7:45 am
Nonstop9h 00m
Rome Fiumicino
Thu 3/26
7:05 am-2:25 pm
1 stop13h 20m
$523
ChicagoRome
ORD - FCO
ORDFCO
Chicago O'Hare Intl
Mon 2/23
3:45 pm-7:45 am
Nonstop9h 00m
Rome Fiumicino
Tue 3/3
9:45 am-1:10 pm
Nonstop10h 25m
$524
ChicagoRome
ORD - FCO
ORDFCO
Chicago O'Hare Intl
Tue 3/3
3:45 pm-7:45 am
Nonstop9h 00m
Rome Fiumicino
Tue 3/31
11:30 am-6:47 pm
1 stop14h 17m
$528
ChicagoRome
ORD - FCO
ORDFCO
Chicago O'Hare Intl
Sun 3/1
9:50 pm-6:15 pm
1 stop13h 25m
Rome Fiumicino
Tue 3/31
9:45 am-1:05 pm
Nonstop10h 20m
$532
ChicagoRome
ORD - FCO
ORDFCO
Chicago O'Hare Intl
Wed 2/18
2:00 pm-11:05 am
1 stop14h 05m
Rome Fiumicino
Tue 3/3
9:45 am-1:10 pm
Nonstop10h 25m
$533
ChicagoFlorence
ORD - FLR
ORDFLR
Chicago O'Hare Intl
Tue 4/7
10:40 am-11:30 am
2 stops17h 50m
Florence Peretola
Tue 4/14
7:55 pm-4:10 pm
1 stop27h 15m
$535
Showing 1-10 of 60 results
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-FCO
MDW-FCO
ORD-PSA
ORD-CIA
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-FCO
MDW-FCO
ORD-PSA
What is the cheapest month to book a flight from Chicago to Tuscany?
Currently, December is the cheapest month in which you can book a flight from Chicago to Tuscany (average of $448). Flying from Chicago to Tuscany in February is currently the most expensive (average of $791). 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.
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 February 3, 2026.
See what other customers who have flown with SWISS, United Airlines, and Lufthansa 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.
Crew
8.3
Entertainment
6.8
Comfort
7.4
Food
7.1
Boarding
7.7
Overall
7.6
Reviews
1 / 20
10.0
ExcellentLeonardo,Aug 2025
AMS - ZRH
Crew
8.3
Entertainment
6.8
Comfort
7.4
Food
7.1
Boarding
7.7
Overall
7.6
Reviews
1 / 20
10.0
ExcellentLeonardo,Aug 2025
AMS - ZRH
Crew
8.3
Entertainment
6.8
Comfort
7.4
Food
7.1
Boarding
7.7
Overall
7.6
Reviews
1 / 20
10.0
ExcellentLeonardo,Aug 2025
AMS - ZRH
Crew
8.3
Entertainment
6.8
Comfort
7.4
Food
7.1
Boarding
7.7
Overall
7.6
Reviews
1 / 20
10.0
ExcellentLeonardo,Aug 2025
AMS - ZRH
Crew
8.3
Entertainment
6.8
Comfort
7.4
Food
7.1
Boarding
7.7
Overall
7.6
Reviews
1 / 20
10.0
ExcellentLeonardo,Aug 2025
AMS - ZRH
Crew
8.3
Entertainment
6.8
Comfort
7.4
Food
7.1
Boarding
7.7
Overall
7.6
Reviews
1 / 20
10.0
ExcellentLeonardo,Aug 2025
AMS - ZRH
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 February 3, 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 February 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$454 | Average$677 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$458 | Average$906 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$491 | Average$853 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$586 | Average$981 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$588 | Average$971 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$630 | Average$1,073 | FlexibilityNo cancel fee | On-time76% | |
| Cheapest$669 | Average$1,102 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$699 | Average$1,167 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$722 | Average$940 | FlexibilityNo cancel fee | On-time81% | |
| Cheapest$741 | Average$1,124 | FlexibilityNo cancel fee | On-time77% |