$276+ 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 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — FLR
Sep 20 — Sep 271
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Tuscany
Cheapest
Best
Last-minute
One-way
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 August 21, 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 August 21, 2026.
This British Airways deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/111:45 am -
2 stops16h 25m
Sun 2/2812:40 pm -
2 stops25h 35m
Deal found 8/21![Multiple Airlines logo]()
$659
This oojo deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 12/138:10 pm -
1 stop15h 35m
Fri 1/85:55 am -
1 stop16h 35m
Deal found 8/19![TAP AIR PORTUGAL logo]()
$668
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/157:25 pm -
1 stop12h 10m
Wed 9/2311:10 am -
1 stop15h 05m
Deal found 8/21![Multiple Airlines logo]()
$669
This Mytrip deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 11/257:15 pm -
3 stops33h 35m
Tue 12/16:15 am -
2 stops17h 30m
Deal found 8/19![Multiple Airlines logo]()
$671
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:00 pm -
1 stop17h 55m
Wed 11/45:55 am -
1 stop16h 35m
Deal found 8/19![TAP AIR PORTUGAL logo]()
$674
This British Airways deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2711:45 am -
2 stops17h 25m
Tue 11/1012:20 pm -
2 stops27h 19m
Deal found 8/20![Multiple Airlines logo]()
$674
This Expedia deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2111:25 am -
1 stop14h 55m
Wed 10/286:40 am -
1 stop18h 40m
Deal found 8/19![Turkish Airlines logo]()
$675
This Super.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:50 pm -
1 stop13h 55m
Thu 8/275:45 pm -
1 stop29h 15m
Deal found 8/17![TAP AIR PORTUGAL logo]()
$677
This Mytrip deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 11/116:30 pm -
1 stop12h 30m
Tue 11/171:55 pm -
2 stops32h 35m
Deal found 8/17![Multiple Airlines logo]()
$679
This Kissandfly.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:50 pm -
1 stop13h 55m
Wed 9/25:45 pm -
1 stop25h 55m
Deal found 8/19![TAP AIR PORTUGAL logo]()
$680
This FlightHub deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 10/216:00 pm -
1 stop15h 45m
Fri 10/305:55 am -
1 stop16h 35m
Deal found 8/17![TAP AIR PORTUGAL logo]()
$682
This Cheapflightsfares deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 10/186:00 pm -
1 stop24h 00m
Fri 10/305:55 am -
1 stop16h 35m
Deal found 8/16![TAP AIR PORTUGAL logo]()
$685
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 August 21, 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 August 21, 2026.
This TAP AIR PORTUGAL deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure TAP AIR PORTUGAL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/158:10 pm -
1 stop15h 35m
Thu 11/197:35 pm -
1 stop26h 55m
Deal found 8/17![TAP AIR PORTUGAL logo]()
$688
This Turkish Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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.
Thu 10/158:10 pm -
1 stop20h 25m
Tue 10/272:50 pm -
1 stop26h 10m
Deal found 8/20![Turkish Airlines logo]()
$750
This Delta deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 2/1010:35 am -
2 stops17h 50m
Wed 2/246:40 am -
2 stops17h 10m
Deal found 8/21![Delta logo]()
$786
This United Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 11/113:40 pm -
Nonstop9h 05m
Wed 11/189:45 am -
Nonstop10h 25m
Deal found 8/18![United Airlines logo]()
$788
This Mytrip deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 11/116:30 pm -
2 stops15h 15m
Wed 11/186:55 am -
2 stops16h 50m
Deal found 8/16![Multiple Airlines logo]()
$801
This Scandinavian Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 10/87:15 pm -
2 stops38h 15m
Thu 10/227:55 pm -
1 stop27h 15m
Deal found 8/17![Scandinavian Airlines logo]()
$813
This ITA Airways deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 10/43:00 pm -
Nonstop9h 25m
Sun 10/119:20 am -
Nonstop10h 50m
Deal found 8/16![ITA Airways logo]()
$896
This Trip.com deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3010:30 pm -
1 stop12h 25m
Wed 10/710:45 am -
1 stop16h 10m
Deal found 8/16![Lufthansa logo]()
$990
This KLM deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/284:50 pm -
1 stop14h 25m
Sun 11/297:45 pm -
1 stop25h 40m
Deal found 8/18![KLM logo]()
$1,016
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1310:01 am -
1 stop19h 39m
Tue 11/2410:00 am -
1 stop15h 04m
Deal found 8/17![Delta logo]()
$802
This United Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 11/253:40 pm -
Nonstop9h 05m
Mon 11/302:10 pm -
1 stop31h 00m
Deal found 8/20![United Airlines logo]()
$823
This Mytrip deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 9/3011:25 am -
2 stops26h 05m
Wed 10/712:15 pm -
2 stops28h 25m
Deal found 8/16![Multiple Airlines logo]()
$825
This Scandinavian Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 10/47:15 pm -
1 stop16h 20m
Sat 10/2410:15 pm -
2 stops26h 30m
Deal found 8/18![Scandinavian Airlines logo]()
$826
This Mytrip deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 10/1111:25 am -
2 stops26h 10m
Sun 10/186:35 am -
2 stops34h 05m
Deal found 8/20![Multiple Airlines logo]()
$841
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 12/11:22 pm -
2 stops15h 03m
Tue 4/66:30 am -
2 stops19h 07m
Deal found 8/18![Delta logo]()
$848
This Turkish Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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.
Sun 10/2512:45 pm -
2 stops23h 30m
Sat 10/316:25 am -
2 stops35h 35m
Deal found 8/16![Turkish Airlines logo]()
$961
This TAP AIR PORTUGAL deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure TAP AIR PORTUGAL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/158:10 pm -
1 stop15h 20m
Thu 11/197:15 pm -
1 stop27h 15m
Deal found 8/20![TAP AIR PORTUGAL logo]()
$964
This Scandinavian Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/710:24 am -
2 stops17h 41m
Wed 10/2111:10 am -
2 stops36h 00m
Deal found 8/20![Scandinavian Airlines logo]()
$890
This United Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 11/183:40 pm -
Nonstop9h 05m
Wed 11/259:45 am -
Nonstop10h 25m
Deal found 8/19![United Airlines logo]()
$904
This KLM deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 9/271:55 pm -
2 stops17h 45m
Mon 10/53:25 pm -
2 stops30h 11m
Deal found 8/18![KLM logo]()
$1,022
This Mytrip deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 11/266:30 pm -
2 stops20h 10m
Tue 12/16:10 am -
2 stops17h 35m
Deal found 8/20![Multiple Airlines logo]()
$855
This CheapTickets deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapTickets is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:30 pm -
1 stop12h 25m
Thu 10/810:40 am -
1 stop16h 15m
Deal found 8/17![Lufthansa logo]()
$1,043
This Turkish Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 10/2311:25 am -
2 stops45h 20m
Sun 11/13:30 pm -
2 stops50h 30m
Deal found 8/20![Turkish Airlines logo]()
$961
This Delta deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 10/193:05 pm -
2 stops16h 20m
Tue 10/276:40 am -
2 stops20h 51m
Deal found 8/19![Delta logo]()
$901
This KAYAK deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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.
Fri 10/236:00 pm -
2 stops35h 10m
Sat 10/318:00 pm -
1 stop27h 45m
Deal found 8/20![Scandinavian Airlines logo]()
$933
This Mytrip deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 10/18:10 pm -
2 stops18h 25m
Thu 10/86:00 am -
2 stops34h 40m
Deal found 8/17![Multiple Airlines logo]()
$866
This United Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 9/214:05 pm -
1 stop18h 55m
Fri 10/210:35 am -
2 stops17h 05m
Deal found 8/20![United Airlines logo]()
$977
This Scandinavian Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/77:15 pm -
2 stops30h 55m
Wed 10/147:55 pm -
2 stops32h 36m
Deal found 8/16![Scandinavian Airlines logo]()
$949
This United deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/243:40 pm -
Nonstop9h 05m
Sun 11/298:15 pm -
1 stop27h 00m
Deal found 8/21![Multiple Airlines logo]()
$873
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/62:30 pm -
2 stops16h 55m
Fri 10/166:30 am -
1 stop14h 45m
Deal found 8/17![Delta logo]()
$961
Last-minute flights from Chicago to TuscanyDiscover last-minute flight deals from Chicago to Tuscany. Data last updated August 21, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Tuscany. Data last updated August 21, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:50 pm -
1 stop13h 55m
Thu 8/275:45 pm -
1 stop29h 15m
Deal found 8/17![TAP AIR PORTUGAL logo]()
$677
This Gotogate deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 8/207:50 pm -
1 stop33h 45m
Wed 9/21:35 pm -
1 stop30h 05m
Deal found 8/19![TAP AIR PORTUGAL logo]()
$680
This Cheapflightsfares deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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.
Thu 8/207:50 pm -
1 stop13h 55m
Wed 8/268:00 pm -
1 stop23h 40m
Deal found 8/18![TAP AIR PORTUGAL logo]()
$691
This Gotogate deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/264:40 pm -
1 stop24h 35m
Tue 9/85:50 pm -
1 stop29h 10m
Deal found 8/19![TAP AIR PORTUGAL logo]()
$701
This oojo deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/273:00 pm -
1 stop12h 35m
Wed 9/23:30 pm -
1 stop28h 40m
Deal found 8/20![ITA Airways logo]()
$765
This oojo deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/273:00 pm -
1 stop16h 45m
Thu 9/36:25 am -
1 stop13h 45m
Deal found 8/20![ITA Airways logo]()
$766
This Condor deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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.
Sun 8/306:00 am -
2 stops32h 45m
Wed 9/28:10 am -
2 stops19h 40m
Deal found 8/16![Multiple Airlines logo]()
$803
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/127:25 pm -
1 stop12h 00m
Fri 9/188:20 pm -
1 stop24h 40m
Deal found 8/21![Multiple Airlines logo]()
$682
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/157:25 pm -
1 stop12h 10m
Wed 9/2311:10 am -
1 stop15h 05m
Deal found 8/21![Multiple Airlines logo]()
$669
This Expedia deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/208:10 pm -
1 stop15h 20m
Wed 9/308:05 pm -
1 stop20h 35m
Deal found 8/17![Turkish Airlines logo]()
$688
This oojo deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/267:15 pm -
1 stop16h 50m
Fri 10/97:55 pm -
1 stop27h 15m
Deal found 8/20![Scandinavian Airlines logo]()
$755
This FlightHub deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 9/288:10 pm -
1 stop15h 20m
Wed 11/46:40 am -
1 stop35h 20m
Deal found 8/16![Turkish Airlines logo]()
$697
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 August 21, 2026.
Search for one-way flight options from Chicago to Tuscany. Find affordable one-way fares based on user searches. Data last updated August 21, 2026.
This Mytrip deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 11/166:30 pm -
1 stop12h 30m
Deal found 8/18![Icelandair logo]()
$276
This Mytrip deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 11/26:30 pm -
1 stop12h 30m
Deal found 8/16![Icelandair logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/98:11 pm -
2 stops59h 19m
Deal found 8/16![Multiple Airlines logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:11 pm -
2 stops59h 19m
Deal found 8/20![Multiple Airlines logo]()
$282
This oojo deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 11/116:30 pm -
1 stop12h 30m
Deal found 8/18![Icelandair logo]()
$284
This KAYAK deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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.
Thu 10/1511:45 am -
2 stops15h 40m
Deal found 8/16![Aer Lingus logo]()
$285
This oojo deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 10/317:30 pm -
1 stop12h 30m
Deal found 8/17![Icelandair logo]()
$286
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 12/96:15 am -
2 stops28h 25m
Deal found 8/17![Multiple Airlines logo]()
$288
This Kiwi.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 10/198:11 pm -
2 stops46h 14m
Deal found 8/18![Multiple Airlines logo]()
$291
This FlightHub deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 11/186:30 pm -
1 stop12h 30m
Deal found 8/20![Icelandair logo]()
$292
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:30 pm -
1 stop12h 30m
Deal found 8/17![Icelandair logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 10/196:15 am -
2 stops25h 15m
Deal found 8/18![Multiple Airlines logo]()
$304
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 August 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $668 (oojo) |
One-way from | $276 (Mytrip) |
Popular in | June |
Cheapest in | January |
Average price | $899 |
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 7,457,451 searches. Data last updated August 21, 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
ChicagoRome
ORD Chicago O'Hare Intl - FCO Rome Fiumicino
ORDFCO
Chicago O'Hare Intl
Sun 11/15
8:10 pm-6:45 pm
1 stop15h 35m
Rome Fiumicino
Thu 11/19
7:35 pm-3:30 pm
1 stop26h 55m
$688
ChicagoRome
ORD Chicago O'Hare Intl - FCO Rome Fiumicino
ORDFCO
Chicago O'Hare Intl
Thu 10/15
8:10 pm-11:35 pm
1 stop20h 25m
Rome Fiumicino
Tue 10/27
2:50 pm-11:00 am
1 stop26h 10m
$750
ChicagoFlorence
MDW Chicago Midway - FLR Florence Peretola
MDWFLR
Chicago Midway
Wed 2/10
10:35 am-11:25 am
2 stops17h 50m
Florence Peretola
Wed 2/24
6:40 am-4:50 pm
2 stops17h 10m
$786
Quickest round-trip
ChicagoRome
ORD Chicago O'Hare Intl - FCO Rome Fiumicino
ORDFCO
Chicago O'Hare Intl
Wed 11/11
3:40 pm-7:45 am
Nonstop9h 05m
Rome Fiumicino
Wed 11/18
9:45 am-1:10 pm
Nonstop10h 25m
$788
ChicagoRome
ORD Chicago O'Hare Intl - CIA Rome Ciampino
ORDCIA
Chicago O'Hare Intl
Wed 11/11
6:30 pm-4:45 pm
2 stops15h 15m
Rome Ciampino
Wed 11/18
6:55 am-4:45 pm
2 stops16h 50m
$801
ChicagoRome
MDW Chicago Midway - FCO Rome Fiumicino
MDWFCO
Chicago Midway
Tue 10/13
10:01 am-12:40 pm
1 stop19h 39m
Rome Fiumicino
Tue 11/24
10:00 am-6:04 pm
1 stop15h 04m
$802
ChicagoFlorence
ORD Chicago O'Hare Intl - FLR Florence Peretola
ORDFLR
Chicago O'Hare Intl
Thu 10/8
7:15 pm-4:30 pm
2 stops38h 15m
Florence Peretola
Thu 10/22
7:55 pm-4:10 pm
1 stop27h 15m
$813
ChicagoRome
ORD Chicago O'Hare Intl - FCO Rome Fiumicino
ORDFCO
Chicago O'Hare Intl
Wed 11/25
3:40 pm-7:45 am
Nonstop9h 05m
Rome Fiumicino
Mon 11/30
2:10 pm-2:10 pm
1 stop31h 00m
$823
ChicagoRome
ORD Chicago O'Hare Intl - CIA Rome Ciampino
ORDCIA
Chicago O'Hare Intl
Wed 9/30
11:25 am-8:30 pm
2 stops26h 05m
Rome Ciampino
Wed 10/7
12:15 pm-9:40 am
2 stops28h 25m
$825
ChicagoRome
ORD Chicago O'Hare Intl - FCO Rome Fiumicino
ORDFCO
Chicago O'Hare Intl
Sun 10/4
7:15 pm-6:35 pm
1 stop16h 20m
Rome Fiumicino
Sat 10/24
10:15 pm-5:45 pm
2 stops26h 30m
$826
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-FCO
ORD-FLR
MDW-FCO
MDW-FLR
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-FCO
ORD-FLR
MDW-FCO
MDW-FLR
What is the cheapest month to book a flight from Chicago to Tuscany?
Currently, November is the cheapest month in which you can book a flight from Chicago to Tuscany (average of $747). Flying from Chicago to Tuscany in June is currently the most expensive (average of $1,451). 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?
Airfare is below average for this route at the moment.
Chicago to Tuscany flights typically cost between $748 and $1,172 in October.The cheapest round-trip price found within the last 5 days was $674 on Multiple Airlines (Oct 27-Nov 10).
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 34 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 August 21, 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.
Overall
7.5
Comfort
7.4
Entertainment
6.8
Crew
8.3
Boarding
7.7
Food
7.1
Reviews
1 / 20
6.0
GoodAnonymous,Jul 2026
LAX - ZRH
Overall
7.5
Comfort
7.4
Entertainment
6.8
Crew
8.3
Boarding
7.7
Food
7.1
Reviews
1 / 20
6.0
GoodAnonymous,Jul 2026
LAX - ZRH
Overall
7.5
Comfort
7.4
Entertainment
6.8
Crew
8.3
Boarding
7.7
Food
7.1
Reviews
1 / 20
6.0
GoodAnonymous,Jul 2026
LAX - ZRH
Overall
7.5
Comfort
7.4
Entertainment
6.8
Crew
8.3
Boarding
7.7
Food
7.1
Reviews
1 / 20
6.0
GoodAnonymous,Jul 2026
LAX - ZRH
Overall
7.5
Comfort
7.4
Entertainment
6.8
Crew
8.3
Boarding
7.7
Food
7.1
Reviews
1 / 20
6.0
GoodAnonymous,Jul 2026
LAX - ZRH
Overall
7.5
Comfort
7.4
Entertainment
6.8
Crew
8.3
Boarding
7.7
Food
7.1
Reviews
1 / 20
6.0
GoodAnonymous,Jul 2026
LAX - 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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Alternative routes for Chicago to Tuscany
See prices for flight routes from nearby airports that may be better suited for you.
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 August 21, 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 7,457,451 searches. Data last updated August 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$443 | Average$662 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$458 | Average$1,046 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$539 | Average$1,081 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$644 | Average$1,208 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$663 | Average$957 | FlexibilityNo cancel fee | On-time76% | |
| Cheapest$697 | Average$1,180 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$758 | Average$965 | FlexibilityNo cancel fee | On-time81% | |
| Cheapest$765 | Average$964 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$799 | Average$1,183 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$809 | Average$1,346 | FlexibilityNo cancel fee | On-timeN/A |