$256+ Cheap flights from Chicago (CHI) to Tuscany
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — FLR
Nov 8 — Nov 151
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
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
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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 October 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 October 9, 2026.
This British Airways deal was found by Cheapflights users on 10/5. 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.
Tue 11/1711:45 am -
2 stops16h 25m
Tue 11/2412:20 pm -
2 stops27h 19m
Deal found 10/5![Multiple Airlines logo]()
$676
This Vliegwinkel deal was found by Cheapflights users on 10/8. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/68:10 pm -
1 stop32h 25m
Thu 11/197:15 pm -
1 stop27h 15m
Deal found 10/8![TAP AIR PORTUGAL logo]()
$680
This Justfly.com deal was found by Cheapflights users on 10/7. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/18:10 pm -
1 stop15h 20m
Tue 11/1012:20 pm -
1 stop34h 10m
Deal found 10/7![TAP AIR PORTUGAL logo]()
$696
This British Airways deal was found by Cheapflights users on 10/8. 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 12/911:45 am -
2 stops16h 50m
Wed 3/312:10 pm -
1 stop14h 05m
Deal found 10/8![Multiple Airlines logo]()
$717
This British Airways deal was found by Cheapflights users on 10/4. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1811:45 am -
2 stops16h 50m
Wed 11/2512:10 pm -
2 stops27h 29m
Deal found 10/4![Multiple Airlines logo]()
$724
This British Airways deal was found by Cheapflights users on 10/6. 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 11/1611:45 am -
2 stops16h 45m
Wed 2/1012:10 pm -
2 stops25h 49m
Deal found 10/6![Multiple Airlines logo]()
$727
This British Airways deal was found by Cheapflights users on 10/6. 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.
Tue 11/1711:45 am -
2 stops16h 25m
Sun 11/2212:40 pm -
2 stops25h 52m
Deal found 10/6![Multiple Airlines logo]()
$774
This Mytrip deal was found by Cheapflights users on 10/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/156:30 pm -
2 stops17h 10m
Thu 11/193:05 pm -
2 stops31h 25m
Deal found 10/4![Multiple Airlines logo]()
$797
This Kiwi.com deal was found by Cheapflights users on 10/4. 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.
Tue 12/15:40 pm -
1 stop14h 55m
Wed 12/94:00 pm -
2 stops54h 30m
Deal found 10/4![Multiple Airlines logo]()
$861
This Kiwi.com deal was found by Cheapflights users on 10/4. 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.
Wed 11/187:00 pm -
2 stops36h 35m
Wed 11/254:00 pm -
1 stop29h 55m
Deal found 10/4![Multiple Airlines logo]()
$930
This Kiwi.com deal was found by Cheapflights users on 10/8. 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.
Tue 11/175:40 pm -
1 stop14h 55m
Sun 11/223:45 pm -
2 stops50h 50m
Deal found 10/8![Multiple Airlines logo]()
$992
This Cheapflightsfares deal was found by Cheapflights users on 10/6. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/144:05 pm -
1 stop18h 50m
Sun 10/1810:45 am -
2 stops32h 50m
Deal found 10/6![Lufthansa logo]()
$1,090
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 October 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 October 9, 2026.
This British Airways deal was found by Cheapflights users on 10/4. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/911:45 am -
2 stops16h 50m
Wed 3/312:10 pm -
1 stop14h 05m
Deal found 10/4![Multiple Airlines logo]()
$717
This United Airlines deal was found by Cheapflights users on 10/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/197:55 pm -
2 stops35h 55m
Mon 3/292:40 pm -
1 stop29h 15m
Deal found 10/4![United Airlines logo]()
$831
This Delta deal was found by Cheapflights users on 10/8. 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 3/61:30 pm -
2 stops15h 05m
Sat 3/136:50 am -
2 stops19h 34m
Deal found 10/8![Delta logo]()
$851
This British Airways deal was found by Cheapflights users on 10/8. 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.
Fri 3/2610:50 pm -
1 stop29h 15m
Thu 4/112:15 pm -
1 stop35h 10m
Deal found 10/8![British Airways logo]()
$883
This Turkish Airlines deal was found by Cheapflights users on 10/4. 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/209:15 pm -
2 stops35h 30m
Sun 3/283:30 pm -
2 stops49h 05m
Deal found 10/4![Turkish Airlines logo]()
$963
This FlightHub deal was found by Cheapflights users on 10/4. 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 10/237:15 pm -
1 stop34h 00m
Sat 10/318:00 pm -
1 stop27h 45m
Deal found 10/4![Scandinavian Airlines logo]()
$1,107
This British Airways deal was found by Cheapflights users on 10/7. 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.
Wed 1/2011:45 am -
2 stops16h 50m
Mon 3/2912:40 pm -
2 stops16h 51m
Deal found 10/7![Multiple Airlines logo]()
$739
This British Airways deal was found by Cheapflights users on 10/7. 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 11/1611:45 am -
2 stops16h 45m
Wed 2/1012:10 pm -
1 stop13h 35m
Deal found 10/7![Multiple Airlines logo]()
$776
This United Airlines deal was found by Cheapflights users on 10/7. 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.
Mon 1/49:50 pm -
1 stop11h 30m
Tue 1/126:30 am -
1 stop15h 50m
Deal found 10/7![United Airlines logo]()
$887
This United Airlines deal was found by Cheapflights users on 10/7. 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.
Mon 1/49:50 pm -
1 stop11h 30m
Mon 1/112:20 pm -
1 stop27h 45m
Deal found 10/7![United Airlines logo]()
$919
This British Airways deal was found by Cheapflights users on 10/5. 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.
Tue 3/2311:45 am -
2 stops17h 25m
Sat 4/37:10 am -
1 stop15h 45m
Deal found 10/5![Multiple Airlines logo]()
$839
This United Airlines deal was found by Cheapflights users on 10/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/197:55 pm -
2 stops35h 55m
Sat 3/272:20 pm -
2 stops34h 01m
Deal found 10/4![United Airlines logo]()
$922
This Kiwi.com deal was found by Cheapflights users on 10/7. 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 1/59:00 pm -
2 stops34h 40m
Thu 1/143:05 pm -
1 stop30h 50m
Deal found 10/7![Multiple Airlines logo]()
$852
This British Airways deal was found by Cheapflights users on 10/5. 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.
Tue 1/1911:45 am -
2 stops16h 25m
Mon 5/247:05 am -
2 stops19h 18m
Deal found 10/5![Multiple Airlines logo]()
$898
This Kiwi.com deal was found by Cheapflights users on 10/4. 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.
Wed 11/187:00 pm -
2 stops36h 35m
Wed 11/254:00 pm -
1 stop29h 55m
Deal found 10/4![Multiple Airlines logo]()
$930
This Mytrip deal was found by Cheapflights users on 10/8. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:30 pm -
2 stops16h 30m
Sun 11/229:00 pm -
3 stops25h 00m
Deal found 10/8![Multiple Airlines logo]()
$1,033
Last-minute flights from Chicago to TuscanyDiscover last-minute flight deals from Chicago to Tuscany. Data last updated October 9, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Tuscany. Data last updated October 9, 2026 and is based on user searches.
This Gotogate deal was found by Cheapflights users on 10/8. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/94:05 pm -
1 stop18h 50m
Thu 10/2210:40 am -
1 stop16h 15m
Deal found 10/8![Lufthansa logo]()
$1,101
This Cheapflightsfares deal was found by Cheapflights users on 10/6. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/144:05 pm -
1 stop18h 50m
Sun 10/1810:45 am -
2 stops32h 50m
Deal found 10/6![Lufthansa logo]()
$1,090
This Justfly.com deal was found by Cheapflights users on 10/7. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/18:10 pm -
1 stop15h 20m
Tue 11/1012:20 pm -
1 stop34h 10m
Deal found 10/7![TAP AIR PORTUGAL logo]()
$696
This Vliegwinkel deal was found by Cheapflights users on 10/8. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/68:10 pm -
1 stop32h 25m
Thu 11/197:15 pm -
1 stop27h 15m
Deal found 10/8![TAP AIR PORTUGAL logo]()
$680
This Mytrip deal was found by Cheapflights users on 10/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/156:30 pm -
2 stops17h 10m
Thu 11/193:05 pm -
2 stops31h 25m
Deal found 10/4![Multiple Airlines logo]()
$797
This British Airways deal was found by Cheapflights users on 10/6. 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 11/1611:45 am -
2 stops16h 45m
Wed 2/1012:10 pm -
1 stop13h 35m
Deal found 10/6![Multiple Airlines logo]()
$717
This British Airways deal was found by Cheapflights users on 10/8. 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.
Tue 11/1711:45 am -
2 stops16h 25m
Tue 11/2412:20 pm -
2 stops27h 19m
Deal found 10/8![Multiple Airlines logo]()
$621
This Kiwi.com deal was found by Cheapflights users on 10/8. 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.
Tue 11/175:40 pm -
1 stop14h 55m
Sun 11/223:45 pm -
2 stops50h 50m
Deal found 10/8![Multiple Airlines logo]()
$992
This British Airways deal was found by Cheapflights users on 10/4. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1811:45 am -
2 stops16h 50m
Wed 11/2512:10 pm -
2 stops27h 29m
Deal found 10/4![Multiple Airlines logo]()
$724
This Kiwi.com deal was found by Cheapflights users on 10/4. 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.
Wed 11/187:00 pm -
2 stops36h 35m
Wed 11/254:00 pm -
1 stop29h 55m
Deal found 10/4![Multiple Airlines logo]()
$930
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 October 9, 2026.
Search for one-way flight options from Chicago to Tuscany. Find affordable one-way fares based on user searches. Data last updated October 9, 2026.
This British Airways deal was found by Cheapflights users on 10/5. 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.
Tue 1/1211:45 am -
2 stops16h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Multiple Airlines logo]()
$256
This British Airways deal was found by Cheapflights users on 10/8. 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.
Mon 1/1111:45 am -
2 stops16h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$257
This BusinessClass deal was found by Cheapflights users on 10/8. 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 BusinessClass is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/188:45 pm -
2 stops31h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![British Airways logo]()
$288
This British Airways deal was found by Cheapflights users on 10/6. 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 1/2111:45 am -
2 stops17h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Multiple Airlines logo]()
$306
This British Airways deal was found by Cheapflights users on 10/8. 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.
Tue 1/1911:45 am -
2 stops16h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$312
This British Airways deal was found by Cheapflights users on 10/4. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/611:48 am -
2 stops16h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Multiple Airlines logo]()
$328
This Cheapflightsfares deal was found by Cheapflights users on 10/5. 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.
Tue 1/126:50 pm -
1 stop16h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![SWISS logo]()
$331
This Booking.com deal was found by Cheapflights users on 10/8. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/189:50 pm -
1 stop11h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Lufthansa logo]()
$336
This Air France deal was found by Cheapflights users on 10/8. 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/116:25 pm -
1 stop18h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Air France logo]()
$339
This Expedia deal was found by Cheapflights users on 10/6. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/215:10 pm -
1 stop11h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![British Airways logo]()
$373
This Expedia deal was found by Cheapflights users on 10/5. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/1210:34 am -
2 stops18h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![British Airways logo]()
$377
This Expedia deal was found by Cheapflights users on 10/5. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/116:50 pm -
1 stop30h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![SWISS logo]()
$380
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 October 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $649 (British Airways) |
One-way from | $256 (British Airways) |
Popular in | December |
Cheapest in | February |
Average price | $1,064 |
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 October 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 Chicago O'Hare Intl - FLR Florence Peretola
ORDFLR
Chicago O'Hare Intl
Sun 3/14
11:45 am-10:50 am
2 stops17h 05m
Florence Peretola
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$256
Quickest round-trip
ChicagoFlorence
ORD Chicago O'Hare Intl - FLR Florence Peretola
ORDFLR
Chicago O'Hare Intl
Tue 1/19
11:45 am-11:10 am
2 stops16h 25m
Florence Peretola
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$312
ChicagoFlorence
ORD Chicago O'Hare Intl - FLR Florence Peretola
ORDFLR
Chicago O'Hare Intl
Tue 4/6
11:48 am-11:35 am
2 stops16h 47m
Florence Peretola
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$328
ChicagoFlorence
ORD Chicago O'Hare Intl - FLR Florence Peretola
ORDFLR
Chicago O'Hare Intl
Wed 3/31
7:05 pm-10:00 am
2 stops31h 55m
Florence Peretola
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$418
ChicagoFlorence
ORD Chicago O'Hare Intl - FLR Florence Peretola
ORDFLR
Chicago O'Hare Intl
Tue 11/17
11:45 am-11:10 am
2 stops16h 25m
Florence Peretola
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$469
ChicagoFlorence
ORD Chicago O'Hare Intl - FLR Florence Peretola
ORDFLR
Chicago O'Hare Intl
Mon 12/28
11:45 am-11:30 am
2 stops16h 45m
Florence Peretola
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$469
ChicagoFlorence
ORD Chicago O'Hare Intl - FLR Florence Peretola
ORDFLR
Chicago O'Hare Intl
Tue 10/20
2:40 pm-2:10 pm
1 stop16h 30m
Florence Peretola
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$537
ChicagoFlorence
ORD Chicago O'Hare Intl - FLR Florence Peretola
ORDFLR
Chicago O'Hare Intl
Tue 10/20
8:10 pm-6:15 pm
2 stops39h 05m
Florence Peretola
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$540
ChicagoFlorence
ORD Chicago O'Hare Intl - FLR Florence Peretola
ORDFLR
Chicago O'Hare Intl
Wed 12/9
11:45 am-11:35 am
2 stops16h 50m
Florence Peretola
Wed 3/3
12:10 pm-7:15 pm
1 stop14h 05m
$717
ChicagoFlorence
ORD Chicago O'Hare Intl - FLR Florence Peretola
ORDFLR
Chicago O'Hare Intl
Wed 1/20
11:45 am-11:35 am
2 stops16h 50m
Florence Peretola
Mon 3/29
12:40 pm-10:31 pm
2 stops16h 51m
$739
Showing 1-10 of 24 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
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
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 $869). Flying from Chicago to Tuscany in June is currently the most expensive (average of $1,474). 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 $1,018 and $1,212 in February.The cheapest round-trip price found within the last 5 days was $649 on Multiple Airlines (Feb 7-Feb 11).
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 32 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 October 9, 2026.
See what other customers who have flown with Delta,SWISS, andScandinavian 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.
Boarding
8.1
Comfort
7.8
Food
7.2
Overall
7.8
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Boarding
8.1
Comfort
7.8
Food
7.2
Overall
7.8
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Boarding
8.1
Comfort
7.8
Food
7.2
Overall
7.8
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Boarding
8.1
Comfort
7.8
Food
7.2
Overall
7.8
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Boarding
8.1
Comfort
7.8
Food
7.2
Overall
7.8
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Boarding
8.1
Comfort
7.8
Food
7.2
Overall
7.8
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
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
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 October 9, 2026.
Popular flight searches
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Top 9 airlines flying from Chicago to Tuscany
Discover the top 9 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 October 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$443 | Average$692 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$539 | Average$1,208 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$624 | Average$1,078 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$663 | Average$1,036 | FlexibilityNo cancel fee | On-time76% | |
| Cheapest$758 | Average$963 | FlexibilityNo cancel fee | On-time81% | |
| Cheapest$798 | Average$981 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$826 | Average$1,210 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$860 | Average$1,300 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$890 | Average$1,183 | FlexibilityNo cancel fee | On-time77% |