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$373+ Cheap flights from Tuscany to Chicago (CHI)

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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
FLR — CHI
Apr 25 — May 21
Sat 4/25
Sat 5/2
1 adult, Economy
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Cheap flight deals from Tuscany to Chicago

Cheapest flights from Tuscany to Chicago
Explore the most affordable flight options available from Tuscany to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 26, 2026.

This eDestinos deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/213:45 pm
FCO
-
ORD
1 stop33h 30m
Icelandair
Tue 4/287:25 pm
ORD
-
FCO
1 stop12h 10m
Icelandair
Deal found 3/22$491
This Mytrip deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/103:45 pm
FCO
-
ORD
1 stop12h 40m
Icelandair
Sun 4/1910:25 pm
ORD
-
FCO
1 stop33h 10m
Icelandair
Deal found 3/25$523
This lol.travel deal was found by Cheapflights users on 3/21. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:00 pm
FLR
-
ORD
1 stop25h 10m
ITA Airways
Thu 5/73:00 pm
ORD
-
FLR
1 stop16h 45m
ITA Airways
Deal found 3/21$526
This lol.travel deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/176:50 pm
FLR
-
ORD
1 stop28h 15m
TAP AIR PORTUGAL
Fri 4/246:00 pm
ORD
-
FLR
1 stop17h 00m
TAP AIR PORTUGAL
Deal found 3/26$529
This Mytrip deal was found by Cheapflights users on 3/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/23:45 pm
FCO
-
ORD
1 stop12h 40m
Icelandair
Wed 9/167:25 pm
ORD
-
FCO
1 stop12h 10m
Icelandair
Deal found 3/21$536
This Mytrip deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/213:45 pm
FCO
-
ORD
1 stop33h 30m
Icelandair
Wed 6/310:25 pm
ORD
-
FCO
1 stop18h 10m
Icelandair
Deal found 3/22$539
This Gotogate deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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.
Tue 5/193:45 pm
FCO
-
ORD
1 stop12h 40m
Icelandair
Tue 5/267:25 pm
ORD
-
FCO
1 stop12h 10m
Icelandair
Deal found 3/23$540
This Gotogate deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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.
Sat 5/23:45 pm
FCO
-
ORD
1 stop33h 30m
Icelandair
Sun 5/1710:25 pm
ORD
-
FCO
1 stop33h 10m
Icelandair
Deal found 3/24$542
This FlightHub deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 8/263:45 pm
FCO
-
ORD
1 stop12h 40m
Icelandair
Sat 9/127:25 pm
ORD
-
FCO
1 stop12h 10m
Icelandair
Deal found 3/23$546
This lol.travel deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/157:05 am
FLR
-
ORD
1 stop13h 45m
British Airways
Sun 4/195:00 pm
ORD
-
FLR
1 stop22h 20m
British Airways
Deal found 3/25$645
This lol.travel deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/17:05 am
FLR
-
ORD
1 stop18h 10m
British Airways
Tue 4/79:15 pm
ORD
-
FLR
1 stop18h 05m
British Airways
Deal found 3/24$647
This American Airlines deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/312:50 pm
PSA
-
ORD
1 stop30h 35m
American Airlines
Tue 4/710:30 pm
ORD
-
PSA
1 stop29h 50m
American Airlines
Deal found 3/24$656

Find flight deals from Tuscany to Chicago

Keep the following information in mind while searching for Tuscany to Chicago flight deals. Data was last updated March 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$491
(eDestinos)

One-way from

$373
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$901
Provider with most accurate pricing for Florence Peretola-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Florence Peretola-Chicago (CHI) flights.
Search Deals
From Tuscany to Chicago (CHI)
Search Deals
One-way flight from Tuscany to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($26 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Tuscany to Chicago 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 March 26, 2026.
Use the filters below to find and compare flights from Tuscany to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Fri 4/17

6:50 pm-4:05 pm

1 stop28h 15m

Chicago O'Hare Intl

Fri 4/24

6:00 pm-6:00 pm

1 stop17h 00m

$529

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Fri 4/17

3:45 pm-9:25 pm

1 stop12h 40m

Chicago O'Hare Intl

Mon 4/20

7:25 pm-2:35 pm

1 stop12h 10m

$556

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Tue 5/12

3:45 pm-6:15 pm

1 stop33h 30m

Chicago O'Hare Intl

Sun 5/31

10:25 pm-2:35 pm

1 stop33h 10m

$575

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Tue 4/21

10:00 am-1:30 pm

Nonstop10h 30m

Chicago O'Hare Intl

Tue 4/28

9:15 pm-5:15 pm

1 stop13h 00m

$651

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Thu 4/16

6:30 am-2:15 pm

1 stop14h 45m

Chicago O'Hare Intl

Wed 4/29

6:00 am-6:50 am

1 stop17h 50m

$654

PisaChicago

PSA - ORD

PSAORD

Pisa Gal Galilei

Wed 4/22

12:05 pm-12:20 pm

1 stop31h 15m

Chicago O'Hare Intl

Sun 4/26

8:30 am-8:00 pm

2 stops28h 30m

$656

PisaChicago

PSA - ORD

PSAORD

Pisa Gal Galilei

Thu 4/16

3:30 pm-5:35 pm

1 stop33h 05m

Chicago O'Hare Intl

Sun 4/19

8:35 pm-11:30 am

1 stop31h 55m

$657

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Thu 4/9

6:30 am-4:49 pm

2 stops17h 19m

Chicago O'Hare Intl

Wed 4/22

8:15 am-7:35 am

1 stop16h 20m

$658
Quickest round-trip

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Fri 4/17

10:00 am-1:30 pm

Nonstop10h 30m

Chicago O'Hare Intl

Mon 4/20

4:55 pm-9:10 am

Nonstop9h 15m

$660

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Thu 9/3

12:15 pm-7:26 pm

1 stop14h 11m

Chicago O'Hare Intl

Tue 9/22

1:15 pm-3:10 pm

2 stops18h 55m

$668

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/21

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Tuscany to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Tuscany with our price prediction graph.
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 Tuscany to Chicago

How much does it cost to fly round-trip from Tuscany to Chicago?

Related info for your journey

Find useful and relevant information for your journey from Tuscany to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Tuscany to Chicago?

    TAP AIR PORTUGAL, Icelandair, and British Airways can get you from Tuscany to Chicago in just under 10h 30m. Your travel time can differ by up to 17h 45m. The distance between Tuscany and Chicago is about 4808 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Tuscany to Chicago one-way?

    The cheapest airline one-way is American Airlines, with whom users have recently found tickets for as low as $445. However, be on the lookout for offers from British Airways and Lufthansa, as they are both options that can get you from Tuscany to Chicago for a low price.

  • What are the most popular routes from Tuscany to Chicago?

    When deciding which route to take from Tuscany to Chicago consider Rome Fiumicino - Chicago O'Hare Intl, Rome Fiumicino - Chicago Midway or Rome Ciampino - Chicago O'Hare Intl as they are the most popular.

  • Can I find deals for flights from Tuscany to Chicago that include hotel bookings?

    Yes. In addition to deals on Tuscany to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Tuscany to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Tuscany to Chicago.

  • Can I find deals for business class flights from Tuscany to Chicago?

    Yes. Cheapflights offers flight deals from Tuscany to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Tuscany to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Vicenza to O'Hare Intl flights
Naples to O'Hare Intl flights
Malpensa to St. Louis flights
Leonardo da Vinci/Fiumicino to St. Louis flights
Florence to St. Louis flights

Top airline flying from Tuscany to Chicago

Discover the top airline that operate flights from Tuscany to Chicago. 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 March 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$755Average$807FlexibilityNo cancel feeOn-time71%

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