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$406+ 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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
FLR — CHI
Jun 9 — Jun 161
Tue 6/9
Tue 6/16
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 May 10, 2026.

This ITA Airways deal was found by Cheapflights users on 5/7. 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:00 pm
FLR
-
ORD
1 stop25h 10m
ITA Airways
Sun 9/273:00 pm
ORD
-
FLR
1 stop12h 40m
ITA Airways
Deal found 5/7$599
This American Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/87:35 am
FCO
-
ORD
2 stops21h 00m
American Airlines
Sun 9/205:50 pm
ORD
-
FCO
1 stop18h 30m
American Airlines
Deal found 5/6$647
This British Airways deal was found by Cheapflights users on 5/7. 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.
Thu 5/1410:00 am
FCO
-
ORD
Nonstop10h 30m
British Airways
Thu 5/289:15 pm
ORD
-
FCO
1 stop30h 00m
British Airways
Deal found 5/7$648
This lol.travel deal was found by Cheapflights users on 5/7. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/216:25 am
FLR
-
ORD
1 stop13h 45m
ITA Airways
Thu 5/283:00 pm
ORD
-
FLR
1 stop20h 15m
ITA Airways
Deal found 5/7$648
This British Airways deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/1710:00 am
FCO
-
ORD
Nonstop10h 30m
British Airways
Sun 6/76:10 pm
ORD
-
FCO
1 stop21h 30m
British Airways
Deal found 5/9$649
This lol.travel deal was found by Cheapflights users on 5/6. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2812:20 pm
FCO
-
ORD
1 stop13h 25m
British Airways
Fri 12/48:40 pm
ORD
-
FCO
1 stop13h 15m
British Airways
Deal found 5/6$650
This American Airlines deal was found by Cheapflights users on 5/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/147:35 am
FCO
-
ORD
1 stop13h 50m
American Airlines
Thu 5/284:55 pm
ORD
-
FCO
Nonstop9h 15m
American Airlines
Deal found 5/5$653
This American Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/510:00 am
FCO
-
ORD
Nonstop10h 30m
American Airlines
Mon 9/214:55 pm
ORD
-
FCO
Nonstop9h 15m
American Airlines
Deal found 5/6$654
This Iberia deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/167:35 am
FCO
-
ORD
1 stop13h 50m
Iberia
Sat 5/3010:53 am
ORD
-
FCO
1 stop15h 57m
Iberia
Deal found 5/9$656
This Finnair deal was found by Cheapflights users on 5/8. 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 Finnair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/1510:00 am
FCO
-
ORD
Nonstop10h 30m
Finnair
Thu 5/284:55 pm
ORD
-
FCO
Nonstop9h 15m
Finnair
Deal found 5/8$657
This Ovago deal was found by Cheapflights users on 5/8. 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 Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/87:10 am
FCO
-
ORD
1 stop14h 50m
British Airways
Sat 6/209:15 pm
ORD
-
FCO
1 stop15h 50m
British Airways
Deal found 5/8$658
This Delta deal was found by Cheapflights users on 5/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:10 am
FCO
-
MDW
2 stops19h 27m
Delta
Sun 11/291:00 pm
MDW
-
FCO
1 stop13h 35m
Delta
Deal found 5/5$687

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 May 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$599
(ITA Airways)

One-way from

$406
(Kiwi.com)

Popular in

April

Cheapest in

October

Average price

$761
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. 20% potential increase in price ($214 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($61 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 10, 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

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Thu 9/17

11:05 am-2:35 pm

Nonstop10h 30m

Chicago O'Hare Intl

Tue 9/22

4:55 pm-9:10 am

Nonstop9h 15m

$654

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Mon 9/21

3:45 pm-6:15 pm

1 stop33h 30m

Chicago O'Hare Intl

Wed 9/30

7:25 pm-2:35 pm

1 stop12h 10m

$657

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Fri 8/28

3:45 pm-9:25 pm

1 stop12h 40m

Chicago O'Hare Intl

Mon 8/31

10:25 pm-2:35 pm

1 stop33h 10m

$661

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Thu 10/8

3:20 pm-11:15 pm

1 stop14h 55m

Chicago O'Hare Intl

Mon 10/12

3:50 pm-7:55 am

Nonstop9h 05m

$699

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Fri 9/18

6:30 am-6:41 pm

2 stops19h 11m

Chicago O'Hare Intl

Fri 10/2

1:15 pm-12:40 pm

1 stop16h 25m

$721

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

Thu 10/8

1:10 pm-9:45 pm

1 stop15h 35m

Chicago Midway

Mon 10/12

1:05 pm-11:00 am

2 stops14h 55m

$721

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Wed 8/26

6:30 am-6:46 pm

2 stops19h 16m

Chicago O'Hare Intl

Sat 9/12

6:10 pm-4:00 pm

2 stops14h 50m

$722

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Thu 6/4

6:30 am-4:29 pm

2 stops16h 59m

Chicago O'Hare Intl

Sat 6/13

9:00 am-7:35 am

1 stop15h 35m

$725

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

Sun 8/23

9:00 am-6:33 pm

1 stop16h 33m

Chicago Midway

Sun 9/6

5:59 pm-2:25 pm

2 stops13h 26m

$725

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Tue 9/15

10:35 am-9:36 pm

2 stops18h 01m

Chicago O'Hare Intl

Thu 9/24

4:20 pm-11:45 am

1 stop12h 25m

$727

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/10

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

What is the cheapest month to book a flight from Tuscany to Chicago?

Currently, February is the cheapest month in which you can book a flight from Tuscany to Chicago (average of $559). Flying from Tuscany to Chicago in April is currently the most expensive (average of $793). 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 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?

    British Airways, Icelandair, and United Airlines can get you from Tuscany to Chicago in just under 10h 30m. Your travel time can differ by up to 23h. 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 Iberia and British Airways, 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 Florence Peretola - 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.

  • What is the cheapest month to book a flight from Tuscany to Chicago?

    Currently, February is the cheapest month in which you can book a flight from Tuscany to Chicago (average of $559). Flying from Tuscany to Chicago in April is currently the most expensive (average of $793). 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.

See more FAQs

Traveling to a place near Chicago?

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

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 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
Leonardo da Vinci/Fiumicino to St. Louis flights
Malpensa 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 May 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$755Average$807FlexibilityNo cancel feeOn-time71%

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