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$467+ 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 2/1. Fares are subject to change and may not be available on all flights or dates of travel.
FLR — CHI
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Cheap flight deals from Tuscany to Chicago

Keep the following information in mind while searching for Tuscany to Chicago flight deals. Data was last updated November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$474
(Booking.com)

One-way from

$467
(Kiwi.com)

Popular in

July

Cheapest in

February

Average price

$661
Provider with most accurate pricing for Florence Peretola-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Florence Peretola-Chicago (CHI) flights.
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From Tuscany to Chicago (CHI)
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One-way flight from Tuscany to Chicago (CHI)
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Highest demand for flights based on searches. 11% potential increase in price ($91 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find 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 November 3, 2025.

This Booking.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/47:15 pmFLR - ORD
1 stop27h 10mTAP AIR PORTUGAL
Wed 12/107:10 pmORD - FLR
1 stop16h 20mTAP AIR PORTUGAL
Deal found 11/2$474
This Kiwi.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/237:10 pmFCO - ORD
1 stop29h 49mMultiple Airlines
Fri 11/2811:48 amORD - FCO
1 stop19h 42mMultiple Airlines
Deal found 11/1$582
This Gotogate deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2311:25 amFCO - ORD
1 stop12h 55mIcelandair
Sat 1/176:30 pmORD - FCO
1 stop12h 30mIcelandair
Deal found 11/1$587
This lol.travel deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/47:10 pmFLR - ORD
2 stops32h 13mITA Airways
Wed 12/109:19 amORD - FLR
2 stops18h 36mITA Airways
Deal found 11/2$591
This Mytrip deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/811:45 amFCO - ORD
2 stops33h 35mMultiple Airlines
Mon 11/245:20 pmORD - FCO
2 stops19h 35mMultiple Airlines
Deal found 11/1$604
This Kiwi.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/237:10 pmFCO - ORD
1 stop29h 49mMultiple Airlines
Sat 1/108:36 amORD - FCO
1 stop22h 54mMultiple Airlines
Deal found 11/2$607
This Mytrip deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/410:00 pmFCO - ORD
1 stop23h 00mMultiple Airlines
Tue 12/93:50 pmORD - FCO
1 stop11h 50mMultiple Airlines
Deal found 11/2$613
This lol.travel deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/207:05 amFCO - ORD
2 stops16h 47mAir Canada
Wed 12/312:50 pmORD - FCO
1 stop13h 35mAir Canada
Deal found 11/1$620
This Gotogate deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/227:05 amFCO - ORD
1 stop13h 05mLufthansa
Sat 1/174:20 pmORD - FCO
1 stop18h 40mLufthansa
Deal found 11/1$624
This Trip.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/247:10 pmFCO - MDW
1 stop23h 32mMultiple Airlines
Thu 12/47:44 amMDW - FCO
1 stop23h 46mMultiple Airlines
Deal found 11/1$624
This lol.travel deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/207:05 amFCO - ORD
2 stops17h 43mAir Canada
Thu 12/43:55 pmORD - FCO
1 stop12h 00mAir Canada
Deal found 11/2$625
This United Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/127:05 amFCO - ORD
1 stop13h 05mUnited Airlines
Mon 1/191:00 pmORD - FCO
1 stop11h 55mUnited Airlines
Deal found 11/1$626

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 November 3, 2025.
Use the filters below to find and compare flights from Tuscany to Chicago that are best for you.

Fly from

Tuscany

Fly to

Chicago

Route

Depart

Return

Price

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 12/4

7:15 pm-3:25 pm

1 stop27h 10m

Chicago O'Hare Intl

Wed 12/10

7:10 pm-6:30 pm

1 stop16h 20m

$476

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 12/4

7:10 pm-8:23 pm

2 stops32h 13m

Chicago O'Hare Intl

Wed 12/10

9:19 am-10:55 am

2 stops18h 36m

$591

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Mon 2/2

7:05 am-3:20 pm

1 stop15h 15m

Chicago O'Hare Intl

Sun 2/15

10:35 am-9:25 am

1 stop15h 50m

$632

PisaChicago

PSA - ORD

PSAORD

Pisa Gal Galilei

Thu 11/13

12:30 pm-3:25 pm

1 stop33h 55m

Chicago O'Hare Intl

Tue 11/18

5:40 pm-11:35 am

2 stops34h 55m

$633

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Thu 11/13

9:35 am-4:20 pm

1 stop13h 45m

Chicago O'Hare Intl

Wed 11/26

3:45 pm-7:45 am

Nonstop9h 00m

$636

PisaChicago

PSA - ORD

PSAORD

Pisa Gal Galilei

Thu 11/20

12:30 pm-3:25 pm

1 stop33h 55m

Chicago O'Hare Intl

Mon 11/24

6:35 pm-11:35 am

2 stops58h 00m

$638

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 11/20

6:35 am-8:05 pm

1 stop20h 30m

Chicago O'Hare Intl

Sat 12/13

8:15 pm-1:35 pm

2 stops34h 20m

$638

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Mon 1/26

7:50 am-1:50 pm

1 stop13h 00m

Chicago O'Hare Intl

Tue 2/3

11:38 am-11:25 am

2 stops16h 47m

$639

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Thu 11/13

12:20 pm-6:25 pm

1 stop13h 05m

Chicago O'Hare Intl

Thu 2/12

6:50 pm-2:00 pm

1 stop12h 10m

$639

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Thu 11/13

12:20 pm-6:25 pm

1 stop13h 05m

Chicago O'Hare Intl

Thu 12/11

9:00 am-7:55 am

2 stops15h 55m

$639

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 60 results
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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
No data available for this route at this time. Please check back soon.

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, ITA Airways, and United Airlines can get you from Tuscany to Chicago in just under 15h 15m. Your travel time can differ by up to 16h 58m. 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 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
Merrillville
Lansing
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.
Malpensa to O'Hare Intl flights
Vicenza to O'Hare Intl flights
Bergamo to O'Hare Intl flights
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Leonardo da Vinci/Fiumicino to O'Hare Intl flights
Vicenza to Midway flights
Ciampino to O'Hare Intl flights
Leonardo da Vinci/Fiumicino to Midway flights
Leonardo da Vinci/Fiumicino to St. Louis flights
Verona to O'Hare Intl flights
Bologna to O'Hare Intl flights
Florence to O'Hare Intl flights
Turin to O'Hare Intl flights
Malpensa to St. Louis flights
Bari to O'Hare Intl flights
Palermo to O'Hare Intl flights
Naples to O'Hare Intl flights
Genoa to O'Hare Intl flights
Vicenza to St. Louis flights
Genoa to Midway flights
Catania to O'Hare Intl flights
Pisa to O'Hare Intl flights
Ancona to O'Hare Intl flights
Malpensa to Moline flights
Florence to St. Louis flights

Top 2 airlines flying from Tuscany to Chicago

Discover the top 2 airlines 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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
SWISSCheapest$600Average$942FlexibilityNo cancel feeOn-time79%
American AirlinesCheapest$762Average$807FlexibilityNo cancel feeOn-time71%

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