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$330+ 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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
FLR — CHI
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
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 September 16, 2025.

Round-trip from

$439
(lol.travel)

One-way from

$330
(Kiwi.com)

Popular in

July

Cheapest in

February

Average price

$693
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. 12% potential increase in price ($96 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 16, 2025.

This lol.travel deal was found by Cheapflights users on 9/16. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/67:15 pmFLR - ORD
1 stop27h 00mTAP AIR PORTUGAL
Wed 11/127:10 pmORD - FLR
1 stop16h 20mTAP AIR PORTUGAL
Deal found 9/16$437
This lol.travel deal was found by Cheapflights users on 9/15. 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.
Sun 11/236:30 amFLR - ORD
2 stops15h 25mAir Canada
Sun 11/3010:00 amORD - FLR
2 stops16h 40mAir Canada
Deal found 9/15$552
This Gotogate deal was found by Cheapflights users on 9/14. 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.
Mon 10/203:45 pmFCO - ORD
1 stop33h 30mIcelandair
Tue 11/46:30 pmORD - FCO
1 stop12h 30mIcelandair
Deal found 9/14$560
This Mytrip deal was found by Cheapflights users on 9/15. 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 10/1510:20 amFCO - ORD
2 stops33h 15mMultiple Airlines
Sat 10/256:15 pmORD - FCO
1 stop18h 30mMultiple Airlines
Deal found 9/15$564
This lol.travel deal was found by Cheapflights users on 9/15. 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 10/311:30 amFCO - ORD
1 stop29h 21mAir Canada
Sun 10/1910:40 amORD - FCO
1 stop15h 35mAir Canada
Deal found 9/15$566
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/226:25 amFCO - ORD
2 stops37h 10mMultiple Airlines
Thu 11/66:40 amORD - FCO
1 stop24h 50mMultiple Airlines
Deal found 9/15$567
This lol.travel deal was found by Cheapflights users on 9/15. 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 10/311:30 amFCO - ORD
1 stop27h 31mAir Canada
Tue 10/710:40 amORD - FCO
1 stop15h 35mAir Canada
Deal found 9/15$569
This Booking.com deal was found by Cheapflights users on 9/15. 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.
Wed 10/157:10 amFCO - ORD
1 stop12h 45mLufthansa
Sat 10/2510:50 pmORD - FCO
1 stop13h 25mLufthansa
Deal found 9/15$571
This Flighttix deal was found by Cheapflights users on 9/14. 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 Flighttix is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/239:45 amFCO - ORD
Nonstop10h 30mLufthansa
Thu 11/63:45 pmORD - FCO
Nonstop9h 00mLufthansa
Deal found 9/14$572
This Gotogate deal was found by Cheapflights users on 9/15. 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 11/236:30 amFLR - ORD
1 stop13h 40mLufthansa
Sun 11/309:50 pmORD - FLR
1 stop17h 10mLufthansa
Deal found 9/15$572
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Thu 10/237:10 amFCO - ORD
1 stop12h 45mUnited Airlines
Sat 11/812:00 pmORD - FCO
1 stop15h 55mUnited Airlines
Deal found 9/15$573
This American Airlines deal was found by Cheapflights users on 9/13. 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 11/2012:30 pmPSA - ORD
2 stops36h 15mAmerican Airlines
Mon 11/245:40 pmORD - PSA
2 stops58h 55mAmerican Airlines
Deal found 9/13$573

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 September 16, 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 11/6

7:15 pm-3:15 pm

1 stop27h 00m

Chicago O'Hare Intl

Wed 11/12

7:10 pm-6:30 pm

1 stop16h 20m

$437

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Sun 11/23

6:30 am-2:55 pm

2 stops15h 25m

Chicago O'Hare Intl

Sun 11/30

10:00 am-9:40 am

2 stops16h 40m

$564

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Sun 11/23

6:30 am-1:10 pm

1 stop13h 40m

Chicago O'Hare Intl

Sun 11/30

9:50 pm-4:30 pm

1 stop11h 40m

$572

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Wed 11/5

7:05 am-8:05 pm

1 stop20h 00m

Chicago O'Hare Intl

Wed 11/12

1:00 pm-8:30 am

1 stop12h 30m

$573

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

8:50 pm-11:35 am

2 stops55h 45m

$573

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Thu 11/6

9:40 am-8:05 pm

1 stop17h 25m

Chicago O'Hare Intl

Sun 11/16

3:07 pm-10:55 am

1 stop12h 48m

$573

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Thu 11/6

9:40 am-8:05 pm

1 stop17h 25m

Chicago O'Hare Intl

Tue 11/11

3:45 pm-7:45 am

Nonstop9h 00m

$573

PisaChicago

PSA - ORD

PSAORD

Pisa Gal Galilei

Thu 11/20

12:30 pm-7:23 pm

2 stops37h 53m

Chicago O'Hare Intl

Mon 11/24

8:47 pm-11:35 am

2 stops55h 48m

$575

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 11/6

3:20 pm-3:25 pm

1 stop31h 05m

Chicago O'Hare Intl

Wed 11/12

3:08 pm-2:05 pm

2 stops15h 57m

$575

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 2/19

6:30 am-3:20 pm

1 stop15h 50m

Chicago O'Hare Intl

Mon 2/23

9:17 am-1:45 pm

2 stops21h 28m

$576

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

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

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, Air Canada, and Lufthansa can get you from Tuscany to Chicago in just under 13h 40m. Your travel time can differ by up to 13h 20m. The distance between Tuscany and Chicago is about 4680 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 Turkish Airlines, with whom users have recently found tickets for as low as $539. However, be on the lookout for offers from American Airlines and Delta, 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 Midway 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, August is the cheapest month in which you can book a flight from Tuscany to Chicago (average of $245). Flying from Tuscany to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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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.
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