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$260+ 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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
FLR — CHI
Mar 6 — Mar 131
Fri 3/6
Fri 3/13
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 February 4, 2026.

This Finnair deal was found by Cheapflights users on 2/1. 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 Finnair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:55 am
FCO
-
ORD
1 stop17h 40m
Multiple Airlines
Fri 10/25:55 pm
ORD
-
FCO
1 stop13h 40m
Multiple Airlines
Deal found 2/1$499
This lol.travel deal was found by Cheapflights users on 2/3. 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.
Tue 4/218:00 pm
FCO
-
ORD
1 stop27h 00m
TAP AIR PORTUGAL
Sun 4/266:00 pm
ORD
-
FCO
1 stop15h 40m
TAP AIR PORTUGAL
Deal found 2/3$536
This lol.travel deal was found by Cheapflights users on 2/3. 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.
Tue 2/104:40 pm
FCO
-
ORD
1 stop29h 20m
TAP AIR PORTUGAL
Fri 2/208:15 pm
ORD
-
FCO
1 stop20h 50m
TAP AIR PORTUGAL
Deal found 2/3$542
This Mytrip deal was found by Cheapflights users on 2/1. 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.
Thu 3/511:25 am
FCO
-
ORD
1 stop12h 55m
Icelandair
Tue 3/177:30 pm
ORD
-
FCO
1 stop12h 30m
Icelandair
Deal found 2/1$560
This FlightHub deal was found by Cheapflights users on 2/3. 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 5/226:20 am
FCO
-
ORD
1 stop22h 05m
Icelandair
Thu 5/287:25 pm
ORD
-
FCO
1 stop12h 10m
Icelandair
Deal found 2/3$574
This Icelandair deal was found by Cheapflights users on 2/3. 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 Icelandair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1811:25 am
FCO
-
ORD
1 stop12h 55m
Icelandair
Mon 3/307:25 pm
ORD
-
FCO
1 stop12h 10m
Icelandair
Deal found 2/3$580
This Expedia deal was found by Cheapflights users on 2/3. 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.
Wed 2/116:00 am
FCO
-
ORD
1 stop16h 00m
TAP AIR PORTUGAL
Sat 4/116:15 pm
ORD
-
FCO
1 stop17h 40m
TAP AIR PORTUGAL
Deal found 2/3$582
This Finnair deal was found by Cheapflights users on 2/2. 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 Finnair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:10 am
FCO
-
ORD
1 stop18h 05m
Multiple Airlines
Wed 9/305:50 pm
ORD
-
FCO
1 stop14h 25m
Multiple Airlines
Deal found 2/2$590
This lol.travel deal was found by Cheapflights users on 2/1. 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.
Wed 8/266:25 am
FLR
-
ORD
1 stop13h 45m
ITA Airways
Wed 9/29:20 am
ORD
-
FLR
2 stops22h 25m
ITA Airways
Deal found 2/1$590
This lol.travel deal was found by Cheapflights users on 2/2. 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 2/269:40 am
FCO
-
ORD
2 stops17h 05m
Air Canada
Tue 3/33:55 pm
ORD
-
FCO
1 stop12h 00m
Air Canada
Deal found 2/2$596
This Gotogate deal was found by Cheapflights users on 2/1. 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.
Mon 8/313:45 pm
FCO
-
ORD
1 stop12h 40m
Icelandair
Fri 9/1110:25 pm
ORD
-
FCO
1 stop33h 10m
Icelandair
Deal found 2/1$598
This lol.travel deal was found by Cheapflights users on 2/2. 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.
Mon 3/29:45 am
FCO
-
ORD
2 stops17h 00m
Air Canada
Mon 3/912:50 pm
ORD
-
FCO
2 stops13h 50m
Air Canada
Deal found 2/2$601

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 February 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$536
(lol.travel)

One-way from

$260
(Trip.com)

Popular in

December

Cheapest in

February

Average price

$581
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. 8% potential increase in price ($66 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($30 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 February 4, 2026.
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 2/19

6:30 am-1:25 pm

1 stop13h 55m

Chicago O'Hare Intl

Mon 2/23

3:51 pm-1:45 pm

2 stops14h 54m

$620

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

$626

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Wed 3/4

6:00 am-3:00 pm

1 stop16h 00m

Chicago O'Hare Intl

Sun 3/8

9:25 pm-6:45 pm

1 stop15h 20m

$630

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Sat 3/14

2:15 pm-11:44 pm

2 stops15h 29m

Chicago O'Hare Intl

Mon 3/23

5:45 pm-1:40 pm

2 stops37h 55m

$630

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Sat 2/14

1:10 pm-10:46 pm

1 stop16h 36m

Chicago O'Hare Intl

Wed 2/18

6:30 pm-7:20 pm

1 stop17h 50m

$632

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Thu 4/9

10:30 am-5:50 pm

1 stop14h 20m

Chicago O'Hare Intl

Sun 4/12

9:30 pm-6:00 pm

1 stop13h 30m

$632

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Thu 3/5

7:05 am-3:20 pm

1 stop15h 15m

Chicago O'Hare Intl

Mon 3/16

6:00 am-8:30 am

1 stop20h 30m

$632

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Tue 3/31

10:00 am-7:55 pm

1 stop16h 55m

Chicago O'Hare Intl

Sun 4/5

3:40 pm-7:55 am

Nonstop9h 15m

$632

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Fri 3/6

7:05 am-1:25 pm

1 stop13h 20m

Chicago O'Hare Intl

Sun 3/15

7:15 am-7:55 am

1 stop18h 40m

$635

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Mon 4/27

6:50 am-10:53 am

2 stops35h 03m

Chicago O'Hare Intl

Tue 5/5

1:06 pm-12:30 pm

2 stops16h 24m

$640

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/1

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?

    United Airlines, Icelandair, and TAP AIR PORTUGAL can get you from Tuscany to Chicago in just under 13h 55m. Your travel time can differ by up to 19h 35m. 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 British Airways, with whom users have recently found tickets for as low as $490. However, be on the lookout for offers from American Airlines and KLM, 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 Ciampino - Chicago O'Hare Intl or Rome Fiumicino - 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.

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

Browse thousands of different options on Cheapflights for your next trip

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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 February 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$755Average$807FlexibilityNo cancel feeOn-time71%

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