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Tuscany

$198+ Cheap flights from Chicago (CHI) to Tuscany

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 11/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — FLR
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Cheap flight deals from Chicago to Tuscany

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

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$408
(oojo)

One-way from

$198
(Trip.com)

Popular in

June

Cheapest in

November

Average price

$741
Provider with most accurate pricing for Chicago (CHI)-Florence Peretola flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Florence Peretola flights.
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From Chicago (CHI) to Tuscany
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One-way flight from Chicago (CHI) to Tuscany
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Highest demand for flights based on searches. 17% potential increase in price ($204 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($40 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 Chicago to Tuscany

Cheapest flights from Chicago to Tuscany
Explore the most affordable flight options available from Chicago to Tuscany. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 3, 2025.

This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/57:10 pmORD - FCO
1 stop16h 35mTAP AIR PORTUGAL
Tue 11/117:35 pmFCO - ORD
1 stop26h 25mTAP AIR PORTUGAL
Deal found 11/2$408
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/107:10 pmORD - FCO
1 stop33h 15mTAP AIR PORTUGAL
Tue 12/237:35 pmFCO - ORD
1 stop26h 25mTAP AIR PORTUGAL
Deal found 11/2$412
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.
Wed 12/37:10 pmORD - FCO
1 stop16h 35mTAP AIR PORTUGAL
Tue 12/167:35 pmFCO - ORD
1 stop26h 25mTAP AIR PORTUGAL
Deal found 11/2$417
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/37:10 pmORD - FCO
1 stop21h 55mTAP AIR PORTUGAL
Thu 12/184:40 pmFCO - ORD
1 stop29h 45mTAP AIR PORTUGAL
Deal found 11/2$423
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/148:15 pmORD - FCO
1 stop20h 50mTAP AIR PORTUGAL
Sun 11/235:45 amFCO - ORD
1 stop16h 00mTAP AIR PORTUGAL
Deal found 11/1$426
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 12/46:30 pmORD - FCO
1 stop12h 30mIcelandair
Thu 12/1811:25 amFCO - ORD
1 stop12h 55mIcelandair
Deal found 11/2$428
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/26:30 pmORD - FCO
1 stop12h 30mIcelandair
Wed 12/1711:25 amFCO - ORD
1 stop12h 55mIcelandair
Deal found 11/2$430
This SmartFares 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/37:00 amORD - FCO
2 stops21h 05mScandinavian Airlines
Thu 12/1111:55 amFCO - ORD
1 stop35h 50mScandinavian Airlines
Deal found 11/2$433
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/246:30 pmORD - FCO
1 stop12h 30mIcelandair
Thu 12/411:25 amFCO - ORD
1 stop12h 55mIcelandair
Deal found 11/1$434
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/77:20 pmORD - FCO
1 stop32h 45mScandinavian Airlines
Fri 12/1211:55 amFCO - ORD
1 stop35h 50mScandinavian Airlines
Deal found 11/2$443
This Ticket 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 Ticket is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/39:50 pmORD - FCO
1 stop18h 10mLufthansa
Wed 11/197:05 amFCO - ORD
1 stop20h 00mLufthansa
Deal found 11/1$446
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.
Fri 11/287:20 pmORD - FLR
1 stop32h 40mScandinavian Airlines
Thu 12/1111:50 amFLR - ORD
2 stops55h 53mScandinavian Airlines
Deal found 11/2$509

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Tuscany 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 Chicago to Tuscany that are best for you.

Fly from

Chicago

Fly to

Tuscany

Route

Depart

Return

Price

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Wed 1/14

5:10 pm-7:20 pm

1 stop19h 10m

Rome Fiumicino

Mon 1/19

12:20 pm-1:50 pm

1 stop32h 30m

$512

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Sun 11/9

7:05 am-8:55 am

1 stop18h 50m

Rome Fiumicino

Tue 11/25

7:05 am-1:10 pm

1 stop13h 05m

$516

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Sat 11/8

5:55 pm-8:55 am

1 stop32h 00m

Rome Fiumicino

Thu 11/20

7:05 am-8:05 pm

1 stop20h 00m

$518

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Wed 12/3

3:45 pm-7:45 am

Nonstop9h 00m

Rome Fiumicino

Tue 12/9

7:05 am-3:20 pm

1 stop15h 15m

$518

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Wed 12/3

3:45 pm-7:45 am

Nonstop9h 00m

Rome Fiumicino

Thu 12/11

9:40 am-3:20 pm

1 stop12h 40m

$518

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Wed 12/3

3:45 pm-7:45 am

Nonstop9h 00m

Rome Fiumicino

Wed 12/17

1:30 pm-8:05 pm

1 stop13h 35m

$518

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Mon 11/10

3:45 pm-7:45 am

Nonstop9h 00m

Rome Fiumicino

Thu 11/20

9:45 am-1:10 pm

Nonstop10h 25m

$522

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Tue 12/2

3:45 pm-7:45 am

Nonstop9h 00m

Rome Fiumicino

Thu 12/11

9:45 am-1:10 pm

Nonstop10h 25m

$522

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Wed 11/12

6:02 am-8:55 am

2 stops19h 53m

Rome Fiumicino

Wed 11/19

7:05 am-1:10 pm

1 stop13h 05m

$522

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Tue 11/11

3:45 pm-7:45 am

Nonstop9h 00m

Rome Fiumicino

Tue 11/25

9:45 am-1:10 pm

Nonstop10h 25m

$522

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

Showing 1-10 of 60 results
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Best time to book a flight from Chicago to Tuscany

Have a flexible travel schedule? Discover the best time to fly to Tuscany from Chicago 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 Chicago to Tuscany

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

Currently, December is the cheapest month in which you can book a flight from Chicago to Tuscany (average of $449). Flying from Chicago to Tuscany in February is currently the most expensive (average of $778). 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.

What is the cheapest time of day to fly from CHI to TO?

Find hourly flight availability from Chicago to Tuscany. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 3, 2025.

One of the essential ways to save on airfare from Chicago to Tuscany is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the morning could potentially save you up to 21% on airfare.

Reviews of airlines servicing Tuscany

Get insights into the airlines that provide service to Tuscany. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Tuscany. Reviews last updated November 3, 2025.
See what other customers who have flown with SWISS, United Airlines, and Lufthansa from Chicago to Tuscany have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
SWISS
7.5
Good
1,775 reviews

Overall

7.5

Entertainment

6.8

Boarding

7.6

Food

7.1

Crew

8.2

Comfort

7.4

Reviews

1 / 20
10.0
Excellent

Leonardo,Aug 2025

AMS - ZRH

Amazing alternative from Europe to Hong Kong. Quick connection (even with a non-European passport) and friendly staff that helped me and my family.
SWISS
7.5
Good
1,775 reviews
SWISS
7.5
Good
1,775 reviews

Overall

7.5

Entertainment

6.8

Boarding

7.6

Food

7.1

Crew

8.2

Comfort

7.4

Reviews

1 / 20
10.0
Excellent

Leonardo,Aug 2025

AMS - ZRH

Amazing alternative from Europe to Hong Kong. Quick connection (even with a non-European passport) and friendly staff that helped me and my family.
United Airlines
7.4
Good
8,994 reviews
SWISS
7.5
Good
1,775 reviews

Overall

7.5

Entertainment

6.8

Boarding

7.6

Food

7.1

Crew

8.2

Comfort

7.4

Reviews

1 / 20
10.0
Excellent

Leonardo,Aug 2025

AMS - ZRH

Amazing alternative from Europe to Hong Kong. Quick connection (even with a non-European passport) and friendly staff that helped me and my family.
Lufthansa
6.8
Okay
7,544 reviews
SWISS
7.5
Good
1,775 reviews

Overall

7.5

Entertainment

6.8

Boarding

7.6

Food

7.1

Crew

8.2

Comfort

7.4

Reviews

1 / 20
10.0
Excellent

Leonardo,Aug 2025

AMS - ZRH

Amazing alternative from Europe to Hong Kong. Quick connection (even with a non-European passport) and friendly staff that helped me and my family.
ITA Airways
6.7
Okay
1,079 reviews
SWISS
7.5
Good
1,775 reviews

Overall

7.5

Entertainment

6.8

Boarding

7.6

Food

7.1

Crew

8.2

Comfort

7.4

Reviews

1 / 20
10.0
Excellent

Leonardo,Aug 2025

AMS - ZRH

Amazing alternative from Europe to Hong Kong. Quick connection (even with a non-European passport) and friendly staff that helped me and my family.
British Airways
6.7
Okay
7,494 reviews
SWISS
7.5
Good
1,775 reviews

Overall

7.5

Entertainment

6.8

Boarding

7.6

Food

7.1

Crew

8.2

Comfort

7.4

Reviews

1 / 20
10.0
Excellent

Leonardo,Aug 2025

AMS - ZRH

Amazing alternative from Europe to Hong Kong. Quick connection (even with a non-European passport) and friendly staff that helped me and my family.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Tuscany. 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 Chicago to Tuscany?

    A quick flight from Chicago to Tuscany can take about 14h 08m. British Airways provides one of the quickest options available for as low as $536. Chicago and Tuscany are separated by a distance of 4810 mi. This flight may include one or multiple stops.

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

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

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Tuscany 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 Chicago to Tuscany?

    Currently, December is the cheapest month in which you can book a flight from Chicago to Tuscany (average of $449). Flying from Chicago to Tuscany in February is currently the most expensive (average of $778). 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

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Alternative routes for Chicago to Tuscany

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Leonardo da Vinci/Fiumicino flights
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Midway to Malpensa flights
St. Louis to Leonardo da Vinci/Fiumicino flights
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Midway to Florence flights
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Midway to Naples flights
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O'Hare Intl to Catania flights
St. Louis to Vicenza flights
O'Hare Intl to Bari flights
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St. Louis to Naples flights
O'Hare Intl to Pisa flights
Peoria to Leonardo da Vinci/Fiumicino flights
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Midway to Catania flights
O'Hare Intl to Verona flights
Midway to Bologna flights
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Midway to Palermo flights
St. Louis to Bologna flights
O'Hare Intl to Trieste flights
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O'Hare Intl to Turin flights
St. Louis to Catania flights
O'Hare Intl to Lamezia Terme flights
Midway to Genoa flights
O'Hare Intl to Brindisi flights
Midway to Turin flights
Evansville to Leonardo da Vinci/Fiumicino flights
O'Hare Intl to Olbia flights
Springfield to Leonardo da Vinci/Fiumicino flights
St. Louis to Verona flights

Top 10 airlines flying from Chicago to Tuscany

Discover the top 10 airlines that operate flights from Chicago to Tuscany. 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
Scandinavian AirlinesCheapest$470Average$678FlexibilityNo cancel feeOn-time77%
KLMCheapest$491Average$875FlexibilityNo cancel feeOn-time75%
British AirwaysCheapest$556Average$987FlexibilityNo cancel feeOn-time70%
Air FranceCheapest$588Average$971FlexibilityNo cancel feeOn-time77%
SWISSCheapest$595Average$1,093FlexibilityNo cancel feeOn-time79%
LufthansaCheapest$630Average$1,075FlexibilityNo cancel feeOn-time76%
United AirlinesCheapest$669Average$1,071FlexibilityNo cancel feeOn-time69%
DeltaCheapest$732Average$1,179FlexibilityNo cancel feeOn-timeN/A
IberiaCheapest$741Average$1,103FlexibilityNo cancel feeOn-time77%
ITA AirwaysCheapest$752Average$958FlexibilityNo cancel feeOn-time81%

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