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Tuscany

$342+ 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 2/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — FLR
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This CrystalTravel deal was found by Cheapflights users on 12/17. 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 CrystalTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:30 pmORD - FCO
1 stop12h 30mIcelandair
Thu 1/2211:25 amFCO - ORD
1 stop12h 55mIcelandair
Deal found 12/17$443
This CrystalTravel deal was found by Cheapflights users on 12/17. 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 CrystalTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/319:50 pmORD - FCO
1 stop13h 25mLufthansa
Thu 1/2212:20 pmFCO - ORD
1 stop13h 05mLufthansa
Deal found 12/17$503
This Mytrip deal was found by Cheapflights users on 12/17. 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 12/317:05 amORD - FCO
1 stop19h 15mMultiple Airlines
Thu 1/227:05 amFCO - ORD
2 stops15h 05mMultiple Airlines
Deal found 12/17$510
This Cheapflightsfares deal was found by Cheapflights users on 12/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:50 pmORD - FCO
2 stops18h 35mSWISS
Thu 1/228:15 pmFCO - ORD
2 stops22h 55mSWISS
Deal found 12/17$535
This KLM deal was found by Cheapflights users on 12/17. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/319:50 amMDW - FCO
1 stop15h 05mKLM
Thu 1/2212:40 pmFCO - MDW
1 stop16h 42mKLM
Deal found 12/17$537
This Delta deal was found by Cheapflights users on 12/17. 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.
Wed 12/313:29 pmMDW - FCO
1 stop12h 01mDelta
Thu 1/226:10 amFCO - MDW
2 stops18h 19mDelta
Deal found 12/17$538
This KAYAK deal was found by Cheapflights users on 12/16. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/284:10 pmORD - FCO
1 stop33h 30mSWISS
Thu 1/88:15 pmFCO - ORD
2 stops24h 55mSWISS
Deal found 12/16$552
This Kiwi.com deal was found by Cheapflights users on 12/17. 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 12/316:50 pmORD - FCO
1 stop17h 35mSWISS
Thu 1/88:15 pmFCO - ORD
2 stops48h 55mSWISS
Deal found 12/17$573
This Cheapflightsfares deal was found by Cheapflights users on 12/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:35 pmORD - FCO
2 stops31h 05mSWISS
Fri 1/98:15 pmFCO - ORD
2 stops27h 45mSWISS
Deal found 12/17$598
This KAYAK deal was found by Cheapflights users on 12/16. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/284:10 pmORD - FCO
1 stop33h 30mSWISS
Sat 1/102:50 pmFCO - ORD
2 stops30h 20mSWISS
Deal found 12/16$602
This Mytrip deal was found by Cheapflights users on 12/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:30 pmORD - CIA
2 stops17h 20mMultiple Airlines
Tue 1/133:30 pmCIA - ORD
3 stops30h 30mMultiple Airlines
Deal found 12/14$670
This Mytrip deal was found by Cheapflights users on 12/17. 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 12/316:30 pmORD - CIA
2 stops19h 05mMultiple Airlines
Thu 1/87:00 amCIA - ORD
3 stops39h 00mMultiple Airlines
Deal found 12/17$820

Find flight deals from Chicago to Tuscany

Keep the following information in mind while searching for Chicago to Tuscany flight deals. Data was last updated December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$407
(Trip.com)

One-way from

$342
(Kiwi.com)

Popular in

June

Cheapest in

November

Average price

$1,366
Provider with most accurate pricing for Chicago (CHI)-Florence Peretola flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Florence Peretola flights.
Search Deals
From Chicago (CHI) to Tuscany
Search Deals
One-way flight from Chicago (CHI) to Tuscany
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($171 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($39 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 18, 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

Sun 4/26

6:00 pm-4:40 pm

1 stop15h 40m

Rome Fiumicino

Fri 5/8

8:00 pm-4:15 pm

1 stop27h 15m

$488

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Sat 1/17

6:30 pm-2:00 pm

1 stop12h 30m

Rome Fiumicino

Thu 2/26

11:25 am-5:20 pm

1 stop12h 55m

$511

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Sun 1/18

5:10 pm-4:55 pm

1 stop16h 45m

Rome Fiumicino

Tue 2/24

7:25 am-1:50 pm

1 stop13h 25m

$513

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Mon 1/26

5:10 pm-4:55 pm

1 stop16h 45m

Rome Fiumicino

Mon 2/9

8:20 pm-2:55 pm

1 stop25h 35m

$513

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Fri 1/30

8:15 pm-6:45 pm

1 stop15h 30m

Rome Fiumicino

Fri 2/6

6:00 am-3:25 pm

1 stop16h 25m

$513

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Tue 3/17

10:50 am-8:55 am

2 stops16h 05m

Rome Fiumicino

Wed 4/1

10:35 am-2:15 pm

1 stop34h 40m

$531

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Tue 3/17

10:50 am-8:55 am

2 stops16h 05m

Rome Fiumicino

Thu 4/2

6:30 am-2:15 pm

1 stop14h 45m

$531

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Wed 3/4

7:00 am-8:55 am

2 stops18h 55m

Rome Fiumicino

Fri 3/20

6:10 am-3:20 pm

1 stop15h 10m

$532

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Mon 3/16

11:15 am-11:00 am

2 stops17h 45m

Rome Fiumicino

Wed 4/1

6:50 am-2:50 pm

1 stop15h 00m

$533

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Sun 3/22

5:59 pm-4:25 pm

2 stops16h 26m

Rome Fiumicino

Wed 4/1

10:35 am-2:15 pm

1 stop34h 40m

$537

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

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 $448). Flying from Chicago to Tuscany in February is currently the most expensive (average of $779). 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 December 18, 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 December 18, 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
1,815 reviews

Entertainment

6.8

Food

7.1

Crew

8.3

Boarding

7.7

Overall

7.5

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
1,815 reviews
SWISS
7.5
Good
1,815 reviews

Entertainment

6.8

Food

7.1

Crew

8.3

Boarding

7.7

Overall

7.5

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
9,093 reviews
SWISS
7.5
Good
1,815 reviews

Entertainment

6.8

Food

7.1

Crew

8.3

Boarding

7.7

Overall

7.5

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
7,635 reviews
SWISS
7.5
Good
1,815 reviews

Entertainment

6.8

Food

7.1

Crew

8.3

Boarding

7.7

Overall

7.5

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
1,108 reviews
SWISS
7.5
Good
1,815 reviews

Entertainment

6.8

Food

7.1

Crew

8.3

Boarding

7.7

Overall

7.5

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
7,585 reviews
SWISS
7.5
Good
1,815 reviews

Entertainment

6.8

Food

7.1

Crew

8.3

Boarding

7.7

Overall

7.5

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 12h 30m. TAP AIR PORTUGAL provides one of the quickest options available for as low as $511. Chicago and Tuscany are separated by a distance of 4808 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Chicago to Tuscany one-way?

    One-way options have recently been found by users for as low as $349 on SWISS. Other airlines that offer cheap prices include Scandinavian Airlines from $367 and British Airways from $468 one-way.

  • 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 $448). Flying from Chicago to Tuscany in February is currently the most expensive (average of $779). 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

Browse thousands of different options on Cheapflights for your next trip

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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.
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Evansville to Leonardo da Vinci/Fiumicino flights
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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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest$470Average$678FlexibilityNo cancel feeOn-time77%
KLMCheapest$491Average$874FlexibilityNo cancel feeOn-time75%
British AirwaysCheapest$556Average$980FlexibilityNo cancel feeOn-time70%
Air FranceCheapest$588Average$971FlexibilityNo cancel feeOn-time77%
SWISSCheapest$595Average$1,088FlexibilityNo cancel feeOn-time79%
LufthansaCheapest$630Average$1,059FlexibilityNo cancel feeOn-time76%
United AirlinesCheapest$669Average$1,082FlexibilityNo cancel feeOn-time69%
DeltaCheapest$699Average$1,166FlexibilityNo cancel feeOn-timeN/A
ITA AirwaysCheapest$726Average$881FlexibilityNo cancel feeOn-time81%
IberiaCheapest$741Average$1,100FlexibilityNo cancel feeOn-time77%

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