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Tuscany

$312+ 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 10/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — FLR
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$637
(Scandinavian Airlines)

One-way from

$312
(Kiwi.com)

Popular in

June

Cheapest in

November

Average price

$1,113
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 ($217 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($33 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Scandinavian Airlines deal was found by Cheapflights users on 4/30. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/147:15 pmORD - FCO
1 stop16h 30mScandinavian Airlines
Sun 8/317:35 pmFCO - ORD
1 stop27h 35mScandinavian Airlines
Deal found 4/30$637
This Turkish Airlines deal was found by Cheapflights users on 4/30. 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/111:45 pmORD - FCO
1 stop16h 45mTurkish Airlines
Sun 10/197:55 pmFCO - ORD
1 stop33h 05mTurkish Airlines
Deal found 4/30$640
This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Sat 8/96:15 pmORD - FCO
1 stop15h 30mTAP AIR PORTUGAL
Sat 8/235:55 amFCO - ORD
1 stop17h 35mTAP AIR PORTUGAL
Deal found 4/30$642
This Delta deal was found by Cheapflights users on 4/30. 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.
Mon 11/109:30 amMDW - FCO
2 stops14h 35mDelta
Sun 11/166:10 amFCO - MDW
2 stops19h 26mDelta
Deal found 4/30$644
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 10/221:55 pmORD - FCO
2 stops18h 05mLufthansa
Sat 11/111:00 amFCO - ORD
2 stops16h 05mLufthansa
Deal found 4/30$649
This Iberia deal was found by Cheapflights users on 4/30. 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/195:20 pmORD - FCO
Nonstop8h 50mIberia
Wed 10/226:25 amFCO - ORD
1 stop14h 05mIberia
Deal found 4/30$651
This Condor deal was found by Cheapflights users on 5/1. 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 Condor is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/58:50 amORD - FCO
2 stops25h 05mMultiple Airlines
Wed 5/78:20 amFCO - ORD
2 stops17h 16mMultiple Airlines
Deal found 5/1$653
This KLM deal was found by Cheapflights users on 4/30. 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.
Mon 11/101:05 pmMDW - FCO
1 stop14h 25mKLM
Mon 11/1712:45 pmFCO - MDW
1 stop15h 59mKLM
Deal found 4/30$670
This Gotogate deal was found by Cheapflights users on 5/1. 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 5/510:30 pmORD - PSA
1 stop12h 05mMultiple Airlines
Tue 5/2010:30 amPSA - ORD
2 stops16h 42mMultiple Airlines
Deal found 5/1$683
This United Airlines deal was found by Cheapflights users on 5/1. 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.
Tue 11/43:45 pmORD - FCO
Nonstop9h 00mUnited Airlines
Sat 11/89:45 amFCO - ORD
Nonstop10h 25mUnited Airlines
Deal found 5/1$689
This Icelandair deal was found by Cheapflights users on 4/30. 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.
Tue 8/57:25 pmORD - FCO
1 stop12h 10mIcelandair
Wed 8/273:45 pmFCO - ORD
1 stop12h 30mIcelandair
Deal found 4/30$690
This Air France deal was found by Cheapflights users on 5/1. 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/53:40 pmMDW - FCO
1 stop11h 50mAir France
Tue 11/1110:05 amFCO - MDW
1 stop15h 31mAir France
Deal found 5/1$695

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 May 1, 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

Thu 8/14

7:15 pm-6:45 pm

1 stop16h 30m

Rome Fiumicino

Sun 8/31

7:35 pm-4:10 pm

1 stop27h 35m

$637

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Wed 10/1

11:45 pm-11:30 pm

1 stop16h 45m

Rome Fiumicino

Sun 10/19

7:55 pm-10:00 pm

1 stop33h 05m

$640

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Sat 8/9

6:15 pm-4:45 pm

1 stop15h 30m

Rome Fiumicino

Sat 8/23

5:55 am-4:30 pm

1 stop17h 35m

$642

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Wed 10/22

1:55 pm-3:00 pm

2 stops18h 05m

Rome Fiumicino

Sat 11/1

11:00 am-9:05 pm

2 stops16h 05m

$649

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Sun 10/19

5:20 pm-9:10 am

Nonstop8h 50m

Rome Fiumicino

Wed 10/22

6:25 am-1:30 pm

1 stop14h 05m

$651

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Fri 8/8

10:15 pm-2:35 pm

1 stop33h 20m

Rome Fiumicino

Sun 8/24

3:45 pm-6:15 pm

1 stop33h 30m

$665

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Mon 5/26

5:51 am-2:30 pm

1 stop25h 39m

Rome Fiumicino

Tue 6/10

7:05 pm-8:07 pm

1 stop32h 02m

$683

ChicagoPisa

ORD - PSA

ORDPSA

Chicago O'Hare Intl

Wed 10/8

7:11 am-9:50 am

2 stops19h 39m

Pisa Gal Galilei

Wed 10/22

10:30 am-8:11 pm

2 stops16h 41m

$700

ChicagoPisa

ORD - PSA

ORDPSA

Chicago O'Hare Intl

Wed 10/1

4:00 pm-5:35 pm

1 stop18h 35m

Pisa Gal Galilei

Wed 10/15

10:30 am-7:55 pm

1 stop16h 25m

$713

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Wed 9/24

9:40 pm-4:45 pm

1 stop12h 05m

Florence Peretola

Fri 10/3

6:40 am-12:55 pm

1 stop13h 15m

$715

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

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, November is the cheapest month in which you can book a flight from Chicago to Tuscany (average of $766). Flying from Chicago to Tuscany in June is currently the most expensive (average of $1,337). 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 May 1, 2025.

When flying from Chicago to Tuscany, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Tuscany by month

Plan your trip to Tuscany by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Tuscany ranges from 1.2 - 3.9 inches per month. October is typically the wettest month, when rainfall can reach 3.9 in. July is typically the driest time to visit Tuscany when rainfall is around 1.2 in.

Temperature in Tuscany by month

Plan your trip to Tuscany by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Tuscany, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 75.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 41.0 F).

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 May 1, 2025.
Get a feel of what it's like to fly with Delta, Porter Airlines and KLM from Chicago to Tuscany by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,934 reviews

Food

7.3

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Food

7.3

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Porter Airlines
8.0
Very good
285 reviews
Delta
8.0
Very good
7,934 reviews

Food

7.3

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
KLM
7.8
Good
1,334 reviews
Delta
8.0
Very good
7,934 reviews

Food

7.3

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Austrian Airlines
7.6
Good
781 reviews
Delta
8.0
Very good
7,934 reviews

Food

7.3

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Finnair
7.6
Good
1,275 reviews
Delta
8.0
Very good
7,934 reviews

Food

7.3

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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.

  • 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 $368 on Scandinavian Airlines. Other airlines that offer cheap prices include TAP AIR PORTUGAL from $460 and Delta from $463 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, November is the cheapest month in which you can book a flight from Chicago to Tuscany (average of $766). Flying from Chicago to Tuscany in June is currently the most expensive (average of $1,337). 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
O'Hare Intl to Malpensa flights
Midway to Leonardo da Vinci/Fiumicino flights
O'Hare Intl to Linate flights
O'Hare Intl to Vicenza flights
O'Hare Intl to Naples flights
O'Hare Intl to Florence flights
St. Louis to Leonardo da Vinci/Fiumicino flights
Midway to Malpensa flights
Midway to Linate flights
Midway to Vicenza flights
O'Hare Intl to Bergamo flights
Midway to Naples flights
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Midway to Catania flights
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O'Hare Intl to Olbia flights
Moline to Leonardo da Vinci/Fiumicino flights
Midway to Pisa flights
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Midway to Turin flights
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Peoria to Leonardo da Vinci/Fiumicino flights
St. Louis to Ciampino 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest$521Average$774FlexibilityNo cancel feeOn-time77%
KLMCheapest$691Average$1,063FlexibilityNo cancel feeOn-time75%
British AirwaysCheapest$710Average$1,132FlexibilityNo cancel feeOn-time70%
LufthansaCheapest$722Average$1,181FlexibilityNo cancel feeOn-time76%
SWISSCheapest$727Average$1,344FlexibilityNo cancel feeOn-time79%
ITA AirwaysCheapest$730Average$1,009FlexibilityNo cancel feeOn-time81%
DeltaCheapest$730Average$1,158FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$737Average$1,213FlexibilityNo cancel feeOn-time69%
Air FranceCheapest$748Average$1,174FlexibilityNo cancel feeOn-time77%
IberiaCheapest$792Average$1,092FlexibilityNo cancel feeOn-time77%

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