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Tuscany

$323+ 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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — FLR
Apr 29 — May 61
Tue 4/29
Tue 5/6
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 April 24, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$632
(Expedia)

One-way from

$335
(Kiwi.com)

Popular in

June

Cheapest in

November

Average price

$906
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 ($214 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 April 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 April 24, 2025.

This Air Canada deal was found by Cheapflights users on 4/23. 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 Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/62:00 pmORD - FCO
1 stop14h 05mAir Canada
Thu 11/1311:10 amFCO - ORD
2 stops27h 55mAir Canada
Deal found 4/23$624
This Scandinavian Airlines deal was found by Cheapflights users on 4/23. 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.
Sat 11/87:20 pmORD - FCO
2 stops40h 35mScandinavian Airlines
Thu 11/1311:55 amFCO - ORD
1 stop35h 50mScandinavian Airlines
Deal found 4/23$625
This oojo deal was found by Cheapflights users on 4/22. 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.
Thu 8/77:25 pmORD - FCO
1 stop12h 10mIcelandair
Mon 8/183:45 pmFCO - ORD
1 stop33h 30mIcelandair
Deal found 4/22$626
This Delta deal was found by Cheapflights users on 4/23. 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.
Tue 12/21:05 pmMDW - FCO
1 stop14h 25mDelta
Sun 12/712:45 pmFCO - MDW
1 stop15h 59mDelta
Deal found 4/23$626
This FlightHub deal was found by Cheapflights users on 4/23. 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.
Tue 10/217:50 pmORD - FCO
1 stop15h 30mTurkish Airlines
Sun 10/2611:20 amFCO - ORD
1 stop29h 50mTurkish Airlines
Deal found 4/23$629
This United Airlines deal was found by Cheapflights users on 4/23. 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.
Sun 11/93:45 pmORD - FCO
Nonstop9h 00mUnited Airlines
Tue 11/119:45 amFCO - ORD
Nonstop10h 25mUnited Airlines
Deal found 4/23$630
This FlightHub deal was found by Cheapflights users on 4/21. 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 8/277:00 amORD - PSA
2 stops20h 55mScandinavian Airlines
Sun 9/711:45 amPSA - ORD
1 stop35h 25mScandinavian Airlines
Deal found 4/21$632
This Condor deal was found by Cheapflights users on 4/23. 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.
Tue 5/68:45 amORD - FCO
2 stops25h 10mMultiple Airlines
Thu 5/88:20 amFCO - ORD
2 stops17h 16mMultiple Airlines
Deal found 4/23$633
This oojo deal was found by Cheapflights users on 4/23. 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 10/176:00 pmORD - FCO
1 stop23h 10mTAP AIR PORTUGAL
Sat 10/258:00 pmFCO - ORD
1 stop27h 00mTAP AIR PORTUGAL
Deal found 4/23$635
This Lufthansa deal was found by Cheapflights users on 4/23. 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 Lufthansa is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/133:35 pmORD - FCO
1 stop11h 25mLufthansa
Sun 11/21:20 pmFCO - ORD
1 stop12h 05mLufthansa
Deal found 4/23$647
This Mytrip deal was found by Cheapflights users on 4/22. 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 6/312:00 pmORD - PSA
2 stops26h 30mMultiple Airlines
Tue 6/101:55 pmPSA - ORD
2 stops33h 15mMultiple Airlines
Deal found 4/22$714
This oojo deal was found by Cheapflights users on 4/23. 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 8/133:00 pmORD - FCO
Nonstop9h 25mITA Airways
Wed 8/279:25 amFCO - ORD
Nonstop10h 45mITA Airways
Deal found 4/23$726

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 April 24, 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

Sat 5/10

8:15 pm-6:45 pm

1 stop15h 30m

Rome Fiumicino

Sat 5/17

7:35 pm-6:25 pm

1 stop29h 50m

$632

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Tue 5/6

8:45 am-4:55 pm

2 stops25h 10m

Rome Fiumicino

Thu 5/8

8:20 am-6:36 pm

2 stops17h 16m

$633

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Mon 7/21

6:10 pm-12:10 am

1 stop23h 00m

Rome Fiumicino

Thu 7/31

5:45 pm-4:10 pm

1 stop29h 25m

$678

ChicagoPisa

ORD - PSA

ORDPSA

Chicago O'Hare Intl

Tue 6/3

12:00 pm-9:30 pm

2 stops26h 30m

Pisa Gal Galilei

Tue 6/10

1:55 pm-4:10 pm

2 stops33h 15m

$714

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Thu 8/28

7:00 am-11:30 am

2 stops21h 30m

Florence Peretola

Sun 9/7

7:55 pm-4:10 pm

1 stop27h 15m

$727

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Sun 10/12

7:05 pm-9:45 am

1 stop31h 40m

Florence Peretola

Tue 11/4

2:40 pm-4:15 pm

1 stop32h 35m

$733

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Wed 5/14

10:31 am-6:40 am

1 stop13h 09m

Rome Fiumicino

Tue 5/20

3:10 pm-5:29 pm

1 stop33h 19m

$736

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Sun 10/12

9:40 pm-4:45 pm

1 stop12h 05m

Florence Peretola

Fri 11/7

1:05 pm-6:25 pm

1 stop12h 20m

$739

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Sat 10/11

9:12 pm-9:40 am

2 stops29h 28m

Florence Peretola

Wed 11/5

2:15 pm-8:57 am

2 stops25h 42m

$745

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Sat 9/13

7:15 pm-10:40 pm

2 stops20h 25m

Florence Peretola

Sun 9/28

3:30 pm-4:10 pm

2 stops31h 40m

$761

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

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 $1,387). 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 April 24, 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 April 24, 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
7,920 reviews

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

7.9

Boarding

8.2

Food

7.3

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
7,920 reviews
Delta
8.0
Very good
7,920 reviews

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

7.9

Boarding

8.2

Food

7.3

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
284 reviews
Delta
8.0
Very good
7,920 reviews

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

7.9

Boarding

8.2

Food

7.3

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
1,333 reviews
Delta
8.0
Very good
7,920 reviews

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

7.9

Boarding

8.2

Food

7.3

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
780 reviews
Delta
8.0
Very good
7,920 reviews

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

7.9

Boarding

8.2

Food

7.3

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.
SWISS
7.5
Good
1,582 reviews
Delta
8.0
Very good
7,920 reviews

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

7.9

Boarding

8.2

Food

7.3

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 $460 on TAP AIR PORTUGAL. Other airlines that offer cheap prices include WestJet from $503 and Delta from $506 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 $1,387). 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
Midway to Leonardo da Vinci/Fiumicino flights
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St. Louis to Leonardo da Vinci/Fiumicino flights
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St. Louis to Bergamo flights
Midway to Turin flights
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Midway to Pisa 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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest$521Average$773FlexibilityNo cancel feeOn-time77%
KLMCheapest$691Average$1,065FlexibilityNo cancel feeOn-time75%
British AirwaysCheapest$710Average$1,133FlexibilityNo cancel feeOn-time70%
LufthansaCheapest$722Average$1,176FlexibilityNo cancel feeOn-time76%
DeltaCheapest$730Average$1,158FlexibilityNo cancel feeOn-timeN/A
ITA AirwaysCheapest$730Average$1,012FlexibilityNo cancel feeOn-time81%
United AirlinesCheapest$737Average$1,219FlexibilityNo cancel feeOn-time69%
SWISSCheapest$746Average$1,357FlexibilityNo cancel feeOn-time79%
Air FranceCheapest$748Average$1,163FlexibilityNo cancel feeOn-time77%
IberiaCheapest$792Average$1,092FlexibilityNo cancel feeOn-time77%

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