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$274+ 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 3/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — FLR
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$549
(United Airlines)

One-way from

$274
(Kiwi.com)

Popular in

June

Cheapest in

November

Average price

$848
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. 22% potential increase in price ($285 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($37 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This Mytrip deal was found by Cheapflights users on 2/20. 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.
Sun 3/307:20 amORD - FCO
1 stop18h 55mMultiple Airlines
Mon 4/78:10 pmFCO - ORD
1 stop23h 00mMultiple Airlines
Deal found 2/20$550
This FlightHub deal was found by Cheapflights users on 2/20. 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 4/257:15 pmORD - FCO
2 stops34h 15mScandinavian Airlines
Wed 5/77:35 pmFCO - ORD
1 stop27h 35mScandinavian Airlines
Deal found 2/20$553
This oojo deal was found by Cheapflights users on 2/20. 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 4/276:00 pmORD - FCO
1 stop18h 05mTAP AIR PORTUGAL
Tue 5/68:00 pmFCO - ORD
1 stop27h 10mTAP AIR PORTUGAL
Deal found 2/20$554
This United Airlines deal was found by Cheapflights users on 2/20. 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 2/238:45 amORD - FCO
1 stop16h 45mUnited Airlines
Wed 4/212:25 pmFCO - ORD
2 stops28h 21mUnited Airlines
Deal found 2/20$555
This Kiwi.com deal was found by Cheapflights users on 2/19. 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.
Tue 3/1112:55 pmORD - FCO
1 stop23h 30mTurkish Airlines
Tue 3/182:50 pmFCO - ORD
1 stop26h 20mTurkish Airlines
Deal found 2/19$558
This KLM deal was found by Cheapflights users on 2/20. 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 4/29:54 amMDW - FCO
1 stop14h 41mKLM
Wed 4/99:45 amFCO - MDW
1 stop19h 36mKLM
Deal found 2/20$560
This Delta deal was found by Cheapflights users on 2/20. 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 3/109:54 amMDW - FCO
1 stop17h 31mDelta
Wed 3/269:20 amFCO - MDW
1 stop19h 03mDelta
Deal found 2/20$561
This Air Canada deal was found by Cheapflights users on 2/20. 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.
Mon 3/179:50 amORD - FCO
1 stop17h 10mAir Canada
Wed 4/212:25 pmFCO - ORD
1 stop16h 41mAir Canada
Deal found 2/20$569
This Delta deal was found by Cheapflights users on 2/20. 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 11/57:00 amORD - FCO
1 stop18h 55mDelta
Wed 11/2610:15 amFCO - ORD
1 stop18h 55mDelta
Deal found 2/20$571
This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
Tue 3/47:05 pmORD - FCO
1 stop11h 55mSWISS
Wed 3/129:40 amFCO - ORD
1 stop13h 35mSWISS
Deal found 2/20$575
This StudentUniverse deal was found by Cheapflights users on 2/20. 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 StudentUniverse is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/99:15 pmORD - FCO
2 stops30h 40mFinnair
Mon 3/176:40 pmFCO - ORD
2 stops27h 05mFinnair
Deal found 2/20$584
This Cheapflightsfares deal was found by Cheapflights users on 2/20. 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.
Thu 4/35:11 pmORD - FCO
1 stop11h 09mIberia
Wed 4/911:05 amFCO - ORD
Nonstop10h 25mIberia
Deal found 2/20$592

Find flights from Chicago to Tuscany within your budget

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 February 20, 2025.

Fly from

Chicago

Fly to

Tuscany

Route

Depart

Return

Price

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Sun 3/30

7:20 am-9:15 am

1 stop18h 55m

Rome Fiumicino

Mon 4/7

8:10 pm-12:10 pm

1 stop23h 00m

$550

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Fri 4/25

7:15 pm-12:30 pm

2 stops34h 15m

Rome Fiumicino

Wed 5/7

7:35 pm-4:10 pm

1 stop27h 35m

$553

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Sun 4/27

6:00 pm-7:05 pm

1 stop18h 05m

Rome Fiumicino

Tue 5/6

8:00 pm-4:10 pm

1 stop27h 10m

$554

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Mon 3/10

4:45 pm-7:45 am

Nonstop9h 00m

Rome Fiumicino

Tue 3/18

9:45 am-2:05 pm

Nonstop10h 20m

$556

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Tue 3/11

12:55 pm-6:25 pm

1 stop23h 30m

Rome Fiumicino

Tue 3/18

2:50 pm-11:10 am

1 stop26h 20m

$558

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 4/2

9:54 am-7:35 am

1 stop14h 41m

Rome Fiumicino

Wed 4/9

9:45 am-10:21 pm

1 stop19h 36m

$560

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Mon 3/10

9:54 am-9:25 am

1 stop17h 31m

Rome Fiumicino

Wed 3/26

9:20 am-10:23 pm

1 stop19h 03m

$561

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Mon 3/17

7:20 am-9:00 am

2 stops19h 40m

Rome Fiumicino

Tue 4/1

11:30 am-10:06 pm

2 stops17h 36m

$569

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Mon 3/10

6:00 am-6:05 am

1 stop18h 05m

Rome Fiumicino

Thu 3/20

9:20 am-5:19 pm

1 stop13h 59m

$571

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Tue 3/4

7:05 pm-2:00 pm

1 stop11h 55m

Rome Fiumicino

Wed 3/12

9:40 am-5:15 pm

1 stop13h 35m

$575

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

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.

Travel insights for flights from Chicago to Tuscany

Get recent, data-driven insights about flights from Chicago to Tuscany including ideal travel times, pricing trends, and more.

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 $1,451). 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 February 20, 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 February 20, 2025.
Get a feel of what it's like to fly with Delta, KLM and Finnair 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
8,220 reviews

Crew

8.5

Food

7.3

Comfort

8.0

Overall

8.0

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
8,220 reviews
Delta
8.0
Very good
8,220 reviews

Crew

8.5

Food

7.3

Comfort

8.0

Overall

8.0

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
1,333 reviews
Delta
8.0
Very good
8,220 reviews

Crew

8.5

Food

7.3

Comfort

8.0

Overall

8.0

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
1,273 reviews
Delta
8.0
Very good
8,220 reviews

Crew

8.5

Food

7.3

Comfort

8.0

Overall

8.0

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
773 reviews
Delta
8.0
Very good
8,220 reviews

Crew

8.5

Food

7.3

Comfort

8.0

Overall

8.0

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.

SWISS
7.5
Good
1,568 reviews
Delta
8.0
Very good
8,220 reviews

Crew

8.5

Food

7.3

Comfort

8.0

Overall

8.0

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 $363 on Icelandair. Other airlines that offer cheap prices include Lufthansa from $364 and Scandinavian Airlines from $367 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 $1,451). 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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Midway to Naples flights
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Moline to Leonardo da Vinci/Fiumicino flights
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Midway to Genoa flights
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O'Hare Intl to Turin flights
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Midway to Turin flights
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St. Louis to Pisa flights
Moline to Vicenza 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest$508Average$804FlexibilityNo cancel feeOn-time77%
Air FranceCheapest$680Average$1,066FlexibilityNo cancel feeOn-time77%
KLMCheapest$702Average$1,079FlexibilityNo cancel feeOn-time75%
British AirwaysCheapest$730Average$1,392FlexibilityNo cancel feeOn-time70%
ITA AirwaysCheapest$734Average$1,029FlexibilityNo cancel feeOn-time81%
United AirlinesCheapest$737Average$1,248FlexibilityNo cancel feeOn-time69%
DeltaCheapest$754Average$1,128FlexibilityNo cancel feeOn-timeN/A
IberiaCheapest$763Average$1,060FlexibilityNo cancel feeOn-time77%
LufthansaCheapest$853Average$1,278FlexibilityNo cancel feeOn-time76%
SWISSCheapest$872Average$1,412FlexibilityNo cancel feeOn-time79%
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