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Tuscany

$270+ 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 8/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — FLR
Jun 23 — Jun 301
Mon 6/23
Mon 6/30
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 June 18, 2025.

Round-trip from

$506
(Scandinavian Airlines)

One-way from

$270
(Kiwi.com)

Popular in

June

Cheapest in

November

Average price

$1,359
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. 15% potential increase in price ($175 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($35 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 18, 2025.

This Scandinavian Airlines deal was found by Cheapflights users on 6/17. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/287:15 pmORD - FLR
1 stop16h 35mScandinavian Airlines
Sun 10/57:55 pmFLR - ORD
1 stop27h 15mScandinavian Airlines
Deal found 6/17$476
This Mytrip deal was found by Cheapflights users on 6/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/148:40 amORD - FLR
2 stops25h 50mMultiple Airlines
Tue 10/216:50 amFLR - ORD
2 stops17h 43mMultiple Airlines
Deal found 6/16$511
This oojo deal was found by Cheapflights users on 6/18. 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 9/46:00 pmORD - FLR
1 stop17h 30mTAP AIR PORTUGAL
Sun 9/217:15 pmFLR - ORD
1 stop28h 25mTAP AIR PORTUGAL
Deal found 6/18$527
This CrystalTravel deal was found by Cheapflights users on 6/16. 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 CrystalTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/59:50 pmORD - FLR
1 stop15h 50mLufthansa
Wed 11/1210:20 amFLR - ORD
1 stop16h 45mLufthansa
Deal found 6/16$571
This United Airlines deal was found by Cheapflights users on 6/18. 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.
Wed 10/157:05 pmORD - FLR
1 stop12h 00mUnited Airlines
Tue 11/46:30 amFLR - ORD
1 stop13h 40mUnited Airlines
Deal found 6/18$601
This Gotogate deal was found by Cheapflights users on 6/18. 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.
Fri 8/83:00 pmORD - FLR
1 stop20h 15mITA Airways
Thu 8/2111:20 amFLR - ORD
1 stop32h 50mITA Airways
Deal found 6/18$604
This SWISS deal was found by Cheapflights users on 6/16. 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 SWISS is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/237:05 pmORD - FLR
1 stop12h 05mSWISS
Mon 12/13:00 pmFLR - ORD
1 stop32h 15mSWISS
Deal found 6/16$608
This Iberia deal was found by Cheapflights users on 6/18. 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.
Wed 9/244:30 pmORD - FLR
1 stop18h 40mIberia
Thu 10/96:50 amFLR - ORD
1 stop18h 25mIberia
Deal found 6/18$613
This Air Canada deal was found by Cheapflights users on 6/18. 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.
Sat 10/189:12 pmORD - FLR
2 stops29h 28mAir Canada
Wed 11/52:15 pmFLR - ORD
2 stops24h 43mAir Canada
Deal found 6/18$621
This British Airways deal was found by Cheapflights users on 6/17. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/187:15 pmORD - FLR
1 stop20h 05mBritish Airways
Wed 7/27:05 amFLR - ORD
1 stop14h 40mBritish Airways
Deal found 6/17$645
This Gotogate deal was found by Cheapflights users on 6/17. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/34:55 pmORD - PSA
1 stop20h 00mBritish Airways
Tue 8/198:10 pmPSA - ORD
1 stop26h 45mBritish Airways
Deal found 6/17$647
This American Airlines deal was found by Cheapflights users on 6/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/37:15 pmORD - PSA
1 stop17h 40mAmerican Airlines
Tue 8/198:10 pmPSA - ORD
1 stop25h 30mAmerican Airlines
Deal found 6/18$649

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 June 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

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Sun 9/28

7:15 pm-6:50 pm

1 stop16h 35m

Florence Peretola

Sun 10/5

7:55 pm-4:10 pm

1 stop27h 15m

$476

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Tue 10/14

8:40 am-5:30 pm

2 stops25h 50m

Florence Peretola

Tue 10/21

6:50 am-5:33 pm

2 stops17h 43m

$511

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Thu 9/4

6:00 pm-6:30 pm

1 stop17h 30m

Florence Peretola

Sun 9/21

7:15 pm-4:40 pm

1 stop28h 25m

$527

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Wed 11/5

9:50 pm-8:40 pm

1 stop15h 50m

Florence Peretola

Wed 11/12

10:20 am-8:05 pm

1 stop16h 45m

$571

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Wed 10/15

7:05 pm-2:05 pm

1 stop12h 00m

Florence Peretola

Tue 11/4

6:30 am-1:10 pm

1 stop13h 40m

$601

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Fri 8/8

3:00 pm-6:15 pm

1 stop20h 15m

Florence Peretola

Thu 8/21

11:20 am-1:10 pm

1 stop32h 50m

$604

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Sun 11/23

7:05 pm-2:10 pm

1 stop12h 05m

Florence Peretola

Mon 12/1

3:00 pm-4:15 pm

1 stop32h 15m

$608

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Wed 9/24

4:30 pm-6:10 pm

1 stop18h 40m

Florence Peretola

Thu 10/9

6:50 am-6:15 pm

1 stop18h 25m

$613

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Sat 10/18

9:12 pm-9:40 am

2 stops29h 28m

Florence Peretola

Wed 11/5

2:15 pm-7:58 am

2 stops24h 43m

$621

ChicagoPisa

ORD - PSA

ORDPSA

Chicago O'Hare Intl

Sun 8/3

4:55 pm-7:55 pm

1 stop20h 00m

Pisa Gal Galilei

Tue 8/19

8:10 pm-3:55 pm

1 stop26h 45m

$647

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/17

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 $1,300). 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 June 18, 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 June 18, 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
7,964 reviews

Food

7.3

Crew

8.5

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,964 reviews
Delta
8.0
Very good
7,964 reviews

Food

7.3

Crew

8.5

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Porter Airlines
8.0
Very good
289 reviews
Delta
8.0
Very good
7,964 reviews

Food

7.3

Crew

8.5

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
KLM
7.8
Good
1,363 reviews
Delta
8.0
Very good
7,964 reviews

Food

7.3

Crew

8.5

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Austrian Airlines
7.6
Good
804 reviews
Delta
8.0
Very good
7,964 reviews

Food

7.3

Crew

8.5

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Finnair
7.6
Good
1,292 reviews
Delta
8.0
Very good
7,964 reviews

Food

7.3

Crew

8.5

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 $304 on TAP AIR PORTUGAL. Other airlines that offer cheap prices include Turkish Airlines from $316 and Scandinavian Airlines from $365 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 $1,300). 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 Naples flights
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O'Hare Intl to Vicenza flights
O'Hare Intl to Florence flights
St. Louis to Leonardo da Vinci/Fiumicino flights
Midway to Malpensa flights
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Midway to Vicenza flights
Midway to Naples flights
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Midway to Palermo flights
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Midway to Bologna flights
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O'Hare Intl to Cagliari flights
O'Hare Intl to Turin flights
Midway to Turin flights
Peoria to Leonardo da Vinci/Fiumicino flights
Moline to Leonardo da Vinci/Fiumicino flights
St. Louis to Bergamo flights
Midway to Genoa flights
St. Louis to Catania flights
St. Louis to Ciampino 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 June 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest$470Average$765FlexibilityNo cancel feeOn-time77%
KLMCheapest$491Average$1,023FlexibilityNo cancel feeOn-time75%
Air FranceCheapest$594Average$1,091FlexibilityNo cancel feeOn-time77%
British AirwaysCheapest$627Average$1,115FlexibilityNo cancel feeOn-time70%
LufthansaCheapest$684Average$1,231FlexibilityNo cancel feeOn-time76%
SWISSCheapest$710Average$1,166FlexibilityNo cancel feeOn-time79%
DeltaCheapest$711Average$1,164FlexibilityNo cancel feeOn-timeN/A
ITA AirwaysCheapest$730Average$979FlexibilityNo cancel feeOn-time81%
United AirlinesCheapest$737Average$1,210FlexibilityNo cancel feeOn-time69%
IberiaCheapest$793Average$1,102FlexibilityNo cancel feeOn-time77%

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