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$346+ Cheap flights from Tuscany to Chicago (CHI)

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 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
FLR — CHI
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
1 adult, Economy
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Cheap flight deals from Tuscany to Chicago

Keep the following information in mind while searching for Tuscany to Chicago flight deals. Data was last updated July 30, 2025.

Round-trip from

$570
(lol.travel)

One-way from

$346
(Mytrip)

Popular in

July

Cheapest in

February

Average price

$821
From Tuscany to Chicago (CHI)
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One-way flight from Tuscany to Chicago (CHI)
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Highest demand for flights based on searches. 11% potential increase in price ($88 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from Tuscany to Chicago

Cheapest flights from Tuscany to Chicago
Explore the most affordable flight options available from Tuscany to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 30, 2025.

This lol.travel deal was found by Cheapflights users on 7/29. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/117:00 pmFLR - ORD
1 stop25h 10mITA Airways
Mon 9/153:00 pmORD - FLR
1 stop20h 15mITA Airways
Deal found 7/29$570
This Scandinavian Airlines deal was found by Cheapflights users on 7/29. 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.
Fri 10/177:40 pmFLR - ORD
1 stop27h 30mScandinavian Airlines
Sat 10/258:20 pmORD - FLR
1 stop32h 40mScandinavian Airlines
Deal found 7/29$571
This United Airlines deal was found by Cheapflights users on 7/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/146:40 amFLR - ORD
1 stop15h 15mUnited Airlines
Mon 8/187:05 pmORD - FLR
1 stop12h 00mUnited Airlines
Deal found 7/30$591
This American Airlines deal was found by Cheapflights users on 7/29. 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.
Mon 10/208:40 pmPSA - ORD
1 stop24h 10mAmerican Airlines
Wed 10/296:10 pmORD - PSA
1 stop11h 25mAmerican Airlines
Deal found 7/29$604
This British Airways deal was found by Cheapflights users on 7/29. 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 10/2212:35 pmPSA - ORD
1 stop12h 40mBritish Airways
Wed 10/296:10 pmORD - PSA
1 stop11h 25mBritish Airways
Deal found 7/29$606
This Booking.com deal was found by Cheapflights users on 7/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/236:30 amFLR - ORD
2 stops20h 00mAir Canada
Sun 11/302:00 pmORD - FLR
2 stops16h 35mAir Canada
Deal found 7/29$611
This British Airways deal was found by Cheapflights users on 7/29. 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.
Thu 9/117:05 amFLR - ORD
1 stop18h 10mBritish Airways
Fri 11/2111:48 amORD - FLR
2 stops23h 07mBritish Airways
Deal found 7/29$613
This Delta deal was found by Cheapflights users on 7/30. 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.
Sat 8/236:30 amFCO - MDW
2 stops19h 07mDelta
Sat 9/66:17 pmMDW - FCO
2 stops14h 43mDelta
Deal found 7/30$617
This Lufthansa deal was found by Cheapflights users on 7/29. 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.
Fri 8/297:10 amFCO - ORD
1 stop14h 45mLufthansa
Sun 9/143:05 pmORD - FCO
1 stop19h 45mLufthansa
Deal found 7/29$618
This Gotogate deal was found by Cheapflights users on 7/29. 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 11/233:05 pmFLR - ORD
1 stop29h 55mMultiple Airlines
Sun 11/306:50 pmORD - FLR
1 stop12h 20mMultiple Airlines
Deal found 7/29$618
This British Airways deal was found by Cheapflights users on 7/30. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/69:00 pmFCO - ORD
2 stops27h 54mBritish Airways
Sun 8/3110:35 pmORD - FCO
1 stop17h 15mBritish Airways
Deal found 7/30$619
This American Airlines deal was found by Cheapflights users on 7/28. 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.
Fri 8/2911:05 amFCO - ORD
Nonstop10h 25mAmerican Airlines
Sun 9/149:24 amORD - FCO
1 stop14h 41mAmerican Airlines
Deal found 7/28$620

Cheapflights Fare Finder

 
Customize your flight search to find flights from Tuscany to Chicago 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 July 30, 2025.
Use the filters below to find and compare flights from Tuscany to Chicago that are best for you.

Fly from

Tuscany

Fly to

Chicago

Route

Depart

Return

Price

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 9/11

7:00 pm-1:10 pm

1 stop25h 10m

Chicago O'Hare Intl

Mon 9/15

3:00 pm-6:15 pm

1 stop20h 15m

$570

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Fri 10/17

7:40 pm-4:10 pm

1 stop27h 30m

Chicago O'Hare Intl

Sat 10/25

8:20 pm-11:00 am

1 stop32h 40m

$571

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 8/14

6:40 am-2:55 pm

1 stop15h 15m

Chicago O'Hare Intl

Mon 8/18

7:05 pm-2:05 pm

1 stop12h 00m

$591

PisaChicago

PSA - ORD

PSAORD

Pisa Gal Galilei

Mon 10/20

8:40 pm-1:50 pm

1 stop24h 10m

Chicago O'Hare Intl

Tue 10/28

9:45 pm-11:35 am

1 stop31h 50m

$604

PisaChicago

PSA - ORD

PSAORD

Pisa Gal Galilei

Wed 10/22

12:35 pm-6:15 pm

1 stop12h 40m

Chicago O'Hare Intl

Thu 10/30

9:45 pm-10:10 am

1 stop30h 25m

$606

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Sun 11/23

6:30 am-7:30 pm

2 stops20h 00m

Chicago O'Hare Intl

Sun 11/30

2:00 pm-1:35 pm

2 stops16h 35m

$611

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Thu 9/11

7:05 am-3:55 pm

1 stop15h 50m

Chicago O'Hare Intl

Mon 11/24

8:45 pm-11:20 am

1 stop31h 35m

$613

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

Sat 8/23

6:30 am-6:37 pm

2 stops19h 07m

Chicago Midway

Sat 9/6

6:17 pm-4:00 pm

2 stops14h 43m

$617

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Fri 8/29

7:10 am-2:55 pm

1 stop14h 45m

Chicago O'Hare Intl

Sun 9/14

3:05 pm-5:50 pm

1 stop19h 45m

$618

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

Sun 11/23

3:05 pm-2:00 pm

1 stop29h 55m

Chicago O'Hare Intl

Sun 11/30

6:50 pm-2:10 pm

1 stop12h 20m

$618

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 56 results
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Best time to book a flight from Tuscany to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Tuscany 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 Tuscany to Chicago

How much does it cost to fly round-trip from Tuscany to Chicago?

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated July 30, 2025.
See what other customers who have flown with Delta, KLM, and Austrian Airlines from Tuscany to Chicago 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.
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Delta
8.0
Very good
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
KLM
7.8
Good
1,383 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Austrian Airlines
7.6
Good
823 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
SWISS
7.5
Good
1,686 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
United Airlines
7.4
Good
8,896 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.

Related info for your journey

Find useful and relevant information for your journey from Tuscany to Chicago. 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 Tuscany to Chicago one-way?

    The cheapest airline one-way is TAP AIR PORTUGAL, with whom users have recently found tickets for as low as $491. However, be on the lookout for offers from Icelandair and Aer Lingus, as they are both options that can get you from Tuscany to Chicago for a low price.

  • What are the most popular routes from Tuscany to Chicago?

    When deciding which route to take from Tuscany to Chicago consider Rome Fiumicino - Chicago O'Hare Intl, Rome Ciampino - Chicago O'Hare Intl or Rome Fiumicino - Chicago Midway as they are the most popular.

  • Can I find deals for flights from Tuscany to Chicago that include hotel bookings?

    Yes. In addition to deals on Tuscany to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Tuscany to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Tuscany to Chicago.

  • Can I find deals for business class flights from Tuscany to Chicago?

    Yes. Cheapflights offers flight deals from Tuscany to Chicago 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 Tuscany to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Tuscany to Chicago (average of $245). Flying from Tuscany to Chicago in March is currently the most expensive (average of $321). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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Alternative routes for Tuscany to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Malpensa to O'Hare Intl flights
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