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Tuscany

$221+ 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 11/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — FLR
ago. 19 — ago. 261
mar. 8/19
mar. 8/26
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 agosto 14, 2025.

Round-trip from

$449
(oojo)

One-way from

$221
(Mytrip)

Popular in

June

Cheapest in

November

Average price

$904
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. 16% potential increase in price ($185 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($36 potential savings vs. average RT price).
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Average for round-trip flights in August 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 agosto 14, 2025.

This oojo deal was found by Cheapflights users on 8/14. 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.
lun. 12/297:20 pmORD - FCO
2 stops17h 05mScandinavian Airlines
dom. 1/117:20 pmFCO - ORD
2 stops28h 25mScandinavian Airlines
Deal found 8/14$450
This oojo deal was found by Cheapflights users on 8/14. 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.
mar. 10/217:15 pmORD - FCO
1 stop16h 30mScandinavian Airlines
dom. 10/2610:30 amFCO - ORD
2 stops37h 25mScandinavian Airlines
Deal found 8/14$451
This oojo deal was found by Cheapflights users on 8/12. 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.
vie. 11/77:20 pmORD - FCO
1 stop32h 35mScandinavian Airlines
vie. 11/1411:55 amFCO - ORD
1 stop35h 50mScandinavian Airlines
Deal found 8/12$452
This Delta deal was found by Cheapflights users on 8/11. 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.
lun. 10/275:51 pmORD - FCO
2 stops16h 34mDelta
mar. 11/46:10 amFCO - ORD
2 stops21h 13mDelta
Deal found 8/11$453
This Delta deal was found by Cheapflights users on 8/12. 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.
vie. 11/289:30 amMDW - FCO
2 stops17h 15mDelta
mar. 12/910:05 amFCO - MDW
1 stop15h 31mDelta
Deal found 8/12$453
This oojo deal was found by Cheapflights users on 8/12. 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.
sáb. 10/117:15 pmORD - FCO
2 stops17h 45mScandinavian Airlines
vie. 10/247:35 pmFCO - ORD
1 stop27h 35mScandinavian Airlines
Deal found 8/12$454
This oojo deal was found by Cheapflights users on 8/12. 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.
mié. 10/2911:10 pmORD - FCO
1 stop29h 55mScandinavian Airlines
vie. 11/710:05 amFCO - ORD
2 stops37h 40mScandinavian Airlines
Deal found 8/12$455
This Gurufare deal was found by Cheapflights users on 8/13. 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 Gurufare is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/156:30 pmORD - FCO
1 stop12h 30mIcelandair
mié. 11/1911:25 amFCO - ORD
1 stop12h 55mIcelandair
Deal found 8/13$456
This United Airlines deal was found by Cheapflights users on 8/11. 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.
vie. 10/317:00 pmORD - FCO
1 stop21h 50mUnited Airlines
jue. 11/69:45 amFCO - ORD
Nonstop10h 25mUnited Airlines
Deal found 8/11$457
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
dom. 10/267:50 pmORD - FCO
1 stop12h 10mMultiple Airlines
vie. 11/78:05 pmFCO - ORD
1 stop24h 55mMultiple Airlines
Deal found 8/13$458
This oojo deal was found by Cheapflights users on 8/12. 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.
vie. 10/106:00 pmORD - FCO
1 stop23h 10mTAP AIR PORTUGAL
mar. 11/114:40 pmFCO - ORD
1 stop29h 20mTAP AIR PORTUGAL
Deal found 8/12$459
This Ovago deal was found by Cheapflights users on 8/12. 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 Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/283:45 pmORD - FCO
Nonstop9h 00mSWISS
mar. 12/99:35 amFCO - ORD
1 stop13h 45mSWISS
Deal found 8/12$460

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 agosto 14, 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

lun. 10/27

5:51 pm-4:25 pm

2 stops16h 34m

Rome Fiumicino

mar. 11/4

6:10 am-8:23 pm

2 stops21h 13m

$453

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

lun. 10/27

1:08 pm-9:10 am

2 stops14h 02m

Rome Fiumicino

mié. 11/5

6:10 am-4:15 pm

2 stops17h 05m

$453

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

vie. 10/31

7:00 pm-10:50 pm

1 stop21h 50m

Rome Fiumicino

jue. 11/6

9:45 am-1:10 pm

Nonstop10h 25m

$457

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

mié. 11/12

3:45 pm-7:45 am

Nonstop9h 00m

Rome Fiumicino

dom. 11/16

1:45 pm-8:05 pm

1 stop13h 20m

$457

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

mar. 11/11

6:30 pm-2:00 pm

1 stop12h 30m

Rome Fiumicino

dom. 11/23

11:25 am-5:20 pm

1 stop12h 55m

$463

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

mar. 11/11

6:30 pm-2:00 pm

1 stop12h 30m

Rome Fiumicino

jue. 11/20

6:15 am-5:20 pm

1 stop18h 05m

$463

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

lun. 11/3

6:30 pm-2:00 pm

1 stop12h 30m

Rome Fiumicino

dom. 11/9

11:25 am-5:20 pm

1 stop12h 55m

$463

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

sáb. 11/8

6:30 pm-2:00 pm

1 stop12h 30m

Rome Fiumicino

mié. 11/19

11:25 am-5:20 pm

1 stop12h 55m

$463

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

mar. 11/11

6:30 pm-2:00 pm

1 stop12h 30m

Rome Fiumicino

sáb. 11/15

11:25 am-5:20 pm

1 stop12h 55m

$463

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

mar. 11/11

6:30 pm-2:00 pm

1 stop12h 30m

Rome Fiumicino

sáb. 11/22

11:25 am-5:20 pm

1 stop12h 55m

$463

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

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 $1,296). 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 agosto 14, 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.

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 agosto 14, 2025.
See what other customers who have flown with SWISS, United Airlines, and Lufthansa from Chicago to Tuscany 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.
SWISS
7.6
Good
1,699 reviews

Boarding

7.7

Comfort

7.4

Entertainment

6.8

Food

7.1

Overall

7.6

Crew

8.2

Reviews

1 / 20
2.0
Mediocre

Jeff,Feb 2025

BER - ZRH

Ground and flight crew are lazy. No food. Late. Ryanair is better.
SWISS
7.6
Good
1,699 reviews
SWISS
7.6
Good
1,699 reviews

Boarding

7.7

Comfort

7.4

Entertainment

6.8

Food

7.1

Overall

7.6

Crew

8.2

Reviews

1 / 20
2.0
Mediocre

Jeff,Feb 2025

BER - ZRH

Ground and flight crew are lazy. No food. Late. Ryanair is better.
United Airlines
7.4
Good
8,916 reviews
SWISS
7.6
Good
1,699 reviews

Boarding

7.7

Comfort

7.4

Entertainment

6.8

Food

7.1

Overall

7.6

Crew

8.2

Reviews

1 / 20
2.0
Mediocre

Jeff,Feb 2025

BER - ZRH

Ground and flight crew are lazy. No food. Late. Ryanair is better.
Lufthansa
6.8
Okay
7,317 reviews
SWISS
7.6
Good
1,699 reviews

Boarding

7.7

Comfort

7.4

Entertainment

6.8

Food

7.1

Overall

7.6

Crew

8.2

Reviews

1 / 20
2.0
Mediocre

Jeff,Feb 2025

BER - ZRH

Ground and flight crew are lazy. No food. Late. Ryanair is better.
ITA Airways
6.7
Okay
1,018 reviews
SWISS
7.6
Good
1,699 reviews

Boarding

7.7

Comfort

7.4

Entertainment

6.8

Food

7.1

Overall

7.6

Crew

8.2

Reviews

1 / 20
2.0
Mediocre

Jeff,Feb 2025

BER - ZRH

Ground and flight crew are lazy. No food. Late. Ryanair is better.
British Airways
6.7
Okay
7,266 reviews
SWISS
7.6
Good
1,699 reviews

Boarding

7.7

Comfort

7.4

Entertainment

6.8

Food

7.1

Overall

7.6

Crew

8.2

Reviews

1 / 20
2.0
Mediocre

Jeff,Feb 2025

BER - ZRH

Ground and flight crew are lazy. No food. Late. Ryanair is better.

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 $222 on TAP AIR PORTUGAL. Other airlines that offer cheap prices include British Airways from $446 and Delta from $487 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 $1,296). 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.
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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 agosto 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest$470Average$695FlexibilityNo cancel feeOn-time77%
KLMCheapest$491Average$965FlexibilityNo cancel feeOn-time75%
Air FranceCheapest$594Average$971FlexibilityNo cancel feeOn-time77%
British AirwaysCheapest$627Average$1,110FlexibilityNo cancel feeOn-time70%
LufthansaCheapest$630Average$1,099FlexibilityNo cancel feeOn-time76%
DeltaCheapest$699Average$1,169FlexibilityNo cancel feeOn-timeN/A
SWISSCheapest$708Average$1,169FlexibilityNo cancel feeOn-time79%
United AirlinesCheapest$728Average$1,080FlexibilityNo cancel feeOn-time69%
ITA AirwaysCheapest$752Average$976FlexibilityNo cancel feeOn-time81%
IberiaCheapest$777Average$1,099FlexibilityNo cancel feeOn-time77%

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