HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Tuscany

$344+ 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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — FLR
abr. 5 — abr. 121
sáb. 4/5
sáb. 4/12
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Tuscany with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 marzo 31, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$568
(oojo)

One-way from

$344
(Kiwi.com)

Popular in

June

Cheapest in

November

Average price

$1,021
Provider with most accurate pricing for Chicago (CHI)-Florence Peretola flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Florence Peretola flights.
Search Deals
From Chicago (CHI) to Tuscany
Search Deals
One-way flight from Chicago (CHI) to Tuscany
Search Deals
Highest demand for flights based on searches. 20% potential increase in price ($266 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($33 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2025
Search Deals

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 marzo 31, 2025.

This United deal was found by Cheapflights users on 3/31. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/23:50 pmORD - FCO
Nonstop8h 55mUnited Airlines
jue. 11/1312:15 pmFCO - ORD
1 stop14h 17mUnited Airlines
Deal found 3/31$564
This Air Canada deal was found by Cheapflights users on 3/31. 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.
dom. 11/27:20 amORD - FCO
1 stop19h 40mAir Canada
jue. 11/131:30 pmFCO - ORD
2 stops28h 28mAir Canada
Deal found 3/31$566
This United deal was found by Cheapflights users on 3/31. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 3/313:35 pmORD - FCO
Nonstop9h 20mMultiple Airlines
lun. 4/78:10 pmFCO - ORD
1 stop26h 45mMultiple Airlines
Deal found 3/31$568
This FlightHub deal was found by Cheapflights users on 3/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/256:15 pmORD - FCO
1 stop15h 35mTAP AIR PORTUGAL
mié. 11/56:00 amFCO - ORD
1 stop16h 30mTAP AIR PORTUGAL
Deal found 3/30$570
This FlightHub deal was found by Cheapflights users on 3/31. 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.
mié. 9/247:50 pmORD - FCO
1 stop20h 40mTurkish Airlines
vie. 10/33:30 pmFCO - ORD
1 stop37h 30mTurkish Airlines
Deal found 3/31$571
This Air Serbia deal was found by Cheapflights users on 3/30. 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 Air Serbia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/1111:20 pmORD - FCO
1 stop13h 20mAir Serbia
vie. 10/179:00 pmFCO - ORD
1 stop31h 00mAir Serbia
Deal found 3/30$573
This KLM deal was found by Cheapflights users on 3/30. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/112:51 pmMDW - FCO
1 stop15h 14mKLM
mar. 4/811:35 amFCO - MDW
1 stop17h 51mKLM
Deal found 3/30$573
This Delta deal was found by Cheapflights users on 3/30. 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.
mar. 4/110:55 amORD - FCO
1 stop12h 30mDelta
lun. 4/712:45 pmFCO - ORD
1 stop32h 55mDelta
Deal found 3/30$576
This Delta deal was found by Cheapflights users on 3/31. 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.
mar. 4/19:25 amMDW - FCO
2 stops15h 10mDelta
mar. 4/89:45 amFCO - MDW
1 stop19h 41mDelta
Deal found 3/31$577
This oojo deal was found by Cheapflights users on 3/30. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/207:15 pmORD - FCO
1 stop16h 30mScandinavian Airlines
sáb. 9/2711:55 amFCO - ORD
1 stop35h 15mScandinavian Airlines
Deal found 3/30$578
This SWISS deal was found by Cheapflights users on 3/31. 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.
dom. 10/268:05 pmORD - FCO
1 stop11h 55mSWISS
lun. 11/38:00 pmFCO - ORD
1 stop27h 15mSWISS
Deal found 3/31$586
This Lufthansa deal was found by Cheapflights users on 3/30. 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 Lufthansa is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 3/3010:30 pmORD - FCO
1 stop12h 20mLufthansa
mar. 4/812:50 pmFCO - ORD
1 stop12h 25mLufthansa
Deal found 3/30$594

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 marzo 31, 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. 4/21

7:15 pm-6:45 pm

1 stop16h 30m

Rome Fiumicino

vie. 5/9

7:35 pm-4:10 pm

1 stop27h 35m

$568

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

mar. 4/29

5:55 am-12:20 am

2 stops35h 25m

Rome Fiumicino

jue. 5/1

7:05 pm-7:03 am

1 stop18h 58m

$576

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

sáb. 4/19

6:15 pm-7:00 pm

1 stop17h 45m

Rome Fiumicino

mar. 4/29

5:45 pm-4:10 pm

1 stop29h 25m

$599

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

vie. 4/4

3:35 pm-7:55 am

Nonstop9h 20m

Rome Fiumicino

mar. 4/8

9:45 am-1:00 pm

Nonstop10h 15m

$608

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

jue. 4/3

9:45 pm-9:15 am

2 stops28h 30m

Rome Fiumicino

mar. 4/8

11:30 am-10:47 am

1 stop30h 17m

$612

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

jue. 4/3

10:30 pm-5:50 pm

1 stop12h 20m

Rome Fiumicino

mié. 4/9

12:50 pm-6:15 pm

1 stop12h 25m

$621

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

jue. 4/3

6:35 pm-8:50 am

1 stop31h 15m

Rome Fiumicino

lun. 4/7

9:40 am-12:10 pm

1 stop33h 30m

$636

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

dom. 4/6

1:57 pm-10:05 am

1 stop13h 08m

Rome Fiumicino

mar. 4/15

10:10 am-5:55 pm

1 stop14h 45m

$642

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

mié. 5/7

3:00 pm-7:25 am

Nonstop9h 25m

Rome Fiumicino

mié. 5/14

9:25 am-1:10 pm

Nonstop10h 45m

$643

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

mar. 4/8

9:45 am-11:05 am

1 stop18h 20m

Rome Fiumicino

mar. 4/22

6:30 am-2:40 pm

1 stop15h 10m

$645

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/30

Showing 1-10 of 60 results
1
2
3
...
6

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 $1,413). 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 marzo 31, 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 marzo 31, 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
7,899 reviews

Comfort

8.0

Food

7.3

Overall

8.0

Boarding

8.2

Crew

8.5

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
7,899 reviews
Delta
8.0
Very good
7,899 reviews

Comfort

8.0

Food

7.3

Overall

8.0

Boarding

8.2

Crew

8.5

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.
Porter Airlines
7.9
Good
277 reviews
Delta
8.0
Very good
7,899 reviews

Comfort

8.0

Food

7.3

Overall

8.0

Boarding

8.2

Crew

8.5

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
1,321 reviews
Delta
8.0
Very good
7,899 reviews

Comfort

8.0

Food

7.3

Overall

8.0

Boarding

8.2

Crew

8.5

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.
Air Transat
7.8
Good
381 reviews
Delta
8.0
Very good
7,899 reviews

Comfort

8.0

Food

7.3

Overall

8.0

Boarding

8.2

Crew

8.5

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
1,267 reviews
Delta
8.0
Very good
7,899 reviews

Comfort

8.0

Food

7.3

Overall

8.0

Boarding

8.2

Crew

8.5

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 $388 on WestJet. Other airlines that offer cheap prices include Scandinavian Airlines from $397 and TAP AIR PORTUGAL from $401 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 $1,413). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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
O'Hare Intl to Malpensa flights
O'Hare Intl to Linate flights
O'Hare Intl to Vicenza flights
O'Hare Intl to Florence flights
Midway to Malpensa flights
O'Hare Intl to Naples flights
St. Louis to Leonardo da Vinci/Fiumicino flights
Midway to Linate flights
Midway to Vicenza flights
O'Hare Intl to Ciampino flights
O'Hare Intl to Palermo flights
Midway to Naples flights
Midway to Florence flights
O'Hare Intl to Bergamo flights
O'Hare Intl to Bologna flights
O'Hare Intl to Catania flights
O'Hare Intl to Bari flights
St. Louis to Malpensa flights
St. Louis to Florence flights
St. Louis to Linate flights
Midway to Bologna flights
Midway to Catania flights
O'Hare Intl to Pisa flights
Midway to Palermo flights
St. Louis to Vicenza flights
O'Hare Intl to Verona flights
St. Louis to Naples flights
Midway to Bari flights
O'Hare Intl to Lamezia Terme flights
O'Hare Intl to Genoa flights
O'Hare Intl to Turin flights
O'Hare Intl to Trieste flights
O'Hare Intl to Cagliari flights
Midway to Pisa flights
O'Hare Intl to Olbia flights
Moline to Leonardo da Vinci/Fiumicino flights
O'Hare Intl to Treviso A. Canova flights
St. Louis to Catania flights
O'Hare Intl to Brindisi flights
St. Louis to Bergamo flights
Midway to Genoa flights
St. Louis to Pisa flights
Midway to Turin flights
Peoria to Leonardo da Vinci/Fiumicino flights
St. Louis to Bologna 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 marzo 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest$557Average$783FlexibilityNo cancel feeOn-time77%
KLMCheapest$702Average$1,075FlexibilityNo cancel feeOn-time75%
British AirwaysCheapest$730Average$1,407FlexibilityNo cancel feeOn-time70%
ITA AirwaysCheapest$736Average$1,032FlexibilityNo cancel feeOn-time81%
United AirlinesCheapest$737Average$1,232FlexibilityNo cancel feeOn-time69%
DeltaCheapest$749Average$1,136FlexibilityNo cancel feeOn-timeN/A
Air FranceCheapest$752Average$1,134FlexibilityNo cancel feeOn-time77%
SWISSCheapest$772Average$1,428FlexibilityNo cancel feeOn-time79%
IberiaCheapest$792Average$1,099FlexibilityNo cancel feeOn-time77%
LufthansaCheapest$810Average$1,197FlexibilityNo cancel feeOn-time76%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.