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Tuscany

$290+ 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 4/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — FLR
Apr 26 — May 31
Sun 4/26
Sun 5/3
1 adult, Economy
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Cheap 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 March 27, 2026.

This FlightHub deal was found by Cheapflights users on 3/23. 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.
Wed 4/158:10 pm
ORD
-
FCO
1 stop15h 15m
Turkish Airlines
Thu 4/233:10 pm
FCO
-
ORD
1 stop25h 30m
Turkish Airlines
Deal found 3/23$575
This FlightHub deal was found by Cheapflights users on 3/23. 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.
Tue 4/148:10 pm
ORD
-
FCO
1 stop20h 25m
Turkish Airlines
Tue 4/218:00 pm
FCO
-
ORD
1 stop20h 40m
Turkish Airlines
Deal found 3/23$578
This oojo deal was found by Cheapflights users on 3/22. 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.
Wed 4/156:00 pm
ORD
-
FCO
1 stop15h 45m
TAP AIR PORTUGAL
Fri 4/245:55 am
FCO
-
ORD
1 stop17h 05m
TAP AIR PORTUGAL
Deal found 3/22$582
This FlightHub deal was found by Cheapflights users on 3/25. 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 10/211:25 am
ORD
-
FCO
1 stop19h 45m
Turkish Airlines
Tue 10/1310:45 am
FCO
-
ORD
1 stop29h 55m
Turkish Airlines
Deal found 3/25$585
This Kiwi.com deal was found by Cheapflights users on 3/24. 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.
Mon 4/278:10 pm
ORD
-
FCO
1 stop15h 15m
Turkish Airlines
Thu 5/78:00 pm
FCO
-
ORD
1 stop20h 40m
Turkish Airlines
Deal found 3/24$586
This FlightHub deal was found by Cheapflights users on 3/25. 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.
Tue 4/218:10 pm
ORD
-
FCO
1 stop15h 15m
Turkish Airlines
Sun 5/37:05 am
FCO
-
ORD
1 stop33h 35m
Turkish Airlines
Deal found 3/25$587
This FlightHub deal was found by Cheapflights users on 3/23. 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.
Mon 11/167:20 pm
ORD
-
FCO
1 stop32h 45m
Scandinavian Airlines
Tue 12/811:55 am
FCO
-
ORD
1 stop36h 00m
Scandinavian Airlines
Deal found 3/23$588
This FlightHub deal was found by Cheapflights users on 3/23. 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.
Sat 10/107:15 pm
ORD
-
FCO
2 stops41h 05m
Scandinavian Airlines
Sun 10/189:30 am
FCO
-
ORD
1 stop13h 40m
Scandinavian Airlines
Deal found 3/23$589
This oojo deal was found by Cheapflights users on 3/25. 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.
Sat 4/116:05 pm
ORD
-
FCO
1 stop23h 10m
TAP AIR PORTUGAL
Sat 4/185:55 am
FCO
-
ORD
1 stop17h 10m
TAP AIR PORTUGAL
Deal found 3/25$592
This FlightHub deal was found by Cheapflights users on 3/24. 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.
Sun 4/128:10 pm
ORD
-
FCO
1 stop15h 15m
Turkish Airlines
Sun 4/197:05 am
FCO
-
ORD
1 stop33h 35m
Turkish Airlines
Deal found 3/24$593
This KAYAK deal was found by Cheapflights users on 3/23. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/158:15 pm
ORD
-
FCO
1 stop15h 30m
TAP AIR PORTUGAL
Thu 12/107:35 pm
FCO
-
ORD
1 stop26h 55m
TAP AIR PORTUGAL
Deal found 3/23$594
This FlightHub deal was found by Cheapflights users on 3/25. 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.
Sat 4/256:05 pm
ORD
-
FCO
1 stop33h 15m
TAP AIR PORTUGAL
Wed 5/64:45 am
FCO
-
ORD
1 stop18h 15m
TAP AIR PORTUGAL
Deal found 3/25$595

Find flight deals from Chicago to Tuscany

Keep the following information in mind while searching for Chicago to Tuscany flight deals. Data was last updated March 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$575
(FlightHub)

One-way from

$290
(Kiwi.com)

Popular in

June

Cheapest in

November

Average price

$913
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. 14% potential increase in price ($151 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($34 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

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 March 27, 2026.
Use the filters below to find and compare flights from Chicago to Tuscany that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Fri 9/11

7:15 pm-4:40 pm

2 stops38h 25m

Rome Fiumicino

Fri 9/25

9:40 am-10:06 pm

2 stops19h 26m

$722

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Wed 4/15

2:12 pm-10:10 am

1 stop12h 58m

Rome Fiumicino

Mon 4/20

9:00 am-5:58 pm

1 stop15h 58m

$757

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Wed 9/9

4:40 pm-8:40 am

1 stop33h 00m

Florence Peretola

Sun 9/20

8:15 pm-2:30 pm

1 stop25h 15m

$787

ChicagoRome

ORD - CIA

ORDCIA

Chicago O'Hare Intl

Tue 4/21

3:45 pm-8:20 pm

3 stops21h 35m

Rome Ciampino

Tue 4/28

8:55 am-7:55 pm

2 stops18h 00m

$808

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Wed 4/8

8:10 pm-6:15 pm

2 stops39h 05m

Florence Peretola

Wed 4/15

2:55 pm-6:15 pm

2 stops34h 20m

$847

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Sat 4/11

8:10 pm-10:40 pm

2 stops43h 30m

Florence Peretola

Wed 4/15

11:25 am-6:15 pm

2 stops37h 50m

$847

ChicagoRome

ORD - CIA

ORDCIA

Chicago O'Hare Intl

Tue 4/21

7:25 pm-8:20 pm

2 stops17h 55m

Rome Ciampino

Sat 4/25

8:05 am-9:15 pm

2 stops20h 10m

$865

ChicagoRome

ORD - CIA

ORDCIA

Chicago O'Hare Intl

Thu 5/7

7:25 pm-9:15 pm

3 stops18h 50m

Rome Ciampino

Tue 5/19

6:15 am-6:15 pm

3 stops19h 00m

$883

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Sat 9/5

8:10 pm-10:40 pm

2 stops43h 30m

Florence Peretola

Sat 9/12

6:25 am-9:40 am

2 stops58h 15m

$887

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Mon 4/20

11:25 am-6:15 pm

2 stops23h 50m

Florence Peretola

Fri 5/1

11:25 am-9:40 am

2 stops29h 15m

$887

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/26

Showing 1-10 of 60 resultsSorted by cheapest first
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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, April is the cheapest month in which you can book a flight from Chicago to Tuscany (average of $473). Flying from Chicago to Tuscany in February is currently the most expensive (average of $879). 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.

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

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 March 27, 2026.
See what other customers who have flown with SWISS,United Airlines, andLufthansa 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
7.5
Good
1,905 reviews

Comfort

7.4

Entertainment

6.8

Boarding

7.7

Overall

7.5

Food

7.1

Crew

8.3

Reviews

1 / 20
10.0
Excellent

Thomas,Mar 2026

BOS - ZRH

The business class seats on the new Swiss A350 are hard as a rock. Seems like a bit of a miss on the new "Swiss Senses" experience. Other than that, excellent service.
SWISS
7.5
Good
1,905 reviews
SWISS
7.5
Good
1,905 reviews

Comfort

7.4

Entertainment

6.8

Boarding

7.7

Overall

7.5

Food

7.1

Crew

8.3

Reviews

1 / 20
10.0
Excellent

Thomas,Mar 2026

BOS - ZRH

The business class seats on the new Swiss A350 are hard as a rock. Seems like a bit of a miss on the new "Swiss Senses" experience. Other than that, excellent service.
United Airlines
7.4
Good
9,491 reviews
SWISS
7.5
Good
1,905 reviews

Comfort

7.4

Entertainment

6.8

Boarding

7.7

Overall

7.5

Food

7.1

Crew

8.3

Reviews

1 / 20
10.0
Excellent

Thomas,Mar 2026

BOS - ZRH

The business class seats on the new Swiss A350 are hard as a rock. Seems like a bit of a miss on the new "Swiss Senses" experience. Other than that, excellent service.
Lufthansa
6.8
Okay
7,871 reviews
SWISS
7.5
Good
1,905 reviews

Comfort

7.4

Entertainment

6.8

Boarding

7.7

Overall

7.5

Food

7.1

Crew

8.3

Reviews

1 / 20
10.0
Excellent

Thomas,Mar 2026

BOS - ZRH

The business class seats on the new Swiss A350 are hard as a rock. Seems like a bit of a miss on the new "Swiss Senses" experience. Other than that, excellent service.
ITA Airways
6.7
Okay
1,173 reviews
SWISS
7.5
Good
1,905 reviews

Comfort

7.4

Entertainment

6.8

Boarding

7.7

Overall

7.5

Food

7.1

Crew

8.3

Reviews

1 / 20
10.0
Excellent

Thomas,Mar 2026

BOS - ZRH

The business class seats on the new Swiss A350 are hard as a rock. Seems like a bit of a miss on the new "Swiss Senses" experience. Other than that, excellent service.
British Airways
6.7
Okay
7,822 reviews
SWISS
7.5
Good
1,905 reviews

Comfort

7.4

Entertainment

6.8

Boarding

7.7

Overall

7.5

Food

7.1

Crew

8.3

Reviews

1 / 20
10.0
Excellent

Thomas,Mar 2026

BOS - ZRH

The business class seats on the new Swiss A350 are hard as a rock. Seems like a bit of a miss on the new "Swiss Senses" experience. Other than that, excellent service.

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.

  • How long is the flight from Chicago to Tuscany?

    A quick flight from Chicago to Tuscany can take about 12h 58m. Scandinavian Airlines provides one of the quickest options available for as low as $757. Chicago and Tuscany are separated by a distance of 4810 mi. This flight may include one or multiple stops.

  • 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 $349 on SWISS. Other airlines that offer cheap prices include Scandinavian Airlines from $367 and United Airlines from $522 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 - Rome Ciampino 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, April is the cheapest month in which you can book a flight from Chicago to Tuscany (average of $473). Flying from Chicago to Tuscany in February is currently the most expensive (average of $879). 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.

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 March 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest$443Average$646FlexibilityNo cancel feeOn-time77%
British AirwaysCheapest$458Average$840FlexibilityNo cancel feeOn-time70%
Air FranceCheapest$478Average$799FlexibilityNo cancel feeOn-time77%
KLMCheapest$491Average$850FlexibilityNo cancel feeOn-time75%
SWISSCheapest$586Average$1,069FlexibilityNo cancel feeOn-time79%
LufthansaCheapest$630Average$1,053FlexibilityNo cancel feeOn-time76%
United AirlinesCheapest$669Average$1,093FlexibilityNo cancel feeOn-time69%
IberiaCheapest$687Average$1,036FlexibilityNo cancel feeOn-time77%
ITA AirwaysCheapest$758Average$940FlexibilityNo cancel feeOn-time81%
DeltaCheapest$782Average$1,167FlexibilityNo cancel feeOn-timeN/A

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