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$327+ Cheap flights from Italy 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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
NAP — CHI
Apr 25 — May 21
Sat 4/25
Sat 5/2
1 adult, Economy
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Cheap flight deals from Italy to Chicago

Cheapest flights from Italy to Chicago
Explore the most affordable flight options available from Italy to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 26, 2026.

This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/213:45 pm
FCO
-
ORD
1 stop33h 30m
Icelandair
Tue 4/287:25 pm
ORD
-
FCO
1 stop12h 10m
Icelandair
Deal found 3/22$491
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/103:45 pm
FCO
-
ORD
1 stop12h 40m
Icelandair
Sun 4/1910:25 pm
ORD
-
FCO
1 stop33h 10m
Icelandair
Deal found 3/25$523
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/167:15 pm
VCE
-
ORD
1 stop27h 45m
TAP AIR PORTUGAL
Sat 5/26:05 pm
ORD
-
VCE
1 stop33h 40m
TAP AIR PORTUGAL
Deal found 3/23$530
This lol.travel deal was found by Cheapflights users on 3/21. 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.
Fri 5/16:00 pm
LIN
-
ORD
1 stop26h 10m
ITA Airways
Thu 5/73:00 pm
ORD
-
LIN
1 stop12h 10m
ITA Airways
Deal found 3/21$530
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/84:20 pm
MXP
-
ORD
1 stop32h 55m
Icelandair
Sun 10/187:25 pm
ORD
-
MXP
1 stop12h 45m
Icelandair
Deal found 3/25$534
This Mytrip deal was found by Cheapflights users on 3/21. 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.
Wed 9/23:45 pm
FCO
-
ORD
1 stop12h 40m
Icelandair
Wed 9/167:25 pm
ORD
-
FCO
1 stop12h 10m
Icelandair
Deal found 3/21$536
This lol.travel 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:00 pm
LIN
-
ORD
1 stop25h 10m
ITA Airways
Mon 5/113:00 pm
ORD
-
LIN
1 stop13h 40m
ITA Airways
Deal found 3/24$536
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/213:45 pm
FCO
-
ORD
1 stop33h 30m
Icelandair
Wed 6/310:25 pm
ORD
-
FCO
1 stop18h 10m
Icelandair
Deal found 3/22$539
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/193:45 pm
FCO
-
ORD
1 stop12h 40m
Icelandair
Tue 5/267:25 pm
ORD
-
FCO
1 stop12h 10m
Icelandair
Deal found 3/23$540
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/23:45 pm
FCO
-
ORD
1 stop33h 30m
Icelandair
Sun 5/1710:25 pm
ORD
-
FCO
1 stop33h 10m
Icelandair
Deal found 3/24$542
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 8/263:45 pm
FCO
-
ORD
1 stop12h 40m
Icelandair
Sat 9/127:25 pm
ORD
-
FCO
1 stop12h 10m
Icelandair
Deal found 3/23$546
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/46:15 am
VCE
-
ORD
1 stop13h 55m
ITA Airways
Mon 5/113:00 pm
ORD
-
VCE
1 stop20h 25m
ITA Airways
Deal found 3/23$556

Find flight deals from Italy to Chicago

Keep the following information in mind while searching for Italy to Chicago flight deals. Data was last updated March 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$491
(eDestinos)

One-way from

$327
(Kiwi.com)

Popular in

January

Cheapest in

May

Average price

$738

Good round-trip deal

$788 or less

Good one-way deal

$576 or less
Provider with most accurate pricing for Rome (ROM)-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Rome (ROM)-Chicago (CHI) flights.
Search Deals
From Italy to Chicago (CHI)
Search Deals
One-way flight from Italy to Chicago (CHI)
Search Deals
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
Price to beat on a round-trip flight from Italy to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Italy to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Italy 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 March 26, 2026.
Use the filters below to find and compare flights from Italy to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Fri 4/17

3:45 pm-9:25 pm

1 stop12h 40m

Chicago O'Hare Intl

Mon 4/20

7:25 pm-2:35 pm

1 stop12h 10m

$556

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Tue 5/12

3:45 pm-6:15 pm

1 stop33h 30m

Chicago O'Hare Intl

Sun 5/31

10:25 pm-2:35 pm

1 stop33h 10m

$575

VeniceChicago

VCE - ORD

VCEORD

Venice Marco Polo

Sun 8/23

12:15 pm-11:12 pm

1 stop17h 57m

Chicago O'Hare Intl

Sat 8/29

8:45 pm-10:05 pm

1 stop18h 20m

$646

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Tue 4/21

10:00 am-1:30 pm

Nonstop10h 30m

Chicago O'Hare Intl

Tue 4/28

9:15 pm-5:15 pm

1 stop13h 00m

$651

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Thu 4/16

6:30 am-2:15 pm

1 stop14h 45m

Chicago O'Hare Intl

Wed 4/29

6:00 am-6:50 am

1 stop17h 50m

$654

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Thu 4/9

6:30 am-4:49 pm

2 stops17h 19m

Chicago O'Hare Intl

Wed 4/22

8:15 am-7:35 am

1 stop16h 20m

$658
Quickest round-trip

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Fri 4/17

10:00 am-1:30 pm

Nonstop10h 30m

Chicago O'Hare Intl

Mon 4/20

4:55 pm-9:10 am

Nonstop9h 15m

$660

MilanChicago

LIN - ORD

LINORD

Milan Linate

Thu 4/9

10:10 pm-2:15 pm

1 stop23h 05m

Chicago O'Hare Intl

Mon 4/13

5:10 pm-1:55 pm

1 stop13h 45m

$662

MilanChicago

LIN - ORD

LINORD

Milan Linate

Thu 4/9

6:40 am-2:15 pm

1 stop14h 35m

Chicago O'Hare Intl

Wed 4/22

5:10 pm-11:20 am

1 stop11h 10m

$663

MilanChicago

LIN - ORD

LINORD

Milan Linate

Thu 4/9

10:10 pm-2:15 pm

1 stop23h 05m

Chicago O'Hare Intl

Wed 4/22

4:50 pm-3:55 pm

1 stop16h 05m

$665

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 Italy to Chicago

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

What is the cheapest month to book a flight from Italy to Chicago?

Currently, September is the cheapest month in which you can book a flight from Italy to Chicago (average of $396). Flying from Italy to Chicago in January is currently the most expensive (average of $621). 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 IT to CHI?

Find hourly flight availability from Italy to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 26, 2026.

When flying from Italy to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

How often are flights from Italy to Chicago delayed?

About 20% of weekly flights between Italy and Chicago have experienced delays in the past year, with the average delay time being 193 minutes.

What is the most punctual flight time for Italy to Chicago flights?

Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Thursday tends to have the lowest number of delays on this route, whereas Monday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Italy to Chicago flights?

Over the last year, Ethiopian Air have had the lowest number of delays on this route, with just 13% of flights being delayed.

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 March 26, 2026.
Read reviews from past customers who have flown Turkish Airlines,United Airlines, andLufthansa from Italy to Chicago. 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.
Turkish Airlines
7.4
Good
4,282 reviews

Food

7.5

Boarding

7.3

Overall

7.4

Comfort

7.3

Entertainment

7.5

Crew

7.8

Reviews

1 / 20
8.0
Excellent

Muhammad,Jan 2026

ORD - DFW

Great, customer service agent at O’hare was able to change the flight due to snow storm. Thank you
Turkish Airlines
7.4
Good
4,282 reviews
Turkish Airlines
7.4
Good
4,282 reviews

Food

7.5

Boarding

7.3

Overall

7.4

Comfort

7.3

Entertainment

7.5

Crew

7.8

Reviews

1 / 20
8.0
Excellent

Muhammad,Jan 2026

ORD - DFW

Great, customer service agent at O’hare was able to change the flight due to snow storm. Thank you
United Airlines
7.4
Good
9,494 reviews
Turkish Airlines
7.4
Good
4,282 reviews

Food

7.5

Boarding

7.3

Overall

7.4

Comfort

7.3

Entertainment

7.5

Crew

7.8

Reviews

1 / 20
8.0
Excellent

Muhammad,Jan 2026

ORD - DFW

Great, customer service agent at O’hare was able to change the flight due to snow storm. Thank you
Lufthansa
6.8
Okay
7,871 reviews
Turkish Airlines
7.4
Good
4,282 reviews

Food

7.5

Boarding

7.3

Overall

7.4

Comfort

7.3

Entertainment

7.5

Crew

7.8

Reviews

1 / 20
8.0
Excellent

Muhammad,Jan 2026

ORD - DFW

Great, customer service agent at O’hare was able to change the flight due to snow storm. Thank you
ITA Airways
6.7
Okay
1,173 reviews
Turkish Airlines
7.4
Good
4,282 reviews

Food

7.5

Boarding

7.3

Overall

7.4

Comfort

7.3

Entertainment

7.5

Crew

7.8

Reviews

1 / 20
8.0
Excellent

Muhammad,Jan 2026

ORD - DFW

Great, customer service agent at O’hare was able to change the flight due to snow storm. Thank you
British Airways
6.7
Okay
7,822 reviews
Turkish Airlines
7.4
Good
4,282 reviews

Food

7.5

Boarding

7.3

Overall

7.4

Comfort

7.3

Entertainment

7.5

Crew

7.8

Reviews

1 / 20
8.0
Excellent

Muhammad,Jan 2026

ORD - DFW

Great, customer service agent at O’hare was able to change the flight due to snow storm. Thank you

Related info for your journey

Find useful and relevant information for your journey from Italy to Chicago. 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 Italy to Chicago?

    There are many flights that can get you from Italy to Chicago in 12h 40m. Fly via Icelandair, British Airways, or Delta to get the fastest option. The distance between Italy and Chicago is about 4808 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Italy to Chicago one-way?

    The cheapest airline one-way is Icelandair, with whom users have recently found tickets for as low as $334. However, be on the lookout for offers from Iberia and American Airlines, as they are both options that can get you from Italy to Chicago for a low price.

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

    While some choose either Milan Malpensa - Chicago O'Hare Intl or Milan Linate - Chicago Midway, Rome Fiumicino - Chicago O'Hare Intl is the most popular route from Italy to Chicago.

  • What are the cheapest flights from Italy to Chicago?

    The cheapest flight price from Italy to Chicago is $510. On average you can expect to pay $1,197. The most popular route, (Rome Fiumicino - Chicago O'Hare Intl), can usually be booked for $523.

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from Italy to Chicago (average of $396). Flying from Italy to Chicago in January is currently the most expensive (average of $621). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Top 5 airlines flying from Italy to Chicago

Discover the top 5 airlines that operate flights from Italy to Chicago. 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 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$537Average$829FlexibilityNo cancel feeOn-time71%
British AirwaysCheapest$545Average$724FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$651Average$831FlexibilityNo cancel feeOn-time69%
LufthansaCheapest$690Average$710FlexibilityNo cancel feeOn-time76%
IberiaCheapest$722Average$747FlexibilityNo cancel feeOn-time77%

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