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$339+ Cheap flights from Chicago (CHI) to Italy

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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — NAP
Jun 9 — Jun 161
Tue 6/9
Tue 6/16
1 adult, Economy
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Cheap flight deals from Chicago to Italy

Cheapest flights from Chicago to Italy
Explore the most affordable flight options available from Chicago to Italy. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 10, 2026.

This FlightHub deal was found by Cheapflights users on 5/5. 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 9/77:15 pm
ORD
-
MXP
1 stop12h 50m
Scandinavian Airlines
Mon 9/143:55 pm
MXP
-
ORD
2 stops37h 11m
Scandinavian Airlines
Deal found 5/5$738
This FlightHub deal was found by Cheapflights users on 5/5. 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 8/237:15 pm
ORD
-
MXP
2 stops17h 35m
Scandinavian Airlines
Wed 8/269:20 am
MXP
-
ORD
2 stops19h 30m
Scandinavian Airlines
Deal found 5/5$740
This oojo deal was found by Cheapflights users on 5/5. 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.
Sun 10/117:15 pm
ORD
-
MXP
2 stops17h 35m
Scandinavian Airlines
Sat 10/249:20 am
MXP
-
ORD
1 stop13h 50m
Scandinavian Airlines
Deal found 5/5$749
This FlightHub deal was found by Cheapflights users on 5/6. 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.
Thu 9/178:10 pm
ORD
-
MXP
1 stop29h 30m
Turkish Airlines
Tue 9/2910:40 am
MXP
-
ORD
1 stop30h 00m
Turkish Airlines
Deal found 5/6$752
This Kiwi.com deal was found by Cheapflights users on 5/6. 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.
Thu 9/247:15 pm
ORD
-
MXP
1 stop12h 50m
Scandinavian Airlines
Sat 10/39:05 pm
MXP
-
ORD
2 stops26h 05m
Scandinavian Airlines
Deal found 5/6$756
This oojo deal was found by Cheapflights users on 5/5. 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 8/227:15 pm
ORD
-
MXP
1 stop11h 55m
Scandinavian Airlines
Sun 8/303:00 pm
MXP
-
ORD
1 stop32h 10m
Scandinavian Airlines
Deal found 5/5$758
This FlightHub deal was found by Cheapflights users on 5/9. 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 8/267:15 pm
ORD
-
MXP
2 stops32h 40m
Scandinavian Airlines
Mon 9/78:00 pm
MXP
-
ORD
1 stop27h 10m
Scandinavian Airlines
Deal found 5/9$762
This Justfly.com deal was found by Cheapflights users on 5/6. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:15 pm
ORD
-
MXP
2 stops32h 40m
Scandinavian Airlines
Sun 10/116:50 pm
MXP
-
ORD
2 stops52h 20m
Scandinavian Airlines
Deal found 5/6$763
This FlightHub deal was found by Cheapflights users on 5/6. 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 9/257:15 pm
ORD
-
MXP
1 stop30h 15m
Scandinavian Airlines
Mon 10/58:00 pm
MXP
-
ORD
1 stop27h 10m
Scandinavian Airlines
Deal found 5/6$764
This Kiwi.com deal was found by Cheapflights users on 5/7. 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.
Sat 8/84:20 pm
ORD
-
LIN
1 stop14h 50m
Austrian Airlines
Sat 8/228:00 pm
LIN
-
ORD
1 stop24h 20m
Austrian Airlines
Deal found 5/7$764
This Gotogate deal was found by Cheapflights users on 5/8. 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.
Mon 8/35:35 pm
ORD
-
LIN
2 stops14h 05m
Air Canada
Wed 8/196:50 am
LIN
-
ORD
2 stops15h 05m
Air Canada
Deal found 5/8$766
This Gotogate deal was found by Cheapflights users on 5/8. 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.
Mon 8/33:35 pm
ORD
-
LIN
1 stop10h 35m
Lufthansa
Wed 8/1910:35 am
LIN
-
ORD
1 stop16h 20m
Lufthansa
Deal found 5/8$767

Find flight deals from Chicago to Italy

Keep the following information in mind while searching for Chicago to Italy flight deals. Data was last updated May 10, 2026.

Most accurate provider

Ovago
3 stars

Most trusted provider

Ovago
3 stars

Round-trip from

$748
(oojo)

One-way from

$339
(Kiwi.com)

Popular in

June

Cheapest in

November

Average price

$871

Good round-trip deal

$889 or less

Good one-way deal

$528 or less
Provider with most accurate pricing for Chicago (CHI)-Rome (ROM) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Rome (ROM) flights.
Search Deals
From Chicago (CHI) to Italy
Search Deals
One-way flight from Chicago (CHI) to Italy
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($164 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Italy.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Italy.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Italy 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 May 10, 2026.
Use the filters below to find and compare flights from Chicago to Italy that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Wed 10/21

5:10 pm-11:20 am

1 stop11h 10m

Milan Linate

Thu 11/5

10:55 am-8:24 pm

2 stops16h 29m

$800

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Tue 7/21

3:45 pm-7:55 am

Nonstop9h 10m

Rome Fiumicino

Tue 8/4

6:50 am-2:55 pm

1 stop15h 05m

$835

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Fri 8/14

9:15 pm-4:30 pm

1 stop12h 15m

Rome Fiumicino

Sat 8/29

10:00 am-1:30 pm

Nonstop10h 30m

$841

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sat 7/25

5:30 pm-10:00 am

Nonstop9h 30m

Naples

Fri 8/21

8:05 pm-3:55 pm

1 stop26h 50m

$871

ChicagoRome

ORD - CIA

ORDCIA

Chicago O'Hare Intl

Wed 9/2

9:00 pm-8:20 pm

2 stops16h 20m

Rome Ciampino

Thu 9/24

6:05 am-6:15 pm

3 stops43h 10m

$891

ChicagoRome

ORD - CIA

ORDCIA

Chicago O'Hare Intl

Thu 9/24

7:25 pm-8:30 pm

2 stops18h 05m

Rome Ciampino

Wed 9/30

4:00 pm-11:50 am

1 stop26h 50m

$894

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Sat 7/25

11:10 am-11:25 am

2 stops17h 15m

Rome Fiumicino

Wed 8/5

10:35 am-9:52 pm

2 stops18h 17m

$903

ChicagoRome

ORD - CIA

ORDCIA

Chicago O'Hare Intl

Wed 9/9

10:30 pm-9:55 pm

2 stops16h 25m

Rome Ciampino

Thu 9/17

6:05 am-6:15 pm

3 stops43h 10m

$905

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Sun 8/2

3:40 pm-11:45 am

1 stop13h 05m

Rome Fiumicino

Sat 8/15

9:45 am-1:15 pm

Nonstop10h 30m

$907

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sun 8/2

3:35 pm-12:20 pm

1 stop13h 45m

Naples

Wed 9/30

6:00 am-11:30 pm

2 stops24h 30m

$922

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/5

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Chicago to Italy

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

How far ahead should I book a flight from Chicago to Italy?

The best time to book flights from Chicago to Italy is 84 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, November is the cheapest month in which you can book a flight from Chicago to Italy (average of $560). Flying from Chicago to Italy in June is currently the most expensive (average of $1,088). 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 IT?

Find hourly flight availability from Chicago to Italy. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 10, 2026.

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

Weekly flight availability from Chicago to Italy

Explore weekly flight availability from Chicago to Italy. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 10, 2026.

The most flights from CHI to IT0 are scheduled on a Monday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (4 on average).

How often are flights from Chicago to Italy delayed?

About 31% of weekly flights between Chicago and Italy have experienced delays in the past year, with the average delay time being 166 minutes.

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

Historically, flights departing in the early afternoon 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?

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

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

Over the last year, United Airlines have had the lowest number of delays on this route, with just 30% of flights being delayed.

Reviews of airlines servicing Italy

Get insights into the airlines that provide service to Italy. 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 Italy. Reviews last updated May 10, 2026.
Peruse reviews from past customers who have flown with Turkish Airlines,United Airlines, andAmerican Airlines from Chicago to Italy to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Turkish Airlines
7.4
Good
4,356 reviews

Comfort

7.3

Entertainment

7.5

Food

7.5

Boarding

7.3

Crew

7.8

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Anonymous,May 2026

DEN - IST

The seat assignments that were booked well in advance and paid extra for were all changed and incorrect. This includes the bassinet we requested at time of booking being unavailable and the row we selected not being in the bassinet aisle.
Turkish Airlines
7.4
Good
4,356 reviews
Turkish Airlines
7.4
Good
4,356 reviews

Comfort

7.3

Entertainment

7.5

Food

7.5

Boarding

7.3

Crew

7.8

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Anonymous,May 2026

DEN - IST

The seat assignments that were booked well in advance and paid extra for were all changed and incorrect. This includes the bassinet we requested at time of booking being unavailable and the row we selected not being in the bassinet aisle.
United Airlines
7.4
Good
9,694 reviews
Turkish Airlines
7.4
Good
4,356 reviews

Comfort

7.3

Entertainment

7.5

Food

7.5

Boarding

7.3

Crew

7.8

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Anonymous,May 2026

DEN - IST

The seat assignments that were booked well in advance and paid extra for were all changed and incorrect. This includes the bassinet we requested at time of booking being unavailable and the row we selected not being in the bassinet aisle.
American Airlines
7.1
Good
11,667 reviews
Turkish Airlines
7.4
Good
4,356 reviews

Comfort

7.3

Entertainment

7.5

Food

7.5

Boarding

7.3

Crew

7.8

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Anonymous,May 2026

DEN - IST

The seat assignments that were booked well in advance and paid extra for were all changed and incorrect. This includes the bassinet we requested at time of booking being unavailable and the row we selected not being in the bassinet aisle.
Lufthansa
6.8
Okay
7,985 reviews
Turkish Airlines
7.4
Good
4,356 reviews

Comfort

7.3

Entertainment

7.5

Food

7.5

Boarding

7.3

Crew

7.8

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Anonymous,May 2026

DEN - IST

The seat assignments that were booked well in advance and paid extra for were all changed and incorrect. This includes the bassinet we requested at time of booking being unavailable and the row we selected not being in the bassinet aisle.
ITA Airways
6.7
Okay
1,213 reviews
Turkish Airlines
7.4
Good
4,356 reviews

Comfort

7.3

Entertainment

7.5

Food

7.5

Boarding

7.3

Crew

7.8

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Anonymous,May 2026

DEN - IST

The seat assignments that were booked well in advance and paid extra for were all changed and incorrect. This includes the bassinet we requested at time of booking being unavailable and the row we selected not being in the bassinet aisle.

Related info for your journey

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

    Delta, United Airlines, and British Airways can get you from Chicago to Italy in just under 9h 10m. Your travel time can differ by up to 3h 05m. Chicago and Italy are separated by a distance of 4808 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    $186 is the cheapest one-way deal found within the past few days, from TAP AIR PORTUGAL. You may also be able to find cheap deals on Icelandair and ITA Airways, with prices starting from $193 and $196, respectively.

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

    Most travelers choose Chicago O'Hare Intl - Rome Fiumicino, Chicago O'Hare Intl - Milan Malpensa or Chicago Midway - Rome Fiumicino when deciding on the best route from Chicago to Italy.

  • What are the cheapest flights from Chicago to Italy?

    Looking at all options, your cheapest flight can be booked for $736. While the most popular route (Chicago O'Hare Intl - Rome Fiumicino) can be booked for $603 on average, our data indicates $1,264 when flying from Chicago to Italy.

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

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

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

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

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

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

    Currently, November is the cheapest month in which you can book a flight from Chicago to Italy (average of $560). Flying from Chicago to Italy in June is currently the most expensive (average of $1,088). 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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Top 10 airlines flying from Chicago to Italy

Discover the top 10 airlines that operate flights from Chicago to Italy. 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 May 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
TAP AIR PORTUGALCheapest$337Average$527FlexibilityNo cancel feeOn-timeN/A
Turkish AirlinesCheapest$375Average$672FlexibilityNo cancel feeOn-time77%
Air CanadaCheapest$384Average$914FlexibilityNo cancel feeOn-time67%
IcelandairCheapest$395Average$680FlexibilityNo cancel feeOn-time76%
Scandinavian AirlinesCheapest$410Average$582FlexibilityNo cancel feeOn-time77%
KLMCheapest$455Average$878FlexibilityNo cancel feeOn-time75%
British AirwaysCheapest$455Average$830FlexibilityNo cancel feeOn-time70%
Air FranceCheapest$458Average$791FlexibilityNo cancel feeOn-time77%
DeltaCheapest$462Average$859FlexibilityNo cancel feeOn-timeN/A
SWISSCheapest$491Average$987FlexibilityNo cancel feeOn-time79%

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