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$289+ 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 4/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — NAP
Apr 26 — May 31
Sun 4/26
Sun 5/3
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 March 27, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/26. 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.
Sun 8/162:20 pm
ORD
-
PMO
1 stop11h 40m
Multiple Airlines
Thu 8/278:10 pm
PMO
-
ORD
1 stop24h 10m
Multiple Airlines
Deal found 3/26$480
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/162:20 pm
ORD
-
PMO
1 stop11h 40m
SWISS
Thu 8/279:45 am
PMO
-
ORD
1 stop13h 10m
SWISS
Deal found 3/25$486
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/152:20 pm
ORD
-
PMO
1 stop11h 40m
Multiple Airlines
Wed 4/229:45 am
PMO
-
ORD
2 stops16h 40m
Multiple Airlines
Deal found 3/24$517
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/164:20 pm
ORD
-
PMO
1 stop33h 30m
Austrian Airlines
Thu 8/278:10 pm
PMO
-
ORD
2 stops29h 27m
Austrian Airlines
Deal found 3/25$527
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:15 pm
ORD
-
MXP
1 stop12h 50m
Scandinavian Airlines
Wed 11/1811:15 am
MXP
-
ORD
1 stop12h 30m
Scandinavian Airlines
Deal found 3/22$528
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/67:20 pm
ORD
-
MXP
2 stops34h 35m
Scandinavian Airlines
Mon 11/238:00 pm
MXP
-
ORD
1 stop27h 45m
Scandinavian Airlines
Deal found 3/22$529
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/411:25 am
ORD
-
NAP
1 stop20h 10m
Turkish Airlines
Thu 10/158:45 pm
NAP
-
ORD
1 stop19h 55m
Turkish Airlines
Deal found 3/22$529
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/97:20 pm
ORD
-
MXP
1 stop30h 05m
Scandinavian Airlines
Wed 11/258:00 pm
MXP
-
ORD
1 stop27h 45m
Scandinavian Airlines
Deal found 3/22$530
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/137:20 pm
ORD
-
MXP
2 stops34h 35m
Scandinavian Airlines
Wed 11/2512:55 pm
MXP
-
ORD
2 stops34h 50m
Scandinavian Airlines
Deal found 3/22$531
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 9/228:10 pm
ORD
-
NAP
1 stop16h 35m
Turkish Airlines
Tue 9/299:30 am
NAP
-
ORD
1 stop31h 10m
Turkish Airlines
Deal found 3/23$531
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.
Thu 11/57:20 pm
ORD
-
MXP
2 stops17h 35m
Scandinavian Airlines
Mon 11/98:00 pm
MXP
-
ORD
1 stop27h 45m
Scandinavian Airlines
Deal found 3/23$532
This SmartFares 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/172:20 pm
ORD
-
PMO
1 stop16h 45m
Multiple Airlines
Wed 8/266:10 pm
PMO
-
ORD
1 stop25h 25m
Multiple Airlines
Deal found 3/24$535

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 March 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$481
(Kiwi.com)

One-way from

$289
(Kiwi.com)

Popular in

June

Cheapest in

November

Average price

$718

Good round-trip deal

$783 or less

Good one-way deal

$558 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. 20% potential increase in price ($183 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($21 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 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 March 27, 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

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Tue 5/5

11:25 am-2:35 pm

1 stop20h 10m

Naples

Tue 5/19

8:45 pm-9:40 am

1 stop19h 55m

$664

ChicagoVenice

ORD - VCE

ORDVCE

Chicago O'Hare Intl

Thu 4/16

8:10 pm-7:00 pm

1 stop15h 50m

Venice Marco Polo

Wed 4/29

9:55 am-9:40 am

1 stop30h 45m

$692

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Sat 4/18

11:25 am-8:25 am

1 stop14h 00m

Palermo Punta Raisi

Wed 4/22

7:35 pm-9:40 am

1 stop21h 05m

$694

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Tue 8/18

5:25 pm-10:00 am

Nonstop9h 35m

Naples

Tue 8/25

3:00 pm-6:50 pm

Nonstop10h 50m

$700

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

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Sun 4/26

7:04 am-10:30 am

2 stops20h 26m

Palermo Punta Raisi

Mon 5/4

2:55 pm-3:55 pm

1 stop32h 00m

$746

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Mon 8/17

5:25 pm-10:00 am

Nonstop9h 35m

Naples

Mon 8/24

3:00 pm-6:50 pm

Nonstop10h 50m

$750

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

ChicagoPalermo

ORD - PMO

ORDPMO

Chicago O'Hare Intl

Mon 4/13

8:10 pm-6:35 pm

1 stop15h 25m

Palermo Punta Raisi

Tue 4/28

7:20 am-9:40 am

2 stops33h 20m

$790

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 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

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

Currently, December is the cheapest month in which you can book a flight from Chicago to Italy (average of $346). Flying from Chicago to Italy in June is currently the most expensive (average of $701). 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 March 27, 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.

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 164 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 March 27, 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
4,282 reviews

Overall

7.4

Food

7.5

Comfort

7.3

Entertainment

7.5

Boarding

7.3

Crew

7.8

Reviews

1 / 20
8.0
Excellent

Cathy,Mar 2026

DFW - ATH

I really enjoyed the food . It's just too hard to eat in such a confined space. Baring in mind, I was not in business class. Crew was very friendly.
Turkish Airlines
7.4
Good
4,282 reviews
Turkish Airlines
7.4
Good
4,282 reviews

Overall

7.4

Food

7.5

Comfort

7.3

Entertainment

7.5

Boarding

7.3

Crew

7.8

Reviews

1 / 20
8.0
Excellent

Cathy,Mar 2026

DFW - ATH

I really enjoyed the food . It's just too hard to eat in such a confined space. Baring in mind, I was not in business class. Crew was very friendly.
United Airlines
7.4
Good
9,494 reviews
Turkish Airlines
7.4
Good
4,282 reviews

Overall

7.4

Food

7.5

Comfort

7.3

Entertainment

7.5

Boarding

7.3

Crew

7.8

Reviews

1 / 20
8.0
Excellent

Cathy,Mar 2026

DFW - ATH

I really enjoyed the food . It's just too hard to eat in such a confined space. Baring in mind, I was not in business class. Crew was very friendly.
American Airlines
7.1
Good
11,502 reviews
Turkish Airlines
7.4
Good
4,282 reviews

Overall

7.4

Food

7.5

Comfort

7.3

Entertainment

7.5

Boarding

7.3

Crew

7.8

Reviews

1 / 20
8.0
Excellent

Cathy,Mar 2026

DFW - ATH

I really enjoyed the food . It's just too hard to eat in such a confined space. Baring in mind, I was not in business class. Crew was very friendly.
Lufthansa
6.8
Okay
7,871 reviews
Turkish Airlines
7.4
Good
4,282 reviews

Overall

7.4

Food

7.5

Comfort

7.3

Entertainment

7.5

Boarding

7.3

Crew

7.8

Reviews

1 / 20
8.0
Excellent

Cathy,Mar 2026

DFW - ATH

I really enjoyed the food . It's just too hard to eat in such a confined space. Baring in mind, I was not in business class. Crew was very friendly.
ITA Airways
6.7
Okay
1,173 reviews
Turkish Airlines
7.4
Good
4,282 reviews

Overall

7.4

Food

7.5

Comfort

7.3

Entertainment

7.5

Boarding

7.3

Crew

7.8

Reviews

1 / 20
8.0
Excellent

Cathy,Mar 2026

DFW - ATH

I really enjoyed the food . It's just too hard to eat in such a confined space. Baring in mind, I was not in business class. Crew was very friendly.

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?

    Turkish Airlines, British Airways, and Scandinavian Airlines can get you from Chicago to Italy in just under 9h 35m. Your travel time can differ by up to 28h 50m. Chicago and Italy are separated by a distance of 4929 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 $561. While the most popular route (Chicago O'Hare Intl - Rome Fiumicino) can be booked for $548 on average, our data indicates $894 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, December is the cheapest month in which you can book a flight from Chicago to Italy (average of $346). Flying from Chicago to Italy in June is currently the most expensive (average of $701). 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 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 March 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
TAP AIR PORTUGALCheapest$337Average$526FlexibilityNo cancel feeOn-timeN/A
Turkish AirlinesCheapest$375Average$692FlexibilityNo cancel feeOn-time77%
Air CanadaCheapest$384Average$897FlexibilityNo cancel feeOn-time67%
IcelandairCheapest$395Average$686FlexibilityNo cancel feeOn-time76%
Scandinavian AirlinesCheapest$403Average$527FlexibilityNo cancel feeOn-time77%
SWISSCheapest$414Average$1,023FlexibilityNo cancel feeOn-time79%
KLMCheapest$455Average$878FlexibilityNo cancel feeOn-time75%
British AirwaysCheapest$455Average$799FlexibilityNo cancel feeOn-time70%
Air FranceCheapest$458Average$719FlexibilityNo cancel feeOn-time77%
DeltaCheapest$462Average$793FlexibilityNo cancel feeOn-timeN/A

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