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$262+ 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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
NAP — CHI
Mar 10 — Mar 171
Tue 3/10
Tue 3/17
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 February 8, 2026.

This Mytrip deal was found by Cheapflights users on 2/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/712:05 pm
VCE
-
ORD
1 stop33h 40m
TAP AIR PORTUGAL
Fri 2/208:15 pm
ORD
-
VCE
1 stop13h 45m
TAP AIR PORTUGAL
Deal found 2/6$483
This Finnair deal was found by Cheapflights users on 2/6. 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 Finnair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/247:30 pm
MXP
-
ORD
1 stop24h 00m
Multiple Airlines
Mon 8/3110:35 pm
ORD
-
MXP
1 stop18h 00m
Multiple Airlines
Deal found 2/6$506
This Finnair deal was found by Cheapflights users on 2/8. 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 Finnair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/411:10 am
LIN
-
ORD
1 stop14h 05m
Multiple Airlines
Sun 9/209:00 pm
ORD
-
LIN
1 stop13h 15m
Multiple Airlines
Deal found 2/8$509
This Finnair deal was found by Cheapflights users on 2/7. 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 Finnair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:55 am
FCO
-
ORD
1 stop17h 40m
Multiple Airlines
Fri 10/210:35 pm
ORD
-
FCO
1 stop13h 45m
Multiple Airlines
Deal found 2/7$522
This Finnair deal was found by Cheapflights users on 2/7. 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 Finnair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/19:50 am
VCE
-
ORD
2 stops33h 35m
Multiple Airlines
Wed 4/88:35 pm
ORD
-
VCE
1 stop15h 45m
Multiple Airlines
Deal found 2/7$523
This Gotogate deal was found by Cheapflights users on 2/6. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/210:55 pm
MXP
-
ORD
1 stop26h 20m
Icelandair
Mon 6/1510:25 pm
ORD
-
MXP
1 stop16h 30m
Icelandair
Deal found 2/6$534
This Kiwi.com deal was found by Cheapflights users on 2/6. 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.
Tue 4/218:00 pm
MXP
-
ORD
1 stop27h 00m
TAP AIR PORTUGAL
Wed 5/66:00 pm
ORD
-
MXP
1 stop18h 00m
TAP AIR PORTUGAL
Deal found 2/6$541
This lol.travel deal was found by Cheapflights users on 2/7. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/218:00 pm
FCO
-
ORD
1 stop27h 00m
TAP AIR PORTUGAL
Sun 5/36:00 pm
ORD
-
FCO
1 stop23h 15m
TAP AIR PORTUGAL
Deal found 2/7$542
This lol.travel deal was found by Cheapflights users on 2/8. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/116:00 am
FCO
-
ORD
1 stop16h 00m
TAP AIR PORTUGAL
Wed 2/187:10 pm
ORD
-
FCO
1 stop21h 55m
TAP AIR PORTUGAL
Deal found 2/8$543
This lol.travel deal was found by Cheapflights users on 2/7. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/218:00 pm
FCO
-
ORD
1 stop27h 00m
TAP AIR PORTUGAL
Sat 5/26:15 pm
ORD
-
FCO
1 stop33h 05m
TAP AIR PORTUGAL
Deal found 2/7$546
This Trip.com deal was found by Cheapflights users on 2/6. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/14:20 pm
MXP
-
ORD
1 stop12h 05m
Icelandair
Mon 6/157:25 pm
ORD
-
MXP
1 stop19h 30m
Icelandair
Deal found 2/6$547
This lol.travel deal was found by Cheapflights users on 2/8. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/171:35 pm
FCO
-
ORD
1 stop33h 40m
TAP AIR PORTUGAL
Sun 4/266:00 pm
ORD
-
FCO
1 stop23h 15m
TAP AIR PORTUGAL
Deal found 2/8$550

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 February 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$477
(Mytrip)

One-way from

$262
(Kiwi.com)

Popular in

January

Cheapest in

April

Average price

$639

Good round-trip deal

$695 or less

Good one-way deal

$494 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
Highest demand for flights based on searches. 0% potential increase in price ($6 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 February 8, 2026.
Use the filters below to find and compare flights from Italy to Chicago that are best for you.

Fly from

Italy

Fly to

Chicago

Route

Depart

Return

Price

VeniceChicago

VCE - ORD

VCEORD

Venice Marco Polo

Sat 4/18

7:10 pm-4:00 pm

1 stop27h 50m

Chicago O'Hare Intl

Sun 5/3

6:00 pm-10:45 am

1 stop33h 45m

$477

VeniceChicago

VCE - ORD

VCEORD

Venice Marco Polo

Wed 4/1

9:50 am-12:25 pm

2 stops33h 35m

Chicago O'Hare Intl

Wed 4/8

8:35 pm-7:20 pm

1 stop15h 45m

$523

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Fri 5/22

10:55 pm-6:15 pm

1 stop26h 20m

Chicago O'Hare Intl

Mon 6/1

10:25 pm-9:55 pm

1 stop16h 30m

$568

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Sat 5/16

4:20 pm-6:15 pm

1 stop32h 55m

Chicago O'Hare Intl

Tue 5/26

10:25 pm-3:10 pm

1 stop33h 45m

$569

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Tue 4/14

8:00 pm-4:10 pm

1 stop27h 10m

Chicago O'Hare Intl

Sat 4/18

7:15 pm-2:10 pm

1 stop11h 55m

$593

MilanChicago

LIN - ORD

LINORD

Milan Linate

Thu 5/21

7:25 am-6:15 pm

1 stop17h 50m

Chicago O'Hare Intl

Sun 5/31

5:00 pm-1:35 pm

1 stop13h 35m

$595

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Thu 2/26

11:15 am-4:45 pm

1 stop12h 30m

Chicago O'Hare Intl

Mon 3/2

7:20 pm-7:10 pm

1 stop16h 50m

$603

MilanChicago

LIN - ORD

LINORD

Milan Linate

Fri 4/24

6:40 am-2:15 pm

1 stop14h 35m

Chicago O'Hare Intl

Sun 4/26

1:36 pm-11:20 am

2 stops14h 44m

$616

MilanChicago

LIN - ORD

LINORD

Milan Linate

Fri 4/24

6:40 am-2:15 pm

1 stop14h 35m

Chicago O'Hare Intl

Sun 4/26

5:10 pm-1:55 pm

1 stop13h 45m

$617

VeniceChicago

VCE - ORD

VCEORD

Venice Marco Polo

Wed 3/18

6:30 am-3:20 pm

1 stop14h 50m

Chicago O'Hare Intl

Mon 4/27

4:50 pm-10:55 am

1 stop11h 05m

$620

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/5

Showing 1-10 of 60 results
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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 February 8, 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 19% of weekly flights between Italy and Chicago have experienced delays in the past year, with the average delay time being 191 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 10% 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 February 8, 2026.
Read reviews from past customers who have flown United Airlines, Turkish Airlines, and Lufthansa 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.
United Airlines
7.4
Good
9,256 reviews

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Crew

8.1

Food

6.6

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,256 reviews
United Airlines
7.4
Good
9,256 reviews

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Crew

8.1

Food

6.6

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Turkish Airlines
7.3
Good
4,207 reviews
United Airlines
7.4
Good
9,256 reviews

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Crew

8.1

Food

6.6

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Lufthansa
6.8
Okay
7,775 reviews
United Airlines
7.4
Good
9,256 reviews

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Crew

8.1

Food

6.6

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
ITA Airways
6.7
Okay
1,145 reviews
United Airlines
7.4
Good
9,256 reviews

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Crew

8.1

Food

6.6

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
British Airways
6.7
Okay
7,720 reviews
United Airlines
7.4
Good
9,256 reviews

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Crew

8.1

Food

6.6

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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 26h 20m. Fly via TAP AIR PORTUGAL, Icelandair, or Scandinavian Airlines to get the fastest option. The distance between Italy and Chicago is about 4508 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 United Airlines, with whom users have recently found tickets for as low as $98. However, be on the lookout for offers from Delta 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 Rome Fiumicino - 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 $419. On average you can expect to pay $620. The most popular route, (Rome Fiumicino - Chicago O'Hare Intl), can usually be booked for $536.

  • 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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Alternative routes for Italy to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Amsterdam to O'Hare Intl flights
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Munich to Midway flights
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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 February 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$536Average$835FlexibilityNo cancel feeOn-time71%
British AirwaysCheapest$545Average$745FlexibilityNo cancel feeOn-time70%
LufthansaCheapest$639Average$723FlexibilityNo cancel feeOn-time76%
United AirlinesCheapest$639Average$827FlexibilityNo cancel feeOn-time69%
IberiaCheapest$692Average$747FlexibilityNo cancel feeOn-time77%

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