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$306+ 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
NAP — CHI
Apr 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
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Cheap flight deals from Italy to Chicago

Keep the following information in mind while searching for Italy to Chicago flight deals. Data was last updated April 24, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$524
(Scandinavian Airlines)

One-way from

$306
(Kiwi.com)

Popular in

August

Cheapest in

February

Average price

$611

Good round-trip deal

$647 or less

Good one-way deal

$658 or less
Provider with most accurate pricing for Rome (ROM)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Rome (ROM)-Chicago (CHI) flights.
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From Italy to Chicago (CHI)
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One-way flight from Italy to Chicago (CHI)
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Highest demand for flights based on searches. 6% potential increase in price ($51 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Italy to Chicago (CHI).
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Price to beat on a one-way flight from Italy to Chicago (CHI).
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Find 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 April 24, 2025.

This Scandinavian Airlines deal was found by Cheapflights users on 4/23. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2310:50 amVCE - ORD
1 stop12h 20mScandinavian Airlines
Sat 10/187:15 pmORD - VCE
1 stop31h 45mScandinavian Airlines
Deal found 4/23$524
This FlightHub deal was found by Cheapflights users on 4/23. 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 9/178:45 pmMXP - ORD
2 stops26h 25mScandinavian Airlines
Sun 9/217:15 pmORD - MXP
1 stop30h 20mScandinavian Airlines
Deal found 4/23$524
This Icelandair deal was found by Cheapflights users on 4/23. 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 Icelandair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/273:10 pmMXP - ORD
1 stop34h 05mIcelandair
Fri 10/1710:15 pmORD - MXP
1 stop33h 15mIcelandair
Deal found 4/23$529
This American Airlines deal was found by Cheapflights users on 4/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/253:00 pmNAP - ORD
Nonstop10h 40mAmerican Airlines
Sun 8/319:15 pmORD - NAP
1 stop15h 10mAmerican Airlines
Deal found 4/23$539
This Cheapflightsfares deal was found by Cheapflights users on 4/23. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/208:05 amVCE - ORD
1 stop17h 10mMultiple Airlines
Fri 10/39:15 pmORD - VCE
1 stop11h 15mMultiple Airlines
Deal found 4/23$541
This American Airlines deal was found by Cheapflights users on 4/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2512:15 pmVCE - ORD
1 stop17h 36mAmerican Airlines
Wed 10/155:06 pmORD - VCE
2 stops18h 54mAmerican Airlines
Deal found 4/23$543
This Cheapflightsfares deal was found by Cheapflights users on 4/23. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1111:05 amFCO - ORD
Nonstop10h 25mIberia
Sun 9/145:10 pmORD - FCO
Nonstop9h 00mIberia
Deal found 4/23$546
This American Airlines deal was found by Cheapflights users on 4/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/177:25 amLIN - ORD
1 stop13h 25mAmerican Airlines
Sun 9/2110:35 pmORD - LIN
1 stop11h 40mAmerican Airlines
Deal found 4/24$546
This American Airlines deal was found by Cheapflights users on 4/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2211:10 amMXP - ORD
1 stop30h 59mAmerican Airlines
Fri 6/65:45 pmORD - MXP
1 stop22h 15mAmerican Airlines
Deal found 4/23$546
This Booking.com deal was found by Cheapflights users on 4/23. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/217:35 amVCE - ORD
1 stop13h 15mBritish Airways
Fri 10/38:40 pmORD - VCE
1 stop11h 50mBritish Airways
Deal found 4/23$548
This Iberia deal was found by Cheapflights users on 4/23. 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/86:50 amNAP - ORD
1 stop14h 25mMultiple Airlines
Mon 5/127:15 pmORD - NAP
1 stop19h 45mMultiple Airlines
Deal found 4/23$550
This Iberia deal was found by Cheapflights users on 4/22. 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/611:10 amMXP - ORD
1 stop13h 24mMultiple Airlines
Tue 5/137:10 pmORD - MXP
1 stop17h 55mMultiple Airlines
Deal found 4/22$550

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 April 24, 2025.
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

Tue 9/23

10:50 am-4:10 pm

1 stop12h 20m

Chicago O'Hare Intl

Sat 10/18

7:15 pm-10:00 am

1 stop31h 45m

$524

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Wed 9/17

8:45 pm-4:10 pm

2 stops26h 25m

Chicago O'Hare Intl

Sun 9/21

7:15 pm-8:35 am

1 stop30h 20m

$524

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Sat 9/27

3:10 pm-6:15 pm

1 stop34h 05m

Chicago O'Hare Intl

Fri 10/17

10:15 pm-2:30 pm

1 stop33h 15m

$529

NaplesChicago

NAP - ORD

NAPORD

Naples

Mon 8/25

3:00 pm-6:40 pm

Nonstop10h 40m

Chicago O'Hare Intl

Sun 8/31

9:15 pm-7:25 pm

1 stop15h 10m

$539

VeniceChicago

VCE - ORD

VCEORD

Venice Marco Polo

Sat 9/20

8:05 am-6:15 pm

1 stop17h 10m

Chicago O'Hare Intl

Fri 10/3

9:15 pm-3:30 pm

1 stop11h 15m

$541

VeniceChicago

VCE - ORD

VCEORD

Venice Marco Polo

Thu 9/25

12:15 pm-10:51 pm

1 stop17h 36m

Chicago O'Hare Intl

Wed 10/15

8:35 pm-10:15 pm

1 stop18h 40m

$543

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Thu 9/11

11:05 am-2:30 pm

Nonstop10h 25m

Chicago O'Hare Intl

Sun 9/14

5:10 pm-9:10 am

Nonstop9h 00m

$546

MilanChicago

LIN - ORD

LINORD

Milan Linate

Wed 9/17

7:25 am-1:50 pm

1 stop13h 25m

Chicago O'Hare Intl

Sun 9/21

10:35 pm-5:15 pm

1 stop11h 40m

$546

VeniceChicago

VCE - ORD

VCEORD

Venice Marco Polo

Sun 9/21

7:35 am-1:50 pm

1 stop13h 15m

Chicago O'Hare Intl

Fri 10/3

8:40 pm-3:30 pm

1 stop11h 50m

$548

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 5/8

6:50 am-2:15 pm

1 stop14h 25m

Chicago O'Hare Intl

Mon 5/12

7:15 pm-10:00 pm

1 stop19h 45m

$550

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

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, August is the cheapest month in which you can book a flight from Italy to Chicago (average of $245). Flying from Italy to Chicago in March is currently the most expensive (average of $321). 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 April 24, 2025.

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.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 April 24, 2025.
Peruse reviews from past customers who have flown with Emirates, Delta and KLM from Italy to Chicago to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Emirates
8.0
Very good
3,206 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.3

Entertainment

8.2

Food

7.8

Reviews

1 / 20
2.0
Mediocre

Anonymous,Jun 2024

DXB - IAH

It was not a good experience the seats were small and uncomfortable the food was not good and they forgot to serve me my breakfast - there were 5 us in 2 rows that they just completely skipped us. Very disappointed.
Emirates
8.0
Very good
3,206 reviews
Emirates
8.0
Very good
3,206 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.3

Entertainment

8.2

Food

7.8

Reviews

1 / 20
2.0
Mediocre

Anonymous,Jun 2024

DXB - IAH

It was not a good experience the seats were small and uncomfortable the food was not good and they forgot to serve me my breakfast - there were 5 us in 2 rows that they just completely skipped us. Very disappointed.
Delta
8.0
Very good
7,920 reviews
Emirates
8.0
Very good
3,206 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.3

Entertainment

8.2

Food

7.8

Reviews

1 / 20
2.0
Mediocre

Anonymous,Jun 2024

DXB - IAH

It was not a good experience the seats were small and uncomfortable the food was not good and they forgot to serve me my breakfast - there were 5 us in 2 rows that they just completely skipped us. Very disappointed.
KLM
7.8
Good
1,333 reviews
Emirates
8.0
Very good
3,206 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.3

Entertainment

8.2

Food

7.8

Reviews

1 / 20
2.0
Mediocre

Anonymous,Jun 2024

DXB - IAH

It was not a good experience the seats were small and uncomfortable the food was not good and they forgot to serve me my breakfast - there were 5 us in 2 rows that they just completely skipped us. Very disappointed.
Air Transat
7.8
Good
385 reviews
Emirates
8.0
Very good
3,206 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.3

Entertainment

8.2

Food

7.8

Reviews

1 / 20
2.0
Mediocre

Anonymous,Jun 2024

DXB - IAH

It was not a good experience the seats were small and uncomfortable the food was not good and they forgot to serve me my breakfast - there were 5 us in 2 rows that they just completely skipped us. Very disappointed.
LOT
7.6
Good
1,066 reviews
Emirates
8.0
Very good
3,206 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.3

Entertainment

8.2

Food

7.8

Reviews

1 / 20
2.0
Mediocre

Anonymous,Jun 2024

DXB - IAH

It was not a good experience the seats were small and uncomfortable the food was not good and they forgot to serve me my breakfast - there were 5 us in 2 rows that they just completely skipped us. Very disappointed.

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.

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

    The cheapest airline one-way is TAP AIR PORTUGAL, with whom users have recently found tickets for as low as $388. However, be on the lookout for offers from Air Serbia and Icelandair, 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 Rome Fiumicino - Chicago O'Hare Intl or Milan Linate - Chicago O'Hare Intl, Milan Malpensa - 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 $527. On average you can expect to pay $1,085. The most popular route, (Milan Malpensa - Chicago O'Hare Intl), can usually be booked for $483.

  • 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, August is the cheapest month in which you can book a flight from Italy to Chicago (average of $245). Flying from Italy to Chicago in March is currently the most expensive (average of $321). 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 Italy?

Book flights to Italy if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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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Krakow to O'Hare Intl flights
Amsterdam to O'Hare Intl flights
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Frankfurt-Hahn to O'Hare Intl flights
Linate to O'Hare Intl flights
Berlin to O'Hare Intl flights
Edinburgh to O'Hare Intl flights
Vicenza to O'Hare Intl flights
Oslo Gardermoen to O'Hare Intl flights
Bruxelles-National to Midway flights
Stansted to O'Hare Intl flights
Bergamo to O'Hare Intl flights
Munich to Midway flights
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Copenhagen to O'Hare Intl flights
Istanbul to Midway flights
Leonardo da Vinci/Fiumicino to Midway flights
Belgrade to O'Hare Intl flights
Sabiha Gokcen to O'Hare Intl flights

Top 8 airlines flying from Italy to Chicago

Discover the top 8 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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
FinnairCheapest$391Average$416FlexibilityNo cancel feeOn-time76%
American AirlinesCheapest$407Average$883FlexibilityNo cancel feeOn-time71%
British AirwaysCheapest$416Average$762FlexibilityNo cancel feeOn-time70%
TAP AIR PORTUGALCheapest$537Average$564FlexibilityNo cancel feeOn-timeN/A
IberiaCheapest$550Average$738FlexibilityNo cancel feeOn-time77%
ITA AirwaysCheapest$550Average$684FlexibilityNo cancel feeOn-time81%
United AirlinesCheapest$571Average$804FlexibilityNo cancel feeOn-time69%
LufthansaCheapest$625Average$848FlexibilityNo cancel feeOn-time76%

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