HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$307+ 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 6/2. Fares are subject to change and may not be available on all flights or dates of travel.
NAP — CHI
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Italy to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 May 1, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$534
(Cheapflightsfares)

One-way from

$307
(Kiwi.com)

Popular in

August

Cheapest in

February

Average price

$627

Good round-trip deal

$664 or less

Good one-way deal

$678 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. 6% potential increase in price ($49 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2025
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

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 May 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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 5/1012:15 pmVCE - ORD
1 stop17h 53mMultiple Airlines
Thu 6/510:30 pmORD - VCE
1 stop18h 20mMultiple Airlines
Deal found 4/29$534
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Sun 5/1112:15 pmVCE - ORD
1 stop17h 53mAmerican Airlines
Tue 5/278:30 pmORD - VCE
1 stop16h 30mAmerican Airlines
Deal found 4/29$540
This British Airways deal was found by Cheapflights users on 4/29. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2011:10 amMXP - ORD
1 stop13h 24mBritish Airways
Tue 5/2710:25 pmORD - MXP
1 stop12h 40mBritish Airways
Deal found 4/29$544
This lol.travel deal was found by Cheapflights users on 4/30. 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 5/1611:05 amFCO - ORD
Nonstop10h 25mIberia
Sun 6/14:45 pmORD - FCO
Nonstop9h 15mIberia
Deal found 4/30$545
This British Airways deal was found by Cheapflights users on 4/30. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/167:50 amNAP - ORD
1 stop15h 05mBritish Airways
Sun 6/18:30 pmORD - NAP
1 stop18h 30mBritish Airways
Deal found 4/30$546
This Iberia deal was found by Cheapflights users on 4/29. 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.
Sun 9/217:35 amVCE - ORD
1 stop13h 15mBritish Airways
Fri 10/39:15 pmORD - VCE
1 stop11h 15mBritish Airways
Deal found 4/29$547
This United Airlines deal was found by Cheapflights users on 4/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/249:45 amFCO - ORD
Nonstop10h 25mUnited Airlines
Sat 5/246:30 pmORD - FCO
1 stop32h 45mUnited Airlines
Deal found 4/30$548
This American Airlines deal was found by Cheapflights users on 4/30. 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 stop14h 25mAmerican Airlines
Sun 9/218:40 pmORD - LIN
1 stop13h 35mAmerican Airlines
Deal found 4/30$548
This Cheapflightsfares deal was found by Cheapflights users on 4/28. 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.
Mon 5/197:35 amFCO - ORD
1 stop13h 40mMultiple Airlines
Mon 5/2610:25 pmORD - FCO
1 stop14h 40mMultiple Airlines
Deal found 4/28$549
This Booking.com deal was found by Cheapflights users on 4/29. 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.
Thu 5/2211:05 amFCO - ORD
Nonstop10h 25mBritish Airways
Fri 6/69:15 pmORD - FCO
1 stop12h 10mBritish Airways
Deal found 4/29$550
This British Airways deal was found by Cheapflights users on 4/30. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/811:05 amLIN - ORD
1 stop12h 55mBritish Airways
Mon 5/125:40 pmORD - LIN
1 stop12h 55mBritish Airways
Deal found 4/30$550
This American Airlines deal was found by Cheapflights users on 4/30. 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 9/1811:05 amFCO - ORD
Nonstop10h 25mAmerican Airlines
Fri 10/38:40 pmORD - FCO
1 stop14h 20mAmerican Airlines
Deal found 4/30$551

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 May 1, 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

Sat 5/10

12:15 pm-11:08 pm

1 stop17h 53m

Chicago O'Hare Intl

Thu 6/5

10:30 pm-11:50 pm

1 stop18h 20m

$534

VeniceChicago

VCE - ORD

VCEORD

Venice Marco Polo

Sun 5/11

12:15 pm-11:08 pm

1 stop17h 53m

Chicago O'Hare Intl

Tue 5/27

8:30 pm-8:00 pm

1 stop16h 30m

$540

MilanChicago

LIN - ORD

LINORD

Milan Linate

Wed 9/17

7:25 am-3:55 pm

1 stop15h 30m

Chicago O'Hare Intl

Sun 9/21

10:35 pm-5:15 pm

1 stop11h 40m

$541

MilanChicago

LIN - ORD

LINORD

Milan Linate

Wed 9/10

11:10 am-6:15 pm

1 stop14h 05m

Chicago O'Hare Intl

Wed 10/8

7:15 pm-1:35 pm

1 stop11h 20m

$544

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Tue 5/20

11:10 am-5:34 pm

1 stop13h 24m

Chicago O'Hare Intl

Tue 5/27

10:25 pm-6:05 pm

1 stop12h 40m

$544

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Fri 5/16

11:05 am-2:30 pm

Nonstop10h 25m

Chicago O'Hare Intl

Sun 6/1

4:45 pm-9:00 am

Nonstop9h 15m

$545

NaplesChicago

NAP - ORD

NAPORD

Naples

Fri 5/16

7:50 am-3:55 pm

1 stop15h 05m

Chicago O'Hare Intl

Sun 6/1

8:30 pm-10:00 pm

1 stop18h 30m

$546

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Sat 5/24

9:45 am-1:10 pm

Nonstop10h 25m

Chicago O'Hare Intl

Sat 5/24

6:30 pm-10:15 am

1 stop32h 45m

$548

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Mon 5/19

7:35 am-2:15 pm

1 stop13h 40m

Chicago O'Hare Intl

Mon 5/26

10:25 pm-8:05 pm

1 stop14h 40m

$549

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Thu 9/18

11:05 am-2:30 pm

Nonstop10h 25m

Chicago O'Hare Intl

Fri 10/3

8:40 pm-6:00 pm

1 stop14h 20m

$551

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 60 results
1
2
3
...
6

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 May 1, 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 May 1, 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
3,215 reviews

Boarding

8.1

Comfort

8.0

Food

7.8

Entertainment

8.2

Crew

8.3

Overall

8.0

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
3,215 reviews
Emirates
8.0
Very good
3,215 reviews

Boarding

8.1

Comfort

8.0

Food

7.8

Entertainment

8.2

Crew

8.3

Overall

8.0

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
7,934 reviews
Emirates
8.0
Very good
3,215 reviews

Boarding

8.1

Comfort

8.0

Food

7.8

Entertainment

8.2

Crew

8.3

Overall

8.0

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
1,334 reviews
Emirates
8.0
Very good
3,215 reviews

Boarding

8.1

Comfort

8.0

Food

7.8

Entertainment

8.2

Crew

8.3

Overall

8.0

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
1,069 reviews
Emirates
8.0
Very good
3,215 reviews

Boarding

8.1

Comfort

8.0

Food

7.8

Entertainment

8.2

Crew

8.3

Overall

8.0

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.
Austrian Airlines
7.6
Good
781 reviews
Emirates
8.0
Very good
3,215 reviews

Boarding

8.1

Comfort

8.0

Food

7.8

Entertainment

8.2

Crew

8.3

Overall

8.0

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 Air Serbia, with whom users have recently found tickets for as low as $405. However, be on the lookout for offers from Icelandair and Aer Lingus, 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 $695. On average you can expect to pay $1,054. The most popular route, (Milan Malpensa - Chicago O'Hare Intl), can usually be booked for $477.

  • 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

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.

Alternative routes for Italy to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Heathrow to O'Hare Intl flights
Charles de Gaulle to O'Hare Intl flights
Frankfurt to O'Hare Intl flights
Madrid to O'Hare Intl flights
Frederic Chopin to O'Hare Intl flights
Bruxelles-National to O'Hare Intl flights
Charles de Gaulle to Midway flights
Orly to O'Hare Intl flights
Gatwick to O'Hare Intl flights
Zurich to O'Hare Intl flights
Amsterdam to O'Hare Intl flights
London City to O'Hare Intl flights
Heathrow to Midway flights
Munich to O'Hare Intl flights
Malpensa to O'Hare Intl flights
Dublin to O'Hare Intl flights
Istanbul to O'Hare Intl flights
Krakow to O'Hare Intl flights
Vienna to O'Hare Intl flights
Athens to O'Hare Intl flights
Frederic Chopin to Midway flights
Leonardo da Vinci/Fiumicino to O'Hare Intl flights
Madrid to Midway flights
Barcelona-El Prat to O'Hare Intl flights
Linate to O'Hare Intl flights
Bruxelles-National to Midway flights
Beauvais-Tille to O'Hare Intl flights
Stansted to O'Hare Intl flights
Frankfurt-Hahn to O'Hare Intl flights
Bergamo to O'Hare Intl flights
Barcelona-El Prat to Midway flights
Vicenza to O'Hare Intl flights
Berlin to O'Hare Intl flights
Luton to O'Hare Intl flights
Amsterdam to Midway flights
Belgrade to O'Hare Intl flights
Copenhagen to O'Hare Intl flights
Edinburgh to O'Hare Intl flights
Lyon to O'Hare Intl flights
Heathrow to St. Louis flights
Frankfurt to St. Louis 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FinnairCheapest$391Average$416FlexibilityNo cancel feeOn-time76%
American AirlinesCheapest$407Average$883FlexibilityNo cancel feeOn-time71%
British AirwaysCheapest$416Average$759FlexibilityNo 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$803FlexibilityNo cancel feeOn-time69%
LufthansaCheapest$639Average$838FlexibilityNo cancel feeOn-time76%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.