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$283+ 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 9/8. Fares are subject to change and may not be available on all flights or dates of travel.
NAP — CHI
Jun 21 — Jun 281
Sat 6/21
Sat 6/28
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 June 16, 2025.

Round-trip from

$369
(lol.travel)

One-way from

$283
(Kiwi.com)

Popular in

August

Cheapest in

February

Average price

$789

Good round-trip deal

$664 or less

Good one-way deal

$483 or less
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 ($48 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 June 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 June 16, 2025.

This lol.travel deal was found by Cheapflights users on 6/14. 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.
Thu 9/187:10 pmVCE - ORD
1 stop28h 20mTAP AIR PORTUGAL
Fri 9/266:00 pmORD - VCE
1 stop33h 45mTAP AIR PORTUGAL
Deal found 6/14$369
This Expedia deal was found by Cheapflights users on 6/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/512:10 pmVCE - ORD
1 stop13h 50mAer Lingus
Fri 9/199:15 pmORD - VCE
1 stop18h 55mAer Lingus
Deal found 6/14$556
This Expedia deal was found by Cheapflights users on 6/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/711:40 amNAP - ORD
1 stop14h 20mAer Lingus
Tue 10/143:45 pmORD - NAP
1 stop11h 55mAer Lingus
Deal found 6/14$574
This Expedia deal was found by Cheapflights users on 6/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/712:00 pmNAP - ORD
1 stop15h 17mBritish Airways
Tue 10/145:06 pmORD - NAP
2 stops18h 04mBritish Airways
Deal found 6/14$589
This American Airlines deal was found by Cheapflights users on 6/14. 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.
Tue 10/73:00 pmNAP - ORD
Nonstop10h 40mAmerican Airlines
Tue 10/147:00 amORD - NAP
1 stop20h 00mAmerican Airlines
Deal found 6/14$595
This Cheapflightsfares deal was found by Cheapflights users on 6/14. 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 9/216:25 amVCE - ORD
1 stop14h 50mMultiple Airlines
Sat 10/410:35 pmORD - VCE
1 stop15h 05mMultiple Airlines
Deal found 6/14$603
This lol.travel deal was found by Cheapflights users on 6/16. 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.
Sun 8/248:50 pmMXP - ORD
1 stop22h 05mBritish Airways
Tue 9/29:15 pmORD - MXP
1 stop19h 30mBritish Airways
Deal found 6/16$604
This Icelandair deal was found by Cheapflights users on 6/14. 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.
Thu 8/213:10 pmMXP - ORD
1 stop13h 05mIcelandair
Mon 9/110:15 pmORD - MXP
1 stop16h 45mIcelandair
Deal found 6/14$606
This Delta deal was found by Cheapflights users on 6/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/206:00 amVCE - ORD
1 stop15h 10mDelta
Fri 10/36:10 pmORD - VCE
2 stops16h 10mDelta
Deal found 6/14$607
This lol.travel deal was found by Cheapflights users on 6/16. 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.
Thu 10/27:50 amLIN - ORD
1 stop13h 25mMultiple Airlines
Wed 10/158:35 pmORD - LIN
1 stop11h 30mMultiple Airlines
Deal found 6/16$608
This Delta deal was found by Cheapflights users on 6/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/176:40 amLIN - ORD
1 stop15h 00mDelta
Sun 9/215:45 pmORD - LIN
2 stops13h 10mDelta
Deal found 6/16$610
This KLM deal was found by Cheapflights users on 6/16. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/112:05 pmVCE - ORD
1 stop31h 05mKLM
Fri 10/241:30 pmORD - VCE
1 stop12h 50mKLM
Deal found 6/16$611

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 June 16, 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

Thu 9/18

7:10 pm-4:30 pm

1 stop28h 20m

Chicago O'Hare Intl

Fri 9/26

6:00 pm-10:45 am

1 stop33h 45m

$369

VeniceChicago

VCE - ORD

VCEORD

Venice Marco Polo

Fri 9/5

12:10 pm-7:00 pm

1 stop13h 50m

Chicago O'Hare Intl

Fri 9/19

9:15 pm-11:10 pm

1 stop18h 55m

$556

NaplesChicago

NAP - ORD

NAPORD

Naples

Tue 10/7

11:40 am-7:00 pm

1 stop14h 20m

Chicago O'Hare Intl

Tue 10/14

3:45 pm-10:40 am

1 stop11h 55m

$574

NaplesChicago

NAP - ORD

NAPORD

Naples

Tue 10/7

12:00 pm-8:17 pm

1 stop15h 17m

Chicago O'Hare Intl

Tue 10/14

5:06 pm-6:10 pm

2 stops18h 04m

$589

NaplesChicago

NAP - ORD

NAPORD

Naples

Tue 10/7

3:00 pm-6:40 pm

Nonstop10h 40m

Chicago O'Hare Intl

Tue 10/14

7:00 am-10:00 am

1 stop20h 00m

$595

VeniceChicago

VCE - ORD

VCEORD

Venice Marco Polo

Sun 9/21

6:25 am-2:15 pm

1 stop14h 50m

Chicago O'Hare Intl

Sat 10/4

10:35 pm-8:40 pm

1 stop15h 05m

$603

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Sun 8/24

8:50 pm-11:55 am

1 stop22h 05m

Chicago O'Hare Intl

Tue 9/2

9:15 pm-11:45 pm

1 stop19h 30m

$604

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Thu 8/21

3:10 pm-9:15 pm

1 stop13h 05m

Chicago O'Hare Intl

Mon 9/1

10:15 pm-10:00 pm

1 stop16h 45m

$606

VeniceChicago

VCE - ORD

VCEORD

Venice Marco Polo

Sat 9/20

6:00 am-2:10 pm

1 stop15h 10m

Chicago O'Hare Intl

Fri 10/3

6:10 pm-5:20 pm

2 stops16h 10m

$607

MilanChicago

LIN - ORD

LINORD

Milan Linate

Thu 10/2

7:50 am-2:15 pm

1 stop13h 25m

Chicago O'Hare Intl

Wed 10/15

8:35 pm-3:05 pm

1 stop11h 30m

$608

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/15

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 June 16, 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.

Weekly flight availability from Italy to Chicago

Explore weekly flight availability from Italy to Chicago. 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 June 16, 2025.

The most flights from IT0 to CHI are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

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 June 16, 2025.
Peruse reviews from past customers who have flown with Emirates, Delta and Alaska Airlines 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
8.1
Very good
3,267 reviews

Crew

8.3

Comfort

8.0

Boarding

8.1

Entertainment

8.2

Overall

8.1

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
8.1
Very good
3,267 reviews
Emirates
8.1
Very good
3,267 reviews

Crew

8.3

Comfort

8.0

Boarding

8.1

Entertainment

8.2

Overall

8.1

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
7,963 reviews
Emirates
8.1
Very good
3,267 reviews

Crew

8.3

Comfort

8.0

Boarding

8.1

Entertainment

8.2

Overall

8.1

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.
Alaska Airlines
8.0
Very good
10,000 reviews
Emirates
8.1
Very good
3,267 reviews

Crew

8.3

Comfort

8.0

Boarding

8.1

Entertainment

8.2

Overall

8.1

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
1,361 reviews
Emirates
8.1
Very good
3,267 reviews

Crew

8.3

Comfort

8.0

Boarding

8.1

Entertainment

8.2

Overall

8.1

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
1,080 reviews
Emirates
8.1
Very good
3,267 reviews

Crew

8.3

Comfort

8.0

Boarding

8.1

Entertainment

8.2

Overall

8.1

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 $434. 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 Venice Marco Polo - 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 $382. On average you can expect to pay $746. The most popular route, (Milan Malpensa - Chicago O'Hare Intl), can usually be booked for $366.

  • 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
Lansing
Benton Harbor
Porter
Hammond
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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Top 7 airlines flying from Italy to Chicago

Discover the top 7 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 June 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
British AirwaysCheapest$525Average$728FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$536Average$828FlexibilityNo cancel feeOn-time71%
TAP AIR PORTUGALCheapest$537Average$564FlexibilityNo cancel feeOn-timeN/A
IberiaCheapest$550Average$711FlexibilityNo cancel feeOn-time77%
United AirlinesCheapest$611Average$824FlexibilityNo cancel feeOn-time69%
LufthansaCheapest$639Average$838FlexibilityNo cancel feeOn-time76%
ITA AirwaysCheapest$658Average$715FlexibilityNo cancel feeOn-time81%

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