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$294+ 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 2/10. Fares are subject to change and may not be available on all flights or dates of travel.
NAP — CHI
Dec 10 — Dec 171
Wed 12/10
Wed 12/17
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 November 10, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$469
(oojo)

One-way from

$294
(Kiwi.com)

Popular in

August

Cheapest in

February

Average price

$703

Good round-trip deal

$707 or less

Good one-way deal

$450 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. 4% potential increase in price ($35 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 10, 2025.

This oojo deal was found by Cheapflights users on 11/9. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/412:05 pmVCE - ORD
1 stop34h 20mTAP AIR PORTUGAL
Sun 12/78:25 pmORD - VCE
1 stop13h 35mTAP AIR PORTUGAL
Deal found 11/9$469
This lol.travel deal was found by Cheapflights users on 11/8. 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.
Sat 11/225:50 pmVCE - ORD
1 stop27h 55mTAP AIR PORTUGAL
Fri 12/58:15 pmORD - VCE
1 stop13h 45mTAP AIR PORTUGAL
Deal found 11/8$483
This Mytrip deal was found by Cheapflights users on 11/10. 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.
Thu 12/45:45 amBGY - ORD
2 stops18h 35mMultiple Airlines
Wed 12/106:30 pmORD - BGY
2 stops19h 30mMultiple Airlines
Deal found 11/10$552
This Mytrip deal was found by Cheapflights users on 11/10. 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.
Wed 11/2611:10 amBGY - ORD
1 stop13h 45mMultiple Airlines
Sun 11/303:50 pmORD - BGY
1 stop12h 10mMultiple Airlines
Deal found 11/10$579
This Kiwi.com deal was found by Cheapflights users on 11/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/227:10 pmFCO - ORD
1 stop24h 46mMultiple Airlines
Sat 1/1712:05 pmORD - FCO
2 stops28h 25mMultiple Airlines
Deal found 11/8$583
This Cheapflightsfares deal was found by Cheapflights users on 11/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/176:00 amFCO - ORD
1 stop16h 00mTAP AIR PORTUGAL
Fri 1/168:15 pmORD - FCO
1 stop12h 35mTAP AIR PORTUGAL
Deal found 11/8$584
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 12/117:10 pmFCO - ORD
1 stop26h 47mMultiple Airlines
Mon 4/135:51 pmORD - FCO
1 stop13h 39mMultiple Airlines
Deal found 11/9$585
This lol.travel deal was found by Cheapflights users on 11/9. 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 12/58:00 pmMXP - ORD
1 stop27h 45mScandinavian Airlines
Mon 12/87:20 pmORD - MXP
1 stop32h 05mScandinavian Airlines
Deal found 11/9$586
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 12/147:10 pmFCO - ORD
1 stop34h 01mMultiple Airlines
Mon 4/135:51 pmORD - FCO
1 stop13h 39mMultiple Airlines
Deal found 11/9$587
This Kiwi.com deal was found by Cheapflights users on 11/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/187:10 pmFCO - ORD
1 stop24h 35mMultiple Airlines
Sat 1/1712:05 pmORD - FCO
2 stops28h 25mMultiple Airlines
Deal found 11/8$588
This Mytrip deal was found by Cheapflights users on 11/8. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/119:00 pmMXP - ORD
2 stops25h 25mMultiple Airlines
Wed 1/76:30 pmORD - MXP
2 stops14h 45mMultiple Airlines
Deal found 11/8$589
This Kiwi.com deal was found by Cheapflights users on 11/9. 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.
Fri 12/127:10 pmFCO - ORD
2 stops31h 51mMultiple Airlines
Mon 4/135:51 pmORD - FCO
1 stop13h 39mMultiple Airlines
Deal found 11/9$590

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 November 10, 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 12/4

12:05 pm-3:25 pm

1 stop34h 20m

Chicago O'Hare Intl

Sun 12/7

8:25 pm-5:00 pm

1 stop13h 35m

$469

VeniceChicago

VCE - ORD

VCEORD

Venice Marco Polo

Sat 11/22

5:50 pm-2:45 pm

1 stop27h 55m

Chicago O'Hare Intl

Fri 12/5

8:15 pm-5:00 pm

1 stop13h 45m

$483

BergamoChicago

BGY - ORD

BGYORD

Bergamo Orio Al Serio

Thu 12/4

5:45 am-5:20 pm

2 stops18h 35m

Chicago O'Hare Intl

Wed 12/10

6:30 pm-9:00 pm

2 stops19h 30m

$552

BergamoChicago

BGY - ORD

BGYORD

Bergamo Orio Al Serio

Wed 11/26

11:10 am-5:55 pm

1 stop13h 45m

Chicago O'Hare Intl

Sun 11/30

3:50 pm-11:00 am

1 stop12h 10m

$579

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Mon 2/2

11:25 am-5:20 pm

1 stop12h 55m

Chicago O'Hare Intl

Thu 2/12

6:30 pm-2:00 pm

1 stop12h 30m

$593

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Thu 12/11

11:55 am-4:45 pm

1 stop35h 50m

Chicago O'Hare Intl

Fri 4/17

7:15 pm-8:40 am

1 stop30h 25m

$597

VeniceChicago

VCE - ORD

VCEORD

Venice Marco Polo

Thu 12/4

7:15 pm-8:23 pm

2 stops32h 08m

Chicago O'Hare Intl

Sun 12/7

9:19 am-10:30 am

2 stops18h 11m

$597

MilanChicago

LIN - ORD

LINORD

Milan Linate

Sun 3/29

7:00 am-1:10 pm

1 stop13h 10m

Chicago O'Hare Intl

Sun 4/5

3:00 pm-10:10 am

1 stop12h 10m

$597

VeniceChicago

VCE - ORD

VCEORD

Venice Marco Polo

Fri 12/5

5:45 am-5:20 pm

2 stops18h 35m

Chicago O'Hare Intl

Mon 12/8

6:30 pm-11:30 am

3 stops34h 00m

$612

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Fri 4/17

12:15 pm-4:10 pm

2 stops34h 55m

Chicago O'Hare Intl

Fri 4/24

7:15 pm-1:05 pm

2 stops34h 50m

$614

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/9

Showing 1-10 of 60 results
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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, February is the cheapest month in which you can book a flight from Italy to Chicago (average of $257). Flying from Italy to Chicago in December is currently the most expensive (average of $567). 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 November 10, 2025.

When flying from Italy to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 19% versus a flight in the afternoon.

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 November 10, 2025.
Read reviews from past customers who have flown United Airlines, American 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
9,012 reviews

Crew

8.1

Entertainment

7.1

Overall

7.4

Comfort

7.3

Boarding

7.7

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
9,012 reviews
United Airlines
7.4
Good
9,012 reviews

Crew

8.1

Entertainment

7.1

Overall

7.4

Comfort

7.3

Boarding

7.7

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
American Airlines
7.2
Good
11,045 reviews
United Airlines
7.4
Good
9,012 reviews

Crew

8.1

Entertainment

7.1

Overall

7.4

Comfort

7.3

Boarding

7.7

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
Lufthansa
6.8
Okay
7,565 reviews
United Airlines
7.4
Good
9,012 reviews

Crew

8.1

Entertainment

7.1

Overall

7.4

Comfort

7.3

Boarding

7.7

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
ITA Airways
6.7
Okay
1,082 reviews
United Airlines
7.4
Good
9,012 reviews

Crew

8.1

Entertainment

7.1

Overall

7.4

Comfort

7.3

Boarding

7.7

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
British Airways
6.7
Okay
7,510 reviews
United Airlines
7.4
Good
9,012 reviews

Crew

8.1

Entertainment

7.1

Overall

7.4

Comfort

7.3

Boarding

7.7

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

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 12h 55m. Fly via TAP AIR PORTUGAL, Icelandair, or Scandinavian Airlines to get the fastest option. The distance between Italy and Chicago is about 4808 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the most popular routes from Italy to Chicago?

    While some choose either Milan Malpensa - Chicago O'Hare Intl or Venice Marco Polo - Chicago O'Hare Intl, 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 $417. On average you can expect to pay $706. The most popular route, (Rome Fiumicino - Chicago O'Hare Intl), can usually be booked for $533.

  • 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, February is the cheapest month in which you can book a flight from Italy to Chicago (average of $257). Flying from Italy to Chicago in December is currently the most expensive (average of $567). 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
Hammond
Porter
Benton Harbor
Merrillville

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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.
Frankfurt to O'Hare Intl flights
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Frederic Chopin to Midway flights
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Orly to O'Hare Intl flights
Vienna to O'Hare Intl flights
Gatwick to O'Hare Intl flights
Charles de Gaulle to Midway flights
Heathrow to Midway flights
London City to O'Hare Intl flights
Krakow to O'Hare Intl flights
Barcelona-El Prat to O'Hare Intl flights
Leonardo da Vinci/Fiumicino to O'Hare Intl flights
Frankfurt-Hahn to O'Hare Intl flights
Bruxelles-National to O'Hare Intl flights
Athens to O'Hare Intl flights
Modlin to O'Hare Intl flights
Dublin to O'Hare Intl flights
Stansted to O'Hare Intl flights
Luton to O'Hare Intl flights
Malpensa to O'Hare Intl flights
Amsterdam to O'Hare Intl flights
Madrid to Midway flights
Istanbul to O'Hare Intl flights
Skopje to O'Hare Intl flights
Barcelona-El Prat to Midway flights
Berlin to O'Hare Intl flights
Copenhagen to O'Hare Intl flights
Beauvais-Tille to O'Hare Intl flights
Sofia to O'Hare Intl flights
Belgrade to O'Hare Intl flights
Munich to Midway flights
Hamburg to O'Hare Intl flights
Frankfurt to St. Louis flights
Oslo Gardermoen to O'Hare Intl flights
Linate to O'Hare Intl flights
Vicenza to O'Hare Intl flights
Ciampino to O'Hare Intl flights
Duesseldorf Intl to O'Hare Intl flights

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 November 10, 2025.
AirlineCheapestAverageFlexibilityOn-time
British AirwaysCheapest$525Average$725FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$536Average$768FlexibilityNo cancel feeOn-time71%
IberiaCheapest$550Average$726FlexibilityNo cancel feeOn-time77%
United AirlinesCheapest$585Average$862FlexibilityNo cancel feeOn-time69%
SWISSCheapest$600Average$942FlexibilityNo cancel feeOn-time79%

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