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$305+ 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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
NAP — CHI
Oct 26 — Nov 21
Sun 10/26
Sun 11/2
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 September 26, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$469
(Mytrip)

One-way from

$305
(Kiwi.com)

Popular in

August

Cheapest in

February

Average price

$647

Good round-trip deal

$682 or less

Good one-way deal

$590 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 ($45 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 26, 2025.

This Mytrip deal was found by Cheapflights users on 9/25. 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 11/1512:05 pmVCE - ORD
1 stop33h 40mTAP AIR PORTUGAL
Fri 11/288:15 pmORD - VCE
1 stop13h 45mTAP AIR PORTUGAL
Deal found 9/25$469
This Vliegwinkel deal was found by Cheapflights users on 9/25. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1512:50 pmVCE - ORD
2 stops35h 30mMultiple Airlines
Fri 11/286:30 pmORD - VCE
2 stops16h 00mMultiple Airlines
Deal found 9/25$485
This Mytrip deal was found by Cheapflights users on 9/25. 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 11/1211:10 amBGY - ORD
1 stop13h 45mMultiple Airlines
Wed 11/197:40 pmORD - BGY
1 stop18h 20mMultiple Airlines
Deal found 9/25$532
This lol.travel deal was found by Cheapflights users on 9/25. 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 12/510:30 amVCE - ORD
1 stop16h 35mUnited Airlines
Mon 12/812:00 pmORD - VCE
1 stop13h 55mUnited Airlines
Deal found 9/25$535
This Ticket deal was found by Cheapflights users on 9/25. 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 Ticket is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1510:35 amVCE - ORD
2 stops15h 55mAir Canada
Fri 11/2810:38 amORD - VCE
2 stops16h 07mAir Canada
Deal found 9/25$553
This Netflights deal was found by Cheapflights users on 9/25. 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 Netflights is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/711:00 amFCO - ORD
1 stop16h 34mBritish Airways
Mon 2/26:45 pmORD - FCO
1 stop15h 10mBritish Airways
Deal found 9/25$557
This Kiwi.com deal was found by Cheapflights users on 9/25. 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.
Wed 11/57:10 pmFCO - ORD
1 stop24h 35mMultiple Airlines
Sun 11/96:40 amORD - FCO
1 stop24h 50mMultiple Airlines
Deal found 9/25$560
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/85:15 pmFCO - ORD
2 stops28h 30mMultiple Airlines
Sat 11/156:40 amORD - FCO
1 stop24h 50mMultiple Airlines
Deal found 9/24$561
This lol.travel deal was found by Cheapflights users on 9/24. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/139:45 amFCO - ORD
Nonstop10h 30mUnited Airlines
Mon 10/279:00 amORD - FCO
1 stop17h 30mUnited Airlines
Deal found 9/24$562
This FlightHub deal was found by Cheapflights users on 9/24. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2111:20 amVCE - ORD
1 stop12h 25mScandinavian Airlines
Sun 11/237:20 pmORD - VCE
1 stop32h 10mScandinavian Airlines
Deal found 9/24$562
This lol.travel deal was found by Cheapflights users on 9/25. 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.
Mon 12/11:30 pmFCO - ORD
1 stop28h 40mUnited Airlines
Mon 12/83:45 pmORD - FCO
Nonstop9h 00mUnited Airlines
Deal found 9/25$563
This lol.travel deal was found by Cheapflights users on 9/25. 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 10/169:45 amFCO - ORD
Nonstop10h 30mUnited Airlines
Wed 10/2910:50 pmORD - FCO
1 stop13h 25mUnited Airlines
Deal found 9/25$565

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 September 26, 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 11/15

8:25 pm-4:20 pm

1 stop26h 55m

Chicago O'Hare Intl

Fri 11/28

6:50 pm-2:10 pm

1 stop12h 20m

$570

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Mon 11/10

1:30 pm-8:05 pm

1 stop13h 35m

Chicago O'Hare Intl

Mon 11/17

3:45 pm-7:45 am

Nonstop9h 00m

$571

BergamoChicago

BGY - ORD

BGYORD

Bergamo Orio Al Serio

Mon 11/10

11:25 am-5:55 pm

1 stop13h 30m

Chicago O'Hare Intl

Mon 11/17

3:50 pm-11:20 am

1 stop12h 30m

$571

VeniceChicago

VCE - ORD

VCEORD

Venice Marco Polo

Fri 12/5

6:30 am-2:20 pm

1 stop14h 50m

Chicago O'Hare Intl

Mon 12/8

10:31 am-11:45 am

2 stops18h 14m

$574

VeniceChicago

VCE - ORD

VCEORD

Venice Marco Polo

Fri 12/5

6:30 am-2:20 pm

1 stop14h 50m

Chicago O'Hare Intl

Mon 12/8

5:20 pm-11:45 am

1 stop11h 25m

$574

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Fri 11/21

9:10 am-8:05 pm

1 stop17h 55m

Chicago O'Hare Intl

Sat 1/10

7:15 am-9:55 am

1 stop19h 40m

$575

VeniceChicago

VCE - ORD

VCEORD

Venice Marco Polo

Thu 2/19

6:55 am-1:50 pm

1 stop13h 55m

Chicago O'Hare Intl

Mon 2/23

8:45 pm-8:20 pm

1 stop16h 35m

$576

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Mon 2/2

7:05 am-3:20 pm

1 stop15h 15m

Chicago O'Hare Intl

Mon 2/9

11:15 am-7:55 am

2 stops13h 40m

$576

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Sun 11/23

10:25 am-5:45 pm

1 stop14h 20m

Chicago O'Hare Intl

Sun 1/11

8:45 pm-8:00 pm

1 stop16h 15m

$577

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Sat 11/22

10:25 am-5:45 pm

1 stop14h 20m

Chicago O'Hare Intl

Sat 1/10

9:45 pm-8:40 pm

1 stop15h 55m

$577

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/24

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 September 26, 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 September 26, 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).

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 September 26, 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
8,928 reviews

Food

6.6

Crew

8.1

Boarding

7.7

Overall

7.4

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
United Airlines
7.4
Good
8,928 reviews
United Airlines
7.4
Good
8,928 reviews

Food

6.6

Crew

8.1

Boarding

7.7

Overall

7.4

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,928 reviews

Food

6.6

Crew

8.1

Boarding

7.7

Overall

7.4

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
Lufthansa
6.8
Okay
7,428 reviews
United Airlines
7.4
Good
8,928 reviews

Food

6.6

Crew

8.1

Boarding

7.7

Overall

7.4

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
ITA Airways
6.7
Okay
1,048 reviews
United Airlines
7.4
Good
8,928 reviews

Food

6.6

Crew

8.1

Boarding

7.7

Overall

7.4

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
British Airways
6.7
Okay
7,399 reviews
United Airlines
7.4
Good
8,928 reviews

Food

6.6

Crew

8.1

Boarding

7.7

Overall

7.4

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.

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 13h 35m. Fly via SWISS, Lufthansa, or Delta 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 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 $361. However, be on the lookout for offers from Aer Lingus and British Airways, 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 Milan Linate - 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 $562. On average you can expect to pay $1,083. The most popular route, (Rome Fiumicino - Chicago O'Hare Intl), can usually be booked for $435.

  • 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
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 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 September 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
British AirwaysCheapest$525Average$709FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$536Average$768FlexibilityNo cancel feeOn-time71%
IberiaCheapest$550Average$772FlexibilityNo cancel feeOn-time77%
United AirlinesCheapest$585Average$823FlexibilityNo cancel feeOn-time69%
ITA AirwaysCheapest$658Average$715FlexibilityNo cancel feeOn-time81%

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