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$242+ 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 5/13. Fares are subject to change and may not be available on all flights or dates of travel.
NAP — CHI
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Cheap 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 December 23, 2025.

This lol.travel deal was found by Cheapflights users on 12/21. 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.
Wed 12/246:20 amMXP - ORD
1 stop15h 40mTAP AIR PORTUGAL
Wed 12/317:10 pmORD - MXP
1 stop14h 45mTAP AIR PORTUGAL
Deal found 12/21$716
This oojo deal was found by Cheapflights users on 12/22. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/237:35 pmFCO - ORD
1 stop31h 25mLOT
Thu 1/19:55 pmORD - FCO
1 stop29h 55mLOT
Deal found 12/22$774
This Kiwi.com deal was found by Cheapflights users on 12/21. 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 12/246:20 amMXP - ORD
1 stop15h 40mMultiple Airlines
Wed 12/316:30 pmORD - MXP
2 stops18h 00mMultiple Airlines
Deal found 12/21$776
This lol.travel deal was found by Cheapflights users on 12/20. 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.
Tue 12/235:45 pmMXP - ORD
1 stop28h 15mTAP AIR PORTUGAL
Sun 12/288:25 pmORD - MXP
1 stop20h 10mTAP AIR PORTUGAL
Deal found 12/20$786
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/314:55 pmVCE - ORD
1 stop28h 15mLufthansa
Mon 1/56:00 pmORD - VCE
1 stop11h 20mLufthansa
Deal found 12/22$809
This Gotogate deal was found by Cheapflights users on 12/22. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/268:00 pmMXP - ORD
1 stop27h 45mScandinavian Airlines
Mon 1/267:20 pmORD - MXP
1 stop32h 05mScandinavian Airlines
Deal found 12/22$811
This United Airlines deal was found by Cheapflights users on 12/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/319:45 amMXP - ORD
2 stops33h 01mUnited Airlines
Tue 1/66:00 pmORD - MXP
2 stops30h 30mUnited Airlines
Deal found 12/22$821
This lol.travel deal was found by Cheapflights users on 12/20. 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 12/266:20 amMXP - ORD
1 stop16h 05mTAP AIR PORTUGAL
Sun 12/288:25 pmORD - MXP
1 stop20h 10mTAP AIR PORTUGAL
Deal found 12/20$823
This FlightHub deal was found by Cheapflights users on 12/21. 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 12/314:55 pmVCE - ORD
1 stop28h 15mLufthansa
Sun 1/46:00 pmORD - VCE
1 stop15h 15mLufthansa
Deal found 12/21$847
This United Airlines deal was found by Cheapflights users on 12/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/311:20 pmBLQ - ORD
1 stop31h 50mUnited Airlines
Mon 1/53:20 pmORD - BLQ
1 stop11h 10mUnited Airlines
Deal found 12/22$852
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/266:00 amFCO - ORD
1 stop16h 25mMultiple Airlines
Sun 12/2810:35 pmORD - FCO
1 stop17h 15mMultiple Airlines
Deal found 12/22$867
This Gotogate deal was found by Cheapflights users on 12/21. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/226:45 amFCO - ORD
1 stop34h 20mTurkish Airlines
Wed 1/711:50 amORD - FCO
1 stop15h 00mTurkish Airlines
Deal found 12/21$878

Find flight deals from Italy to Chicago

Keep the following information in mind while searching for Italy to Chicago flight deals. Data was last updated December 23, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$452
(lol.travel)

One-way from

$242
(Kiwi.com)

Popular in

August

Cheapest in

April

Average price

$691

Good round-trip deal

$697 or less

Good one-way deal

$512 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. 4% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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

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 December 23, 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

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Tue 2/17

4:40 pm-3:00 pm

1 stop29h 20m

Chicago O'Hare Intl

Wed 3/4

7:10 pm-12:05 am

1 stop21h 55m

$538

BolognaChicago

BLQ - ORD

BLQORD

Bologna Guglielmo Marconi

Thu 2/5

8:00 pm-4:45 pm

1 stop27h 45m

Chicago O'Hare Intl

Sat 2/14

7:20 pm-7:20 pm

1 stop17h 00m

$563

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Mon 1/26

11:25 am-5:20 pm

1 stop12h 55m

Chicago O'Hare Intl

Thu 2/5

6:30 pm-2:00 pm

1 stop12h 30m

$573

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Sun 2/1

11:15 am-4:55 pm

1 stop12h 40m

Chicago O'Hare Intl

Sat 2/7

7:20 pm-7:10 pm

1 stop16h 50m

$586

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Thu 2/19

11:15 am-4:45 pm

1 stop12h 30m

Chicago O'Hare Intl

Sun 2/22

7:10 pm-7:10 pm

1 stop17h 00m

$586

VeniceChicago

VCE - ORD

VCEORD

Venice Marco Polo

Sat 1/17

10:50 am-5:00 pm

1 stop13h 10m

Chicago O'Hare Intl

Fri 1/30

4:14 pm-4:55 pm

2 stops17h 41m

$587

VeniceChicago

VCE - ORD

VCEORD

Venice Marco Polo

Wed 3/11

6:55 am-4:25 pm

1 stop15h 30m

Chicago O'Hare Intl

Mon 3/23

9:45 pm-4:50 pm

1 stop13h 05m

$587

BolognaChicago

BLQ - ORD

BLQORD

Bologna Guglielmo Marconi

Thu 2/12

8:00 pm-4:45 pm

1 stop27h 45m

Chicago O'Hare Intl

Mon 2/16

7:20 pm-7:20 pm

1 stop17h 00m

$594

BolognaChicago

BLQ - ORD

BLQORD

Bologna Guglielmo Marconi

Wed 2/18

7:20 am-7:42 pm

2 stops19h 22m

Chicago O'Hare Intl

Wed 2/25

9:45 pm-10:50 pm

1 stop18h 05m

$595

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Mon 2/2

9:15 am-4:45 pm

1 stop14h 30m

Chicago O'Hare Intl

Fri 2/6

7:20 pm-7:10 pm

1 stop16h 50m

$598

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

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, September is the cheapest month in which you can book a flight from Italy to Chicago (average of $409). Flying from Italy to Chicago in December is currently the most expensive (average of $578). 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 December 23, 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 20% versus a flight in the afternoon.

How often are flights from Italy to Chicago delayed?

About 18% of weekly flights between Italy and Chicago have experienced delays in the past year, with the average delay time being 184 minutes.

What is the most punctual flight time for Italy to Chicago flights?

Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Thursday tends to have the lowest number of delays on this route, whereas Monday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Italy to Chicago flights?

Over the last year, Ethiopian Air have had the lowest number of delays on this route, with just 11% of flights being delayed.

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 December 23, 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
9,107 reviews

Comfort

7.3

Overall

7.4

Crew

8.1

Entertainment

7.1

Food

6.6

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
United Airlines
7.4
Good
9,107 reviews
United Airlines
7.4
Good
9,107 reviews

Comfort

7.3

Overall

7.4

Crew

8.1

Entertainment

7.1

Food

6.6

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
American Airlines
7.2
Good
11,050 reviews
United Airlines
7.4
Good
9,107 reviews

Comfort

7.3

Overall

7.4

Crew

8.1

Entertainment

7.1

Food

6.6

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
Lufthansa
6.8
Okay
7,649 reviews
United Airlines
7.4
Good
9,107 reviews

Comfort

7.3

Overall

7.4

Crew

8.1

Entertainment

7.1

Food

6.6

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
ITA Airways
6.7
Okay
1,112 reviews
United Airlines
7.4
Good
9,107 reviews

Comfort

7.3

Overall

7.4

Crew

8.1

Entertainment

7.1

Food

6.6

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
British Airways
6.7
Okay
7,607 reviews
United Airlines
7.4
Good
9,107 reviews

Comfort

7.3

Overall

7.4

Crew

8.1

Entertainment

7.1

Food

6.6

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.

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, Scandinavian Airlines, or Icelandair 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 Delta, with whom users have recently found tickets for as low as $113. However, be on the lookout for offers from American Airlines and Southwest, 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 Linate - Chicago Midway or Bergamo Orio Al Serio - 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 $459. On average you can expect to pay $667. The most popular route, (Milan Malpensa - Chicago O'Hare Intl), can usually be booked for $496.

  • 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, September is the cheapest month in which you can book a flight from Italy to Chicago (average of $409). Flying from Italy to Chicago in December is currently the most expensive (average of $578). 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
Merrillville
Hammond
Porter
Benton Harbor

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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 December 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
British AirwaysCheapest$525Average$736FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$536Average$768FlexibilityNo cancel feeOn-time71%
IberiaCheapest$550Average$726FlexibilityNo cancel feeOn-time77%
United AirlinesCheapest$585Average$821FlexibilityNo cancel feeOn-time69%
LufthansaCheapest$690Average$710FlexibilityNo cancel feeOn-time76%

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