HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$314+ 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 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
NAP — CHI
Aug 16 — Aug 231
Sat 8/16
Sat 8/23
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 August 11, 2025.

Round-trip from

$486
(Flightnetwork)

One-way from

$314
(Trip.com)

Popular in

August

Cheapest in

February

Average price

$802

Good round-trip deal

$633 or less

Good one-way deal

$692 or less
From Italy to Chicago (CHI)
Search Deals
One-way flight from Italy to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($39 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 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 August 11, 2025.

This Flightnetwork deal was found by Cheapflights users on 8/9. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/117:10 pmVCE - ORD
1 stop28h 00mTAP AIR PORTUGAL
Sat 9/276:15 pmORD - VCE
1 stop33h 30mTAP AIR PORTUGAL
Deal found 8/9$486
This SWISS deal was found by Cheapflights users on 8/9. 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 SWISS is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/129:35 amNAP - ORD
1 stop13h 20mSWISS
Sun 9/217:05 pmORD - NAP
1 stop30h 40mSWISS
Deal found 8/9$508
This Mytrip deal was found by Cheapflights users on 8/10. 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 9/42:50 pmNAP - ORD
1 stop32h 05mSWISS
Mon 9/87:05 pmORD - NAP
1 stop30h 40mSWISS
Deal found 8/10$527
This Mytrip deal was found by Cheapflights users on 8/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1810:15 amBGY - ORD
2 stops18h 00mMultiple Airlines
Thu 9/257:25 pmORD - BGY
2 stops20h 15mMultiple Airlines
Deal found 8/9$531
This lol.travel deal was found by Cheapflights users on 8/11. 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 9/1011:35 amNAP - ORD
1 stop15h 36mUnited Airlines
Wed 9/171:12 pmORD - NAP
1 stop15h 28mUnited Airlines
Deal found 8/11$534
This lol.travel deal was found by Cheapflights users on 8/10. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/29:45 amNAP - ORD
1 stop15h 49mUnited Airlines
Mon 10/64:00 pmORD - NAP
1 stop12h 40mUnited Airlines
Deal found 8/10$536
This lol.travel deal was found by Cheapflights users on 8/11. 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 9/259:45 amNAP - ORD
1 stop15h 49mUnited Airlines
Thu 10/210:40 amORD - NAP
1 stop13h 20mUnited Airlines
Deal found 8/11$539
This lol.travel deal was found by Cheapflights users on 8/11. 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 8/279:45 amNAP - ORD
1 stop15h 24mUnited Airlines
Sun 8/317:35 pmORD - NAP
1 stop33h 05mUnited Airlines
Deal found 8/11$540
This lol.travel deal was found by Cheapflights users on 8/10. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/411:35 amNAP - ORD
1 stop15h 36mAir Canada
Mon 9/86:06 pmORD - NAP
2 stops32h 34mAir Canada
Deal found 8/10$548
This American Airlines deal was found by Cheapflights users on 8/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/23:00 pmNAP - ORD
Nonstop10h 50mAmerican Airlines
Mon 10/64:55 pmORD - NAP
1 stop12h 05mAmerican Airlines
Deal found 8/10$553
This lol.travel deal was found by Cheapflights users on 8/9. 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.
Thu 9/1110:55 amVCE - ORD
1 stop16h 00mUnited Airlines
Sat 9/278:45 amORD - VCE
2 stops17h 20mUnited Airlines
Deal found 8/9$556
This United Airlines deal was found by Cheapflights users on 8/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/236:40 amNAP - ORD
2 stops20h 31mUnited Airlines
Tue 9/3012:50 pmORD - NAP
2 stops15h 50mUnited Airlines
Deal found 8/9$558

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 August 11, 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 9/11

7:10 pm-4:10 pm

1 stop28h 00m

Chicago O'Hare Intl

Sat 9/27

6:15 pm-10:45 am

1 stop33h 30m

$486

NaplesChicago

NAP - ORD

NAPORD

Naples

Fri 9/12

9:35 am-3:55 pm

1 stop13h 20m

Chicago O'Hare Intl

Sun 9/21

7:05 pm-8:45 am

1 stop30h 40m

$508

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 9/4

2:50 pm-3:55 pm

1 stop32h 05m

Chicago O'Hare Intl

Mon 9/8

7:05 pm-8:45 am

1 stop30h 40m

$527

BergamoChicago

BGY - ORD

BGYORD

Bergamo Orio Al Serio

Thu 9/18

10:15 am-9:15 pm

2 stops18h 00m

Chicago O'Hare Intl

Thu 9/25

7:25 pm-10:40 pm

2 stops20h 15m

$531

NaplesChicago

NAP - ORD

NAPORD

Naples

Wed 9/10

11:35 am-8:11 pm

1 stop15h 36m

Chicago O'Hare Intl

Wed 9/17

1:12 pm-11:40 am

1 stop15h 28m

$534

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 10/2

9:45 am-6:34 pm

1 stop15h 49m

Chicago O'Hare Intl

Mon 10/6

4:00 pm-11:40 am

1 stop12h 40m

$536

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 9/25

9:45 am-6:34 pm

1 stop15h 49m

Chicago O'Hare Intl

Thu 10/2

10:40 am-7:00 am

1 stop13h 20m

$539

NaplesChicago

NAP - ORD

NAPORD

Naples

Wed 8/27

9:45 am-6:09 pm

1 stop15h 24m

Chicago O'Hare Intl

Sun 8/31

7:35 pm-11:40 am

1 stop33h 05m

$540

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 9/4

11:35 am-8:11 pm

1 stop15h 36m

Chicago O'Hare Intl

Mon 9/8

6:06 pm-9:40 am

2 stops32h 34m

$548

NaplesChicago

NAP - ORD

NAPORD

Naples

Thu 10/2

3:00 pm-6:50 pm

Nonstop10h 50m

Chicago O'Hare Intl

Mon 10/6

4:55 pm-12:00 pm

1 stop12h 05m

$553

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/10

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 August 11, 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 August 11, 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 August 11, 2025.
Read reviews from past customers who have flown Emirates, Delta, and KLM 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.
Emirates
8.1
Very good
3,314 reviews

Comfort

8.0

Crew

8.3

Entertainment

8.2

Overall

8.1

Food

7.9

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jun 2025

ATH - EWR

Best flight I taken. Airline stewards were very attentive and creative a very comfortable environment. Food was plentiful, gave a variety for each meal and delicious.
Emirates
8.1
Very good
3,314 reviews
Emirates
8.1
Very good
3,314 reviews

Comfort

8.0

Crew

8.3

Entertainment

8.2

Overall

8.1

Food

7.9

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jun 2025

ATH - EWR

Best flight I taken. Airline stewards were very attentive and creative a very comfortable environment. Food was plentiful, gave a variety for each meal and delicious.
Delta
8.0
Very good
7,978 reviews
Emirates
8.1
Very good
3,314 reviews

Comfort

8.0

Crew

8.3

Entertainment

8.2

Overall

8.1

Food

7.9

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jun 2025

ATH - EWR

Best flight I taken. Airline stewards were very attentive and creative a very comfortable environment. Food was plentiful, gave a variety for each meal and delicious.
KLM
7.8
Good
1,381 reviews
Emirates
8.1
Very good
3,314 reviews

Comfort

8.0

Crew

8.3

Entertainment

8.2

Overall

8.1

Food

7.9

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jun 2025

ATH - EWR

Best flight I taken. Airline stewards were very attentive and creative a very comfortable environment. Food was plentiful, gave a variety for each meal and delicious.
Austrian Airlines
7.6
Good
825 reviews
Emirates
8.1
Very good
3,314 reviews

Comfort

8.0

Crew

8.3

Entertainment

8.2

Overall

8.1

Food

7.9

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jun 2025

ATH - EWR

Best flight I taken. Airline stewards were very attentive and creative a very comfortable environment. Food was plentiful, gave a variety for each meal and delicious.
Finnair
7.6
Good
1,321 reviews
Emirates
8.1
Very good
3,314 reviews

Comfort

8.0

Crew

8.3

Entertainment

8.2

Overall

8.1

Food

7.9

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jun 2025

ATH - EWR

Best flight I taken. Airline stewards were very attentive and creative a very comfortable environment. Food was plentiful, gave a variety for each meal and delicious.

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 most popular routes from Italy to Chicago?

    While some choose either Milan Linate - Chicago O'Hare Intl 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 $538. On average you can expect to pay $748. The most popular route, (Milan Malpensa - Chicago O'Hare Intl), can usually be booked for $450.

  • 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
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
Frederic Chopin to O'Hare Intl flights
Madrid to O'Hare Intl flights
Munich to O'Hare Intl flights
Frederic Chopin to Midway flights
Orly to O'Hare Intl flights
Malpensa to O'Hare Intl flights
Gatwick to O'Hare Intl flights
London City to O'Hare Intl flights
Heathrow to Midway flights
Barcelona-El Prat to O'Hare Intl flights
Dublin to O'Hare Intl flights
Athens to O'Hare Intl flights
Zurich to O'Hare Intl flights
Charles de Gaulle to Midway flights
Madrid to Midway flights
Vienna to O'Hare Intl flights
Beauvais-Tille to O'Hare Intl flights
Krakow to O'Hare Intl flights
Bruxelles-National to O'Hare Intl flights
Istanbul to O'Hare Intl flights
Bergamo to O'Hare Intl flights
Frankfurt-Hahn to O'Hare Intl flights
Leonardo da Vinci/Fiumicino to O'Hare Intl flights
Linate to O'Hare Intl flights
Vilnius to O'Hare Intl flights
Modlin to O'Hare Intl flights
Barcelona-El Prat to Midway flights
Luton to O'Hare Intl flights
Vicenza to O'Hare Intl flights
Munich to Midway flights
Berlin to O'Hare Intl flights
Stansted to O'Hare Intl flights
Amsterdam to O'Hare Intl flights
Sofia to O'Hare Intl flights
Manchester to O'Hare Intl flights
Duesseldorf Intl to O'Hare Intl flights
Oslo Gardermoen to O'Hare Intl flights
Bruxelles-National to Midway flights
Duesseldorf Intl to Midway flights

Top 6 airlines flying from Italy to Chicago

Discover the top 6 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 August 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
British AirwaysCheapest$525Average$693FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$536Average$775FlexibilityNo cancel feeOn-time71%
IberiaCheapest$550Average$772FlexibilityNo cancel feeOn-time77%
United AirlinesCheapest$611Average$823FlexibilityNo cancel feeOn-time69%
LufthansaCheapest$639Average$795FlexibilityNo cancel feeOn-time76%
ITA AirwaysCheapest$658Average$715FlexibilityNo cancel feeOn-time81%

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.