HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$235+ 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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
NAP — CHI
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
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 March 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$497
(Gotogate)

One-way from

$235
(Kiwi.com)

Popular in

August

Cheapest in

February

Average price

$709

Good round-trip deal

$661 or less

Good one-way deal

$685 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. 7% potential increase in price ($57 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 28, 2025.

This Gotogate deal was found by Cheapflights users on 3/27. 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.
Thu 5/1510:50 amVCE - ORD
1 stop12h 20mScandinavian Airlines
Sat 5/317:15 pmORD - VCE
1 stop16h 50mScandinavian Airlines
Deal found 3/27$497
This Flysmarter deal was found by Cheapflights users on 3/27. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/59:50 amVCE - ORD
1 stop15h 00mMultiple Airlines
Mon 5/128:30 pmORD - VCE
1 stop18h 45mMultiple Airlines
Deal found 3/27$501
This British Airways deal was found by Cheapflights users on 3/27. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/208:05 amVCE - ORD
1 stop13h 45mBritish Airways
Sun 9/288:40 pmORD - VCE
1 stop12h 35mBritish Airways
Deal found 3/27$517
This American Airlines deal was found by Cheapflights users on 3/27. 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.
Sun 9/216:25 amVCE - ORD
1 stop14h 50mAmerican Airlines
Fri 10/310:35 pmORD - VCE
1 stop15h 00mAmerican Airlines
Deal found 3/27$518
This Iberia deal was found by Cheapflights users on 3/26. 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/211:10 amMXP - ORD
1 stop13h 23mMultiple Airlines
Wed 4/94:55 pmORD - MXP
1 stop23h 45mMultiple Airlines
Deal found 3/26$521
This British Airways deal was found by Cheapflights users on 3/27. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1811:05 amLIN - ORD
1 stop12h 55mBritish Airways
Sun 9/2110:35 pmORD - LIN
1 stop11h 40mBritish Airways
Deal found 3/27$522
This American Airlines deal was found by Cheapflights users on 3/26. 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.
Sun 9/2110:25 amMXP - ORD
1 stop14h 50mAmerican Airlines
Sat 9/2710:35 pmORD - MXP
1 stop14h 25mAmerican Airlines
Deal found 3/26$522
This British Airways deal was found by Cheapflights users on 3/27. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/177:50 amLIN - ORD
1 stop13h 25mMultiple Airlines
Sun 9/2110:35 pmORD - LIN
1 stop11h 40mMultiple Airlines
Deal found 3/27$523
This Priceline deal was found by Cheapflights users on 3/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/158:25 amMXP - ORD
1 stop12h 25mBritish Airways
Tue 4/2210:20 pmORD - MXP
1 stop14h 45mBritish Airways
Deal found 3/26$528
This Booking.com deal was found by Cheapflights users on 3/27. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/223:10 pmMXP - ORD
1 stop13h 05mIcelandair
Wed 5/287:25 pmORD - MXP
1 stop11h 45mIcelandair
Deal found 3/27$530
This oojo deal was found by Cheapflights users on 3/27. 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 5/88:45 pmMXP - ORD
2 stops26h 25mScandinavian Airlines
Mon 5/127:15 pmORD - MXP
2 stops17h 40mScandinavian Airlines
Deal found 3/27$533
This Booking.com deal was found by Cheapflights users on 3/26. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/177:40 pmMXP - ORD
1 stop26h 30mLOT
Fri 9/269:40 pmORD - MXP
1 stop14h 15mLOT
Deal found 3/26$535

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 March 28, 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 5/15

10:50 am-4:10 pm

1 stop12h 20m

Chicago O'Hare Intl

Sat 5/31

7:15 pm-7:05 pm

1 stop16h 50m

$497

VeniceChicago

VCE - ORD

VCEORD

Venice Marco Polo

Mon 5/5

9:50 am-5:50 pm

1 stop15h 00m

Chicago O'Hare Intl

Mon 5/12

8:30 pm-10:15 pm

1 stop18h 45m

$501

VeniceChicago

VCE - ORD

VCEORD

Venice Marco Polo

Sat 9/20

8:05 am-2:50 pm

1 stop13h 45m

Chicago O'Hare Intl

Sun 9/28

8:40 pm-4:15 pm

1 stop12h 35m

$517

VeniceChicago

VCE - ORD

VCEORD

Venice Marco Polo

Sun 9/21

6:25 am-2:15 pm

1 stop14h 50m

Chicago O'Hare Intl

Fri 10/3

10:35 pm-8:35 pm

1 stop15h 00m

$518

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Wed 4/9

11:10 am-5:39 pm

1 stop13h 29m

Chicago O'Hare Intl

Wed 4/16

4:55 pm-11:40 pm

1 stop23h 45m

$521

MilanChicago

LIN - ORD

LINORD

Milan Linate

Thu 9/18

11:05 am-5:00 pm

1 stop12h 55m

Chicago O'Hare Intl

Sun 9/21

10:35 pm-5:15 pm

1 stop11h 40m

$522

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Sun 9/21

10:25 am-6:15 pm

1 stop14h 50m

Chicago O'Hare Intl

Sat 9/27

10:35 pm-8:00 pm

1 stop14h 25m

$522

MilanChicago

LIN - ORD

LINORD

Milan Linate

Wed 9/17

7:50 am-2:15 pm

1 stop13h 25m

Chicago O'Hare Intl

Sun 9/21

10:35 pm-5:15 pm

1 stop11h 40m

$523

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Tue 4/15

8:25 am-1:50 pm

1 stop12h 25m

Chicago O'Hare Intl

Tue 4/22

10:20 pm-8:05 pm

1 stop14h 45m

$528

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Thu 5/22

3:10 pm-9:15 pm

1 stop13h 05m

Chicago O'Hare Intl

Wed 5/28

7:25 pm-2:10 pm

1 stop11h 45m

$530

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/27

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 $323). 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 March 28, 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.

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 March 28, 2025.
Peruse reviews from past customers who have flown with Delta, Emirates and KLM 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.
Delta
8.0
Very good
7,896 reviews

Crew

8.5

Food

7.3

Overall

8.0

Entertainment

7.9

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,896 reviews
Delta
8.0
Very good
7,896 reviews

Crew

8.5

Food

7.3

Overall

8.0

Entertainment

7.9

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Emirates
8.0
Very good
3,190 reviews
Delta
8.0
Very good
7,896 reviews

Crew

8.5

Food

7.3

Overall

8.0

Entertainment

7.9

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
KLM
7.8
Good
1,321 reviews
Delta
8.0
Very good
7,896 reviews

Crew

8.5

Food

7.3

Overall

8.0

Entertainment

7.9

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Air Transat
7.8
Good
381 reviews
Delta
8.0
Very good
7,896 reviews

Crew

8.5

Food

7.3

Overall

8.0

Entertainment

7.9

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
LOT
7.6
Good
1,063 reviews
Delta
8.0
Very good
7,896 reviews

Crew

8.5

Food

7.3

Overall

8.0

Entertainment

7.9

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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 $335. However, be on the lookout for offers from Air Serbia and Icelandair, 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 Milan Linate - 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 $527. On average you can expect to pay $758. The most popular route, (Milan Malpensa - Chicago O'Hare Intl), can usually be booked for $405.

  • 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 $323). 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
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.
Frankfurt to O'Hare Intl flights
Charles de Gaulle to O'Hare Intl flights
Heathrow to O'Hare Intl flights
Frederic Chopin to O'Hare Intl flights
Madrid to O'Hare Intl flights
Frederic Chopin to Midway flights
Orly to O'Hare Intl flights
Bruxelles-National to O'Hare Intl flights
Malpensa to O'Hare Intl flights
Istanbul to O'Hare Intl flights
Gatwick to O'Hare Intl flights
Zurich to O'Hare Intl flights
Leonardo da Vinci/Fiumicino to O'Hare Intl flights
Barcelona-El Prat to O'Hare Intl flights
Munich to O'Hare Intl flights
Krakow to O'Hare Intl flights
Amsterdam to O'Hare Intl flights
Charles de Gaulle to Midway flights
Vienna to O'Hare Intl flights
London City to O'Hare Intl flights
Heathrow to Midway flights
Athens to O'Hare Intl flights
Dublin to O'Hare Intl flights
Frankfurt to St. Louis flights
Beauvais-Tille to O'Hare Intl flights
Barcelona-El Prat to Midway flights
Duesseldorf Intl to O'Hare Intl flights
Bruxelles-National to Midway flights
Linate to O'Hare Intl flights
Frankfurt-Hahn to O'Hare Intl flights
Madrid to Midway flights
Stansted to O'Hare Intl flights
Copenhagen to O'Hare Intl flights
Istanbul to Midway flights
Leonardo da Vinci/Fiumicino to Midway flights
Otopeni Intl to O'Hare Intl flights
Modlin to O'Hare Intl flights
Lisbon to O'Hare Intl flights
Berlin to O'Hare Intl flights
Duesseldorf Intl to Midway flights
Vicenza to O'Hare Intl flights
Belgrade to O'Hare Intl flights
Prague to O'Hare Intl flights
Luton to O'Hare Intl flights

Top 8 airlines flying from Italy to Chicago

Discover the top 8 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 March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
FinnairCheapest$391Average$416FlexibilityNo cancel feeOn-time76%
American AirlinesCheapest$407Average$801FlexibilityNo cancel feeOn-time71%
British AirwaysCheapest$416Average$762FlexibilityNo cancel feeOn-time70%
ITA AirwaysCheapest$535Average$665FlexibilityNo cancel feeOn-time81%
TAP AIR PORTUGALCheapest$537Average$564FlexibilityNo cancel feeOn-timeN/A
IberiaCheapest$553Average$724FlexibilityNo cancel feeOn-time77%
LufthansaCheapest$625Average$848FlexibilityNo cancel feeOn-time76%
United AirlinesCheapest$625Average$855FlexibilityNo cancel feeOn-time69%
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.