HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Italy

$244+ Cheap flights from Chicago (CHI) to Italy

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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — VCE
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Italy 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 Chicago to Italy

Keep the following information in mind while searching for Chicago to Italy flight deals. Data was last updated February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$375
(SWISS)

One-way from

$244
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$554

Good round-trip deal

$848 or less

Good one-way deal

$513 or less
Provider with most accurate pricing for Chicago (CHI)-Rome (ROM) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Rome (ROM) flights.
Search Deals
From Chicago (CHI) to Italy
Search Deals
One-way flight from Chicago (CHI) to Italy
Search Deals
Highest demand for flights based on searches. 25% potential increase in price ($265 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($36 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Italy.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Italy.
Search Deals

Find flight deals from Chicago to Italy

Cheapest flights from Chicago to Italy
Explore the most affordable flight options available from Chicago to Italy. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 20, 2025.

This SWISS deal was found by Cheapflights users on 2/20. 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 SWISS is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/62:20 pmORD - NAP
1 stop11h 25mSWISS
Sun 4/137:35 pmNAP - ORD
1 stop23h 35mSWISS
Deal found 2/20$375
This Kiwi.com deal was found by Cheapflights users on 2/18. 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 3/27:40 pmORD - MXP
2 stops16h 10mScandinavian Airlines
Thu 3/2011:20 amMXP - ORD
1 stop13h 30mScandinavian Airlines
Deal found 2/18$502
This Gotogate deal was found by Cheapflights users on 2/19. 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.
Sun 4/136:00 pmORD - MXP
1 stop34h 00mTAP AIR PORTUGAL
Tue 4/2911:50 amMXP - ORD
1 stop35h 20mTAP AIR PORTUGAL
Deal found 2/19$516
This oojo deal was found by Cheapflights users on 2/19. 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.
Mon 9/157:50 pmORD - MXP
1 stop29h 55mTurkish Airlines
Thu 9/2510:45 amMXP - ORD
1 stop29h 55mTurkish Airlines
Deal found 2/19$518
This Trip.com deal was found by Cheapflights users on 2/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/13:45 pmORD - LIN
1 stop11h 55mAer Lingus
Tue 4/1511:20 amLIN - ORD
1 stop14h 40mAer Lingus
Deal found 2/20$521
This Mytrip deal was found by Cheapflights users on 2/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/67:15 pmORD - VCE
1 stop31h 45mScandinavian Airlines
Sun 4/138:00 pmVCE - ORD
1 stop27h 10mScandinavian Airlines
Deal found 2/20$523
This Mytrip deal was found by Cheapflights users on 2/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/307:20 amORD - FCO
1 stop18h 55mMultiple Airlines
Mon 4/78:10 pmFCO - ORD
1 stop23h 00mMultiple Airlines
Deal found 2/20$550
This FlightHub deal was found by Cheapflights users on 2/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/257:15 pmORD - FCO
2 stops34h 15mScandinavian Airlines
Wed 5/77:35 pmFCO - ORD
1 stop27h 35mScandinavian Airlines
Deal found 2/20$553
This oojo deal was found by Cheapflights users on 2/20. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/276:00 pmORD - FCO
1 stop18h 05mTAP AIR PORTUGAL
Tue 5/68:00 pmFCO - ORD
1 stop27h 10mTAP AIR PORTUGAL
Deal found 2/20$554
This United Airlines deal was found by Cheapflights users on 2/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/238:45 amORD - FCO
1 stop16h 45mUnited Airlines
Wed 4/212:25 pmFCO - ORD
2 stops28h 21mUnited Airlines
Deal found 2/20$555
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 3/1112:55 pmORD - FCO
1 stop23h 30mTurkish Airlines
Tue 3/182:50 pmFCO - ORD
1 stop26h 20mTurkish Airlines
Deal found 2/19$558
This KLM deal was found by Cheapflights users on 2/20. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/29:54 amMDW - FCO
1 stop14h 41mKLM
Wed 4/99:45 amFCO - MDW
1 stop19h 36mKLM
Deal found 2/20$560

Find flights from Chicago to Italy within your budget

Customize your flight search to find flights from Chicago to Italy 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 February 20, 2025.

Fly from

Chicago

Fly to

Italy

Route

Depart

Return

Price

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sun 4/6

2:20 pm-8:45 am

1 stop11h 25m

Naples

Sun 4/13

7:35 pm-12:10 pm

1 stop23h 35m

$375

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sun 3/2

7:40 pm-6:50 pm

2 stops16h 10m

Milan Malpensa

Thu 3/20

11:20 am-6:50 pm

1 stop13h 30m

$502

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sun 4/13

6:00 pm-11:00 am

1 stop34h 00m

Milan Malpensa

Tue 4/29

11:50 am-4:10 pm

1 stop35h 20m

$516

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Tue 4/1

3:45 pm-10:40 am

1 stop11h 55m

Milan Linate

Tue 4/15

11:20 am-7:00 pm

1 stop14h 40m

$521

ChicagoVenice

ORD - VCE

ORDVCE

Chicago O'Hare Intl

Sun 4/6

7:15 pm-10:00 am

1 stop31h 45m

Venice Marco Polo

Sun 4/13

8:00 pm-4:10 pm

1 stop27h 10m

$523

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Tue 3/11

9:30 pm-1:35 pm

1 stop34h 05m

Milan Malpensa

Wed 3/19

6:35 pm-11:10 am

1 stop22h 35m

$533

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Sun 3/30

7:20 am-9:15 am

1 stop18h 55m

Rome Fiumicino

Mon 4/7

8:10 pm-12:10 pm

1 stop23h 00m

$550

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Fri 4/25

7:15 pm-12:30 pm

2 stops34h 15m

Rome Fiumicino

Wed 5/7

7:35 pm-4:10 pm

1 stop27h 35m

$553

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Sun 4/27

6:00 pm-7:05 pm

1 stop18h 05m

Rome Fiumicino

Tue 5/6

8:00 pm-4:10 pm

1 stop27h 10m

$554

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Mon 3/10

4:45 pm-7:45 am

Nonstop9h 00m

Rome Fiumicino

Tue 3/18

9:45 am-2:05 pm

Nonstop10h 20m

$556

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 60 results
1
2
3
...
6

Best time to book a flight from Chicago to Italy

Have a flexible travel schedule? Discover the best time to fly to Italy from Chicago 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.

Travel insights for flights from Chicago to Italy

Get recent, data-driven insights about flights from Chicago to Italy including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Chicago to Italy?

Currently, January is the cheapest month in which you can book a flight from Chicago to Italy (average of $665). Flying from Chicago to Italy in June is currently the most expensive (average of $1,353). 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 CHI to IT?

Find hourly flight availability from Chicago to Italy. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 20, 2025.

When flying from Chicago to Italy, 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 Italy by month

Plan your trip to Italy by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Italy ranges from 0.6 - 4.4 inches per month. November is typically the wettest month, when rainfall can reach 4.4 in. June is typically the driest time to visit Italy when rainfall is around 0.6 in.

Temperature in Italy by month

Plan your trip to Italy by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Italy, use this chart to help with planning. For those seeking warmer temperatures, August is the ideal time of year to visit, when temperatures reach an average of 75.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 46.4 F).

Reviews of airlines servicing Italy

Get insights into the airlines that provide service to Italy. 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 Italy. Reviews last updated February 20, 2025.
Get a feel of what it's like to fly with Singapore Airlines, Delta and KLM from Chicago to Italy by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Singapore Airlines
8.1
Very good
1,301 reviews

Boarding

8.2

Entertainment

8.0

Comfort

8.0

Crew

8.6

Food

7.7

Overall

8.1

Reviews

1 / 20

6.0
Good

Gina,Dec 2024

BLR - SIN

Overall the experience was good. First flight of 17 hours had no entertainment since Singapore airline has technical issues. Was informed that passengers would get a $350 voucher for future flight. Uncertain how that is being distributed but would like to understand if an email is required from my end or if it is an automatic email sent to me by Singapore Airlines. -Gina Robles

Singapore Airlines
8.1
Very good
1,301 reviews
Singapore Airlines
8.1
Very good
1,301 reviews

Boarding

8.2

Entertainment

8.0

Comfort

8.0

Crew

8.6

Food

7.7

Overall

8.1

Reviews

1 / 20

6.0
Good

Gina,Dec 2024

BLR - SIN

Overall the experience was good. First flight of 17 hours had no entertainment since Singapore airline has technical issues. Was informed that passengers would get a $350 voucher for future flight. Uncertain how that is being distributed but would like to understand if an email is required from my end or if it is an automatic email sent to me by Singapore Airlines. -Gina Robles

Delta
8.0
Very good
8,219 reviews
Singapore Airlines
8.1
Very good
1,301 reviews

Boarding

8.2

Entertainment

8.0

Comfort

8.0

Crew

8.6

Food

7.7

Overall

8.1

Reviews

1 / 20

6.0
Good

Gina,Dec 2024

BLR - SIN

Overall the experience was good. First flight of 17 hours had no entertainment since Singapore airline has technical issues. Was informed that passengers would get a $350 voucher for future flight. Uncertain how that is being distributed but would like to understand if an email is required from my end or if it is an automatic email sent to me by Singapore Airlines. -Gina Robles

KLM
7.8
Good
1,333 reviews
Singapore Airlines
8.1
Very good
1,301 reviews

Boarding

8.2

Entertainment

8.0

Comfort

8.0

Crew

8.6

Food

7.7

Overall

8.1

Reviews

1 / 20

6.0
Good

Gina,Dec 2024

BLR - SIN

Overall the experience was good. First flight of 17 hours had no entertainment since Singapore airline has technical issues. Was informed that passengers would get a $350 voucher for future flight. Uncertain how that is being distributed but would like to understand if an email is required from my end or if it is an automatic email sent to me by Singapore Airlines. -Gina Robles

LOT
7.6
Good
1,080 reviews
Singapore Airlines
8.1
Very good
1,301 reviews

Boarding

8.2

Entertainment

8.0

Comfort

8.0

Crew

8.6

Food

7.7

Overall

8.1

Reviews

1 / 20

6.0
Good

Gina,Dec 2024

BLR - SIN

Overall the experience was good. First flight of 17 hours had no entertainment since Singapore airline has technical issues. Was informed that passengers would get a $350 voucher for future flight. Uncertain how that is being distributed but would like to understand if an email is required from my end or if it is an automatic email sent to me by Singapore Airlines. -Gina Robles

Finnair
7.6
Good
1,274 reviews
Singapore Airlines
8.1
Very good
1,301 reviews

Boarding

8.2

Entertainment

8.0

Comfort

8.0

Crew

8.6

Food

7.7

Overall

8.1

Reviews

1 / 20

6.0
Good

Gina,Dec 2024

BLR - SIN

Overall the experience was good. First flight of 17 hours had no entertainment since Singapore airline has technical issues. Was informed that passengers would get a $350 voucher for future flight. Uncertain how that is being distributed but would like to understand if an email is required from my end or if it is an automatic email sent to me by Singapore Airlines. -Gina Robles

Related info for your journey

Find useful and relevant information for your journey from Chicago to Italy. 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 Chicago to Italy one-way?

    $363 is the cheapest one-way deal found within the past few days, from Icelandair. You may also be able to find cheap deals on Lufthansa and Scandinavian Airlines, with prices starting from $364 and $365, respectively.

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

    Most travelers choose Chicago O'Hare Intl - Rome Fiumicino, Chicago Midway - Rome Fiumicino or Chicago O'Hare Intl - Milan Malpensa when deciding on the best route from Chicago to Italy.

  • What are the cheapest flights from Chicago to Italy?

    Looking at all options, your cheapest flight can be booked for $696. While the most popular route (Chicago O'Hare Intl - Rome Fiumicino) can be booked for $439 on average our data indicates $1,451 when flying from Chicago to Italy.

  • Can I find deals for flights from Chicago to Italy that include hotel bookings?

    Yes. In addition to deals on Chicago to Italy flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Italy?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Italy.

  • Can I find deals for business class flights from Chicago to Italy?

    Yes. Cheapflights offers flight deals from Chicago to Italy 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 Chicago to Italy?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Italy (average of $665). Flying from Chicago to Italy in June is currently the most expensive (average of $1,353). 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

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 Chicago to Italy

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Heathrow flights
O'Hare Intl to Leonardo da Vinci/Fiumicino flights
O'Hare Intl to Charles de Gaulle flights
O'Hare Intl to Athens flights
O'Hare Intl to Dublin flights
O'Hare Intl to Istanbul flights
O'Hare Intl to Barcelona-El Prat flights
O'Hare Intl to Madrid flights
O'Hare Intl to Frederic Chopin flights
O'Hare Intl to Orly flights
O'Hare Intl to Gatwick flights
O'Hare Intl to London City flights
O'Hare Intl to Amsterdam flights
O'Hare Intl to Lisbon flights
O'Hare Intl to Frankfurt flights
Midway to Charles de Gaulle flights
O'Hare Intl to Zurich flights
Midway to Leonardo da Vinci/Fiumicino flights
Midway to Heathrow flights
O'Hare Intl to Malpensa flights
O'Hare Intl to Krakow flights
Midway to Athens flights
O'Hare Intl to Copenhagen flights
Midway to Dublin flights
O'Hare Intl to Keflavik Intl flights
O'Hare Intl to Edinburgh flights
Midway to Barcelona-El Prat flights
O'Hare Intl to Vienna flights
O'Hare Intl to Oslo Gardermoen flights
O'Hare Intl to Linate flights
O'Hare Intl to Bruxelles-National flights
O'Hare Intl to Sabiha Gokcen flights
O'Hare Intl to Munich flights
Midway to Madrid flights
O'Hare Intl to Vicenza flights
O'Hare Intl to Belgrade flights
Midway to Lisbon flights
Midway to Istanbul flights
St. Louis to Heathrow flights
O'Hare Intl to Prague flights
Midway to Amsterdam flights
Midway to Frederic Chopin flights
O'Hare Intl to Budapest flights
O'Hare Intl to Skopje flights
Midway to Keflavik Intl flights
O'Hare Intl to Geneva flights
O'Hare Intl to Sofia flights
Midway to Oslo Gardermoen flights
O'Hare Intl to Florence flights
O'Hare Intl to Sarajevo flights

Top 10 airlines flying from Chicago to Italy

Discover the top 10 airlines that operate flights from Chicago to Italy. 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
AeroitaliaCheapest$41Average$72FlexibilityNo cancel feeOn-timeN/A
IcelandairCheapest$370Average$783FlexibilityNo cancel feeOn-time76%
TAP AIR PORTUGALCheapest$378Average$604FlexibilityNo cancel feeOn-timeN/A
Scandinavian AirlinesCheapest$432Average$671FlexibilityNo cancel feeOn-time77%
Aer LingusCheapest$506Average$841FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$506Average$1,095FlexibilityNo cancel feeOn-time67%
LufthansaCheapest$508Average$1,109FlexibilityNo cancel feeOn-time76%
SWISSCheapest$509Average$1,178FlexibilityNo cancel feeOn-time79%
Turkish AirlinesCheapest$518Average$657FlexibilityNo cancel feeOn-time77%
British AirwaysCheapest$523Average$1,065FlexibilityNo cancel feeOn-time70%
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.