Italy

$276+ 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 4/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — NAP
Apr 20 — Apr 271
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 April 15, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$582
(Mytrip)

One-way from

$276
(Trip.com)

Popular in

June

Cheapest in

February

Average price

$747

Good round-trip deal

$807 or less

Good one-way deal

$559 or less
Provider with most accurate pricing for Chicago (CHI)-Rome (ROM) flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Rome (ROM) flights.
From Chicago (CHI) to Italy
One-way flight from Chicago (CHI) to Italy
Highest demand for flights based on searches. 24% potential increase in price ($243 potential increase over avg. RT price).
Cheapest flight prices on average. 4% potential price decrease ($34 potential savings vs. average RT price).
Average for round-trip flights in April 2025
Price to beat on a round-trip flight from Chicago (CHI) to Italy.
Price to beat on a one-way flight from Chicago (CHI) to Italy.

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 April 15, 2025.

This oojo deal was found by Cheapflights users on 4/15. 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 10/77:15 pmORD - FCO
1 stop16h 30mScandinavian Airlines
Wed 10/227:35 pmFCO - ORD
1 stop27h 35mScandinavian Airlines
Deal found 4/15$482
This Trip.com deal was found by Cheapflights users on 4/15. 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.
Sun 10/57:15 pmORD - VCE
1 stop31h 45mScandinavian Airlines
Thu 10/1610:50 amVCE - ORD
1 stop12h 20mScandinavian Airlines
Deal found 4/15$504
This oojo deal was found by Cheapflights users on 4/15. 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 8/2410:15 pmORD - FCO
1 stop33h 20mIcelandair
Thu 9/43:45 pmFCO - ORD
1 stop12h 30mIcelandair
Deal found 4/15$545
This Kiwi.com deal was found by Cheapflights users on 4/15. 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 5/108:37 amORD - FCO
1 stop27h 33mMultiple Airlines
Tue 5/131:10 pmFCO - ORD
1 stop24h 32mMultiple Airlines
Deal found 4/15$547
This FlightHub deal was found by Cheapflights users on 4/15. 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.
Tue 9/167:15 pmORD - MXP
1 stop30h 20mScandinavian Airlines
Mon 9/298:05 pmMXP - ORD
1 stop27h 05mScandinavian Airlines
Deal found 4/15$567
This oojo deal was found by Cheapflights users on 4/15. 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 8/148:50 pmORD - FCO
1 stop12h 55mTAP AIR PORTUGAL
Sun 8/245:45 pmFCO - ORD
1 stop29h 55mTAP AIR PORTUGAL
Deal found 4/15$570
This FlightHub deal was found by Cheapflights users on 4/15. 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.
Tue 10/711:25 amORD - FCO
1 stop14h 55mTurkish Airlines
Fri 10/177:55 pmFCO - ORD
1 stop20h 45mTurkish Airlines
Deal found 4/15$574
This Turkish Airlines deal was found by Cheapflights users on 4/14. 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1511:25 amORD - MXP
1 stop19h 45mTurkish Airlines
Tue 9/233:10 pmMXP - ORD
1 stop25h 30mTurkish Airlines
Deal found 4/14$576
This oojo deal was found by Cheapflights users on 4/15. 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.
Sat 10/411:20 pmORD - FCO
1 stop13h 20mAir Serbia
Sat 10/119:25 amFCO - ORD
1 stop18h 35mAir Serbia
Deal found 4/15$576
This British Airways deal was found by Cheapflights users on 4/15. 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.
Sun 5/47:15 pmORD - FCO
1 stop12h 10mBritish Airways
Wed 5/1411:05 amFCO - ORD
Nonstop10h 25mBritish Airways
Deal found 4/15$578
This Mytrip deal was found by Cheapflights users on 4/13. 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 5/75:05 amORD - MXP
3 stops19h 55mMultiple Airlines
Wed 5/149:00 amMXP - ORD
3 stops21h 04mMultiple Airlines
Deal found 4/13$582
This Delta deal was found by Cheapflights users on 4/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/139:39 amORD - FCO
1 stop18h 26mDelta
Tue 5/2011:35 amFCO - ORD
1 stop19h 23mDelta
Deal found 4/15$589

Cheapflights Fare Finder

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 April 15, 2025.
Use the filters below to find and compare flights from Chicago to Italy that are best for you.

Fly from

Chicago

Fly to

Italy

Route

Depart

Return

Price

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Sat 5/10

8:37 am-7:10 pm

1 stop27h 33m

Rome Fiumicino

Tue 5/13

1:10 pm-6:42 am

1 stop24h 32m

$547

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Sun 5/4

7:15 pm-2:25 pm

1 stop12h 10m

Rome Fiumicino

Wed 5/14

11:05 am-2:30 pm

Nonstop10h 25m

$578

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Wed 5/7

5:05 am-8:00 am

3 stops19h 55m

Milan Malpensa

Wed 5/14

9:00 am-11:04 pm

3 stops21h 04m

$582

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Tue 5/6

10:37 am-11:25 am

2 stops17h 48m

Milan Malpensa

Thu 5/15

11:20 am-6:25 pm

1 stop14h 05m

$586

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Tue 5/13

9:39 am-11:05 am

1 stop18h 26m

Rome Fiumicino

Tue 5/20

11:35 am-11:58 pm

1 stop19h 23m

$589

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Mon 4/28

9:52 am-7:35 am

1 stop14h 43m

Rome Fiumicino

Wed 5/7

9:45 am-9:28 pm

1 stop18h 43m

$589

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Mon 4/28

9:20 am-7:35 am

2 stops15h 15m

Rome Fiumicino

Wed 5/7

10:10 am-9:28 pm

2 stops18h 18m

$593

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Tue 4/29

9:30 pm-6:00 pm

1 stop13h 30m

Rome Fiumicino

Wed 5/7

6:55 pm-2:40 pm

2 stops26h 45m

$597

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Tue 5/6

5:10 pm-2:50 pm

1 stop14h 40m

Rome Fiumicino

Wed 5/14

9:45 am-6:48 pm

1 stop16h 03m

$598

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Mon 5/5

8:40 am-9:15 am

1 stop17h 35m

Rome Fiumicino

Fri 5/23

7:10 am-8:12 pm

2 stops20h 02m

$599

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/13

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.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Italy

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 $703). Flying from Chicago to Italy in June is currently the most expensive (average of $1,273). 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 April 15, 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 April 15, 2025.
Get a feel of what it's like to fly with Delta, Porter Airlines 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.
8.0
Very good

Food

7.3

Overall

8.0

Entertainment

7.9

Comfort

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
8.0
Very good
8.0
Very good

Food

7.3

Overall

8.0

Entertainment

7.9

Comfort

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
8.0
Very good

Food

7.3

Overall

8.0

Entertainment

7.9

Comfort

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
8.0
Very good

Food

7.3

Overall

8.0

Entertainment

7.9

Comfort

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
8.0
Very good

Food

7.3

Overall

8.0

Entertainment

7.9

Comfort

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
8.0
Very good

Food

7.3

Overall

8.0

Entertainment

7.9

Comfort

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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?

    $320 is the cheapest one-way deal found within the past few days, from TAP AIR PORTUGAL. You may also be able to find cheap deals on Air Serbia and Scandinavian Airlines, with prices starting from $420 and $433, respectively.

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

  • What are the cheapest flights from Chicago to Italy?

    Looking at all options, your cheapest flight can be booked for $574. While the most popular route (Chicago O'Hare Intl - Rome Fiumicino) can be booked for $440 on average our data indicates $1,086 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 $703). Flying from Chicago to Italy in June is currently the most expensive (average of $1,273). 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.

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 April 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
AeroitaliaCheapest$41Average$72FlexibilityNo cancel feeOn-timeN/A
IcelandairCheapest$366Average$688FlexibilityNo cancel feeOn-time76%
TAP AIR PORTUGALCheapest$377Average$598FlexibilityNo cancel feeOn-timeN/A
SWISSCheapest$428Average$1,112FlexibilityNo cancel feeOn-time79%
Scandinavian AirlinesCheapest$429Average$618FlexibilityNo cancel feeOn-time77%
Air CanadaCheapest$500Average$762FlexibilityNo cancel feeOn-time67%
LufthansaCheapest$502Average$1,090FlexibilityNo cancel feeOn-time76%
Aer LingusCheapest$506Average$824FlexibilityNo cancel feeOn-timeN/A
British AirwaysCheapest$517Average$903FlexibilityNo cancel feeOn-time70%
Turkish AirlinesCheapest$518Average$682FlexibilityNo cancel feeOn-time77%

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.