Italy

$278+ 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 7/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — NAP
mar. 30 — abr. 61
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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 marzo 25, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$524
(oojo)

One-way from

$278
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$699

Good round-trip deal

$818 or less

Good one-way deal

$514 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 ($251 potential increase over avg. RT price).
Cheapest flight prices on average. 4% potential price decrease ($35 potential savings vs. average RT price).
Average for round-trip flights in March 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 marzo 25, 2025.

This FlightHub deal was found by Cheapflights users on 3/23. 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.
sáb. 9/67:15 pmORD - VCE
1 stop31h 45mScandinavian Airlines
mar. 9/1610:50 amVCE - ORD
1 stop12h 20mScandinavian Airlines
Deal found 3/23$512
This oojo deal was found by Cheapflights users on 3/23. 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.
lun. 5/57:15 pmORD - MXP
2 stops17h 40mScandinavian Airlines
mié. 5/148:45 pmMXP - ORD
2 stops26h 25mScandinavian Airlines
Deal found 3/23$524
This oojo deal was found by Cheapflights users on 3/24. 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.
dom. 10/268:30 pmORD - LIN
2 stops33h 35mScandinavian Airlines
jue. 11/612:55 pmLIN - ORD
2 stops34h 50mScandinavian Airlines
Deal found 3/24$533
This Justfly.com deal was found by Cheapflights users on 3/23. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/411:45 pmORD - MXP
1 stop26h 00mTurkish Airlines
sáb. 10/116:50 amMXP - ORD
1 stop22h 10mTurkish Airlines
Deal found 3/23$537
This Mytrip deal was found by Cheapflights users on 3/23. 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.
lun. 5/57:15 pmORD - FCO
2 stops21h 20mMultiple Airlines
mié. 5/211:05 pmFCO - ORD
2 stops34h 05mMultiple Airlines
Deal found 3/23$559
This Kiwi.com deal was found by Cheapflights users on 3/22. 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.
mié. 11/58:25 pmORD - FCO
1 stop12h 25mTAP AIR PORTUGAL
mié. 11/126:00 amFCO - ORD
1 stop16h 30mTAP AIR PORTUGAL
Deal found 3/22$560
This British Airways deal was found by Cheapflights users on 3/23. 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.
mar. 3/2510:45 pmORD - FCO
1 stop12h 00mBritish Airways
mié. 4/211:05 amFCO - ORD
Nonstop10h 25mBritish Airways
Deal found 3/23$562
This United Airlines deal was found by Cheapflights users on 3/23. 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.
mié. 3/2611:49 amORD - FCO
1 stop14h 06mUnited Airlines
mar. 4/19:45 amFCO - ORD
Nonstop10h 15mUnited Airlines
Deal found 3/23$563
This FlightHub deal was found by Cheapflights users on 3/24. 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.
mié. 9/2411:45 pmORD - FCO
1 stop26h 35mTurkish Airlines
sáb. 10/410:45 amFCO - ORD
1 stop18h 15mTurkish Airlines
Deal found 3/24$571
This Delta deal was found by Cheapflights users on 3/23. 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.
mar. 3/2512:20 pmORD - FCO
1 stop14h 25mDelta
mar. 4/110:10 amFCO - ORD
1 stop17h 28mDelta
Deal found 3/23$573
This Delta deal was found by Cheapflights users on 3/23. 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.
mar. 3/259:54 amMDW - FCO
1 stop15h 01mDelta
mié. 4/29:45 amFCO - MDW
1 stop19h 38mDelta
Deal found 3/23$573
This Air Canada deal was found by Cheapflights users on 3/24. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/279:30 pmORD - FCO
2 stops29h 30mAir Canada
jue. 11/612:15 pmFCO - ORD
1 stop14h 17mAir Canada
Deal found 3/24$575

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 marzo 25, 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

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

jue. 5/8

7:15 pm-7:55 pm

2 stops17h 40m

Milan Malpensa

jue. 5/15

9:15 am-4:10 pm

1 stop13h 55m

$529

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

lun. 5/5

7:15 pm-11:35 pm

2 stops21h 20m

Rome Fiumicino

mié. 5/21

1:05 pm-4:10 pm

2 stops34h 05m

$559

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

mié. 4/2

7:10 am-9:15 am

2 stops19h 05m

Rome Fiumicino

mié. 4/9

9:45 am-1:00 pm

Nonstop10h 15m

$563

ChicagoVenice

ORD - VCE

ORDVCE

Chicago O'Hare Intl

dom. 5/11

7:15 pm-10:00 am

1 stop31h 45m

Venice Marco Polo

lun. 5/19

10:50 am-4:10 pm

1 stop12h 20m

$563

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

mié. 4/2

11:10 am-9:15 am

2 stops15h 05m

Rome Fiumicino

mié. 4/9

12:25 pm-7:30 pm

1 stop14h 05m

$565

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

dom. 4/27

7:15 pm-11:05 am

1 stop32h 50m

Rome Fiumicino

mié. 5/7

7:35 pm-4:10 pm

1 stop27h 35m

$569

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

mar. 4/1

10:55 am-6:25 am

1 stop12h 30m

Rome Fiumicino

mar. 4/8

9:45 am-6:56 pm

1 stop16h 11m

$573

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

dom. 3/30

12:51 pm-11:05 am

1 stop15h 14m

Rome Fiumicino

mié. 4/9

9:45 am-10:21 pm

1 stop19h 36m

$573

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

mar. 4/1

9:25 am-7:35 am

2 stops15h 10m

Rome Fiumicino

mar. 4/8

10:10 am-10:26 pm

2 stops19h 16m

$577

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

lun. 4/7

3:45 pm-9:55 am

1 stop11h 10m

Milan Malpensa

mié. 4/23

7:30 pm-3:55 pm

1 stop27h 25m

$585

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/24

Showing 1-10 of 60 results
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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 $1,280). 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 marzo 25, 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 marzo 25, 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

Boarding

8.2

Crew

8.5

Entertainment

7.9

Comfort

8.0

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

Boarding

8.2

Crew

8.5

Entertainment

7.9

Comfort

8.0

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

Boarding

8.2

Crew

8.5

Entertainment

7.9

Comfort

8.0

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

Boarding

8.2

Crew

8.5

Entertainment

7.9

Comfort

8.0

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

Boarding

8.2

Crew

8.5

Entertainment

7.9

Comfort

8.0

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

Boarding

8.2

Crew

8.5

Entertainment

7.9

Comfort

8.0

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?

    $290 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 Turkish Airlines and Scandinavian Airlines, with prices starting from $369 and $372, 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 $663. While the most popular route (Chicago O'Hare Intl - Rome Fiumicino) can be booked for $449 on average our data indicates $1,647 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 $1,280). 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

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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 marzo 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
AeroitaliaCheapest$41Average$72FlexibilityNo cancel feeOn-timeN/A
IcelandairCheapest$368Average$713FlexibilityNo cancel feeOn-time76%
TAP AIR PORTUGALCheapest$377Average$598FlexibilityNo cancel feeOn-timeN/A
Scandinavian AirlinesCheapest$430Average$659FlexibilityNo cancel feeOn-time77%
SWISSCheapest$484Average$1,185FlexibilityNo cancel feeOn-time79%
Air CanadaCheapest$500Average$762FlexibilityNo cancel feeOn-time67%
LufthansaCheapest$504Average$1,151FlexibilityNo cancel feeOn-time76%
Aer LingusCheapest$506Average$832FlexibilityNo cancel feeOn-timeN/A
British AirwaysCheapest$517Average$1,064FlexibilityNo cancel feeOn-time70%
Turkish AirlinesCheapest$518Average$650FlexibilityNo cancel feeOn-time77%
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