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$255+ 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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — VCE
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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Cheap flight deals from Chicago to Italy

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Italy (IT0). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.

Round-trip from

$493
(oojo)

One-way from

$255
(Kiwi.com)

Good round-trip deal

$829 or less

Good one-way deal

$520 or less
From Chicago (CHI) to Italy
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One-way flight from Chicago (CHI) to Italy
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Price to beat on a round-trip flight from Chicago (CHI) to Italy.
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Price to beat on a one-way flight from Chicago (CHI) to Italy.
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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 January 21, 2025.

This oojo deal was found by Cheapflights users on 1/21. 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 2/247:40 pmORD - MXP
1 stop16h 30mScandinavian Airlines
Sat 3/18:00 pmMXP - ORD
1 stop28h 50mScandinavian Airlines
Deal found 1/21$493
This Mytrip deal was found by Cheapflights users on 1/20. 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.
Wed 3/56:30 pmORD - MXP
1 stop11h 40mIcelandair
Sun 3/92:10 pmMXP - ORD
1 stop34h 10mIcelandair
Deal found 1/20$524
This Gotogate deal was found by Cheapflights users on 1/21. 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.
Mon 3/102:05 pmORD - FCO
1 stop12h 55mAir Canada
Tue 3/259:40 amFCO - ORD
2 stops15h 57mAir Canada
Deal found 1/21$524
This United Airlines deal was found by Cheapflights users on 1/20. 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.
Wed 3/263:35 pmORD - FCO
1 stop11h 25mUnited Airlines
Thu 4/39:45 amFCO - ORD
Nonstop10h 15mUnited Airlines
Deal found 1/20$526
This CrystalTravel deal was found by Cheapflights users on 1/21. 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 CrystalTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/287:50 pmORD - MXP
1 stop15h 20mTurkish Airlines
Mon 5/128:10 pmMXP - ORD
1 stop20h 40mTurkish Airlines
Deal found 1/21$527
This Mytrip deal was found by Cheapflights users on 1/21. 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 2/267:05 pmORD - FCO
1 stop17h 05mMultiple Airlines
Fri 3/712:15 pmFCO - ORD
1 stop29h 39mMultiple Airlines
Deal found 1/21$527
This oojo deal was found by Cheapflights users on 1/21. 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 2/168:25 pmORD - FCO
1 stop12h 25mTAP AIR PORTUGAL
Sat 2/224:45 pmFCO - ORD
1 stop29h 45mTAP AIR PORTUGAL
Deal found 1/21$529
This oojo deal was found by Cheapflights users on 1/21. 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 10/269:25 pmORD - MXP
1 stop20h 10mTAP AIR PORTUGAL
Thu 11/65:45 pmMXP - ORD
1 stop28h 45mTAP AIR PORTUGAL
Deal found 1/21$531
This Delta deal was found by Cheapflights users on 1/21. 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 3/1812:51 pmMDW - FCO
1 stop14h 34mDelta
Tue 4/19:45 amFCO - MDW
1 stop19h 38mDelta
Deal found 1/21$540
This Kiwi.com deal was found by Cheapflights users on 1/21. 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.
Mon 3/178:05 pmORD - FCO
1 stop17h 05mSWISS
Mon 3/318:10 pmFCO - ORD
1 stop23h 00mSWISS
Deal found 1/21$541
This oojo deal was found by Cheapflights users on 1/20. 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.
Wed 3/511:55 amORD - NAP
1 stop23h 25mTurkish Airlines
Wed 3/129:15 amNAP - ORD
1 stop31h 55mTurkish Airlines
Deal found 1/20$541
This FlightHub deal was found by Cheapflights users on 1/21. 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.
Mon 9/811:45 pmORD - FCO
1 stop16h 45mTurkish Airlines
Mon 9/227:00 amFCO - ORD
1 stop17h 55mTurkish Airlines
Deal found 1/21$548

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Mon 2/24

7:40 pm-7:10 pm

1 stop16h 30m

Milan Malpensa

Sat 3/1

8:00 pm-5:50 pm

1 stop28h 50m

$493

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Wed 5/7

6:00 pm-11:40 am

1 stop34h 40m

Naples

Fri 5/16

12:30 pm-4:30 pm

1 stop35h 00m

$515

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sat 2/15

6:30 pm-1:10 pm

1 stop11h 40m

Milan Malpensa

Sun 2/23

2:10 pm-5:20 pm

1 stop34h 10m

$522

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Mon 3/24

8:30 pm-9:00 am

1 stop30h 30m

Rome Fiumicino

Mon 3/31

3:05 pm-3:55 pm

1 stop31h 50m

$522

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Wed 2/19

7:15 pm-3:50 pm

1 stop13h 35m

Rome Fiumicino

Sat 3/1

7:35 pm-3:30 pm

1 stop26h 55m

$524

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Wed 3/5

11:35 am-10:00 am

1 stop15h 25m

Rome Fiumicino

Wed 3/12

9:45 am-2:05 pm

Nonstop10h 20m

$525

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Wed 3/26

3:35 pm-9:00 am

1 stop11h 25m

Rome Fiumicino

Thu 4/3

9:45 am-1:00 pm

Nonstop10h 15m

$526

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Mon 2/3

11:55 am-1:35 pm

1 stop18h 40m

Milan Malpensa

Mon 5/12

10:45 am-9:50 am

1 stop30h 05m

$532

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Tue 3/18

12:51 pm-9:25 am

1 stop14h 34m

Rome Fiumicino

Tue 4/1

9:45 am-10:23 pm

1 stop19h 38m

$540

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Mon 3/17

8:05 pm-7:10 pm

1 stop17h 05m

Rome Fiumicino

Mon 3/31

8:10 pm-12:10 pm

1 stop23h 00m

$541

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

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.

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 $1,364). 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 January 21, 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 January 21, 2025.
Get a feel of what it's like to fly with United Airlines, Delta and Icelandair 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.
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.9

Reviews

1 / 10

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

Delta
8.0
Very good
8,521 reviews
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.9

Reviews

1 / 10

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

Porter Airlines
7.9
Good
277 reviews
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.9

Reviews

1 / 10

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

KLM
7.8
Good
1,341 reviews
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.9

Reviews

1 / 10

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

Finnair
7.6
Good
1,286 reviews
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.9

Reviews

1 / 10

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

Austrian Airlines
7.6
Good
786 reviews
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.9

Reviews

1 / 10

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?

    $291 is the cheapest one-way deal found within the past few days, from Icelandair. You may also be able to find cheap deals on SWISS and Lufthansa, with prices starting from $291 and $295, 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 $703. While the most popular route (Chicago O'Hare Intl - Rome Fiumicino) can be booked for $451 on average our data indicates $962 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 $1,364). 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.

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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.
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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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
AeroitaliaCheapest$41Average$82FlexibilityNo cancel feeOn-timeN/A
IcelandairCheapest$370Average$788FlexibilityNo cancel feeOn-time76%
TAP AIR PORTUGALCheapest$381Average$788FlexibilityNo cancel feeOn-timeN/A
Scandinavian AirlinesCheapest$430Average$677FlexibilityNo cancel feeOn-time77%
Aer LingusCheapest$506Average$795FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$506Average$1,119FlexibilityNo cancel feeOn-time67%
LufthansaCheapest$510Average$1,123FlexibilityNo cancel feeOn-time76%
KLMCheapest$512Average$890FlexibilityNo cancel feeOn-time75%
Turkish AirlinesCheapest$520Average$696FlexibilityNo cancel feeOn-time77%
United AirlinesCheapest$526Average$1,093FlexibilityNo cancel feeOn-time69%
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