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$229+ 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 10/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — NAP
ago. 12 — ago. 191
mar. 8/12
mar. 8/19
1 adult, Economy
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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 agosto 7, 2025.

Round-trip from

$459
(United Airlines)

One-way from

$228
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$771

Good round-trip deal

$691 or less

Good one-way deal

$369 or less
From Chicago (CHI) to Italy
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One-way flight from Chicago (CHI) to Italy
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Highest demand for flights based on searches. 23% potential increase in price ($232 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($32 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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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 agosto 7, 2025.

This SWISS deal was found by Cheapflights users on 8/6. 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.
jue. 10/307:50 pmORD - FCO
1 stop12h 10mSWISS
mar. 11/119:35 amFCO - ORD
1 stop13h 45mSWISS
Deal found 8/6$465
This FlightHub deal was found by Cheapflights users on 8/5. 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. 10/187:15 pmORD - FCO
1 stop16h 30mScandinavian Airlines
vie. 10/247:35 pmFCO - ORD
1 stop27h 35mScandinavian Airlines
Deal found 8/5$466
This FlightHub deal was found by Cheapflights users on 8/6. 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.
mar. 10/217:15 pmORD - FCO
1 stop32h 50mScandinavian Airlines
dom. 10/2610:30 amFCO - ORD
2 stops37h 25mScandinavian Airlines
Deal found 8/6$467
This oojo deal was found by Cheapflights users on 8/5. 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.
mié. 8/137:25 pmORD - FCO
1 stop12h 10mIcelandair
mié. 8/203:45 pmFCO - ORD
1 stop12h 30mIcelandair
Deal found 8/5$468
This Delta deal was found by Cheapflights users on 8/6. 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.
vie. 10/316:35 pmMDW - FCO
2 stops16h 50mDelta
vie. 11/712:40 pmFCO - MDW
1 stop16h 34mDelta
Deal found 8/6$468
This Kiwi.com deal was found by Cheapflights users on 8/5. 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.
sáb. 10/116:15 pmORD - FCO
1 stop15h 30mTAP AIR PORTUGAL
mié. 10/225:45 pmFCO - ORD
1 stop25h 50mTAP AIR PORTUGAL
Deal found 8/5$469
This Mytrip deal was found by Cheapflights users on 8/5. 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.
sáb. 10/46:15 pmORD - BGY
2 stops23h 10mMultiple Airlines
jue. 10/162:40 pmBGY - ORD
2 stops32h 30mMultiple Airlines
Deal found 8/5$470
This United Airlines deal was found by Cheapflights users on 8/6. 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.
jue. 10/304:45 pmORD - FCO
Nonstop9h 00mUnited Airlines
mié. 11/129:45 amFCO - ORD
Nonstop10h 25mUnited Airlines
Deal found 8/6$470
This Delta deal was found by Cheapflights users on 8/7. 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.
lun. 12/11:05 pmMDW - FCO
1 stop14h 25mDelta
dom. 12/146:00 amFCO - MDW
2 stops19h 07mDelta
Deal found 8/7$470
This Delta deal was found by Cheapflights users on 8/5. 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.
jue. 10/307:30 amORD - FCO
1 stop16h 35mDelta
mar. 11/116:10 amFCO - ORD
2 stops18h 26mDelta
Deal found 8/5$471
This Delta deal was found by Cheapflights users on 8/6. 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.
jue. 10/3010:35 amMDW - FCO
1 stop16h 55mDelta
jue. 11/66:10 amFCO - MDW
2 stops17h 04mDelta
Deal found 8/6$471
This Booking.com deal was found by Cheapflights users on 8/6. 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.
lun. 11/312:50 pmORD - FCO
2 stops21h 20mAir Canada
dom. 11/239:35 amFCO - ORD
2 stops16h 55mAir Canada
Deal found 8/6$472

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 agosto 7, 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

jue. 10/30

7:50 pm-2:00 pm

1 stop12h 10m

Rome Fiumicino

mar. 11/11

9:35 am-4:20 pm

1 stop13h 45m

$465

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

sáb. 10/18

7:15 pm-6:45 pm

1 stop16h 30m

Rome Fiumicino

vie. 10/24

7:35 pm-4:10 pm

1 stop27h 35m

$466

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

mar. 10/21

7:15 pm-11:05 am

1 stop32h 50m

Rome Fiumicino

dom. 10/26

10:30 am-5:55 pm

2 stops37h 25m

$467

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

lun. 11/10

10:35 am-11:45 am

2 stops18h 10m

Rome Fiumicino

sáb. 11/22

10:05 am-4:34 pm

1 stop13h 29m

$468

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

vie. 10/31

6:35 pm-5:25 pm

2 stops16h 50m

Rome Fiumicino

vie. 11/7

12:40 pm-10:14 pm

1 stop16h 34m

$468

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

sáb. 10/11

6:15 pm-4:45 pm

1 stop15h 30m

Rome Fiumicino

mié. 10/22

5:45 pm-12:35 pm

1 stop25h 50m

$469

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

sáb. 10/4

6:15 pm-12:25 am

2 stops23h 10m

Bergamo Orio Al Serio

jue. 10/16

2:40 pm-4:10 pm

2 stops32h 30m

$470

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

jue. 10/30

4:45 pm-7:45 am

Nonstop9h 00m

Rome Fiumicino

jue. 11/13

9:45 am-1:10 pm

Nonstop10h 25m

$470

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

lun. 12/1

1:05 pm-10:30 am

1 stop14h 25m

Rome Fiumicino

dom. 12/14

6:00 am-6:07 pm

2 stops19h 07m

$470

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

jue. 10/30

7:30 am-6:05 am

1 stop16h 35m

Rome Fiumicino

mar. 11/11

6:10 am-5:36 pm

2 stops18h 26m

$471

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/4

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 $1,210). 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 agosto 7, 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.

Weekly flight availability from Chicago to Italy

Explore weekly flight availability from Chicago to Italy. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated agosto 7, 2025.

The most flights from CHI to IT0 are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

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 agosto 7, 2025.
Peruse reviews from past customers who have flown with Delta, Porter Airlines, and KLM from Chicago to Italy to help guide your decision. 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
7,987 reviews

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,987 reviews
Delta
8.0
Very good
7,987 reviews

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Porter Airlines
8.0
Very good
325 reviews
Delta
8.0
Very good
7,987 reviews

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
KLM
7.8
Good
1,382 reviews
Delta
8.0
Very good
7,987 reviews

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Austrian Airlines
7.6
Good
824 reviews
Delta
8.0
Very good
7,987 reviews

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
SWISS
7.6
Good
1,692 reviews
Delta
8.0
Very good
7,987 reviews

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 most popular routes from Chicago to Italy?

    Most travelers choose Chicago O'Hare Intl - Rome Fiumicino, Chicago O'Hare Intl - Milan Malpensa or Chicago Midway - Rome Fiumicino 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 $438. While the most popular route (Chicago O'Hare Intl - Rome Fiumicino) can be booked for $331 on average our data indicates $731 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 $1,210). 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

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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 agosto 7, 2025.
AirlineCheapestAverageFlexibilityOn-time
IcelandairCheapest$365Average$639FlexibilityNo cancel feeOn-time76%
TAP AIR PORTUGALCheapest$372Average$594FlexibilityNo cancel feeOn-timeN/A
SWISSCheapest$413Average$1,058FlexibilityNo cancel feeOn-time79%
Scandinavian AirlinesCheapest$414Average$583FlexibilityNo cancel feeOn-time77%
DeltaCheapest$419Average$1,025FlexibilityNo cancel feeOn-timeN/A
KLMCheapest$455Average$719FlexibilityNo cancel feeOn-time75%
Air FranceCheapest$458Average$876FlexibilityNo cancel feeOn-time77%
Turkish AirlinesCheapest$488Average$663FlexibilityNo cancel feeOn-time77%
Air CanadaCheapest$500Average$672FlexibilityNo cancel feeOn-time67%
Aer LingusCheapest$506Average$852FlexibilityNo cancel feeOn-timeN/A

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