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$297+ 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 8/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — NAP
jul. 22 — jul. 291
mié. 7/22
mié. 7/29
1 adult, Economy
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Cheap 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 junio 22, 2026.

This Kiwi.com deal was found by Cheapflights users on 6/21. 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.
mié. 10/77:15 pm
ORD
-
FLR
1 stop16h 50m
Scandinavian Airlines
vie. 10/167:55 pm
FLR
-
ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/21$590
This Kiwi.com deal was found by Cheapflights users on 6/18. 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.
dom. 10/47:15 pm
ORD
-
FLR
1 stop16h 50m
Scandinavian Airlines
lun. 10/127:55 pm
FLR
-
ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/18$591
This Kiwi.com deal was found by Cheapflights users on 6/18. 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.
mar. 9/297:15 pm
ORD
-
FLR
1 stop16h 50m
Scandinavian Airlines
lun. 10/127:55 pm
FLR
-
ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/18$595
This lol.travel deal was found by Cheapflights users on 6/19. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 8/93:00 pm
ORD
-
NAP
1 stop20h 50m
ITA Airways
mar. 8/253:05 pm
NAP
-
ORD
1 stop29h 05m
ITA Airways
Deal found 6/19$604
This oojo deal was found by Cheapflights users on 6/18. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/77:15 pm
ORD
-
FLR
1 stop16h 50m
Scandinavian Airlines
mié. 10/147:55 pm
FLR
-
ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/18$605
This Kiwi.com deal was found by Cheapflights users on 6/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 10/47:15 pm
ORD
-
NAP
1 stop16h 30m
Scandinavian Airlines
sáb. 10/108:35 pm
NAP
-
ORD
1 stop26h 35m
Scandinavian Airlines
Deal found 6/20$606
This FlightHub deal was found by Cheapflights users on 6/20. 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.
dom. 10/47:15 pm
ORD
-
NAP
1 stop16h 30m
Scandinavian Airlines
lun. 10/127:35 pm
NAP
-
ORD
1 stop27h 35m
Scandinavian Airlines
Deal found 6/20$611
This FlightHub deal was found by Cheapflights users on 6/20. 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.
lun. 10/57:15 pm
ORD
-
NAP
2 stops31h 00m
Scandinavian Airlines
lun. 10/127:35 pm
NAP
-
ORD
1 stop27h 35m
Scandinavian Airlines
Deal found 6/20$613
This Kiwi.com deal was found by Cheapflights users on 6/21. 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.
dom. 8/167:15 pm
ORD
-
FLR
1 stop16h 50m
Scandinavian Airlines
dom. 8/307:55 pm
FLR
-
ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/21$618
This oojo deal was found by Cheapflights users on 6/21. 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.
mar. 8/183:00 pm
ORD
-
NAP
1 stop12h 35m
ITA Airways
mar. 8/253:05 pm
NAP
-
ORD
1 stop29h 05m
ITA Airways
Deal found 6/21$629
This Kiwi.com deal was found by Cheapflights users on 6/18. 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.
sáb. 10/37:15 pm
ORD
-
FLR
1 stop16h 50m
Scandinavian Airlines
lun. 10/127:55 pm
FLR
-
ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 6/18$631
This Justfly.com deal was found by Cheapflights users on 6/21. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/236:00 pm
ORD
-
NAP
1 stop17h 25m
TAP AIR PORTUGAL
sáb. 10/107:10 pm
NAP
-
ORD
1 stop27h 50m
TAP AIR PORTUGAL
Deal found 6/21$635

Find flight deals from Chicago to Italy

Keep the following information in mind while searching for Chicago to Italy flight deals. Data was last updated junio 22, 2026.

Most accurate provider

Ovago
3 stars

Most trusted provider

Ovago
3 stars

Round-trip from

$590
(Kiwi.com)

One-way from

$297
(Kiwi.com)

Popular in

June

Cheapest in

December

Average price

$944

Good round-trip deal

$920 or less

Good one-way deal

$633 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. 18% potential increase in price ($163 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
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

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 junio 22, 2026.
Use the filters below to find and compare flights from Chicago to Italy that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

vie. 8/21

7:15 pm-6:40 pm

1 stop16h 25m

Florence Peretola

lun. 8/24

7:55 pm-4:10 pm

1 stop27h 15m

$636

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

mié. 10/21

5:00 pm-10:20 pm

1 stop22h 20m

Florence Peretola

mié. 11/4

12:10 pm-7:15 am

2 stops26h 05m

$776
Quickest round-trip

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

dom. 8/9

9:40 pm-1:20 pm

Nonstop8h 40m

Milan Malpensa

vie. 8/21

3:20 pm-6:10 pm

Nonstop9h 50m

$777

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

mar. 8/11

9:40 pm-1:20 pm

Nonstop8h 40m

Milan Malpensa

jue. 8/20

3:20 pm-6:10 pm

Nonstop9h 50m

$777

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

lun. 8/10

9:40 pm-1:20 pm

Nonstop8h 40m

Milan Malpensa

lun. 8/24

9:00 am-2:55 pm

1 stop12h 55m

$779

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

mié. 8/19

9:40 pm-4:40 pm

1 stop12h 00m

Milan Malpensa

sáb. 8/22

3:20 pm-6:10 pm

Nonstop9h 50m

$785

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

lun. 8/3

6:00 pm-12:20 pm

1 stop11h 20m

Milan Linate

mié. 8/19

6:50 am-12:55 pm

1 stop13h 05m

$790

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

mié. 10/21

7:05 pm-10:20 pm

1 stop20h 15m

Florence Peretola

mié. 11/4

12:10 pm-1:50 pm

1 stop32h 40m

$791

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

dom. 8/9

12:46 pm-9:25 am

1 stop13h 39m

Milan Malpensa

mar. 8/25

11:40 am-10:36 pm

1 stop17h 56m

$792

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

lun. 8/10

12:46 pm-9:25 am

1 stop13h 39m

Milan Malpensa

jue. 8/20

11:40 am-10:36 pm

1 stop17h 56m

$792

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/21

Showing 1-10 of 60 resultsSorted by cheapest first
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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, November is the cheapest month in which you can book a flight from Chicago to Italy (average of $618). Flying from Chicago to Italy in July is currently the most expensive (average of $1,104). 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 junio 22, 2026.

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 junio 22, 2026.

The most flights from CHI to IT0 are scheduled on a Monday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (4 on average).

How often are flights from Chicago to Italy delayed?

About 31% of weekly flights between Chicago and Italy have experienced delays in the past year, with the average delay time being 165 minutes.

What is the most punctual flight time for Chicago to Italy flights?

Historically, flights departing in the early afternoon are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Wednesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Italy flights?

Over the last year, United Airlines have had the lowest number of delays on this route, with just 31% of flights being delayed.

How far ahead should I book a flight from Chicago to Italy?

The best time to book flights from Chicago to Italy is 18 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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 junio 22, 2026.
Peruse reviews from past customers who have flown with Turkish Airlines,Scandinavian Airlines, andUnited Airlines 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.
Turkish Airlines
7.4
Good
4,409 reviews

Overall

7.4

Crew

7.8

Food

7.5

Comfort

7.3

Entertainment

7.5

Boarding

7.3

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

MIA - IST

The cabin is very clean, the service is great, the food is excellent
Turkish Airlines
7.4
Good
4,409 reviews
Turkish Airlines
7.4
Good
4,409 reviews

Overall

7.4

Crew

7.8

Food

7.5

Comfort

7.3

Entertainment

7.5

Boarding

7.3

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

MIA - IST

The cabin is very clean, the service is great, the food is excellent
Scandinavian Airlines
7.4
Good
1,848 reviews
Turkish Airlines
7.4
Good
4,409 reviews

Overall

7.4

Crew

7.8

Food

7.5

Comfort

7.3

Entertainment

7.5

Boarding

7.3

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

MIA - IST

The cabin is very clean, the service is great, the food is excellent
United Airlines
7.4
Good
9,874 reviews
Turkish Airlines
7.4
Good
4,409 reviews

Overall

7.4

Crew

7.8

Food

7.5

Comfort

7.3

Entertainment

7.5

Boarding

7.3

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

MIA - IST

The cabin is very clean, the service is great, the food is excellent
Lufthansa
6.8
Okay
8,086 reviews
Turkish Airlines
7.4
Good
4,409 reviews

Overall

7.4

Crew

7.8

Food

7.5

Comfort

7.3

Entertainment

7.5

Boarding

7.3

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

MIA - IST

The cabin is very clean, the service is great, the food is excellent
ITA Airways
6.7
Okay
1,265 reviews
Turkish Airlines
7.4
Good
4,409 reviews

Overall

7.4

Crew

7.8

Food

7.5

Comfort

7.3

Entertainment

7.5

Boarding

7.3

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

MIA - IST

The cabin is very clean, the service is great, the food is excellent

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.

  • How long is the flight from Chicago to Italy?

    Scandinavian Airlines, United Airlines, and Delta can get you from Chicago to Italy in just under 8h 40m. Your travel time can differ by up to 7h 45m. Chicago and Italy are separated by a distance of 4508 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Chicago to Italy one-way?

    $59 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on Delta and American Airlines, with prices starting from $105 and $122, 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 most reliable airlines from Chicago to Italy?

    Before booking your flight to Italy from Chicago, check out the most reliable airlines to get you to your destination on time: American Airlines (71%), Finnair (71%), Iberia( 71%).

  • What are the cheapest flights from Chicago to Italy?

    Looking at all options, your cheapest flight can be booked for $552. While the most popular route (Chicago O'Hare Intl - Rome Fiumicino) can be booked for $540 on average, our data indicates $1,014 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, November is the cheapest month in which you can book a flight from Chicago to Italy (average of $618). Flying from Chicago to Italy in July is currently the most expensive (average of $1,104). 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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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 junio 22, 2026.
AirlineCheapestAverageFlexibilityOn-time
TAP AIR PORTUGALCheapest$337Average$524FlexibilityNo cancel feeOn-timeN/A
Turkish AirlinesCheapest$375Average$665FlexibilityNo cancel feeOn-time77%
Air CanadaCheapest$384Average$914FlexibilityNo cancel feeOn-time67%
IcelandairCheapest$395Average$699FlexibilityNo cancel feeOn-time76%
Scandinavian AirlinesCheapest$420Average$619FlexibilityNo cancel feeOn-time77%
KLMCheapest$455Average$793FlexibilityNo cancel feeOn-time75%
British AirwaysCheapest$455Average$863FlexibilityNo cancel feeOn-time70%
SWISSCheapest$491Average$966FlexibilityNo cancel feeOn-time79%
LufthansaCheapest$493Average$1,106FlexibilityNo cancel feeOn-time76%
FinnairCheapest$495Average$1,208FlexibilityNo cancel feeOn-time76%

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