HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Italy

$235+ 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 3/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — NAP
Mar 10 — Mar 171
Tue 3/10
Tue 3/17
1 adult, Economy
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

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 February 8, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/5. 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.
Fri 4/177:15 pm
ORD
-
FLR
1 stop32h 50m
Scandinavian Airlines
Tue 4/217:55 pm
FLR
-
ORD
1 stop27h 15m
Scandinavian Airlines
Deal found 2/5$431
This CrystalTravel deal was found by Cheapflights users on 2/7. 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 CrystalTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/257:20 pm
ORD
-
MXP
1 stop16h 50m
Scandinavian Airlines
Sat 3/711:15 am
MXP
-
ORD
1 stop12h 30m
Scandinavian Airlines
Deal found 2/7$433
This Kiwi.com deal was found by Cheapflights users on 2/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/257:15 pm
ORD
-
MXP
1 stop11h 55m
Scandinavian Airlines
Sat 5/99:20 am
MXP
-
ORD
1 stop13h 50m
Scandinavian Airlines
Deal found 2/6$434
This FlightHub deal was found by Cheapflights users on 2/7. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/27:20 pm
ORD
-
MXP
1 stop16h 50m
Scandinavian Airlines
Fri 3/611:15 am
MXP
-
ORD
1 stop12h 40m
Scandinavian Airlines
Deal found 2/7$437
This Mytrip deal was found by Cheapflights users on 2/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/157:15 pm
ORD
-
MXP
1 stop16h 55m
Scandinavian Airlines
Wed 4/229:20 am
MXP
-
ORD
1 stop13h 50m
Scandinavian Airlines
Deal found 2/6$440
This Kiwi.com deal was found by Cheapflights users on 2/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/98:20 pm
ORD
-
MXP
1 stop16h 50m
Scandinavian Airlines
Mon 3/168:55 am
MXP
-
ORD
1 stop14h 50m
Scandinavian Airlines
Deal found 2/7$441
This oojo deal was found by Cheapflights users on 2/6. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/27:20 pm
ORD
-
MXP
1 stop16h 50m
Scandinavian Airlines
Thu 3/511:15 am
MXP
-
ORD
1 stop12h 30m
Scandinavian Airlines
Deal found 2/6$442
This CrystalTravel deal was found by Cheapflights users on 2/5. 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 CrystalTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/177:15 pm
ORD
-
MXP
1 stop16h 55m
Scandinavian Airlines
Mon 4/209:20 am
MXP
-
ORD
1 stop13h 50m
Scandinavian Airlines
Deal found 2/5$445
This FlightHub deal was found by Cheapflights users on 2/7. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/27:20 pm
ORD
-
MXP
1 stop16h 50m
Scandinavian Airlines
Sat 3/79:15 am
MXP
-
ORD
1 stop14h 30m
Scandinavian Airlines
Deal found 2/7$447
This Mytrip deal was found by Cheapflights users on 2/8. 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.
Mon 3/27:20 pm
ORD
-
MXP
1 stop16h 50m
Scandinavian Airlines
Sun 3/158:00 pm
MXP
-
ORD
1 stop27h 45m
Scandinavian Airlines
Deal found 2/8$448
This FlightHub deal was found by Cheapflights users on 2/7. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/67:15 pm
ORD
-
MXP
2 stops41h 35m
Scandinavian Airlines
Mon 4/209:20 am
MXP
-
ORD
1 stop13h 50m
Scandinavian Airlines
Deal found 2/7$449
This Mytrip deal was found by Cheapflights users on 2/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/46:30 pm
ORD
-
BGY
2 stops22h 40m
Multiple Airlines
Wed 3/116:45 am
BGY
-
ORD
2 stops17h 35m
Multiple Airlines
Deal found 2/7$461

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 February 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$431
(Kiwi.com)

One-way from

$235
(Mytrip)

Popular in

June

Cheapest in

November

Average price

$600

Good round-trip deal

$789 or less

Good one-way deal

$568 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. 22% potential increase in price ($219 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($31 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 February 8, 2026.
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

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Wed 4/22

7:15 pm-11:30 am

1 stop33h 15m

Florence Peretola

Thu 4/30

7:55 pm-4:10 pm

1 stop27h 15m

$481

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Fri 4/10

7:15 pm-9:50 am

2 stops31h 35m

Florence Peretola

Tue 4/14

7:55 pm-4:10 pm

1 stop27h 15m

$488

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Mon 2/23

7:20 pm-8:25 am

1 stop30h 05m

Milan Malpensa

Thu 2/26

11:15 am-4:45 pm

1 stop12h 30m

$500

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Sun 3/1

3:45 pm-7:45 am

Nonstop9h 00m

Rome Fiumicino

Tue 3/10

9:45 am-4:20 pm

1 stop12h 35m

$522

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Mon 2/23

3:45 pm-7:45 am

Nonstop9h 00m

Rome Fiumicino

Tue 3/3

7:05 am-3:20 pm

1 stop15h 15m

$522

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Tue 3/3

3:45 pm-7:45 am

Nonstop9h 00m

Rome Fiumicino

Thu 3/19

9:45 am-2:10 pm

Nonstop10h 25m

$524

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Wed 2/25

6:30 pm-9:20 pm

2 stops19h 50m

Bergamo Orio Al Serio

Wed 3/4

9:00 pm-5:20 pm

2 stops27h 20m

$528

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Sun 2/22

12:45 pm-10:30 am

1 stop14h 45m

Rome Fiumicino

Tue 3/10

9:05 am-5:54 pm

1 stop14h 49m

$531

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Tue 3/24

10:50 pm-11:00 pm

1 stop18h 10m

Rome Fiumicino

Thu 4/2

11:30 am-8:05 pm

1 stop15h 35m

$535

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Mon 3/23

10:40 am-6:05 am

1 stop13h 25m

Rome Fiumicino

Tue 3/31

6:30 am-6:31 pm

2 stops19h 01m

$539

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/6

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 $332). Flying from Chicago to Italy in June is currently the most expensive (average of $573). 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.

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 164 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 morning 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 29% of flights being delayed.

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 February 8, 2026.
Peruse reviews from past customers who have flown with United Airlines, Scandinavian Airlines, and American 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.
United Airlines
7.4
Good
9,256 reviews

Crew

8.1

Overall

7.4

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Food

6.6

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,256 reviews
United Airlines
7.4
Good
9,256 reviews

Crew

8.1

Overall

7.4

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Food

6.6

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
Scandinavian Airlines
7.3
Good
1,678 reviews
United Airlines
7.4
Good
9,256 reviews

Crew

8.1

Overall

7.4

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Food

6.6

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
American Airlines
7.2
Good
11,252 reviews
United Airlines
7.4
Good
9,256 reviews

Crew

8.1

Overall

7.4

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Food

6.6

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
Lufthansa
6.8
Okay
7,775 reviews
United Airlines
7.4
Good
9,256 reviews

Crew

8.1

Overall

7.4

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Food

6.6

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
ITA Airways
6.7
Okay
1,145 reviews
United Airlines
7.4
Good
9,256 reviews

Crew

8.1

Overall

7.4

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Food

6.6

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

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 9h. Your travel time can differ by up to 24h 15m. Chicago and Italy are separated by a distance of 4808 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?

    $186 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 Icelandair and ITA Airways, with prices starting from $193 and $196, 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 $611. While the most popular route (Chicago O'Hare Intl - Rome Fiumicino) can be booked for $423 on average, our data indicates $925 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 $332). Flying from Chicago to Italy in June is currently the most expensive (average of $573). 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.
O'Hare Intl to Heathrow flights
O'Hare Intl to Leonardo da Vinci/Fiumicino flights
O'Hare Intl to Charles de Gaulle flights
O'Hare Intl to Athens flights
O'Hare Intl to Dublin flights
O'Hare Intl to Madrid flights
O'Hare Intl to Barcelona-El Prat flights
O'Hare Intl to Istanbul flights
O'Hare Intl to Orly flights
O'Hare Intl to Gatwick flights
O'Hare Intl to London City flights
O'Hare Intl to Frederic Chopin flights
O'Hare Intl to Stansted flights
O'Hare Intl to Amsterdam flights
O'Hare Intl to Lisbon flights
O'Hare Intl to Krakow flights
O'Hare Intl to Frankfurt flights
O'Hare Intl to Zurich flights
Midway to Leonardo da Vinci/Fiumicino flights
O'Hare Intl to Malpensa flights
Midway to Heathrow flights
Midway to Charles de Gaulle flights
O'Hare Intl to Edinburgh flights
O'Hare Intl to Munich flights
O'Hare Intl to Copenhagen flights
O'Hare Intl to Keflavik Intl flights
Midway to Athens flights
O'Hare Intl to Luton flights
Midway to Dublin flights
Midway to Madrid flights
O'Hare Intl to Linate flights
O'Hare Intl to Bruxelles-National flights
St. Louis to Heathrow flights
O'Hare Intl to Beauvais-Tille flights
O'Hare Intl to Belgrade flights
O'Hare Intl to Vienna flights
O'Hare Intl to Sabiha Gokcen flights
O'Hare Intl to Oslo Gardermoen flights
O'Hare Intl to Vicenza flights
O'Hare Intl to Naples flights
Midway to Barcelona-El Prat flights
O'Hare Intl to Ciampino flights
O'Hare Intl to Katowice flights
O'Hare Intl to Florence flights
O'Hare Intl to Berlin flights
Midway to Lisbon flights
O'Hare Intl to Sofia flights
Midway to Frederic Chopin flights
O'Hare Intl to Geneva flights
Midway to Keflavik Intl flights

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 February 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
IberiaCheapest$230Average$1,174FlexibilityNo cancel feeOn-time77%
TAP AIR PORTUGALCheapest$337Average$471FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$390Average$897FlexibilityNo cancel feeOn-time67%
IcelandairCheapest$392Average$552FlexibilityNo cancel feeOn-time76%
Scandinavian AirlinesCheapest$410Average$554FlexibilityNo cancel feeOn-time77%
SWISSCheapest$414Average$1,014FlexibilityNo cancel feeOn-time79%
KLMCheapest$455Average$865FlexibilityNo cancel feeOn-time75%
British AirwaysCheapest$455Average$874FlexibilityNo cancel feeOn-time70%
Air FranceCheapest$458Average$845FlexibilityNo cancel feeOn-time77%
DeltaCheapest$462Average$1,031FlexibilityNo cancel feeOn-timeN/A

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.