What airlines fly to Italy?

United Airlines, ITA Airways and American Airlines are the top three most popular airlines that fly to Italy from Chicago according to our data. United Airlines is the first choice among our users, with 39% of people opting to fly with this airline when traveling to Italy. Keep in mind that there are 17 different airlines that fly to Italy on a routine basis, so you have a few additional options to choose from.

How many flights depart from Chicago to Italy on average per day?

10 flights are operational daily from Chicago to Italy as of November 2025. The most popular departure time for this route is 3:00PM, with 53% of flights per day taking off in the evening.

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

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 24% of their flights experiencing any sort of delay.

How often are flights from Chicago to Italy delayed?

Historically, on average around 28% of flights between Chicago and Italy have experienced a delay on any given week. The average delay length over the past 12 months has been 164 minutes.

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

Wednesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

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

Generally, flights departing in the early afternoon tend to experience fewer delays. Flights in the morning have, in the past, seen delays more frequently in comparison.

What is the cheapest airline that flies from Chicago to Italy?

Scandinavian Airlines, Air Serbia, and British Airways are the most popular carriers operating from Chicago to Italy

How many flights depart from Chicago to Italy on average per week?

As of November 2025, there are 72 flights per week flying from Chicago to Italy. The most common day of the week flights depart is Mon, with 15% of flights taking off on this day.

When did momondo last update prices for flights from Chicago to Italy?

Prices for flights from Chicago to Italy refresh daily.

How many operators does momondo search for flights from Chicago to Italy?

As of November 2025, there are 17 operators available to choose from for flights from Chicago to Italy.

How old do you have to be to fly from Chicago to Italy?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Italy.

What documentation or ID do you need to fly to Italy?

The travel and health documents you'll need for your trip to Italy may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Italy. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$214 Cheap Flights from Chicago to Italy in 2025/26

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Cheap round-trip flights

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7:00 am - 7:05 pmORD-FLR

29h 05m2 stops

12:20 pm - 4:10 pmFLR-ORD

34h 50m1 stop

$387Scandinavian Airlines

Find Deal

Tue, Apr 7 - Tue, Apr 14

6:59 pm - 10:30 amORD-VCE

32h 31m2 stops

11:05 am - 4:55 pmVCE-ORD

12h 50m1 stop

$401Scandinavian Airlines

Find Deal

Wed, Jan 28 - Sun, Feb 1

10:10 am - 3:25 pmORD-FCO

22h 15m2 stops

11:55 am - 4:10 pmFCO-ORD

35h 15m1 stop

$409Scandinavian Airlines

Find Deal

Wed, Apr 29 - Fri, May 8

7:10 pm - 11:15 amORD-VCE

33h 05m1 stop

5:50 pm - 4:00 pmVCE-ORD

28h 10m1 stop

$417TAP AIR PORTUGAL

Find Deal

Wed, Mar 4 - Tue, Mar 10

6:00 pm - 12:15 amORD-FCO

23h 15m1 stop

8:00 pm - 4:15 pmFCO-ORD

27h 15m1 stop

$420TAP AIR PORTUGAL

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Wed, May 6 - Fri, May 15

3:34 pm - 11:50 amORD-NAP

14h 16m2 stops

2:35 pm - 11:55 amNAP-ORD

28h 20m1 stop

$440American Airlines

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Mon, Mar 16 - Mon, Mar 30

6:40 pm - 2:10 pmORD-NAP

13h 30m1 stop

2:35 pm - 11:55 amNAP-ORD

28h 20m1 stop

$453American Airlines

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Mon, Mar 16 - Mon, Mar 30

5:10 pm - 3:35 pmORD-NAP

15h 25m1 stop

1:55 pm - 1:50 pmNAP-ORD

30h 55m1 stop

$469British Airways

Find Deal

Thu, Jan 15 - Mon, Jan 19

6:00 pm - 12:30 pmORD-NAP

11h 30m1 stop

3:10 pm - 1:10 pmNAP-ORD

29h 00m2 stops

$477Lufthansa

Find Deal

Sun, Jan 18 - Tue, Feb 3

11:44 am - 3:35 pmORD-NAP

20h 51m2 stops

12:40 pm - 5:44 pmNAP-ORD

36h 04m2 stops

$489British Airways

Find Deal

Thu, Jan 8 - Thu, Jan 15

American Airlines flights from Chicago to Italy

Our best American Airlines deals on Chicago to Italy flight tickets

American Airlines

Mar 16

ORD3:34 pmChicago O'Hare Intl

14h 16m

2 stops

NAP11:50 amNaples

Mar 30

NAP2:35 pmNaples

28h 20m

1 stop

ORD11:55 amChicago O'Hare Intl

$440

Find similar

American Airlines

Mar 16

ORD6:40 pmChicago O'Hare Intl

13h 30m

1 stop

NAP2:10 pmNaples

Mar 30

NAP2:35 pmNaples

28h 20m

1 stop

ORD11:55 amChicago O'Hare Intl

$453

Find similar

American Airlines

Dec 2

ORD5:40 pmChicago O'Hare Intl

14h 50m

1 stop

FCO3:30 pmRome Fiumicino

Dec 11

FCO11:00 amRome Fiumicino

17h 29m

2 stops

ORD9:29 pmChicago O'Hare Intl

$469

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British Airways flights from Chicago to Italy

Our best British Airways deals on Chicago to Italy flight tickets

British Airways

Mar 2

ORD5:10 pmChicago O'Hare Intl

12h 40m

1 stop

FCO12:50 pmRome Fiumicino

Mar 13

FCO8:35 amRome Fiumicino

17h 10m

1 stop

ORD7:45 pmChicago O'Hare Intl

$439

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British Airways

Mar 16

ORD6:10 pmChicago O'Hare Intl

21h 45m

1 stop

FCO9:55 pmRome Fiumicino

Mar 23

FCO8:50 pmRome Fiumicino

28h 55m

1 stop

ORD7:45 pmChicago O'Hare Intl

$457

Find similar

British Airways

Jan 15

ORD5:10 pmChicago O'Hare Intl

15h 25m

1 stop

NAP3:35 pmNaples

Jan 19

NAP1:55 pmNaples

30h 55m

1 stop

ORD1:50 pmChicago O'Hare Intl

$469

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Fly from

Fly to

Route

Depart

Return

Price

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Tue 4/7

7:00 am-7:05 pm

2 stops29h 05m

Florence Peretola

Tue 4/14

12:20 pm-4:10 pm

1 stop34h 50m

$387

ChicagoVenice

ORD - VCE

ORDVCE

Chicago O'Hare Intl

Wed 1/28

6:59 pm-10:30 am

2 stops32h 31m

Venice Marco Polo

Sun 2/1

11:05 am-4:55 pm

1 stop12h 50m

$401

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Wed 4/29

10:10 am-3:25 pm

2 stops22h 15m

Rome Fiumicino

Fri 5/8

11:55 am-4:10 pm

1 stop35h 15m

$409

ChicagoVenice

ORD - VCE

ORDVCE

Chicago O'Hare Intl

Wed 3/4

7:10 pm-11:15 am

1 stop33h 05m

Venice Marco Polo

Tue 3/10

5:50 pm-4:00 pm

1 stop28h 10m

$417

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Wed 5/6

6:00 pm-12:15 am

1 stop23h 15m

Rome Fiumicino

Fri 5/15

8:00 pm-4:15 pm

1 stop27h 15m

$420

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Mon 3/16

3:34 pm-11:50 am

2 stops14h 16m

Naples

Mon 3/30

2:35 pm-11:55 am

1 stop28h 20m

$440

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Mon 3/16

6:40 pm-2:10 pm

1 stop13h 30m

Naples

Mon 3/30

2:35 pm-11:55 am

1 stop28h 20m

$453

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Thu 1/15

5:10 pm-3:35 pm

1 stop15h 25m

Naples

Mon 1/19

1:55 pm-1:50 pm

1 stop30h 55m

$469

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sun 1/18

6:00 pm-12:30 pm

1 stop11h 30m

Naples

Tue 2/3

3:10 pm-1:10 pm

2 stops29h 00m

$477

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Thu 1/8

11:44 am-3:35 pm

2 stops20h 51m

Naples

Thu 1/15

12:40 pm-5:44 pm

2 stops36h 04m

$489

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How to get the cheapest flight ticket from Chicago to Italy

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Delays

Other information

What is the cheapest month to fly to Italy?

The cheapest month to fly to Italy from Chicago is in November. Flight prices, which tend to average around $576, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of November, then book flights to Italy from Chicago during January instead. Flights to Italy in January, while not as cheap as those in November, still average around $580.

What is the cheapest day to depart on your flight to Italy?

According to our data, Tuesday is the cheapest day to fly to Italy from Chicago. The lowest ticket price found for a Tuesday departure recently was $909. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. When flying out on a Thursday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Italy for around $1,020.

What is the cheapest time of day to depart on your flight to Italy?

Our data shows that the cheapest Chicago to Italy flights are usually those with departure times in the evening. Our users have found flights to Italy in the evening for as low as $686. In contrast, the most expensive time of day to depart to Italy is in the afternoon when prices are around $960.

What is the cheapest Chicago to Italy flight route?

Fly from Chicago O'Hare Intl to Rome Fiumicino for the best Chicago - Italy flight prices

How far in advance should I book a flight to Italy?

You are more likely to see cheaper flights to Italy from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Italy for around $797 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Italy from Chicago for as low as $772 on momondo.

What cabin class options are available on Chicago to Italy flights?

There are 3 cabin classes available to choose from on Chicago to Italy flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to Italy flights?

No. A direct flight is the cheapest option for a flight between Chicago to Italy.

Cheap Chicago to Italy flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Italy

Best Price Found	$450
Fastest flight time	8h 30m
Direct flights	Every day
Airports in Italy	2 airports

The best one-way flight to Italy from Chicago in the past 72 hours is $450. The best round-trip flight deal from Chicago to Italy found on momondo in the last 72 hours is $734.

The fastest flight from Chicago to Italy takes 8h 30m

Direct flights go from Chicago to Italy every day.

There are 2 airports near Italy: Rome Fiumicino (FCO), Milan Malpensa (MXP)

Search flight deals

When did momondo last update prices for flights from Chicago to Italy?
Prices for flights from Chicago to Italy refresh daily.
How many operators does momondo search for flights from Chicago to Italy?
As of November 2025, there are 17 operators available to choose from for flights from Chicago to Italy.
How old do you have to be to fly from Chicago to Italy?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Italy.
What documentation or ID do you need to fly to Italy?
The travel and health documents you'll need for your trip to Italy may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Italy. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago to Italy?
Based on momondo bookings for flights between Chicago and Italy, the leading plane model is Boeing 787 Dreamliner, making up 43.73% of the total bookings. Other popular models include Boeing 787-8 Dreamliner with 23.47%, Boeing 787-10 Dreamliner with 20.51%, and Airbus A330-900neo with 6.88%.

Best airlines flying from Chicago to Italy

Compare and see reviews for airlines that fly from Chicago to Italy with momondo

Airline	Rating	Free Cancellation	Price
TAP AIR PORTUGAL	PriceFrom $337	Free Cancellation	Rating 7.1 2,075 reviews	Search TAP AIR PORTUGAL flights
Iberia	PriceFrom $354	Free Cancellation	Rating 7.0 3,036 reviews	Search Iberia flights
Air Canada	PriceFrom $390	Free Cancellation	Rating 7.1 10,481 reviews	Search Air Canada flights
Icelandair	PriceFrom $392	Free Cancellation	Rating 7.0 581 reviews	Search Icelandair flights
Scandinavian Airlines	PriceFrom $414	Free Cancellation	Rating 7.4 1,589 reviews	Search Scandinavian Airlines flights
SWISS	PriceFrom $416	Free Cancellation	Rating 7.5 1,797 reviews	Search SWISS flights
Delta	PriceFrom $419	Free Cancellation	Rating 7.9 8,003 reviews	Search Delta flights
KLM	PriceFrom $455	Free Cancellation	Rating 7.7 1,423 reviews	Search KLM flights
Air France	PriceFrom $458	Free Cancellation	Rating 7.4 1,498 reviews	Search Air France flights
Turkish Airlines	PriceFrom $488	Free Cancellation	Rating 7.3 4,063 reviews	Search Turkish Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Italy?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Italy from Chicago.

Can I find flights from Chicago to Italy with flexible booking policies on momondo?

All flight searches from Chicago to Italy on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to Italy?

momondo provides multiple filters to help you find the best flight to Italy from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to Italy right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Italy now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Italy and let you know when they change.

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Find better results for your trip to Italy

Popular cities in Italy

Flights to Romefrom $322

Flights to Milanfrom $327

Flights to Venicefrom $351

Flights to Naplesfrom $329

Flights to Florencefrom $342

Flights to Cataniafrom $357

Flights to Palermofrom $413

Flights to Bolognafrom $344

Flights to Barifrom $391

Flights to Olbiafrom $505

Flights to Pisafrom $411

Flights to Cagliarifrom $420

Cheap flights from Chicago to Italy from $214

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Italy departing on 2/22. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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American Airlines flights from Chicago to Italy

Our best American Airlines deals on Chicago to Italy flight tickets

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Our best British Airways deals on Chicago to Italy flight tickets

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How to get the cheapest flight ticket from Chicago to Italy

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Italy?

What is the cheapest day to depart on your flight to Italy?

What is the cheapest time of day to depart on your flight to Italy?

Our data shows that the cheapest Chicago to Italy flights are usually those with departure times in the evening. Our users have found flights to Italy in the evening for as low as $686. In contrast, the most expensive time of day to depart to Italy is in the afternoon when prices are around $960.

What is the cheapest Chicago to Italy flight route?

Fly from Chicago O'Hare Intl to Rome Fiumicino for the best Chicago - Italy flight prices

How far in advance should I book a flight to Italy?

What cabin class options are available on Chicago to Italy flights?

There are 3 cabin classes available to choose from on Chicago to Italy flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to Italy flights?

No. A direct flight is the cheapest option for a flight between Chicago to Italy.

What is the cheapest airline that flies from Chicago to Italy?

Scandinavian Airlines, Air Serbia, and British Airways are the most popular carriers operating from Chicago to Italy

What airlines fly to Italy?

How often are flights from Chicago to Italy delayed?

Historically, on average around 28% of flights between Chicago and Italy have experienced a delay on any given week. The average delay length over the past 12 months has been 164 minutes.

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

Generally, flights departing in the early afternoon tend to experience fewer delays. Flights in the morning have, in the past, seen delays more frequently in comparison.

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

Wednesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

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

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 24% of their flights experiencing any sort of delay.

How many flights depart from Chicago to Italy on average per day?

10 flights are operational daily from Chicago to Italy as of November 2025. The most popular departure time for this route is 3:00PM, with 53% of flights per day taking off in the evening.

How many flights depart from Chicago to Italy on average per week?

As of November 2025, there are 72 flights per week flying from Chicago to Italy. The most common day of the week flights depart is Mon, with 15% of flights taking off on this day.

Cheap Chicago to Italy flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Italy

Best Price Found

Fastest flight time

Direct flights

Airports in Italy

When did momondo last update prices for flights from Chicago to Italy?

How many operators does momondo search for flights from Chicago to Italy?

How old do you have to be to fly from Chicago to Italy?

What documentation or ID do you need to fly to Italy?

What is the most popular plane model from Chicago to Italy?

Best airlines flying from Chicago to Italy

Compare and see reviews for airlines that fly from Chicago to Italy with momondo

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Italy?

Can I find flights from Chicago to Italy with flexible booking policies on momondo?

How can momondo help me find flights from Chicago to Italy?

I’m not ready to book a flight from Chicago to Italy right now. Can momondo alert me if prices change?

An easier way to manage your Italy trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Italy

Popular cities in Italy

Popular flights according to clicks in the last 7 days on momondo