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

Scandinavian Airlines, Lufthansa, and KLM are the most popular carriers operating from Chicago to Italy

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.

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

As of December 2025, there are 40 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.

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 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?

5 flights are operational daily from Chicago to Italy as of December 2025. The most popular departure time for this route is 3:00PM, with 62% of flights per day taking off in the afternoon.

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.

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.

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 December 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.

$222 Cheap Flights from Chicago to Italy in 2025/26

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Cheap round-trip flights

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10:40 am - 10:30 am

ORD

VCE

16h 50m2 stops

11:20 am - 4:45 pm

VCE

ORD

12h 25m1 stop

$401Scandinavian Airlines

Mon, Feb 2 - Fri, Feb 13

7:10 pm - 6:45 pm

ORD

FCO

16h 35m1 stop

4:40 pm - 4:25 pm

FCO

ORD

29h 45m1 stop

$402TAP AIR PORTUGAL

Wed, Mar 4 - Thu, Mar 12

6:30 pm - 2:00 pm

ORD

FCO

12h 30m1 stop

11:25 am - 5:20 pm

FCO

ORD

12h 55m1 stop

$403Icelandair

Sat, Jan 17 - Mon, Jan 26

6:00 pm - 6:55 pm

ORD

FCO

17h 55m1 stop

4:45 am - 4:00 pm

FCO

ORD

18h 15m1 stop

$404TAP AIR PORTUGAL

Wed, May 6 - Wed, May 13

5:10 pm - 1:05 pm

ORD

NAP

12h 55m1 stop

6:20 am - 2:55 pm

NAP

ORD

15h 35m1 stop

$432American Airlines

Sun, Jan 18 - Tue, Feb 3

11:38 am - 11:45 am

ORD

NAP

41h 07m2 stops

12:40 pm - 1:50 pm

NAP

ORD

32h 10m1 stop

$434British Airways

Tue, Jan 20 - Thu, Feb 5

9:45 pm - 11:45 am

ORD

NAP

31h 00m1 stop

12:40 pm - 1:50 pm

NAP

ORD

32h 10m1 stop

$436British Airways

Tue, Jan 20 - Thu, Feb 5

6:25 pm - 1:05 pm

ORD

NAP

11h 40m1 stop

6:20 am - 2:55 pm

NAP

ORD

15h 35m1 stop

$482American Airlines

Sun, Feb 1 - Sun, Feb 8

9:50 pm - 5:25 pm

ORD

NAP

12h 35m1 stop

6:35 am - 1:10 pm

NAP

ORD

13h 35m1 stop

$484Lufthansa

Tue, Feb 24 - Sun, Mar 1

3:45 pm - 10:40 am

ORD

LIN

11h 55m1 stop

11:20 am - 7:00 pm

LIN

ORD

14h 40m1 stop

$578Aer Lingus

Wed, May 20 - Wed, May 27

American Airlines flights from Chicago to Italy

Our best American Airlines deals on Chicago to Italy flight tickets

American Airlines

Jan 18

ORD5:10 pmChicago O'Hare Intl

12h 55m

1 stop

NAP1:05 pmNaples

Feb 3

NAP6:20 amNaples

15h 35m

1 stop

ORD2:55 pmChicago O'Hare Intl

$432

Find similar

American Airlines

Feb 2

ORD6:25 pmChicago O'Hare Intl

13h 30m

1 stop

FCO2:55 pmRome Fiumicino

Feb 9

FCO7:00 pmRome Fiumicino

26h 55m

1 stop

ORD2:55 pmChicago O'Hare Intl

$457

Find similar

American Airlines

Feb 1

ORD6:25 pmChicago O'Hare Intl

11h 40m

1 stop

NAP1:05 pmNaples

Feb 8

NAP6:20 amNaples

15h 35m

1 stop

ORD2:55 pmChicago O'Hare Intl

$482

Find similar

British Airways flights from Chicago to Italy

Our best British Airways deals on Chicago to Italy flight tickets

British Airways

Jan 20

ORD11:38 amChicago O'Hare Intl

41h 07m

2 stops

NAP11:45 amNaples

Feb 5

NAP12:40 pmNaples

32h 10m

1 stop

ORD1:50 pmChicago O'Hare Intl

$434

Find similar

British Airways

Jan 20

ORD9:45 pmChicago O'Hare Intl

31h 00m

1 stop

NAP11:45 amNaples

Feb 5

NAP12:40 pmNaples

32h 10m

1 stop

ORD1:50 pmChicago O'Hare Intl

$436

Find similar

British Airways

Jan 20

ORD11:38 amChicago O'Hare Intl

41h 07m

2 stops

NAP11:45 amNaples

Feb 5

NAP12:40 pmNaples

36h 02m

2 stops

ORD5:42 pmChicago O'Hare Intl

$437

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Fly from

Fly to

Route

Depart

Return

Price

ChicagoVenice

ORD - VCE

ORDVCE

Chicago O'Hare Intl

Mon 2/2

10:40 am-10:30 am

2 stops16h 50m

Venice Marco Polo

Fri 2/13

11:20 am-4:45 pm

1 stop12h 25m

$401

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Wed 3/4

7:10 pm-6:45 pm

1 stop16h 35m

Rome Fiumicino

Thu 3/12

4:40 pm-4:25 pm

1 stop29h 45m

$402

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Sat 1/17

6:30 pm-2:00 pm

1 stop12h 30m

Rome Fiumicino

Mon 1/26

11:25 am-5:20 pm

1 stop12h 55m

$403

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Wed 5/6

6:00 pm-6:55 pm

1 stop17h 55m

Rome Fiumicino

Wed 5/13

4:45 am-4:00 pm

1 stop18h 15m

$404

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sun 1/18

5:10 pm-1:05 pm

1 stop12h 55m

Naples

Tue 2/3

6:20 am-2:55 pm

1 stop15h 35m

$432

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Tue 1/20

11:38 am-11:45 am

2 stops41h 07m

Naples

Thu 2/5

12:40 pm-1:50 pm

1 stop32h 10m

$434

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Tue 1/20

9:45 pm-11:45 am

1 stop31h 00m

Naples

Thu 2/5

12:40 pm-1:50 pm

1 stop32h 10m

$436

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sun 2/1

6:25 pm-1:05 pm

1 stop11h 40m

Naples

Sun 2/8

6:20 am-2:55 pm

1 stop15h 35m

$482

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Tue 2/24

9:50 pm-5:25 pm

1 stop12h 35m

Naples

Sun 3/1

6:35 am-1:10 pm

1 stop13h 35m

$484

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Wed 5/20

3:45 pm-10:40 am

1 stop11h 55m

Milan Linate

Wed 5/27

11:20 am-7:00 pm

1 stop14h 40m

$578

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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, Monday is the cheapest day to fly to Italy from Chicago. The lowest ticket price found for a Monday 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 $963.

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 $794 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 $766 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	$459
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 $459. The best round-trip flight deal from Chicago to Italy found on momondo in the last 72 hours is $737.

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 December 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 41.59% of the total bookings. Other popular models include Boeing 787-8 Dreamliner with 23.53%, Boeing 787-10 Dreamliner with 21.38%, and Airbus A330-900neo with 8.66%.

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
Iberia	PriceFrom $292	Free Cancellation	Rating 7.0 3,040 reviews	Search Iberia flights
TAP AIR PORTUGAL	PriceFrom $337	Free Cancellation	Rating 7.1 2,081 reviews	Search TAP AIR PORTUGAL flights
Air Canada	PriceFrom $390	Free Cancellation	Rating 7.1 10,500 reviews	Search Air Canada flights
Icelandair	PriceFrom $392	Free Cancellation	Rating 7.0 584 reviews	Search Icelandair flights
Scandinavian Airlines	PriceFrom $414	Free Cancellation	Rating 7.4 1,592 reviews	Search Scandinavian Airlines flights
SWISS	PriceFrom $414	Free Cancellation	Rating 7.5 1,804 reviews	Search SWISS flights
Delta	PriceFrom $419	Free Cancellation	Rating 7.9 8,011 reviews	Search Delta flights
KLM	PriceFrom $455	Free Cancellation	Rating 7.7 1,430 reviews	Search KLM flights
Air France	PriceFrom $458	Free Cancellation	Rating 7.4 1,502 reviews	Search Air France flights
Turkish Airlines	PriceFrom $488	Free Cancellation	Rating 7.3 4,077 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 $323

Flights to Milanfrom $272

Flights to Venicefrom $342

Flights to Naplesfrom $343

Flights to Florencefrom $343

Flights to Cataniafrom $361

Flights to Palermofrom $389

Flights to Bolognafrom $351

Flights to Barifrom $384

Flights to Olbiafrom $433

Flights to Pisafrom $377

Flights to Cagliarifrom $481

Cheap flights from Chicago to Italy from $222

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 3/2. 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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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 $963.

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, Lufthansa, and KLM 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?

5 flights are operational daily from Chicago to Italy as of December 2025. The most popular departure time for this route is 3:00PM, with 62% of flights per day taking off in the afternoon.

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

As of December 2025, there are 40 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