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 36% of people opting to fly with this airline when traveling to Italy. Keep in mind that there are 19 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?

19 flights are operational daily from Chicago to Italy as of August 2025. The most popular departure time for this route is 3:00PM, with 65% of flights per day taking off in the afternoon.

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

TAP AIR PORTUGAL and Turkish Airlines are the most popular carriers operating from Chicago to Italy

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

As of August 2025, there are 139 flights per week flying from Chicago to Italy. The most common day of the week flights depart is Wed, 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 August 2025, there are 19 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.

$177 Cheap Flights from Chicago to Italy in 2025

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Find the cheapest flights from Chicago to Italy

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

7:10 pm - 6:45 pmORD-FCO

16h 35m1 stop

7:35 pm - 3:15 pmFCO-ORD

26h 40m1 stop

$333TAP AIR PORTUGAL

Find Deal

Wed, Dec 3 - Thu, Dec 11

6:15 pm - 12:10 amORD-FCO

22h 55m1 stop

5:45 pm - 12:35 pmFCO-ORD

25h 50m1 stop

$334TAP AIR PORTUGAL

Find Deal

Sat, Oct 11 - Wed, Oct 22

7:10 pm - 11:25 amORD-FCO

33h 15m1 stop

6:00 am - 3:00 pmFCO-ORD

16h 00m1 stop

$338TAP AIR PORTUGAL

Find Deal

Wed, Nov 5 - Wed, Nov 12

3:45 pm - 7:45 amORD-FCO

9h 00mnonstop

9:45 am - 1:10 pmFCO-ORD

10h 25mnonstop

$384United Airlines

Find Deal

Wed, Nov 12 - Thu, Nov 27

8:00 am - 8:30 amORD-FCO

17h 30m1 stop

9:45 am - 1:10 pmFCO-ORD

10h 25mnonstop

$389United Airlines

Find Deal

Mon, Nov 3 - Thu, Nov 13

3:45 pm - 7:45 amORD-FCO

9h 00mnonstop

12:25 pm - 6:25 pmFCO-ORD

13h 00m1 stop

$412Lufthansa

Find Deal

Wed, Nov 12 - Thu, Nov 27

10:50 pm - 6:20 pmORD-FCO

13h 30m1 stop

9:45 am - 1:10 pmFCO-ORD

10h 25mnonstop

$416Lufthansa

Find Deal

Mon, Oct 27 - Wed, Nov 5

10:45 pm - 11:50 amORD-NAP

31h 05m1 stop

12:35 pm - 1:50 pmNAP-ORD

32h 15m1 stop

$513British Airways

Find Deal

Sun, Oct 26 - Sun, Nov 9

5:10 pm - 1:05 pmORD-NAP

12h 55m1 stop

12:40 pm - 1:50 pmNAP-ORD

32h 10m1 stop

$557British Airways

Find Deal

Sun, Feb 8 - Thu, Feb 19

6:45 pm - 5:45 pmORD-LIN

16h 00m1 stop

7:15 am - 5:38 pmLIN-ORD

17h 23m2 stops

$619American Airlines

Find Deal

Sun, Nov 9 - Thu, Nov 20

British Airways flights from Chicago to Italy

Our best British Airways deals on Chicago to Italy flight tickets

British Airways

Oct 26

ORD10:45 pmChicago O'Hare Intl

31h 05m

1 stop

NAP11:50 amNaples

Nov 9

NAP12:35 pmNaples

32h 15m

1 stop

ORD1:50 pmChicago O'Hare Intl

$513

Find similar

British Airways

Aug 19

ORD5:05 pmChicago O'Hare Intl

9h 05m

FCO9:10 amRome Fiumicino

Aug 26

FCO11:05 amRome Fiumicino

10h 25m

ORD2:30 pmChicago O'Hare Intl

$745

Find similar

British Airways

Aug 20

ORD7:15 pmChicago O'Hare Intl

11h 20m

1 stop

LIN1:35 pmMilan Linate

Aug 28

LIN7:25 amMilan Linate

13h 30m

1 stop

ORD1:55 pmChicago O'Hare Intl

$6,179

Find similar

American Airlines flights from Chicago to Italy

Our best American Airlines deals on Chicago to Italy flight tickets

American Airlines

Nov 9

ORD6:45 pmChicago O'Hare Intl

16h 00m

1 stop

LIN5:45 pmMilan Linate

Nov 20

LIN7:15 amMilan Linate

17h 23m

2 stops

ORD5:38 pmChicago O'Hare Intl

$619

Find similar

American Airlines

Aug 23

ORD8:35 pmChicago O'Hare Intl

9h 25m

NAP1:00 pmNaples

Aug 30

NAP3:00 pmNaples

10h 50m

ORD6:50 pmChicago O'Hare Intl

$748

Find similar

American Airlines

Aug 23

ORD8:40 amChicago O'Hare Intl

18h 20m

1 stop

NAP10:00 amNaples

Aug 30

NAP3:00 pmNaples

10h 50m

ORD6:50 pmChicago O'Hare Intl

$753

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Wed 12/3

7:10 pm-6:45 pm

1 stop16h 35m

Rome Fiumicino

Thu 12/11

7:35 pm-3:15 pm

1 stop26h 40m

$333

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Sat 10/11

6:15 pm-12:10 am

1 stop22h 55m

Rome Fiumicino

Wed 10/22

5:45 pm-12:35 pm

1 stop25h 50m

$334

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Wed 11/5

7:10 pm-11:25 am

1 stop33h 15m

Rome Fiumicino

Wed 11/12

6:00 am-3:00 pm

1 stop16h 00m

$338

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Wed 11/12

3:45 pm-7:45 am

Nonstop9h 00m

Rome Fiumicino

Thu 11/27

9:45 am-1:10 pm

Nonstop10h 25m

$384

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Mon 11/3

8:00 am-8:30 am

1 stop17h 30m

Rome Fiumicino

Thu 11/13

9:45 am-1:10 pm

Nonstop10h 25m

$389

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Wed 11/12

3:45 pm-7:45 am

Nonstop9h 00m

Rome Fiumicino

Thu 11/27

12:25 pm-6:25 pm

1 stop13h 00m

$412

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Mon 10/27

10:50 pm-6:20 pm

1 stop13h 30m

Rome Fiumicino

Wed 11/5

9:45 am-1:10 pm

Nonstop10h 25m

$416

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sun 10/26

10:45 pm-11:50 am

1 stop31h 05m

Naples

Sun 11/9

12:35 pm-1:50 pm

1 stop32h 15m

$513

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sun 2/8

5:10 pm-1:05 pm

1 stop12h 55m

Naples

Thu 2/19

12:40 pm-1:50 pm

1 stop32h 10m

$557

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Sun 11/9

6:45 pm-5:45 pm

1 stop16h 00m

Milan Linate

Thu 11/20

7:15 am-5:38 pm

2 stops17h 23m

$619

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Other information

What is the cheapest month to fly to Italy?

The cheapest month to fly to Italy from Chicago is in February. Flight prices, which tend to average around $548, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of February, then book flights to Italy from Chicago during January instead. Flights to Italy in January, while not as cheap as those in February, still average around $567.

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 $884. 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 Saturday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Italy for around $1,002.

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 $942.

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 $795 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 $737 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.

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	$177
Fastest flight time	9h 00m
Direct flights	Every day
Airports in Italy	6 airports

The best one-way flight to Italy from Chicago in the past 72 hours is $177. The best round-trip flight deal from Chicago to Italy found on momondo in the last 72 hours is $333.

The fastest flight from Chicago to Italy takes 9h 00m

Direct flights go from Chicago to Italy every day.

There are 6 airports near Italy: Milan Linate (LIN), Rome Fiumicino (FCO), Milan Malpensa (MXP), Venice Marco Polo (VCE), Naples (NAP), Florence Peretola (FLR)

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 August 2025, there are 19 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 45.98% of the total bookings. Other popular models include Boeing 787-8 Dreamliner with 27.05%, Boeing 787-10 Dreamliner with 15.61%, and Airbus A330 with 8.21%.

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 $365	Free Cancellation	Rating 7.1 1,948 reviews	Search TAP AIR PORTUGAL flights
Icelandair	PriceFrom $379	Free Cancellation	Rating 7.0 526 reviews	Search Icelandair flights
SWISS	PriceFrom $413	Free Cancellation	Rating 7.5 1,699 reviews	Search SWISS flights
Scandinavian Airlines	PriceFrom $414	Free Cancellation	Rating 7.4 1,468 reviews	Search Scandinavian Airlines flights
Delta	PriceFrom $419	Free Cancellation	Rating 8.0 7,980 reviews	Search Delta flights
KLM	PriceFrom $455	Free Cancellation	Rating 7.8 1,381 reviews	Search KLM flights
Air France	PriceFrom $458	Free Cancellation	Rating 7.4 1,467 reviews	Search Air France flights
Iberia	PriceFrom $466	Free Cancellation	Rating 7.0 2,878 reviews	Search Iberia flights
Turkish Airlines	PriceFrom $488	Free Cancellation	Rating 7.3 3,940 reviews	Search Turkish Airlines flights
Air Canada	PriceFrom $500	Free Cancellation	Rating 7.1 9,949 reviews	Search Air Canada 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.

An easier way to manage your Italy trip

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Find better results for your trip to Italy

Popular cities in Italy

Flights to Romefrom $321

Flights to Milanfrom $250

Flights to Venicefrom $344

Flights to Naplesfrom $349

Flights to Florencefrom $334

Flights to Cataniafrom $352

Flights to Palermofrom $406

Flights to Bolognafrom $345

Flights to Barifrom $484

Flights to Olbiafrom $495

Flights to Cagliarifrom $471

Flights to Pisafrom $408

Cheap flights from Chicago to Italy from $177

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 11/28. 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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Big names and deals

Filter for what you want

Filter for what you want

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Find the cheapest flights from Chicago to Italy

Cheap round-trip flights

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British Airways flights from Chicago to Italy

Our best British Airways deals on Chicago to Italy flight tickets

American Airlines flights from Chicago to Italy

Our best American Airlines deals on Chicago to Italy flight tickets

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

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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 $942.

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.

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

TAP AIR PORTUGAL and Turkish Airlines are the most popular carriers operating from Chicago to Italy

What airlines fly to Italy?

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

19 flights are operational daily from Chicago to Italy as of August 2025. The most popular departure time for this route is 3:00PM, with 65% of flights per day taking off in the afternoon.

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

As of August 2025, there are 139 flights per week flying from Chicago to Italy. The most common day of the week flights depart is Wed, 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