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

As of September 2025, there are 140 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 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 38% 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?

20 flights are operational daily from Chicago to Italy as of September 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 is the most popular carrier operating from Chicago to Italy

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 September 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.

$206 Cheap Flights from Chicago to Italy in 2025/26

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Find the cheapest flights from Chicago to Italy

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

8:40 am - 9:15 amORD-FCO

17h 35m1 stop

2:20 pm - 6:25 pmFCO-ORD

35h 05m1 stop

$466Multiple Airlines

Find Deal

Wed, Oct 22 - Mon, Nov 3

8:20 pm - 11:05 amORD-FCO

32h 45m1 stop

11:55 am - 5:45 pmFCO-ORD

35h 50m1 stop

$467Scandinavian Airlines

Find Deal

Sat, Mar 14 - Wed, Mar 18

3:45 pm - 7:45 amORD-FCO

9h 00mnonstop

12:20 pm - 6:25 pmFCO-ORD

13h 05m1 stop

$468Lufthansa

Find Deal

Tue, Nov 11 - Fri, Nov 21

3:45 pm - 7:45 amORD-FCO

9h 00mnonstop

7:05 am - 2:10 pmFCO-ORD

13h 05m1 stop

$478Lufthansa

Find Deal

Tue, Mar 3 - Tue, Mar 10

3:45 pm - 7:45 amORD-FCO

9h 00mnonstop

9:45 am - 2:10 pmFCO-ORD

10h 25mnonstop

$479United Airlines

Find Deal

Mon, Mar 2 - Thu, Mar 12

10:40 am - 9:15 amORD-FCO

15h 35m1 stop

1:30 pm - 1:10 pmFCO-ORD

30h 40m1 stop

$484United Airlines

Find Deal

Tue, Oct 14 - Mon, Nov 3

8:40 pm - 1:00 pmORD-NAP

9h 20mnonstop

3:00 pm - 6:50 pmNAP-ORD

10h 50mnonstop

$557American Airlines

Find Deal

Sun, Sep 28 - Tue, Oct 14

8:40 pm - 1:00 pmORD-NAP

9h 20mnonstop

3:00 pm - 6:50 pmNAP-ORD

10h 50mnonstop

$559American Airlines

Find Deal

Sun, Sep 28 - Tue, Oct 14

8:45 am - 6:55 pmORD-NAP

27h 10m2 stops

7:40 pm - 6:33 pmNAP-ORD

28h 53m2 stops

$565ITA Airways

Find Deal

Sun, Mar 1 - Mon, Mar 9

8:55 am - 10:40 pmORD-NAP

30h 45m2 stops

7:40 pm - 6:33 pmNAP-ORD

28h 53m2 stops

$615ITA Airways

Find Deal

Thu, Mar 5 - Mon, Mar 9

United Airlines flights from Chicago to Italy

Our best United Airlines deals on Chicago to Italy flight tickets

United Airlines

Mar 2

ORD3:45 pmChicago O'Hare Intl

9h 00m

FCO7:45 amRome Fiumicino

Mar 12

FCO9:45 amRome Fiumicino

10h 25m

ORD2:10 pmChicago O'Hare Intl

$479

Find similar

United Airlines

Oct 14

ORD10:40 amChicago O'Hare Intl

15h 35m

1 stop

FCO9:15 amRome Fiumicino

Nov 3

FCO1:30 pmRome Fiumicino

30h 40m

1 stop

ORD1:10 pmChicago O'Hare Intl

$484

Find similar

United Airlines

Oct 26

ORD4:45 pmChicago O'Hare Intl

9h 00m

FCO7:45 amRome Fiumicino

Nov 6

FCO11:00 amRome Fiumicino

19h 43m

1 stop

ORD11:43 pmChicago O'Hare Intl

$489

Find similar

American Airlines flights from Chicago to Italy

Our best American Airlines deals on Chicago to Italy flight tickets

American Airlines

Sep 28

ORD8:40 pmChicago O'Hare Intl

9h 20m

NAP1:00 pmNaples

Oct 14

NAP3:00 pmNaples

10h 50m

ORD6:50 pmChicago O'Hare Intl

$557

Find similar

American Airlines

Sep 28

ORD8:40 pmChicago O'Hare Intl

9h 20m

NAP1:00 pmNaples

Oct 14

NAP3:00 pmNaples

10h 50m

ORD6:50 pmChicago O'Hare Intl

$559

Find similar

American Airlines

Oct 16

ORD8:50 pmChicago O'Hare Intl

9h 10m

NAP1:00 pmNaples

Oct 23

NAP3:00 pmNaples

10h 50m

ORD6:50 pmChicago O'Hare Intl

$563

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Wed 10/22

8:40 am-9:15 am

1 stop17h 35m

Rome Fiumicino

Mon 11/3

2:20 pm-6:25 pm

1 stop35h 05m

$466

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Sat 3/14

8:20 pm-11:05 am

1 stop32h 45m

Rome Fiumicino

Wed 3/18

11:55 am-5:45 pm

1 stop35h 50m

$467

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Tue 11/11

3:45 pm-7:45 am

Nonstop9h 00m

Rome Fiumicino

Fri 11/21

12:20 pm-6:25 pm

1 stop13h 05m

$468

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Tue 3/3

3:45 pm-7:45 am

Nonstop9h 00m

Rome Fiumicino

Tue 3/10

7:05 am-2:10 pm

1 stop13h 05m

$478

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Mon 3/2

3:45 pm-7:45 am

Nonstop9h 00m

Rome Fiumicino

Thu 3/12

9:45 am-2:10 pm

Nonstop10h 25m

$479

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Tue 10/14

10:40 am-9:15 am

1 stop15h 35m

Rome Fiumicino

Mon 11/3

1:30 pm-1:10 pm

1 stop30h 40m

$484

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sun 9/28

8:40 pm-1:00 pm

Nonstop9h 20m

Naples

Tue 10/14

3:00 pm-6:50 pm

Nonstop10h 50m

$557

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sun 9/28

8:40 pm-1:00 pm

Nonstop9h 20m

Naples

Tue 10/14

3:00 pm-6:50 pm

Nonstop10h 50m

$559

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sun 3/1

8:45 am-6:55 pm

2 stops27h 10m

Naples

Mon 3/9

7:40 pm-6:33 pm

2 stops28h 53m

$565

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Thu 3/5

8:55 am-10:40 pm

2 stops30h 45m

Naples

Mon 3/9

7:40 pm-6:33 pm

2 stops28h 53m

$615

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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

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 $554, 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 $572.

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 $891. 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 Friday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Italy for around $1,004.

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 $949.

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 $790 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 $735 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	$461
Fastest flight time	8h 30m
Direct flights	Every day
Airports in Italy	1 airport

The best one-way flight to Italy from Chicago in the past 72 hours is $461. The best round-trip flight deal from Chicago to Italy found on momondo in the last 72 hours is $625.

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

Direct flights go from Chicago to Italy every day.

There is 1 airport near Italy: 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 September 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 46.41% of the total bookings. Other popular models include Boeing 787-8 Dreamliner with 24.87%, Boeing 787-10 Dreamliner with 17.35%, and Airbus A330 with 6.33%.

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 $357	Free Cancellation	Rating 7.1 1,977 reviews	Search TAP AIR PORTUGAL flights
Icelandair	PriceFrom $382	Free Cancellation	Rating 7.0 545 reviews	Search Icelandair flights
SWISS	PriceFrom $413	Free Cancellation	Rating 7.6 1,737 reviews	Search SWISS flights
Scandinavian Airlines	PriceFrom $414	Free Cancellation	Rating 7.4 1,486 reviews	Search Scandinavian Airlines flights
Delta	PriceFrom $419	Free Cancellation	Rating 7.9 7,961 reviews	Search Delta flights
Iberia	PriceFrom $431	Free Cancellation	Rating 7.0 2,925 reviews	Search Iberia flights
KLM	PriceFrom $455	Free Cancellation	Rating 7.8 1,386 reviews	Search KLM flights
Air France	PriceFrom $458	Free Cancellation	Rating 7.4 1,468 reviews	Search Air France flights
Turkish Airlines	PriceFrom $488	Free Cancellation	Rating 7.3 3,965 reviews	Search Turkish Airlines flights
United Airlines	PriceFrom $496	Free Cancellation	Rating 7.4 8,926 reviews	Search United 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 $340

Flights to Milanfrom $314

Flights to Venicefrom $357

Flights to Naplesfrom $357

Flights to Florencefrom $351

Flights to Cataniafrom $438

Flights to Palermofrom $425

Flights to Bolognafrom $346

Flights to Barifrom $436

Flights to Olbiafrom $486

Flights to Cagliarifrom $522

Flights to Pisafrom $375

Cheap flights from Chicago to Italy from $206

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 11/16. 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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Find the cheapest flights from Chicago to Italy

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United Airlines flights from Chicago to Italy

Our best United Airlines 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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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 $949.

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?

TAP AIR PORTUGAL is the most popular carrier operating from Chicago to Italy

What airlines fly to Italy?

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

20 flights are operational daily from Chicago to Italy as of September 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 September 2025, there are 140 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