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

As of November 2025, there are 73 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.

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 55% of flights per day taking off in the afternoon.

Which airline has the best punctuality record on $[0,article:'genitive ']$[0,place:'genitive'] $[1, preposition:'to ']$[1, article:'to ']$[1, place:'to'] 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.

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 18 different airlines that fly to Italy on a routine basis, so you have a few additional options to choose from.

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

Scandinavian Airlines, TAP AIR PORTUGAL, and Air Serbia are the most popular carriers operating from Chicago to Italy

How often are flights $[0, preposition:'from ']$[0, article:'from ']$[0, place:'from'] $[1, preposition:'to ']$[1, article:'to ']$[1, place:'to'] delayed?

Historically, on average around 28% of flights between $[0, place:'genitive'] and $[1, place:'genitive'] 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 $[0,article:'genitive ']$[0,place:'genitive'] $[1, preposition:'to ']$[1, article:'to ']$[1, place:'to'] 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.

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 18 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.

$213 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 amORD-VCE

16h 50m2 stops

11:20 am - 4:45 pmVCE-ORD

12h 25m1 stop

$391Scandinavian Airlines

Find Deal

seg, fev 2 - sex, fev 6

10:10 am - 11:30 amORD-FLR

18h 20m2 stops

7:55 pm - 4:10 pmFLR-ORD

27h 15m1 stop

$398Scandinavian Airlines

Find Deal

ter, abr 7 - ter, abr 14

6:59 pm - 10:30 amORD-VCE

32h 31m2 stops

11:05 am - 4:55 pmVCE-ORD

12h 50m1 stop

$402Scandinavian Airlines

Find Deal

qua, jan 28 - dom, fev 1

7:10 pm - 6:45 pmORD-FCO

16h 35m1 stop

6:00 am - 3:00 pmFCO-ORD

16h 00m1 stop

$413TAP AIR PORTUGAL

Find Deal

qua, dez 3 - qua, dez 10

7:10 pm - 11:25 amORD-FCO

33h 15m1 stop

4:40 pm - 3:00 pmFCO-ORD

29h 20m1 stop

$414TAP AIR PORTUGAL

Find Deal

qua, dez 10 - ter, dez 23

4:20 pm - 1:25 pmORD-NAP

14h 05m1 stop

3:10 pm - 1:10 pmNAP-ORD

29h 00m2 stops

$501Lufthansa

Find Deal

dom, jan 11 - ter, jan 27

3:20 pm - 1:25 pmORD-NAP

15h 05m1 stop

3:10 pm - 2:10 pmNAP-ORD

30h 00m2 stops

$503Lufthansa

Find Deal

dom, jan 11 - seg, jan 26

11:25 am - 2:50 pmORD-NAP

20h 25m1 stop

3:50 pm - 9:40 amNAP-ORD

24h 50m1 stop

$519Turkish Airlines

Find Deal

ter, abr 21 - qua, abr 29

3:00 pm - 6:10 pmORD-LIN

20h 10m1 stop

7:00 am - 1:10 pmLIN-ORD

13h 10m1 stop

$523ITA Airways

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qua, abr 1 - sex, abr 10

8:50 am - 11:40 amORD-LIN

19h 50m2 stops

11:30 am - 1:10 pmLIN-ORD

32h 40m1 stop

$550ITA Airways

Find Deal

dom, abr 26 - ter, mai 12

SWISS flights from Chicago to Italy

Our best SWISS deals on Chicago to Italy flight tickets

SWISS

Jan 11

ORD6:50 pmChicago O'Hare Intl

12h 20m

1 stop

NAP2:10 pmNaples

Jan 30

NAP10:10 amNaples

13h 10m

1 stop

ORD4:20 pmChicago O'Hare Intl

$518

Find similar

SWISS

Jan 14

ORD6:50 pmChicago O'Hare Intl

12h 25m

1 stop

NAP2:15 pmNaples

Jan 21

NAP6:35 amNaples

16h 45m

2 stops

ORD4:20 pmChicago O'Hare Intl

$521

Find similar

SWISS

Jan 12

ORD6:50 pmChicago O'Hare Intl

17h 05m

2 stops

NAP6:55 pmNaples

Jan 26

NAP3:00 pmNaples

32h 20m

1 stop

ORD4:20 pmChicago O'Hare Intl

$528

Find similar

KLM flights from Chicago to Italy

Our best KLM deals on Chicago to Italy flight tickets

KLM

Jan 12

ORD5:55 pmChicago O'Hare Intl

32h 40m

2 stops

NAP9:35 amNaples

Jan 26

NAP1:15 pmNaples

34h 39m

2 stops

ORD4:54 pmChicago O'Hare Intl

$546

Find similar

KLM

Jan 14

ORD1:54 pmChicago O'Hare Intl

14h 36m

2 stops

NAP11:30 amNaples

Jan 21

NAP10:25 amNaples

17h 39m

2 stops

ORD9:04 pmChicago O'Hare Intl

$550

Find similar

KLM

Nov 24

MDW1:15 pmChicago Midway

12h 55m

2 stops

FCO9:10 amRome Fiumicino

Dec 9

FCO6:10 amRome Fiumicino

17h 24m

2 stops

MDW4:34 pmChicago Midway

$579

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Fly from

Fly to

Route

Depart

Return

Price

ChicagoVenice

ORD - VCE

ORDVCE

Chicago O'Hare Intl

seg 2/2

10:40 am-10:30 am

2 stops16h 50m

Venice Marco Polo

sex 2/6

11:20 am-4:45 pm

1 stop12h 25m

$391

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

ter 4/7

10:10 am-11:30 am

2 stops18h 20m

Florence Peretola

ter 4/14

7:55 pm-4:10 pm

1 stop27h 15m

$398

ChicagoVenice

ORD - VCE

ORDVCE

Chicago O'Hare Intl

qua 1/28

6:59 pm-10:30 am

2 stops32h 31m

Venice Marco Polo

dom 2/1

11:05 am-4:55 pm

1 stop12h 50m

$402

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

qua 12/3

7:10 pm-6:45 pm

1 stop16h 35m

Rome Fiumicino

qua 12/10

6:00 am-3:00 pm

1 stop16h 00m

$413

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

qua 12/10

7:10 pm-11:25 am

1 stop33h 15m

Rome Fiumicino

ter 12/23

4:40 pm-3:00 pm

1 stop29h 20m

$414

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

dom 1/11

4:20 pm-1:25 pm

1 stop14h 05m

Naples

ter 1/27

3:10 pm-1:10 pm

2 stops29h 00m

$501

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

dom 1/11

3:20 pm-1:25 pm

1 stop15h 05m

Naples

seg 1/26

3:10 pm-2:10 pm

2 stops30h 00m

$503

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

ter 4/21

11:25 am-2:50 pm

1 stop20h 25m

Naples

qua 4/29

3:50 pm-9:40 am

1 stop24h 50m

$519

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

qua 4/1

3:00 pm-6:10 pm

1 stop20h 10m

Milan Linate

sex 4/10

7:00 am-1:10 pm

1 stop13h 10m

$523

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

dom 4/26

8:50 am-11:40 am

2 stops19h 50m

Milan Linate

ter 5/12

11:30 am-1:10 pm

1 stop32h 40m

$550

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

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 $578, 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 $901. 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 $1,022.

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 $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 $769 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	$481
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 $481. The best round-trip flight deal from Chicago to Italy found on momondo in the last 72 hours is $761.

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 18 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 $338	Free Cancellation	Rating 7.1 2,067 reviews	Search TAP AIR PORTUGAL flights
Air Canada	PriceFrom $390	Free Cancellation	Rating 7.1 10,462 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 1,584 reviews	Search Scandinavian Airlines flights
Iberia	PriceFrom $415	Free Cancellation	Rating 7.0 3,027 reviews	Search Iberia flights
SWISS	PriceFrom $416	Free Cancellation	Rating 7.5 1,788 reviews	Search SWISS flights
Delta	PriceFrom $419	Free Cancellation	Rating 7.9 8,002 reviews	Search Delta flights
Air France	PriceFrom $458	Free Cancellation	Rating 7.4 1,493 reviews	Search Air France flights
Turkish Airlines	PriceFrom $488	Free Cancellation	Rating 7.3 4,043 reviews	Search Turkish Airlines flights
KLM	PriceFrom $491	Free Cancellation	Rating 7.7 1,414 reviews	Search KLM 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 $309

Flights to Venicefrom $356

Flights to Naplesfrom $361

Flights to Florencefrom $354

Flights to Cataniafrom $406

Flights to Palermofrom $406

Flights to Bolognafrom $343

Flights to Barifrom $394

Flights to Olbiafrom $499

Flights to Pisafrom $409

Flights to Cagliarifrom $493

Cheap flights from Chicago to Italy from $212

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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SWISS flights from Chicago to Italy

Our best SWISS deals on Chicago to Italy flight tickets

KLM flights from Chicago to Italy

Our best KLM 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, TAP AIR PORTUGAL, and Air Serbia are the most popular carriers operating from Chicago to Italy

What airlines fly to Italy?

How often are flights $[0, preposition:'from ']$[0, article:'from ']$[0, place:'from'] $[1, preposition:'to ']$[1, article:'to ']$[1, place:'to'] delayed?

Historically, on average around 28% of flights between $[0, place:'genitive'] and $[1, place:'genitive'] 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 $[0,article:'genitive ']$[0,place:'genitive'] $[1, preposition:'to ']$[1, article:'to ']$[1, place:'to'] 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.

Which airline has the best punctuality record on $[0,article:'genitive ']$[0,place:'genitive'] $[1, preposition:'to ']$[1, article:'to ']$[1, place:'to'] 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 55% of flights per day taking off in the afternoon.

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

As of November 2025, there are 73 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