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

Aer Lingus, Air Serbia, and Delta 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.

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 29% of their flights experiencing any sort of delay.

How often are flights from Chicago to Italy delayed?

Historically, on average around 31% 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 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 18 different airlines that fly to Italy on a routine basis, so you have a few additional options to choose from.

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.

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 January 2026, 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.

$219 Cheap Flights from Chicago to Italy in 2026

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Cheap round-trip flights

Enter your travel dates to find the best prices.

6:00 pm - 6:25 pm

ORD

NAP

17h 25m

1 stop

7:10 pm - 4:00 pm

NAP

ORD

27h 50m

1 stop

$411TAP AIR PORTUGAL

Wed, Apr 22 - Sat, May 2

6:00 pm - 6:05 pm

ORD

FLR

17h 05m

1 stop

6:50 pm - 4:00 pm

FLR

ORD

28h 10m

1 stop

$412TAP AIR PORTUGAL

Wed, Apr 22 - Thu, Apr 30

6:00 pm - 11:40 am

ORD

NAP

34h 40m

1 stop

7:10 pm - 4:00 pm

NAP

ORD

27h 50m

1 stop

$415TAP AIR PORTUGAL

Wed, Apr 22 - Sat, May 2

7:20 pm - 9:10 pm

ORD

MXP

18h 50m

1 stop

8:00 pm - 4:45 pm

MXP

ORD

27h 45m

1 stop

$430Scandinavian Airlines

Sat, Feb 7 - Wed, Feb 11

7:15 pm - 11:25 am

ORD

MXP

33h 10m

2 stops

3:55 pm - 4:10 pm

MXP

ORD

31h 15m

1 stop

$437Scandinavian Airlines

Mon, Apr 20 - Thu, Apr 30

9:50 pm - 5:25 pm

ORD

NAP

12h 35m

1 stop

6:15 pm - 7:25 pm

NAP

ORD

31h 10m

1 stop

$480Lufthansa

Tue, Mar 3 - Mon, Mar 9

4:05 pm - 1:25 pm

ORD

NAP

14h 20m

1 stop

6:15 pm - 6:25 pm

NAP

ORD

31h 10m

1 stop

$488Lufthansa

Sun, Feb 1 - Tue, Feb 17

5:10 pm - 1:05 pm

ORD

NAP

12h 55m

1 stop

6:20 am - 2:55 pm

NAP

ORD

15h 35m

1 stop

$508American Airlines

Sun, Feb 1 - Tue, Feb 17

11:50 am - 6:40 pm

ORD

VCE

23h 50m

1 stop

7:40 pm - 6:25 pm

VCE

ORD

29h 45m

1 stop

$537Turkish Airlines

Thu, Jan 29 - Sun, Feb 1

11:25 am - 8:20 am

ORD

VCE

13h 55m

1 stop

9:20 am - 9:40 am

VCE

ORD

31h 20m

1 stop

$538Turkish Airlines

Tue, Mar 31 - Thu, Apr 9

TAP AIR PORTUGAL flights from Chicago to Italy

Our best TAP AIR PORTUGAL deals on Chicago to Italy flight tickets

TAP AIR PORTUGAL

Apr 22

ORD6:00 pmChicago O'Hare Intl

17h 25m

1 stop

NAP6:25 pmNaples

May 2

NAP7:10 pmNaples

27h 50m

1 stop

ORD4:00 pmChicago O'Hare Intl

$411

TAP AIR PORTUGAL

Apr 12

ORD6:00 pmChicago O'Hare Intl

17h 00m

1 stop

FLR6:00 pmFlorence Peretola

Apr 18

FLR6:45 pmFlorence Peretola

28h 15m

1 stop

ORD4:00 pmChicago O'Hare Intl

$412

TAP AIR PORTUGAL

Apr 22

ORD6:00 pmChicago O'Hare Intl

34h 40m

1 stop

NAP11:40 amNaples

May 2

NAP7:10 pmNaples

27h 50m

1 stop

ORD4:00 pmChicago O'Hare Intl

$415

American Airlines flights from Chicago to Italy

Our best American Airlines deals on Chicago to Italy flight tickets

American Airlines

Feb 1

ORD5:10 pmChicago O'Hare Intl

12h 55m

1 stop

NAP1:05 pmNaples

Feb 17

NAP6:20 amNaples

15h 35m

1 stop

ORD2:55 pmChicago O'Hare Intl

$508

American Airlines

Jan 21

ORD4:14 pmChicago O'Hare Intl

15h 41m

2 stops

FCO2:55 pmRome Fiumicino

Feb 3

FCO7:30 amRome Fiumicino

18h 52m

2 stops

ORD7:22 pmChicago O'Hare Intl

$513

American Airlines

Jan 30

ORD5:40 pmChicago O'Hare Intl

21h 45m

1 stop

NAP10:25 pmNaples

Feb 5

NAP6:20 amNaples

20h 50m

2 stops

ORD8:10 pmChicago O'Hare Intl

$585

Fly from

Fly to

Route

Depart

Return

Price

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Wed 4/22

6:00 pm-6:25 pm

1 stop17h 25m

Naples

Sat 5/2

7:10 pm-4:00 pm

1 stop27h 50m

$411

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Wed 4/22

6:00 pm-6:05 pm

1 stop17h 05m

Florence Peretola

Thu 4/30

6:50 pm-4:00 pm

1 stop28h 10m

$412

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Wed 4/22

6:00 pm-11:40 am

1 stop34h 40m

Naples

Sat 5/2

7:10 pm-4:00 pm

1 stop27h 50m

$415

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sat 2/7

7:20 pm-9:10 pm

1 stop18h 50m

Milan Malpensa

Wed 2/11

8:00 pm-4:45 pm

1 stop27h 45m

$430

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Mon 4/20

7:15 pm-11:25 am

2 stops33h 10m

Milan Malpensa

Thu 4/30

3:55 pm-4:10 pm

1 stop31h 15m

$437

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Tue 3/3

9:50 pm-5:25 pm

1 stop12h 35m

Naples

Mon 3/9

6:15 pm-7:25 pm

1 stop31h 10m

$480

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sun 2/1

4:05 pm-1:25 pm

1 stop14h 20m

Naples

Tue 2/17

6:15 pm-6:25 pm

1 stop31h 10m

$488

ChicagoNaples

ORD - NAP

ORDNAP

Chicago O'Hare Intl

Sun 2/1

5:10 pm-1:05 pm

1 stop12h 55m

Naples

Tue 2/17

6:20 am-2:55 pm

1 stop15h 35m

$508

ChicagoVenice

ORD - VCE

ORDVCE

Chicago O'Hare Intl

Thu 1/29

11:50 am-6:40 pm

1 stop23h 50m

Venice Marco Polo

Sun 2/1

7:40 pm-6:25 pm

1 stop29h 45m

$537

ChicagoVenice

ORD - VCE

ORDVCE

Chicago O'Hare Intl

Tue 3/31

11:25 am-8:20 am

1 stop13h 55m

Venice Marco Polo

Thu 4/9

9:20 am-9:40 am

1 stop31h 20m

$538

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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

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 $570, 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 $587.

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 $905. 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 $1,016.

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 $683 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	$568
Fastest flight time	8h 40m
Direct flights	Every day
Airports in Italy	416 airports

The best one-way flight to Italy from Chicago in the past 72 hours is $568. The best round-trip flight deal from Chicago to Italy found on momondo in the last 72 hours is $803.

The fastest flight from Chicago to Italy takes 8h 40m

Direct flights go from Chicago to Italy every day.

There are 416 airports in Italy. From Chicago there are direct flights to 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 January 2026, 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 39.99% of the total bookings. Other popular models include Boeing 787-8 Dreamliner with 23.40%, Boeing 787-10 Dreamliner with 19.37%, and Airbus A330-900neo with 10.47%.

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 $230	Free Cancellation	Rating 7.0 3,087 reviews	Search Iberia flights
TAP AIR PORTUGAL	PriceFrom $337	Free Cancellation	Rating 7.1 2,122 reviews	Search TAP AIR PORTUGAL flights
Air Canada	PriceFrom $390	Free Cancellation	Rating 7.1 10,627 reviews	Search Air Canada flights
Icelandair	PriceFrom $392	Free Cancellation	Rating 7.1 596 reviews	Search Icelandair flights
Scandinavian Airlines	PriceFrom $414	Free Cancellation	Rating 7.3 1,654 reviews	Search Scandinavian Airlines flights
SWISS	PriceFrom $414	Free Cancellation	Rating 7.5 1,850 reviews	Search SWISS flights
KLM	PriceFrom $455	Free Cancellation	Rating 7.7 1,440 reviews	Search KLM flights
Air France	PriceFrom $458	Free Cancellation	Rating 7.4 1,522 reviews	Search Air France flights
British Airways	PriceFrom $458	Free Cancellation	Rating 6.7 7,684 reviews	Search British Airways flights
Delta	PriceFrom $462	Free Cancellation	Rating 7.9 8,057 reviews	Search Delta 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 $299

Flights to Venicefrom $319

Flights to Naplesfrom $328

Flights to Florencefrom $324

Flights to Cataniafrom $362

Flights to Palermofrom $402

Flights to Bolognafrom $354

Flights to Barifrom $384

Flights to Olbiafrom $403

Flights to Pisafrom $376

Flights to Cagliarifrom $397

Cheap flights from Chicago to Italy from $219

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 2/7. 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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TAP AIR PORTUGAL flights from Chicago to Italy

Our best TAP AIR PORTUGAL 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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See travel insights to Italy from

How to get the cheapest flight ticket from Chicago to Italy

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 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?

Aer Lingus, Air Serbia, and Delta 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 31% 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 29% of their flights experiencing any sort of delay.

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