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.

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

6 flights are operational daily from Chicago to Italy as of October 2025. The most popular departure time for this route is 4:00PM, 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 October 2025, there are 44 flights per week flying from Chicago to Italy. The most common day of the week flights depart is Wed, with 25% 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 October 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.

$178 Cheap Flights from Chicago to Italy in 2025/26

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Cheap round-trip flights

Enter your travel dates to find the best prices.

10:24 am - 10:30 amORD-VCE

17h 06m2 stops

11:20 am - 4:45 pmVCE-ORD

12h 25m1 stop

$392Scandinavian Airlines

Find Deal

Thu, Jan 29 - Fri, Feb 6

8:25 pm - 6:45 pmORD-FCO

15h 20m1 stop

7:35 pm - 2:45 pmFCO-ORD

26h 10m1 stop

$408TAP AIR PORTUGAL

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Sun, Nov 9 - Sat, Nov 22

11:50 am - 9:05 amORD-MXP

14h 15m1 stop

6:40 pm - 6:25 pmMXP-ORD

30h 45m1 stop

$496Turkish Airlines

Find Deal

Fri, Nov 14 - Mon, Nov 17

11:50 am - 6:40 pmORD-VCE

23h 50m1 stop

7:40 pm - 10:05 amVCE-ORD

21h 25m1 stop

$497Turkish Airlines

Find Deal

Fri, Nov 14 - Thu, Nov 20

9:50 pm - 4:30 pmORD-FLR

11h 40m1 stop

6:30 am - 1:10 pmFLR-ORD

13h 40m1 stop

$506Lufthansa

Find Deal

Fri, Nov 28 - Fri, Dec 5

9:50 pm - 8:40 pmORD-FLR

15h 50m1 stop

7:10 am - 6:25 pmFLR-ORD

18h 15m1 stop

$509Lufthansa

Find Deal

Thu, Jan 1 - Mon, Jan 19

11:00 am - 2:45 pmORD-FLR

21h 45m2 stops

6:30 am - 6:28 pmFLR-ORD

17h 58m2 stops

$523ITA Airways

Find Deal

Wed, Mar 11 - Wed, Mar 18

6:50 pm - 2:20 pmORD-FLR

12h 30m1 stop

6:35 am - 3:20 pmFLR-ORD

15h 45m1 stop

$534United Airlines

Find Deal

Thu, Dec 11 - Thu, Dec 25

6:20 pm - 4:30 pmORD-FLR

15h 10m2 stops

6:30 am - 8:05 pmFLR-ORD

20h 35m1 stop

$536United Airlines

Find Deal

Mon, Dec 1 - Wed, Dec 10

10:48 am - 10:10 amORD-LIN

16h 22m2 stops

8:00 pm - 6:10 pmLIN-ORD

29h 10m2 stops

$586ITA Airways

Find Deal

Wed, Nov 12 - Tue, Nov 18

Scandinavian Airlines flights from Chicago to Italy

Our best Scandinavian Airlines deals on Chicago to Italy flight tickets

Scandinavian Airlines

Jan 29

ORD10:24 amChicago O'Hare Intl

17h 06m

2 stops

VCE10:30 amVenice Marco Polo

Feb 6

VCE11:20 amVenice Marco Polo

12h 25m

1 stop

ORD4:45 pmChicago O'Hare Intl

$392

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Scandinavian Airlines

Nov 28

ORD7:20 pmChicago O'Hare Intl

31h 55m

1 stop

VCE10:15 amVenice Marco Polo

Dec 11

VCE11:20 amVenice Marco Polo

12h 25m

1 stop

ORD4:45 pmChicago O'Hare Intl

$438

Find similar

Scandinavian Airlines

Nov 14

ORD7:20 pmChicago O'Hare Intl

31h 55m

1 stop

VCE10:15 amVenice Marco Polo

Nov 20

VCE11:20 amVenice Marco Polo

12h 25m

1 stop

ORD4:45 pmChicago O'Hare Intl

$443

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Turkish Airlines flights from Chicago to Italy

Our best Turkish Airlines deals on Chicago to Italy flight tickets

Turkish Airlines

Nov 5

ORD11:50 amChicago O'Hare Intl

18h 40m

1 stop

MXP1:30 pmMilan Malpensa

Nov 10

MXP6:55 amMilan Malpensa

18h 30m

1 stop

ORD6:25 pmChicago O'Hare Intl

$496

Find similar

Turkish Airlines

Nov 14

ORD11:50 amChicago O'Hare Intl

23h 50m

1 stop

VCE6:40 pmVenice Marco Polo

Nov 20

VCE7:40 pmVenice Marco Polo

21h 25m

1 stop

ORD10:05 amChicago O'Hare Intl

$497

Find similar

Turkish Airlines

Nov 4

ORD11:50 amChicago O'Hare Intl

18h 40m

1 stop

MXP1:30 pmMilan Malpensa

Nov 9

MXP10:40 amMilan Malpensa

38h 45m

1 stop

ORD6:25 pmChicago O'Hare Intl

$505

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoVenice

ORD - VCE

ORDVCE

Chicago O'Hare Intl

Thu 1/29

10:24 am-10:30 am

2 stops17h 06m

Venice Marco Polo

Fri 2/6

11:20 am-4:45 pm

1 stop12h 25m

$392

ChicagoRome

ORD - FCO

ORDFCO

Chicago O'Hare Intl

Sun 11/9

8:25 pm-6:45 pm

1 stop15h 20m

Rome Fiumicino

Sat 11/22

7:35 pm-2:45 pm

1 stop26h 10m

$408

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Fri 11/14

11:50 am-9:05 am

1 stop14h 15m

Milan Malpensa

Mon 11/17

6:40 pm-6:25 pm

1 stop30h 45m

$496

ChicagoVenice

ORD - VCE

ORDVCE

Chicago O'Hare Intl

Fri 11/14

11:50 am-6:40 pm

1 stop23h 50m

Venice Marco Polo

Thu 11/20

7:40 pm-10:05 am

1 stop21h 25m

$497

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Fri 11/28

9:50 pm-4:30 pm

1 stop11h 40m

Florence Peretola

Fri 12/5

6:30 am-1:10 pm

1 stop13h 40m

$506

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Thu 1/1

9:50 pm-8:40 pm

1 stop15h 50m

Florence Peretola

Mon 1/19

7:10 am-6:25 pm

1 stop18h 15m

$509

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Wed 3/11

11:00 am-2:45 pm

2 stops21h 45m

Florence Peretola

Wed 3/18

6:30 am-6:28 pm

2 stops17h 58m

$523

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Thu 12/11

6:50 pm-2:20 pm

1 stop12h 30m

Florence Peretola

Thu 12/25

6:35 am-3:20 pm

1 stop15h 45m

$534

ChicagoFlorence

ORD - FLR

ORDFLR

Chicago O'Hare Intl

Mon 12/1

6:20 pm-4:30 pm

2 stops15h 10m

Florence Peretola

Wed 12/10

6:30 am-8:05 pm

1 stop20h 35m

$536

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Wed 11/12

10:48 am-10:10 am

2 stops16h 22m

Milan Linate

Tue 11/18

8:00 pm-6:10 pm

2 stops29h 10m

$586

Flights are sorted by cheapest round-trip flights first.

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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 $571, 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 November instead. Flights to Italy in November, while not as cheap as those in February, still average around $576.

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 $895. 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 $1,019.

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 $959.

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 $791 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 $739 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	$449
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 $449. 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 October 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 44.69% of the total bookings. Other popular models include Boeing 787-8 Dreamliner with 23.04%, Boeing 787-10 Dreamliner with 20.02%, and Airbus A330-900neo with 6.20%.

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 $339	Free Cancellation	Rating 7.1 2,040 reviews	Search TAP AIR PORTUGAL flights
Air Canada	PriceFrom $390	Free Cancellation	Rating 7.1 10,383 reviews	Search Air Canada flights
Icelandair	PriceFrom $392	Free Cancellation	Rating 7.1 562 reviews	Search Icelandair flights
Scandinavian Airlines	PriceFrom $414	Free Cancellation	Rating 7.4 1,548 reviews	Search Scandinavian Airlines flights
SWISS	PriceFrom $416	Free Cancellation	Rating 7.5 1,775 reviews	Search SWISS flights
Delta	PriceFrom $419	Free Cancellation	Rating 7.9 7,998 reviews	Search Delta flights
Iberia	PriceFrom $419	Free Cancellation	Rating 7.0 3,004 reviews	Search Iberia flights
Air France	PriceFrom $458	Free Cancellation	Rating 7.4 1,482 reviews	Search Air France flights
Turkish Airlines	PriceFrom $488	Free Cancellation	Rating 7.3 4,033 reviews	Search Turkish Airlines flights
KLM	PriceFrom $491	Free Cancellation	Rating 7.7 1,406 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.

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 $312

Flights to Milanfrom $312

Flights to Venicefrom $333

Flights to Naplesfrom $331

Flights to Florencefrom $331

Flights to Cataniafrom $371

Flights to Palermofrom $381

Flights to Bolognafrom $334

Flights to Barifrom $399

Flights to Olbiafrom $489

Flights to Pisafrom $421

Flights to Cagliarifrom $484

Cheap flights from Chicago to Italy from $178

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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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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Scandinavian Airlines flights from Chicago to Italy

Our best Scandinavian Airlines deals on Chicago to Italy flight tickets

Turkish Airlines flights from Chicago to Italy

Our best Turkish 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 $959.

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 airlines fly to Italy?

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

6 flights are operational daily from Chicago to Italy as of October 2025. The most popular departure time for this route is 4:00PM, 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 October 2025, there are 44 flights per week flying from Chicago to Italy. The most common day of the week flights depart is Wed, with 25% 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