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

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

How long does it take to fly to Chicago?

Average flight duration from Italy to Chicago depends on which airport you fly into and out of. Flying from Milan to Chicago O'Hare Intl Airport is 9h 40m on average, while flying from Rome to Chicago O'Hare Intl Airport is 10h 25m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

What is the most punctual flight time for Italy to Chicago flights?

Generally, flights departing at night tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

What airlines fly to Chicago?

American Airlines, United Airlines and British Airways are the top three most popular airlines that fly to Chicago from Italy according to our data. American Airlines is the first choice among our users, with 40% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

How often are flights from Italy to Chicago delayed?

Historically, on average around 18% of flights between Italy and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 183 minutes.

What day of the week experiences the fewest flight delays on this route?

Thursday is statistically the day of the week which experiences the fewest number of delays on this flight route. Monday has historically seen more delays on average compared to the rest of the week.

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

As of December 2025, 5 flights take off from Italy and land in Chicago each day. The most common flight departure time for this route is 9:00AM, with 51% of daily flights taking off at noon.

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

As of December 2025, 41 flights take off from Italy and land in Chicago each week. The most common flight departure day for this route is Mon, with 15% of weekly flights taking off on this day.

Which airline has the best punctuality record on Italy to Chicago flights?

According to our data, Ethiopian Air have had the least number of delays on this route over the last 12 months; with about 11% of their flights experiencing any sort of delay.

When did momondo last update prices for flights from Italy to Chicago?

Prices for flights from Italy to Chicago are updated daily.

How many operators does momondo search for flights from Italy to Chicago?

As of December 2025, there are 5 operators available to choose from for flights from Italy to Chicago.

How old do you have to be to fly from Italy to Chicago?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Italy to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents you'll need for your trip to Chicago 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 Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$249 Cheap Flights from Italy to Chicago in 2025/26

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Recent round-trip flight deals from Italy to Chicago

Enter your travel dates to find the best prices.

5:50 pm - 2:45 pmVCE-ORD

27h 55m1 stop

8:15 pm - 5:00 pmORD-VCE

13h 45m1 stop

$439TAP AIR PORTUGAL

Find Deal

Sat, Jan 17 - Fri, Jan 30

5:45 pm - 3:25 pmMXP-ORD

28h 40m1 stop

7:10 pm - 4:55 pmORD-MXP

14h 45m1 stop

$439TAP AIR PORTUGAL

Find Deal

Thu, Jan 15 - Wed, Jan 28

9:15 am - 4:45 pmMXP-ORD

14h 30m1 stop

7:20 pm - 10:25 amORD-MXP

32h 05m1 stop

$501Scandinavian Airlines

Find Deal

Thu, Jan 15 - Thu, Jan 29

10:00 pm - 5:20 pmFCO-ORD

26h 20m2 stops

6:30 pm - 10:05 pmORD-FCO

20h 35m2 stops

$503Multiple Airlines

Find Deal

Thu, Jan 22 - Fri, Jan 30

11:15 am - 4:45 pmMXP-ORD

12h 30m1 stop

7:20 pm - 7:25 pmORD-MXP

17h 05m2 stops

$511Scandinavian Airlines

Find Deal

Sat, Jan 17 - Fri, Jan 23

8:40 am - 5:20 pmBGY-ORD

15h 40m2 stops

6:30 pm - 9:20 pmORD-BGY

19h 50m2 stops

$511Multiple Airlines

Find Deal

Sat, Jan 17 - Fri, Jan 23

7:10 pm - 6:12 pmBLQ-ORD

30h 02m2 stops

11:15 am - 10:20 amORD-BLQ

16h 05m2 stops

$602ITA Airways

Find Deal

Sat, May 9 - Thu, Jun 4

6:25 am - 3:20 pmBLQ-ORD

15h 55m1 stop

9:50 pm - 10:50 pmORD-BLQ

18h 00m1 stop

$603Lufthansa

Find Deal

Thu, Jan 15 - Wed, Jan 21

6:25 am - 3:20 pmBLQ-ORD

15h 55m1 stop

6:00 pm - 12:40 pmORD-BLQ

11h 40m1 stop

$604Lufthansa

Find Deal

Thu, Jan 15 - Thu, Jan 22

2:00 pm - 6:12 pmLIN-ORD

35h 12m2 stops

11:15 am - 10:10 amORD-LIN

15h 55m2 stops

$610ITA Airways

Find Deal

Sat, May 9 - Thu, Jun 4

TAP AIR PORTUGAL flights from Italy to Chicago

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

TAP AIR PORTUGAL

Jan 17

VCE5:50 pmVenice Marco Polo

27h 55m

1 stop

ORD2:45 pmChicago O'Hare Intl

Jan 30

ORD8:15 pmChicago O'Hare Intl

13h 45m

1 stop

VCE5:00 pmVenice Marco Polo

$439

Find similar

TAP AIR PORTUGAL

Jan 21

FCO6:00 amRome Fiumicino

16h 00m

1 stop

ORD3:00 pmChicago O'Hare Intl

Feb 11

ORD7:10 pmChicago O'Hare Intl

13h 40m

1 stop

FCO3:50 pmRome Fiumicino

$440

Find similar

TAP AIR PORTUGAL

Jan 16

FCO6:00 amRome Fiumicino

16h 25m

1 stop

ORD3:25 pmChicago O'Hare Intl

Jan 23

ORD8:15 pmChicago O'Hare Intl

20h 50m

1 stop

FCO12:05 amRome Fiumicino

$441

Find similar

Scandinavian Airlines flights from Italy to Chicago

Our best Scandinavian Airlines deals on Italy to Chicago flight tickets

Scandinavian Airlines

Jan 15

MXP9:15 amMilan Malpensa

14h 30m

1 stop

ORD4:45 pmChicago O'Hare Intl

Jan 29

ORD7:20 pmChicago O'Hare Intl

32h 05m

1 stop

MXP10:25 amMilan Malpensa

$501

Find similar

Scandinavian Airlines

Jan 17

MXP11:15 amMilan Malpensa

12h 30m

1 stop

ORD4:45 pmChicago O'Hare Intl

Jan 23

ORD7:20 pmChicago O'Hare Intl

17h 05m

2 stops

MXP7:25 pmMilan Malpensa

$511

Find similar

Scandinavian Airlines

Jan 15

FCO11:55 amRome Fiumicino

35h 50m

1 stop

ORD4:45 pmChicago O'Hare Intl

Jan 22

ORD7:20 pmChicago O'Hare Intl

32h 30m

1 stop

FCO10:50 amRome Fiumicino

$520

Find similar

Fly from

Fly to

Route

Depart

Return

Price

VeniceChicago

VCE - ORD

VCEORD

Venice Marco Polo

Sat 1/17

5:50 pm-2:45 pm

1 stop27h 55m

Chicago O'Hare Intl

Fri 1/30

8:15 pm-5:00 pm

1 stop13h 45m

$439

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Thu 1/15

5:45 pm-3:25 pm

1 stop28h 40m

Chicago O'Hare Intl

Wed 1/28

7:10 pm-4:55 pm

1 stop14h 45m

$439

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Thu 1/15

9:15 am-4:45 pm

1 stop14h 30m

Chicago O'Hare Intl

Thu 1/29

7:20 pm-10:25 am

1 stop32h 05m

$501

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Thu 1/22

10:00 pm-5:20 pm

2 stops26h 20m

Chicago O'Hare Intl

Fri 1/30

6:30 pm-10:05 pm

2 stops20h 35m

$503

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Sat 1/17

11:15 am-4:45 pm

1 stop12h 30m

Chicago O'Hare Intl

Fri 1/23

7:20 pm-7:25 pm

2 stops17h 05m

$511

BergamoChicago

BGY - ORD

BGYORD

Bergamo Orio Al Serio

Sat 1/17

8:40 am-5:20 pm

2 stops15h 40m

Chicago O'Hare Intl

Fri 1/23

6:30 pm-9:20 pm

2 stops19h 50m

$511

BolognaChicago

BLQ - ORD

BLQORD

Bologna Guglielmo Marconi

Sat 5/9

7:10 pm-6:12 pm

2 stops30h 02m

Chicago O'Hare Intl

Thu 6/4

11:15 am-10:20 am

2 stops16h 05m

$602

BolognaChicago

BLQ - ORD

BLQORD

Bologna Guglielmo Marconi

Thu 1/15

6:25 am-3:20 pm

1 stop15h 55m

Chicago O'Hare Intl

Wed 1/21

9:50 pm-10:50 pm

1 stop18h 00m

$603

BolognaChicago

BLQ - ORD

BLQORD

Bologna Guglielmo Marconi

Thu 1/15

6:25 am-3:20 pm

1 stop15h 55m

Chicago O'Hare Intl

Thu 1/22

6:00 pm-12:40 pm

1 stop11h 40m

$604

MilanChicago

LIN - ORD

LINORD

Milan Linate

Sat 5/9

2:00 pm-6:12 pm

2 stops35h 12m

Chicago O'Hare Intl

Thu 6/4

11:15 am-10:10 am

2 stops15h 55m

$610

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How to get the cheapest flight ticket from Italy to Chicago

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 Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Italy, with most prices found around $591. If you’re not able to fly to Chicago in February, then April is your next best option. Flight prices from Italy to Chicago during April average around $611.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $729. This is often the case because there is less demand to fly during this day of the week. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Italy to Chicago for around $875.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from Italy to Chicago during this time can be as low as $748. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $778.

What is the cheapest Italy to Chicago flight route?

Fly from Rome Fiumicino to Chicago O'Hare Intl for the best Italy - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Italy when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $740 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Italy for as low as $524 on momondo.

What cabin class options are available on Italy to Chicago flights?

There are 3 cabin classes available to choose from on Italy to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Cheap Italy to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Italy to Chicago

Best Price Found	$528
Fastest flight time	9h 40m
Direct flights	Every day
Airports in Chicago	1 airport

The best one-way flight to Chicago from Italy in the past 72 hours is $528. The best round-trip flight deal from Italy to Chicago found on momondo in the last 72 hours is $690.

The fastest flight from Italy to Chicago takes 9h 40m

Direct flights go from Italy to Chicago every day.

There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)

Search flight deals

When did momondo last update prices for flights from Italy to Chicago?
Prices for flights from Italy to Chicago are updated daily.
How many operators does momondo search for flights from Italy to Chicago?
As of December 2025, there are 5 operators available to choose from for flights from Italy to Chicago.
How old do you have to be to fly from Italy to Chicago?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Italy to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents you'll need for your trip to Chicago 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 Chicago. 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 Italy to Chicago?
Based on momondo bookings for flights between Italy and Chicago, the leading plane model is Boeing 787 Dreamliner, making up 35.23% of the total bookings. Other popular models include Boeing 787-8 Dreamliner with 21.53%, Boeing 787-10 Dreamliner with 13.11%, and Boeing 787-9 Dreamliner with 5.19%.

Best airlines flying from Italy to Chicago

Compare and see reviews for airlines that fly from Italy to Chicago with momondo

Airline	Rating	Free Cancellation	Price
British Airways	PriceFrom $525	Free Cancellation	Rating 6.7 7,550 reviews	Search British Airways flights
American Airlines	PriceFrom $536	Free Cancellation	Rating 7.2 11,045 reviews	Search American Airlines flights
Iberia	PriceFrom $550	Free Cancellation	Rating 7.0 3,038 reviews	Search Iberia flights
United Airlines	PriceFrom $585	Free Cancellation	Rating 7.4 9,063 reviews	Search United Airlines flights
SWISS	PriceFrom $600	Free Cancellation	Rating 7.5 1,798 reviews	Search SWISS flights
Lufthansa	PriceFrom $690	Free Cancellation	Rating 6.8 7,603 reviews	Search Lufthansa flights

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New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Italy to Chicago?

Finding the right flight to Chicago from Italy is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Italy to Chicago with flexible booking policies on momondo?

All flight searches from Italy to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Italy to Chicago?

Once all potential Italy to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Italy to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Italy. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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Find better results for your trip to the United States

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Chicago O'Hare Intl Airport

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Flights to Bostonfrom $56

Flights to Atlantafrom $37

Flights to Dallasfrom $53

Flights to Seattlefrom $59

Flights to Denverfrom $49

Cheap flights from Italy to Chicago from $249

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Italy to Chicago departing on 2/3. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

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Price Alerts

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Find the cheapest flights from Italy to Chicago

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Recent one-way flight deals from Italy to Chicago

Recent last minute flight deals from Italy to Chicago

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TAP AIR PORTUGAL flights from Italy to Chicago

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

Scandinavian Airlines flights from Italy to Chicago

Our best Scandinavian Airlines deals on Italy to Chicago flight tickets

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

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How to get the cheapest flight ticket from Italy to Chicago

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 Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Italy, with most prices found around $591. If you’re not able to fly to Chicago in February, then April is your next best option. Flight prices from Italy to Chicago during April average around $611.

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from Italy to Chicago during this time can be as low as $748. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $778.

What is the cheapest Italy to Chicago flight route?

Fly from Rome Fiumicino to Chicago O'Hare Intl for the best Italy - Chicago flight prices

How far in advance should I book a flight to Chicago?

What cabin class options are available on Italy to Chicago flights?

There are 3 cabin classes available to choose from on Italy to Chicago 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 Italy to Chicago?

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

What airlines fly to Chicago?

How often are flights from Italy to Chicago delayed?

Historically, on average around 18% of flights between Italy and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 183 minutes.

What is the most punctual flight time for Italy to Chicago flights?

Generally, flights departing at night tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Thursday is statistically the day of the week which experiences the fewest number of delays on this flight route. Monday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on Italy to Chicago flights?

According to our data, Ethiopian Air have had the least number of delays on this route over the last 12 months; with about 11% of their flights experiencing any sort of delay.

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

As of December 2025, 5 flights take off from Italy and land in Chicago each day. The most common flight departure time for this route is 9:00AM, with 51% of daily flights taking off at noon.

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

As of December 2025, 41 flights take off from Italy and land in Chicago each week. The most common flight departure day for this route is Mon, with 15% of weekly flights taking off on this day.

How long does it take to fly to Chicago?

Cheap Italy to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Italy to Chicago

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

When did momondo last update prices for flights from Italy to Chicago?

How many operators does momondo search for flights from Italy to Chicago?

How old do you have to be to fly from Italy to Chicago?

What documentation or ID do you need to fly to Chicago?

What is the most popular plane model from Italy to Chicago?

Best airlines flying from Italy to Chicago

Compare and see reviews for airlines that fly from Italy to Chicago with momondo

Traveling to a place near Chicago?

Why use momondo?

Why should I use momondo to find a flight deal from Italy to Chicago?

Can I find flights from Italy to Chicago with flexible booking policies on momondo?

How can momondo help me find flights from Italy to Chicago?

I’m not ready to book a flight from Italy to Chicago right now. Can momondo alert me if prices change?

An easier way to manage your Chicago 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 the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago