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

Icelandair, Air Serbia, and TAP AIR PORTUGAL 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 airlines fly to Chicago?

United Airlines, American Airlines and British Airways are the top three most popular airlines that fly to Chicago from Italy 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 Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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.

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.

How often are flights from Italy to Chicago delayed?

Historically, on average around 19% 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 191 minutes.

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 10% of their flights experiencing any sort of delay.

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

As of January 2026, 6 flights take off from Italy and land in Chicago each week. The most common flight departure day for this route is Mon, with 17% of weekly flights taking off on this day.

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 January 2026, 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.

$245 Cheap Flights from Italy to Chicago in 2026

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Find the cheapest flights from Italy to Chicago

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Italy to Chicago

Enter your travel dates to find the best prices.

8:00 pm - 4:00 pm

MXP

ORD

27h 00m

1 stop

6:00 pm - 12:45 am

ORD

MXP

23h 45m

1 stop

$427TAP AIR PORTUGAL

mar., abr. 21 - mié., may. 6

5:50 am - 4:00 pm

MXP

ORD

17h 10m

1 stop

6:15 pm - 11:00 am

ORD

MXP

33h 45m

1 stop

$431TAP AIR PORTUGAL

dom., abr. 19 - sáb., may. 2

5:45 pm - 2:45 pm

MXP

ORD

28h 00m

1 stop

8:25 pm - 11:35 pm

ORD

MXP

20h 10m

1 stop

$438TAP AIR PORTUGAL

sáb., feb. 14 - dom., mar. 1

1:40 pm - 2:31 pm

VCE

ORD

31h 51m

1 stop

9:15 pm - 10:05 pm

ORD

VCE

17h 50m

1 stop

$594British Airways

mié., may. 13 - sáb., may. 23

7:25 am - 3:00 pm

LIN

ORD

14h 35m

1 stop

9:15 pm - 10:10 am

ORD

LIN

29h 55m

1 stop

$601British Airways

dom., abr. 19 - sáb., may. 2

9:00 pm - 1:10 pm

LIN

ORD

23h 10m

1 stop

11:00 am - 10:10 am

ORD

LIN

16h 10m

2 stops

$613ITA Airways

vie., may. 1 - mar., may. 12

6:30 am - 3:20 pm

FLR

ORD

15h 50m

1 stop

6:50 pm - 1:45 pm

ORD

FLR

11h 55m

1 stop

$621United Airlines

jue., feb. 19 - lun., feb. 23

6:30 am - 3:20 pm

FLR

ORD

15h 50m

1 stop

6:50 pm - 1:45 pm

ORD

FLR

11h 55m

1 stop

$622United Airlines

jue., feb. 19 - lun., feb. 23

8:30 pm - 3:25 pm

VCE

ORD

25h 55m

1 stop

5:00 pm - 4:50 pm

ORD

VCE

16h 50m

2 stops

$624American Airlines

jue., feb. 26 - lun., mar. 2

6:55 am - 5:00 pm

VCE

ORD

17h 05m

1 stop

6:30 pm - 4:50 pm

ORD

VCE

15h 20m

1 stop

$625American Airlines

jue., feb. 26 - lun., mar. 2

TAP AIR PORTUGAL flights from Italy to Chicago

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

TAP AIR PORTUGAL

Apr 21

MXP8:00 pmMilan Malpensa

27h 00m

1 stop

ORD4:00 pmChicago O'Hare Intl

May 6

ORD6:00 pmChicago O'Hare Intl

23h 45m

1 stop

MXP12:45 amMilan Malpensa

$427

TAP AIR PORTUGAL

Apr 19

MXP5:50 amMilan Malpensa

17h 10m

1 stop

ORD4:00 pmChicago O'Hare Intl

May 2

ORD6:15 pmChicago O'Hare Intl

33h 45m

1 stop

MXP11:00 amMilan Malpensa

$431

TAP AIR PORTUGAL

Feb 5

FLR7:15 pmFlorence Peretola

27h 10m

1 stop

ORD3:25 pmChicago O'Hare Intl

Feb 11

ORD7:10 pmChicago O'Hare Intl

16h 20m

1 stop

FLR6:30 pmFlorence Peretola

$437

Icelandair flights from Italy to Chicago

Our best Icelandair deals on Italy to Chicago flight tickets

Icelandair

Apr 8

MXP4:20 pmMilan Malpensa

32h 55m

1 stop

ORD6:15 pmChicago O'Hare Intl

Apr 21

ORD7:25 pmChicago O'Hare Intl

12h 45m

1 stop

MXP3:10 pmMilan Malpensa

$518

Icelandair

Jun 6

MXP4:20 pmMilan Malpensa

32h 55m

1 stop

ORD6:15 pmChicago O'Hare Intl

Jun 13

ORD10:25 pmChicago O'Hare Intl

33h 45m

1 stop

MXP3:10 pmMilan Malpensa

$533

Icelandair

Jun 6

MXP4:20 pmMilan Malpensa

32h 55m

1 stop

ORD6:15 pmChicago O'Hare Intl

Jun 14

ORD7:25 pmChicago O'Hare Intl

12h 45m

1 stop

MXP3:10 pmMilan Malpensa

$543

Fly from

Fly to

Route

Depart

Return

Price

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

mar. 4/21

8:00 pm-4:00 pm

1 stop27h 00m

Chicago O'Hare Intl

mié. 5/6

6:00 pm-12:45 am

1 stop23h 45m

$427

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

dom. 4/19

5:50 am-4:00 pm

1 stop17h 10m

Chicago O'Hare Intl

sáb. 5/2

6:15 pm-11:00 am

1 stop33h 45m

$431

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

sáb. 2/14

5:45 pm-2:45 pm

1 stop28h 00m

Chicago O'Hare Intl

dom. 3/1

8:25 pm-11:35 pm

1 stop20h 10m

$438

VeniceChicago

VCE - ORD

VCEORD

Venice Marco Polo

mié. 5/13

1:40 pm-2:31 pm

1 stop31h 51m

Chicago O'Hare Intl

sáb. 5/23

9:15 pm-10:05 pm

1 stop17h 50m

$594

MilanChicago

LIN - ORD

LINORD

Milan Linate

dom. 4/19

7:25 am-3:00 pm

1 stop14h 35m

Chicago O'Hare Intl

sáb. 5/2

9:15 pm-10:10 am

1 stop29h 55m

$601

MilanChicago

LIN - ORD

LINORD

Milan Linate

vie. 5/1

9:00 pm-1:10 pm

1 stop23h 10m

Chicago O'Hare Intl

mar. 5/12

11:00 am-10:10 am

2 stops16h 10m

$613

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

jue. 2/19

6:30 am-3:20 pm

1 stop15h 50m

Chicago O'Hare Intl

lun. 2/23

6:50 pm-1:45 pm

1 stop11h 55m

$621

FlorenceChicago

FLR - ORD

FLRORD

Florence Peretola

jue. 2/19

6:30 am-3:20 pm

1 stop15h 50m

Chicago O'Hare Intl

lun. 2/23

6:50 pm-1:45 pm

1 stop11h 55m

$622

VeniceChicago

VCE - ORD

VCEORD

Venice Marco Polo

jue. 2/26

8:30 pm-3:25 pm

1 stop25h 55m

Chicago O'Hare Intl

lun. 3/2

5:00 pm-4:50 pm

2 stops16h 50m

$624

VeniceChicago

VCE - ORD

VCEORD

Venice Marco Polo

jue. 2/26

6:55 am-5:00 pm

1 stop17h 05m

Chicago O'Hare Intl

lun. 3/2

6:30 pm-4:50 pm

1 stop15h 20m

$625

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 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 April is, on average, the cheapest month to fly to Chicago from Italy, with most prices found around $613. If you’re not able to fly to Chicago in April, then May is your next best option. Flight prices from Italy to Chicago during May average around $617.

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 $879.

What is the cheapest Italy to Chicago flight route?

Fly from Naples 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 $792 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 $594 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.

Can stopping save me money on Italy to Chicago flights?

You could potentially save up to 20% on your flight if you consider stops on a Italy to Chicago flight.

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	$491
Fastest flight time	9h 40m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Italy in the past 72 hours is $491. The best round-trip flight deal from Italy to Chicago found on momondo in the last 72 hours is $695.

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

Direct flights go from Italy to Chicago every day.

There are 3 airports in Chicago. From Italy there are direct flights to 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 January 2026, 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 28.00% of the total bookings. Other popular models include Boeing 787-8 Dreamliner with 14.59%, Boeing 787-10 Dreamliner with 12.65%, and Boeing 787-9 Dreamliner with 11.35%.

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 7,704 reviews	Search British Airways flights
American Airlines	PriceFrom $536	Free Cancellation	Rating 7.2 11,201 reviews	Search American Airlines flights
United Airlines	PriceFrom $585	Free Cancellation	Rating 7.4 9,209 reviews	Search United Airlines flights
Lufthansa	PriceFrom $690	Free Cancellation	Rating 6.8 7,749 reviews	Search Lufthansa flights
Iberia	PriceFrom $692	Free Cancellation	Rating 7.0 3,099 reviews	Search Iberia flights

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Munster

Crown Point

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.

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.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

Popular cities in the United States

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Flights to San Franciscofrom $56

Flights to Las Vegasfrom $40

Flights to Washington, D.C.from $54

Flights to Bostonfrom $52

Flights to Atlantafrom $49

Flights to Dallasfrom $56

Flights to Seattlefrom $56

Flights to Denverfrom $55

Cheap flights from Italy to Chicago from $245

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 4/18. 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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Big names and deals

Filter for what you want

Filter for what you want

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Find the cheapest flights from Italy to Chicago

Recent round-trip flight deals from Italy to Chicago

Recent one-way 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

Icelandair flights from Italy to Chicago

Our best Icelandair 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.

See travel insights to Chicago from

How to get the cheapest flight ticket from Italy to Chicago

What is the cheapest month to fly to Chicago?

The month of April is, on average, the cheapest month to fly to Chicago from Italy, with most prices found around $613. If you’re not able to fly to Chicago in April, then May is your next best option. Flight prices from Italy to Chicago during May average around $617.

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

What is the cheapest Italy to Chicago flight route?

Fly from Naples 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.

Can stopping save me money on Italy to Chicago flights?

You could potentially save up to 20% on your flight if you consider stops on a Italy to Chicago flight.

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

Icelandair, Air Serbia, and TAP AIR PORTUGAL 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 19% 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 191 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 10% of their flights experiencing any sort of delay.

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

As of January 2026, 6 flights take off from Italy and land in Chicago each week. The most common flight departure day for this route is Mon, with 17% 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