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

As of September 2025, 120 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.

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 41% 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.

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

As of September 2025, 17 flights take off from Italy and land in Chicago each day. The most common flight departure time for this route is 9:00AM, with 64% of daily flights taking off at noon.

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 50m 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 cheapest airline that flies from Italy to Chicago?

TAP AIR PORTUGAL and British Airways are the most popular carriers operating from Italy to Chicago

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 September 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.

$327 Cheap Flights from Italy to Chicago in 2025/26

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Italy to Chicago

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Italy to Chicago

11:20 am - 4:45 pmVCE-ORD

12h 25m1 stop

7:20 pm - 10:30 amORD-VCE

32h 10m1 stop

$514Scandinavian Airlines

Find Deal

Fri, Nov 21 - Sun, Nov 23

11:20 am - 4:45 pmVCE-ORD

12h 25m1 stop

7:20 pm - 10:30 amORD-VCE

32h 10m1 stop

$515Scandinavian Airlines

Find Deal

Fri, Nov 21 - Sun, Nov 23

7:10 am - 12:55 pmFCO-ORD

12h 45m1 stop

10:50 pm - 6:15 pmORD-FCO

13h 25m1 stop

$571Lufthansa

Find Deal

Wed, Oct 15 - Sat, Oct 25

7:10 am - 12:55 pmFCO-ORD

12h 45m1 stop

12:00 pm - 10:55 amORD-FCO

15h 55m1 stop

$573United Airlines

Find Deal

Thu, Oct 23 - Sat, Nov 8

7:05 am - 1:10 pmFCO-ORD

13h 05m1 stop

3:45 pm - 7:45 amORD-FCO

9h 00mnonstop

$574United Airlines

Find Deal

Sun, Feb 22 - Mon, Mar 2

6:00 am - 12:55 pmVCE-ORD

13h 55m1 stop

3:35 pm - 9:20 amORD-VCE

10h 45m1 stop

$574Lufthansa

Find Deal

Thu, Oct 16 - Mon, Oct 20

6:50 pm - 1:50 pmFCO-ORD

26h 00m1 stop

6:30 pm - 2:55 pmORD-FCO

13h 25m1 stop

$578British Airways

Find Deal

Mon, Nov 3 - Fri, Nov 14

6:55 am - 1:50 pmFCO-ORD

13h 55m1 stop

2:03 pm - 12:25 pmORD-FCO

15h 22m2 stops

$584British Airways

Find Deal

Tue, Oct 21 - Fri, Nov 7

7:10 pm - 6:30 pmVCE-ORD

30h 20m2 stops

9:20 am - 2:30 pmORD-VCE

23h 10m2 stops

$647ITA Airways

Find Deal

Wed, Oct 15 - Wed, Oct 29

7:30 am - 6:20 pmLIN-ORD

17h 50m2 stops

11:05 am - 10:10 amORD-LIN

16h 05m2 stops

$650ITA Airways

Find Deal

Thu, Oct 2 - Wed, Oct 15

United Airlines flights from Italy to Chicago

Our best United Airlines deals on Italy to Chicago flight tickets

United Airlines

Oct 23

FCO7:10 amRome Fiumicino

12h 45m

1 stop

ORD12:55 pmChicago O'Hare Intl

Nov 8

ORD12:00 pmChicago O'Hare Intl

15h 55m

1 stop

FCO10:55 amRome Fiumicino

$573

Find similar

United Airlines

Feb 22

FCO7:05 amRome Fiumicino

13h 05m

1 stop

ORD1:10 pmChicago O'Hare Intl

Mar 2

ORD3:45 pmChicago O'Hare Intl

9h 00m

FCO7:45 amRome Fiumicino

$574

Find similar

United Airlines

Oct 23

FCO7:10 amRome Fiumicino

12h 45m

1 stop

ORD12:55 pmChicago O'Hare Intl

Nov 6

ORD6:50 pmChicago O'Hare Intl

12h 10m

1 stop

FCO2:00 pmRome Fiumicino

$576

Find similar

Delta flights from Italy to Chicago

Our best Delta deals on Italy to Chicago flight tickets

Delta

Dec 5

VCE6:30 amVenice Marco Polo

14h 50m

1 stop

ORD2:20 pmChicago O'Hare Intl

Dec 8

ORD10:31 amChicago O'Hare Intl

18h 14m

2 stops

VCE11:45 amVenice Marco Polo

$582

Find similar

Delta

Dec 5

VCE6:30 amVenice Marco Polo

16h 48m

2 stops

ORD4:18 pmChicago O'Hare Intl

Dec 8

ORD10:31 amChicago O'Hare Intl

18h 14m

2 stops

VCE11:45 amVenice Marco Polo

$587

Find similar

Delta

Nov 4

FCO6:10 amRome Fiumicino

18h 33m

2 stops

MDW5:43 pmChicago Midway

Nov 17

MDW12:47 pmChicago Midway

12h 08m

1 stop

FCO7:55 amRome Fiumicino

$588

Find similar

Fly from

Fly to

Route

Depart

Return

Price

VeniceChicago

VCE - ORD

VCEORD

Venice Marco Polo

Fri 11/21

11:20 am-4:45 pm

1 stop12h 25m

Chicago O'Hare Intl

Sun 11/23

7:20 pm-10:30 am

1 stop32h 10m

$514

VeniceChicago

VCE - ORD

VCEORD

Venice Marco Polo

Fri 11/21

11:20 am-4:45 pm

1 stop12h 25m

Chicago O'Hare Intl

Sun 11/23

7:20 pm-10:30 am

1 stop32h 10m

$515

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Wed 10/15

7:10 am-12:55 pm

1 stop12h 45m

Chicago O'Hare Intl

Sat 10/25

10:50 pm-6:15 pm

1 stop13h 25m

$571

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Thu 10/23

7:10 am-12:55 pm

1 stop12h 45m

Chicago O'Hare Intl

Sat 11/8

12:00 pm-10:55 am

1 stop15h 55m

$573

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Sun 2/22

7:05 am-1:10 pm

1 stop13h 05m

Chicago O'Hare Intl

Mon 3/2

3:45 pm-7:45 am

Nonstop9h 00m

$574

VeniceChicago

VCE - ORD

VCEORD

Venice Marco Polo

Thu 10/16

6:00 am-12:55 pm

1 stop13h 55m

Chicago O'Hare Intl

Mon 10/20

3:35 pm-9:20 am

1 stop10h 45m

$574

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Mon 11/3

6:50 pm-1:50 pm

1 stop26h 00m

Chicago O'Hare Intl

Fri 11/14

6:30 pm-2:55 pm

1 stop13h 25m

$578

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Tue 10/21

6:55 am-1:50 pm

1 stop13h 55m

Chicago O'Hare Intl

Fri 11/7

2:03 pm-12:25 pm

2 stops15h 22m

$584

VeniceChicago

VCE - ORD

VCEORD

Venice Marco Polo

Wed 10/15

7:10 pm-6:30 pm

2 stops30h 20m

Chicago O'Hare Intl

Wed 10/29

9:20 am-2:30 pm

2 stops23h 10m

$647

MilanChicago

LIN - ORD

LINORD

Milan Linate

Thu 10/2

7:30 am-6:20 pm

2 stops17h 50m

Chicago O'Hare Intl

Wed 10/15

11:05 am-10:10 am

2 stops16h 05m

$650

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

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 $739. This is often the case because there is less demand to fly during this day of the week. When flying out on a Friday, the most expensive travel day of the week, you can expect to see flight prices from Italy to Chicago for around $864.

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 afternoon when prices are around $774.

What is the cheapest Italy to Chicago flight route?

Fly from Milan Malpensa 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 $733 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 $465 on momondo.

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

There are 4 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?

No. A direct flight is the cheapest option for a flight between Italy 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	$623
Fastest flight time	9h 50m
Direct flights	Every day
Airports in Chicago	1 airport

The best one-way flight to Chicago from Italy in the past 72 hours is $623. The best round-trip flight deal from Italy to Chicago found on momondo in the last 72 hours is $479.

The fastest flight from Italy to Chicago takes 9h 50m

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 September 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 36.47% of the total bookings. Other popular models include Boeing 787-8 Dreamliner with 23.02%, Boeing 787-10 Dreamliner with 9.57%, and Boeing 777-200/200ER with 4.58%.

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 7,363 reviews	Search British Airways flights
American Airlines	PriceFrom $536	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Iberia	PriceFrom $550	Free Cancellation	Rating 7.0 2,924 reviews	Search Iberia flights
United Airlines	PriceFrom $585	Free Cancellation	Rating 7.4 8,924 reviews	Search United Airlines flights
ITA Airways	PriceFrom $658	Free Cancellation	Rating 6.7 1,036 reviews	Search ITA Airways flights

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Lansing

Portage

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.

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.

Start using Trips

Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

1 adult

Thu 10/16

Thu 10/23

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

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

Flights to New Yorkfrom $49

Flights to Los Angelesfrom $49

Flights to Miamifrom $49

Flights to Orlandofrom $60

Flights to Las Vegasfrom $48

Flights to San Franciscofrom $53

Flights to Washington, D.C.from $49

Flights to Bostonfrom $62

Flights to Atlantafrom $51

Flights to Dallasfrom $68

Flights to Seattlefrom $69

Flights to Denverfrom $63

Cheap flights from Italy to Chicago from $327

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 11/15. 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

Trusted and free

Price Alerts

Price Alerts

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

Recent last minute flight deals from Italy to Chicago

Recent direct flight deals from Italy to Chicago

United Airlines flights from Italy to Chicago

Our best United Airlines deals on Italy to Chicago flight tickets

Delta flights from Italy to Chicago

Our best Delta deals on Italy to Chicago flight tickets

momondo Fare Finder

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

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 afternoon when prices are around $774.

What is the cheapest Italy to Chicago flight route?

Fly from Milan Malpensa 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 4 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?

No. A direct flight is the cheapest option for a flight between Italy to Chicago.

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

TAP AIR PORTUGAL and British Airways are the most popular carriers operating from Italy to Chicago

What airlines fly to Chicago?

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

As of September 2025, 17 flights take off from Italy and land in Chicago each day. The most common flight departure time for this route is 9:00AM, with 64% of daily flights taking off at noon.

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

As of September 2025, 120 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