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

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

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.

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.

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?

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 week?

As of December 2025, 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 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 184 minutes.

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.

$261 Cheap Flights from Italy to Chicago in 2025/26

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Find the cheapest flights from Italy to Chicago

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One-way

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Recent round-trip flight deals from Italy to Chicago

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5:45 pm - 3:25 pm

BLQ

ORD

28h 40m1 stop

7:10 pm - 4:55 pm

ORD

BLQ

14h 45m1 stop

$453TAP AIR PORTUGAL

Thu, Feb 5 - Wed, Feb 11

5:45 pm - 3:25 pm

BLQ

ORD

28h 40m1 stop

7:10 pm - 12:30 pm

ORD

BLQ

34h 20m1 stop

$457TAP AIR PORTUGAL

Thu, Feb 5 - Wed, Feb 11

7:05 pm - 2:41 pm

FCO

ORD

26h 36m1 stop

4:47 pm - 2:30 pm

ORD

FCO

14h 43m1 stop

$518Multiple Airlines

Tue, Apr 14 - Thu, Apr 23

9:15 am - 4:45 pm

MXP

ORD

14h 30m1 stop

7:20 pm - 8:25 am

ORD

MXP

30h 05m1 stop

$571Scandinavian Airlines

Mon, Feb 9 - Mon, Feb 16

11:15 am - 4:55 pm

MXP

ORD

12h 40m1 stop

8:20 pm - 10:25 am

ORD

MXP

32h 05m1 stop

$581Scandinavian Airlines

Fri, Mar 6 - Sun, Mar 15

10:50 am - 5:00 pm

VCE

ORD

13h 10m1 stop

8:45 pm - 9:25 pm

ORD

VCE

17h 40m1 stop

$588Multiple Airlines

Sat, Jan 17 - Sun, Feb 1

7:15 am - 1:50 pm

BLQ

ORD

13h 35m1 stop

5:10 pm - 11:40 am

ORD

BLQ

11h 30m1 stop

$589British Airways

Mon, Feb 9 - Mon, Feb 16

11:45 am - 6:45 pm

VCE

ORD

14h 00m1 stop

5:10 pm - 1:30 pm

ORD

VCE

13h 20m1 stop

$596British Airways

Mon, Jan 26 - Mon, Feb 2

12:40 pm - 3:25 pm

BLQ

ORD

33h 45m1 stop

11:29 am - 11:40 am

ORD

BLQ

17h 11m2 stops

$615American Airlines

Thu, Feb 5 - Wed, Feb 11

7:20 am - 7:50 pm

BLQ

ORD

19h 30m2 stops

11:38 am - 11:40 am

ORD

BLQ

17h 02m2 stops

$621American Airlines

Thu, Feb 5 - Wed, Feb 11

Delta flights from Italy to Chicago

Our best Delta deals on Italy to Chicago flight tickets

Delta

Feb 5

BLQ6:05 amBologna Guglielmo Marconi

16h 05m

1 stop

ORD3:10 pmChicago O'Hare Intl

Feb 11

ORD7:00 amChicago O'Hare Intl

20h 30m

2 stops

BLQ10:30 amBologna Guglielmo Marconi

$629

Find similar

Delta

Jan 23

MXP6:55 amMilan Malpensa

15h 15m

1 stop

ORD3:10 pmChicago O'Hare Intl

Jan 25

ORD1:58 pmChicago O'Hare Intl

13h 37m

2 stops

MXP10:35 amMilan Malpensa

$632

Find similar

Delta

Apr 10

BLQ9:20 amBologna Guglielmo Marconi

11h 55m

1 stop

ORD2:15 pmChicago O'Hare Intl

Apr 25

ORD12:45 pmChicago O'Hare Intl

18h 10m

2 stops

BLQ1:55 pmBologna Guglielmo Marconi

$634

Find similar

Scandinavian Airlines flights from Italy to Chicago

Our best Scandinavian Airlines deals on Italy to Chicago flight tickets

Scandinavian Airlines

Feb 9

MXP9:15 amMilan Malpensa

14h 30m

1 stop

ORD4:45 pmChicago O'Hare Intl

Feb 16

ORD7:20 pmChicago O'Hare Intl

30h 05m

1 stop

MXP8:25 amMilan Malpensa

$571

Find similar

Scandinavian Airlines

Mar 6

MXP11:15 amMilan Malpensa

12h 40m

1 stop

ORD4:55 pmChicago O'Hare Intl

Mar 15

ORD8:20 pmChicago O'Hare Intl

32h 05m

1 stop

MXP10:25 amMilan Malpensa

$581

Find similar

Scandinavian Airlines

Jan 16

MXP11:15 amMilan Malpensa

12h 30m

1 stop

ORD4:45 pmChicago O'Hare Intl

Jan 29

ORD7:10 pmChicago O'Hare Intl

39h 25m

2 stops

MXP5:35 pmMilan Malpensa

$582

Find similar

Fly from

Fly to

Route

Depart

Return

Price

BolognaChicago

BLQ - ORD

BLQORD

Bologna Guglielmo Marconi

Thu 2/5

5:45 pm-3:25 pm

1 stop28h 40m

Chicago O'Hare Intl

Wed 2/11

7:10 pm-4:55 pm

1 stop14h 45m

$453

BolognaChicago

BLQ - ORD

BLQORD

Bologna Guglielmo Marconi

Thu 2/5

5:45 pm-3:25 pm

1 stop28h 40m

Chicago O'Hare Intl

Wed 2/11

7:10 pm-12:30 pm

1 stop34h 20m

$457

RomeChicago

FCO - ORD

FCOORD

Rome Fiumicino

Tue 4/14

7:05 pm-2:41 pm

1 stop26h 36m

Chicago O'Hare Intl

Thu 4/23

4:47 pm-2:30 pm

1 stop14h 43m

$518

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Mon 2/9

9:15 am-4:45 pm

1 stop14h 30m

Chicago O'Hare Intl

Mon 2/16

7:20 pm-8:25 am

1 stop30h 05m

$571

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Fri 3/6

11:15 am-4:55 pm

1 stop12h 40m

Chicago O'Hare Intl

Sun 3/15

8:20 pm-10:25 am

1 stop32h 05m

$581

VeniceChicago

VCE - ORD

VCEORD

Venice Marco Polo

Sat 1/17

10:50 am-5:00 pm

1 stop13h 10m

Chicago O'Hare Intl

Sun 2/1

8:45 pm-9:25 pm

1 stop17h 40m

$588

BolognaChicago

BLQ - ORD

BLQORD

Bologna Guglielmo Marconi

Mon 2/9

7:15 am-1:50 pm

1 stop13h 35m

Chicago O'Hare Intl

Mon 2/16

5:10 pm-11:40 am

1 stop11h 30m

$589

VeniceChicago

VCE - ORD

VCEORD

Venice Marco Polo

Mon 1/26

11:45 am-6:45 pm

1 stop14h 00m

Chicago O'Hare Intl

Mon 2/2

5:10 pm-1:30 pm

1 stop13h 20m

$596

BolognaChicago

BLQ - ORD

BLQORD

Bologna Guglielmo Marconi

Thu 2/5

12:40 pm-3:25 pm

1 stop33h 45m

Chicago O'Hare Intl

Wed 2/11

11:29 am-11:40 am

2 stops17h 11m

$615

BolognaChicago

BLQ - ORD

BLQORD

Bologna Guglielmo Marconi

Thu 2/5

7:20 am-7:50 pm

2 stops19h 30m

Chicago O'Hare Intl

Wed 2/11

11:38 am-11:40 am

2 stops17h 02m

$621

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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 April is, on average, the cheapest month to fly to Chicago from Italy, with most prices found around $611. 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 $625.

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 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 $788 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 $557 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 3% 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 $682.

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 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 32.86% of the total bookings. Other popular models include Boeing 787-8 Dreamliner with 18.61%, Boeing 787-10 Dreamliner with 13.31%, and Boeing 787-9 Dreamliner with 7.07%.

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 7,616 reviews	Search British Airways flights
American Airlines	PriceFrom $536	Free Cancellation	Rating 7.2 11,071 reviews	Search American Airlines flights
Iberia	PriceFrom $550	Free Cancellation	Rating 7.0 3,059 reviews	Search Iberia flights
United Airlines	PriceFrom $585	Free Cancellation	Rating 7.4 9,114 reviews	Search United Airlines flights
Lufthansa	PriceFrom $690	Free Cancellation	Rating 6.8 7,658 reviews	Search Lufthansa flights

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Valparaiso

Schererville

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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Cheap flights from Italy to Chicago from $261

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 5/6. 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

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Find the cheapest flights from Italy to Chicago

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Delta flights from Italy to Chicago

Our best Delta 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.

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 $611. 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 $625.

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

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.

Can stopping save me money on Italy to Chicago flights?

You could potentially save up to 3% on your flight if you consider stops on a Italy to Chicago flight.

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

TAP AIR PORTUGAL, British Airways, and American Airlines 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 184 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 week?

As of December 2025, 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