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$209 Find cheap flights from Italy to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 6/10. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
mån 6/3
mån 6/10

Search hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
In the last 7 days travelers have searched 43,369,418 times on KAYAK, and here is why:

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Flights to Chicago - Travel Insights & Trends

Get data-powered insights and trends for flights to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest day to fly to Chicago?

The average price of all flights to Chicago clicked on KAYAK for each day over the last 12 months.
Based on KAYAK data, the cheapest day to fly to Chicago is Wednesday where tickets can be as cheap as $671. On the other hand, the most expensive day to fly is Saturday, where prices are $872 on average.

What is the cheapest month to fly to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights to Chicago is January, where tickets cost $536 on average for one-way flights. On the other hand, the most expensive months are August and July, where the average cost of tickets from Italy is $1,147 and $973 respectively. For return trips, the best month to travel is November with an average price of $566.

What is the cheapest time of day to fly to Chicago?

The average price for all flights to Chicago depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.
The cheapest time of day to fly to Chicago is generally in the morning, when flights cost $722 on average. The most expensive time of day to fly to Chicago is generally in the evening, which is peak travel time and where the average cost of a ticket is $875.

What is a good deal for flights to Chicago?

If you’re looking for cheap airfare to Chicago, 25% of our users found tickets to Chicago for the following prices or less: From Milan Malpensa Airport $678 one-way - $829 round-trip, from Rome Fiumicino Airport $720 one-way - $668 round-trip, from Venice Marco Polo Airport $812 one-way - $797 round-trip.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 79 days before departure.

Which is the cheapest airport to fly into in Chicago?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Chicago is Chicago Midway Airport, with an average flight price of $114.

Which airlines fly to Chicago?

Many airlines fly to Chicago, the most common ones being American Airlines, United Airlines, and ITA Airways. See the amount of flights per week for popular airlines flying to Chicago.

Which airline offers the most flights to Chicago?

Of the 14 airlines that fly to Chicago, United Airlines offers the most flights, with around 5,222 per week, followed by American Airlines with 2,596 flights per week.

How many airports are there in Chicago?

There are 3 airports in Chicago: Chicago O'Hare Airport (ORD), Chicago Midway Airport (MDW) and Chicago Greater Rockford Airport (RFD). The busiest airport is Chicago O'Hare Airport (ORD), with 82% of all flights arriving there.

How long is the flight to Chicago?

The duration of your flight to Chicago depends on your departure and arrival airports. Obviously any flights that include a layover will also be longer. The most popular routes to Chicago on KAYAK are from Milan, which takes 9h 35m, Venice, which takes 10h 00m, Rome, which takes 10h 15m, and Naples, which takes 13h 15m.

How many direct flights to Chicago are there each day?

There are around 1,572 direct flights from within Italy to Chicago every day. Most flights depart in the morning, with 6:00 am the most common departure time and 51% of flights departing in the morning.

How many direct flights to Chicago are there each week?

Each week there are around 11,003 direct flights from within Italy to Chicago. The most common day for departures is Tuesday, with 16% of flights taking off on this day.

How many long-haul flights are there to Chicago each week?

There are not any medium-haul (3-6 hour flight duration) or short-haul (up to 3 hour flight duration) flights to Chicago. Instead, there are 40 long-haul flights (6-12 hour flight duration), with the most arriving from Rome.

How many cities have direct flights to Chicago?

From Italy, there are direct flights to Chicago from 2 cities. The city with the most direct flights is Rome, with 33 direct flights each week.

Good to know

Low season

January

High season

August

Cheapest flight

$209
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 37% increase in price.
Flight from Rome Fiumicino Airport to Chicago O'Hare Airport

FAQs - booking Chicago flights

  • Which Chicago airport is closest to central Chicago?

    Chicago is served by 3 major airports. Chicago Midway Airport (9 miles) is the closest to the center of Chicago. Chicago O'Hare Airport is 16 miles from the center and Chicago Greater Rockford is 79 miles away from the center.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $873. The cheapest price found on KAYAK in the last 2 weeks cost $434 and departed from Milan Malpensa Airport.

  • How does KAYAK find such low prices on flights to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Chicago

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Prefer to fly non-stop to Chicago?

Find which airlines fly direct to Chicago, which days they fly and book direct flights.

Nonstop departures

Italy to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

See more direct flights

Nonstop returns

Chicago to Italy

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

See more direct flights
See more direct flights

Top 5 airlines serving from Italy to Chicago

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Italy to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
Scandinavian AirlinesOverall score based on 1431 reviews
7.7Boarding
7.3Comfort
6.8Food
8.1Crew
6.7Entertainment
Airline reviews

Bathrooms weren’t too clean. Onboard entertainment was light. Other than that everything was great. Food, service, comfort and crew. Although it was hard to understand the crew announcements.

10.0 ExcellentAna, May 2024CPH - LAX
Read more about Scandinavian Airlines reviews

Bathrooms weren’t too clean. Onboard entertainment was light. Other than that everything was great. Food, service, comfort and crew. Although it was hard to understand the crew announcements.

Much better, not their fault but my plane was so delayed causing me to have to take this airline rather than my earlier connecting flight

TERRIBLE! Staff was unfriendly, rude, and demeaning. One flight attendant touched me to grab the complimentary blanket off my neck because I couldn't take it home, while a bunch of other people took theirs home. I have never been so ill treated. I am not happy at all. And flight was delayed, no information until short notice for everything. Lost an entire day at my destination. I expect a full refund for that experience. Never will fly with them EVER again

My return flight has been changed to JFK from EWR without any notice or reason

This was my first time flying SAS and used them for 4 flights. The crews, flight and communication was outstanding. I flew premium economy and was extremely impressed by their SAS lounges. I will 100% ise SAS again. Everyone was so pleasant!

I upgraded to economy plus and it’s so worth the price. The crew is exceptional and the food is pretty decent. I would definitely fly with them again.

I had economy plus and it’s definitely worth the price. The seats are so comfortable, so much space, great large TV screens, and you get fed often. Really decent food (although other fish was overcooked.) They do need better movie choices. The crew is the best. Super friendly and accommodating. So much better than most American run Airlines.

They lost my luggage. Tromso in winter without warm clothes is not fun.

I paid for wifi and it worked about a total of 5 min. Feel ripped off

Overall, this flight team did a fantastic job. They came often with the water, coffee and tea. There was no meal choice in coach, but the lasagna lunch was decent. The sandwich snack just before landing was tasty. The baggage bins were large, so no trouble holding carry on luggage.

It was good! Appreciated that it was very on schedule so it made the connecting flight less stressful

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

We were delayed an hour leaving Munich (No fault of the crew). They kept us posted on the status so we knew what was going on, but as a result we missed our connection in Chicago and the communication on connecting flights was pretty poor as we disembarked. It was already stressful and some of that could have been reduced by better communications about where to find transfers, etc.

One problem, but a serious one - the plane is built with electric windows that tint dark to reduce light. Sitting next to the window is VERY UNCOMFORTABLE as it emits so much HEAT in the face when tinted.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

Wifi wasn't working on one of the UA flights after boarding.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Crew was not very helpful. They forgot to serve me coffee and had to wait for a long time.It looked as if they were not very happy with what they were doing.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

The plane was old and in new of a cleaning up and renovating on the interior. Seats and carpets were very worn and dirty looking. Cushioning on the seats was broken down and not as comfortable as newer jet seats. Food was a little below average but okay. Staff were friendly and hard working but did not pick up debris or food they spilled when collecting from the customers. But they were very helpful and professional.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

lounge was the highlight - seats weren't that comfortable - it was a full flight but no complaints

my original flight was cancelled the previous day, and i was rescheduled onto this flight, which left much earlier in the morning, impacting my previous evening and requiring me to get up much earlier in the morning to get to the airport online. This practice happens way way way too much, and it seems on every airline, though AA is probably the worst.

Spending 10 hours on a flight with no video or wifi access due to issues per stewardess was not enjoyable nor acceptable. Will follow up directly with the airline as well

I really did not like being ordered to pull my shade down by the attendants. One of them was very rude to me about it, standing there until I closed it like I was a child brusquely reaching across me to close an adjoining one. They claim it was so people who wanted to could sleep. It’s a 10:30am flight not a red eye. Closing your shade or leaving it up for natural light should be a choice. Ruined my flight!

My baggage did not arrived with me. Took 3 days to get it after so may calls and follow up

The crew was very attentive and kept busy serving a variety of treats!

Terrible. Flight was 3 hours delayed and I missed my other flight to my final destination

Offered vegetable curry when it was actually tofu which I don’t care for.

The flight was good the crew excellent…but take off delayed three hours!!!

Both mine and my husband's chairs were broken. Also it took 2 hours to get our bags after our flight which was wild.

perhaps eye contact with the cabin crew, instead of abruptness and an impatience to serve.

The plane seemed very dated. The entertainment was very limited. There was a school group on our flight and the crew seemed bothered by them. They were not overly friendly or welcoming.

Ok, but no entertainment. Left late, but made up most of the time.

May be it is not an ITA issue, but the bags took long time to go out.

Good. But there food was poor quality and 95% of movies didn't have English subtitles

I thought they had rebranded themselves in every aspect but it was quite the opposite. The food was terrible the service was sub-par. Overall it was not a good experience.

Service from staff was poor, food choices were limited. Air plane was not clean or hygienic and seemed like not cleaned for days. Seats were uncomfortable.

service from stAff was barely there , food choices were limited. AirPlane was not clean and seemed like it was not cleaned for days.. Seats were very uncomfortable.

I paid for premium seats and the last minute they changed the aircraft for a bigger one, they bumped me to another seat which was NOT at all comfortable for an 11 hour flight, will fight for a refund!!

The landing was catastrophic. I was very scared. I thought it were my last lminues. Pilotes should be more experienced

ALL services were good. An announcement should’ve been made at the end of the flight that filling out a customs form would not be necessary anymore for USA travelers entering Philadelphia.

Book cheap flights from Italy to Chicago

Recent round-trip flight deals

 
These are the cheapest round-trip flights to Chicago found on KAYAK in the last 72 hours.
9/12tors
1 stopTAP AIR PORTUGAL
29h 40mMXP-ORD
9/16mån
1 stopTAP AIR PORTUGAL
15h 25mORD-MXP
$438
9/17tis
1 stopIcelandair
12h 45mMXP-ORD
10/20sön
1 stopIcelandair
12h 00mORD-MXP
$478
10/17tors
1 stopScandinavian Airlines
34h 15mMXP-ORD
10/21mån
1 stopScandinavian Airlines
16h 30mORD-MXP
$514
10/17tors
2 stopsScandinavian Airlines
28h 10mMXP-ORD
10/21mån
1 stopScandinavian Airlines
16h 30mORD-MXP
$525
9/15sön
1 stopITA Airways
13h 40mLIN-ORD
10/17tors
1 stopITA Airways
12h 10mORD-LIN
$547
6/3mån
1 stopBritish Airways
13h 20mLIN-ORD
3/12ons
1 stopBritish Airways
13h 25mORD-LIN
$565
9/12tors
1 stopITA Airways
13h 40mLIN-ORD
10/19lör
1 stopITA Airways
12h 10mORD-LIN
$579
9/18ons
nonstopBritish Airways
10h 50mFCO-ORD
10/2ons
1 stopBritish Airways
15h 40mORD-FCO
$585
10/14mån
1 stopAmerican Airlines
27h 07mFCO-ORD
11/14tors
1 stopAmerican Airlines
23h 35mORD-FCO
$680
10/11fre
1 stopAmerican Airlines
29h 55mFCO-ORD
11/11mån
2 stopsAmerican Airlines
16h 40mORD-FCO
$682

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Recent one-way flight deals

 
Only flying one-way? Below are some of the best deals for one-way flights to Chicago found on KAYAK in the last 72 hours.
6/10mån
1 stop
22h 19mFCO-ORD
$209
6/11tis
2 stops
40h 37mFCO-ORD
$238
5/29ons
1 stopScandinavian Airlines
13h 35mMXP-ORD
$531
5/29ons
1 stopScandinavian Airlines
13h 35mMXP-ORD
$533
8/22tors
2 stopsITA Airways
21h 42mVCE-ORD
$580
8/22tors
2 stopsITA Airways
21h 42mVCE-ORD
$582
8/21ons
nonstopBritish Airways
10h 25mFCO-ORD
$682
5/22ons
nonstopBritish Airways
10h 25mFCO-ORD
$715
7/31ons
nonstopAmerican Airlines
10h 00mVCE-ORD
$1,180
7/31ons
1 stopAmerican Airlines
14h 40mVCE-ORD
$1,190

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Last minute flights to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights to Chicago that are departing in the next 10 days.
5/9tors
nonstopIberia
10h 25mFCO-ORD
5/16tors
multi-stopIberia
15h 50mORD-FCO
$597
5/9tors
multi-stopIberia
15h 00mFCO-ORD
5/16tors
multi-stopIberia
15h 50mORD-FCO
$606
5/9tors
multi-stopUnited Airlines
17h 12mFCO-ORD
5/16tors
multi-stopUnited Airlines
14h 00mORD-FCO
$651
5/9tors
multi-stop
17h 34mMXP-ORD
5/16tors
multi-stop
14h 25mORD-MXP
$676
5/9tors
multi-stopAmerican Airlines
19h 49mMXP-ORD
5/16tors
multi-stopAmerican Airlines
34h 25mORD-MXP
$702
5/9tors
nonstopBritish Airways
10h 25mFCO-ORD
5/13mån
multi-stopBritish Airways
16h 45mORD-FCO
$724
5/9tors
nonstopITA Airways
10h 50mFCO-ORD
5/13mån
nonstopITA Airways
9h 20mORD-FCO
$728
5/9tors
nonstopUnited Airlines
9h 35mMXP-ORD
5/16tors
multi-stopUnited Airlines
13h 05mORD-MXP
$749
5/9tors
multi-stopITA Airways
24h 10mLIN-ORD
5/16tors
multi-stopITA Airways
16h 10mORD-LIN
$766
5/7tis
multi-stopAmerican Airlines
13h 35mMXP-ORD
5/14tis
multi-stopAmerican Airlines
16h 10mORD-MXP
$771

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