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$258 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 9/6. 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
sáb. 6/29
sáb. 7/6

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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 42,686,544 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 $635. On the other hand, the most expensive day to fly is Saturday, where prices are $884 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 $559.

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 $700 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 $848.

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 Rome Fiumicino Airport $745 one-way - $706 round-trip, from Venice Marco Polo Airport $819 one-way - $416 round-trip, from Milan Malpensa Airport $1,174 one-way - $832 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 $107.

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 4,400 per week, followed by American Airlines with 2,642 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 83% 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 Rome, which takes 10h 15m, Milan, which takes 11h 27m, Naples, which takes 13h 35m, and Bergamo, which takes 14h 45m.

How many direct flights to Chicago are there each day?

There are around 1,404 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 50% of flights departing in the morning.

How many direct flights to Chicago are there each week?

Each week there are around 9,822 direct flights from within Italy to Chicago. The most common day for departures is Friday, with 15% 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 63 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 3 cities. The city with the most direct flights is Rome, with 35 direct flights each week.

Good to know

Low season

January

High season

August

Cheapest flight

$258
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 30% 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 $939. The cheapest price found on KAYAK in the last 2 weeks cost $391 and departed from Venice Marco Polo 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, +79 more

ANA, Aer Lingus, +80 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 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, +79 more

ANA, Aer Lingus, +80 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 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 1402 reviews
7.3Comfort
7.7Boarding
6.8Food
8.1Crew
6.7Entertainment
Airline reviews

Other than a delay that had nothing to do with the staff, it was a very pleasant experience.

10.0 ExcellentMike, May 2024CPH - FCO
Read more about Scandinavian Airlines reviews

Other than a delay that had nothing to do with the staff, it was a very pleasant experience.

SAS is the representation of the Scandinavian minimalism, which I like. I wished they had a more relaxed policy on free water distribution beyond one bottle (500 ml) per person and two drinks, including water, per overseas flight.

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.

Left on time. Arrived early. Turbulence coming in and gate not open due to early arrival but expected.

The CX617 from HK to BKK was delayed more than 1.5 hours.

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.

Crew was very nice and helpful. It was a good flight experience.

Efficient boarding. Good flight but seats were quite uncomfortable considering we'd already been sitting on two flights, total 13 hours or so. Would have liked to have prices on the menu of amenities on the plane. We could have used more water. Restrooms and nonalcoholic beverages at no extra cost, not much else. I realize these were discount tickets, and the airline has to break even, so I can't say we were expecting amenities to be plentiful. Still, it's nice with long flights to discover a few. Very pleasant crew though.

Will try to not fly with them again. Delays because of weather but got redirected to an airport where I could not make connection.

Staff didn’t care in business class. Closed the door on my mom while she was on the jetbridge and flight attendant told me she would make it from the connecting flight. They lied. My luggage was damaged on arrival. No success in filing damage claim.

Crew was super rude in business class. Not friendly or helpful. Luggage was damaged and was told to file with United and that was unsuccessful.

my flight was at 3:45 after that they delayed to 4:40 I have transit from Chicago to Frankfurt and Frankfurt to vina airport from vina to Erbil buy the Time I come to Frankfort my other flight left me I have to stay at airport all day with my 5 kids ask for help no one help me I spent at airport almost $450 just for food was horrible flight ever I call and ask for hotel from united customer service they been telling me we can’t provide any hotel I need some refund or fixed my flight when I return to America need some one respond my email

The crew member put her luggage and boxes behind my seat so I was able to recline while the passenger in front of me did for 8 hours. My knees were forced against the seat for hours :(. Dude sitting next to me hasn't showered in weeks so I almost threw up.

I always try to book flights that don’t charge for baggage. Yet I was charged $75 for this flight.

Our flight to Chicago O'Hare was delayed an hour, causing us to miss our connection to MSP and spend an extra 3 hours at O'Hare so we could board a plane with a damaged door and wait another 45 minutes or so. The crew was great, the food decent, The drinks were great: 2 glasses of a nice South African Shiraz, an ice cold can of Beck's Beer, and Dewar's White Label on the rocks.

A350 has great entertainment. Make sure to watch the plane's external tail and nose camera's on landing and take off. Seats were a little hard for a 10 hour flight. I am gluten intolerant, they had good alternative meals for me on the flight.

There was nothing to like besides the crew. The comfort of the airplane was poor (seat did not work properly and it was not comfortable). The “entertainment” system did not work! On a flight that last nearly eight hours, (which is advertised as having excellent entertainment options), that is unacceptable! Passengers should have been given free WiFi for the flight. The food served on the flight was below school lunch grade food. (With one exception, the ice cream snack). The chicken entree was tough and nearly impossible to cut and eat. The “pizza” served later in the flight was worse. The chicken pizza had a dry crust and the “toppings” were equally not enjoyable. The amount of chicken and cheese were almost non existent. Overall not a flight we would want to repeat!!

There was a problem in the luggage because there were not porters

2-1/2 hours on tarmac after arrival to DFW, lost connection to London, 3 hours wait for customer assistance, stayed on our own account in DFW, no replacement flight for 5 days, had to cancel the entire travel and return to Monterrey today.

My worst flying experience so far. This flight was delayed a total of 42 hours and diverted to New York before it was finally cancelled. It was delayed 4 and a half hours in London. As we were scanning our boarding passes at the gate they advised that the flight was being diverted to JFK since the delays caused us to missed the open hours for Charlotte international customs and immigration. We were assured multiple times by airport personnel, flight attendants, and the Pilot that we would land at JFK go through customs and immigration and then reboard the plane to fly to Charlotte in the same night. When we landed in New York the pilot advised us as we were retrieving our carry on luggage that we were delayed till 10am the next morning and to see guest services to get a room for the night. During this time I had to purchase a room for a family member in Charlotte which drove over 4 and a half hours to pick us up from Charlotte. This could have been avoided if American Airlines had been up front about the delay. Then after standing in line for over 2 and a half hours at guest services we were taken by taxi to a hotel 30 minutes out of the way. Luckily I looked for other flights that night and found one at 8 am to get on. The initial flight which we were scheduled to fly to charlotte in was delayed 12 more times and was finally cancelled 42 hours after it was supposed to land. I am unaware of what happened to the guest that were supposed to fly on the flight after we were placed on another flight but 42 hours in delays for a direct flight is absolutely ridiculous.

The boarding to Gatwick was a breeze but the boarding from Gatwick was a nightmare. The onboard service to Gatwick had a lot to be desired but the onboard sevice from Gatwick was amazing ! Very nice,friendly and funny ! Would I recommend BA to anyone.? ! Yes I would!

Is it American Airlines or British Airways? This is so confusing. I got it from Portugal.

Appreciate free wine and entertainment plus good meals. Also leg room

Really quick check in and security at Heathrow Terminal 5. Staff on board were lovely and very friendly. Could have provided a few more drinks on the flight but they were available at the back of the plane.

they are improving. The crew from Charlotte to Tampa was outstanding. SMILING and trying to be helpful with the customers.

It was a flight operated by Aer Linus for BA and the plane and crew were very good but the food selection was average.

It was a short haul trip, so food and entertainment weren’t a big issue

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

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.
8/30vie.
1 stopTAP AIR PORTUGAL
26h 45mMXP-ORD
9/9lun.
1 stopTAP AIR PORTUGAL
23h 35mORD-MXP
$478
11/15vie.
1 stopAer Lingus
13h 20mFCO-ORD
11/22vie.
1 stopAer Lingus
12h 00mORD-FCO
$488
11/20mié.
2 stopsScandinavian Airlines
36h 10mLIN-ORD
11/24dom.
2 stopsScandinavian Airlines
32h 55mORD-LIN
$495
11/17dom.
1 stopScandinavian Airlines
13h 45mMXP-ORD
11/24dom.
1 stopScandinavian Airlines
16h 00mORD-MXP
$501
9/1dom.
1 stopITA Airways
13h 40mLIN-ORD
9/8dom.
1 stopITA Airways
20h 10mORD-LIN
$513
7/12vie.
1 stopITA Airways
13h 40mBLQ-ORD
9/16lun.
1 stopITA Airways
16h 50mORD-BLQ
$520
7/18jue.
nonstopBritish Airways
10h 00mVCE-ORD
9/8dom.
1 stopBritish Airways
14h 25mORD-VCE
$535
8/4dom.
1 stopBritish Airways
26h 20mLIN-ORD
8/31sáb.
1 stopBritish Airways
18h 30mORD-LIN
$535
6/18mar.
2 stopsAmerican Airlines
25h 58mVCE-ORD
6/24lun.
2 stopsAmerican Airlines
19h 25mORD-VCE
$554
6/9dom.
2 stopsAmerican Airlines
24h 04mFCO-ORD
6/24lun.
1 stopAmerican Airlines
17h 45mORD-FCO
$565

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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.
9/6vie.
1 stop
22h 19mFCO-ORD
$258
9/6vie.
2 stops
31h 02mFCO-ORD
$280
6/13jue.
2 stops
44h 39mFCO-MDW
$298
11/4lun.
1 stopScandinavian Airlines
13h 45mMXP-ORD
$497
6/20jue.
1 stopITA Airways
25h 00mVCE-ORD
$529
9/9lun.
1 stopITA Airways
13h 40mLIN-ORD
$562
7/19vie.
nonstopBritish Airways
10h 00mVCE-ORD
$587
8/22jue.
nonstopBritish Airways
10h 00mVCE-ORD
$588
9/5jue.
nonstopAmerican Airlines
10h 00mVCE-ORD
$935
6/6jue.
nonstopAmerican Airlines
10h 00mVCE-ORD
$1,105

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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.
6/4mar.
multi-stopAir Canada
14h 01mMXP-ORD
6/11mar.
multi-stopAir Canada
11h 25mORD-MXP
$547
6/4mar.
nonstop
9h 45mMXP-ORD
6/11mar.
multi-stop
11h 25mORD-MXP
$569
6/4mar.
multi-stopAmerican Airlines
15h 10mMXP-ORD
6/11mar.
multi-stopAmerican Airlines
16h 25mORD-MXP
$588
6/3lun.
multi-stopBritish Airways
22h 15mBLQ-ORD
6/10lun.
multi-stopBritish Airways
18h 20mORD-BLQ
$711
6/3lun.
multi-stopBritish Airways
25h 15mBLQ-ORD
6/10lun.
multi-stopBritish Airways
18h 20mORD-BLQ
$714
5/31vie.
multi-stopScandinavian Airlines
28h 50mMXP-ORD
6/13jue.
multi-stopScandinavian Airlines
16h 30mORD-MXP
$723
5/31vie.
multi-stopScandinavian Airlines
28h 50mMXP-ORD
6/13jue.
multi-stopScandinavian Airlines
37h 10mORD-MXP
$765
6/3lun.
nonstopITA Airways
10h 50mFCO-ORD
8/18dom.
nonstopITA Airways
9h 20mORD-FCO
$766
6/4mar.
multi-stopAmerican Airlines
15h 10mMXP-ORD
6/7vie.
multi-stopAmerican Airlines
14h 40mORD-MXP
$868
6/4mar.
multi-stopITA Airways
13h 40mLIN-ORD
6/11mar.
multi-stopITA Airways
13h 10mORD-LIN
$3,315

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