$307 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 6/2. 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.
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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
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Cheap Flight Deals from Italy to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Italy to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Italy to Chicago

KAYAK's recommended round-trip deals from the most popular airlines that fly from Italy to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Icelandair Logo
3:10 pm - 9:15 pmMXP-ORD
13h 05m1 stop
Icelandair Logo
10:15 pm - 10:00 pmORD-MXP
16h 45m1 stop
$483Icelandair
Find Deal
Thu, Jun 5 - Mon, Jun 16
Icelandair Logo
3:10 pm - 9:15 pmMXP-ORD
13h 05m1 stop
Icelandair Logo
7:25 pm - 2:10 pmORD-MXP
11h 45m1 stop
$484Icelandair
Find Deal
Thu, May 15 - Wed, May 28
British Airways Logo
11:10 am - 5:34 pmMXP-ORD
13h 24m1 stop
British Airways Logo
10:25 pm - 6:05 pmORD-MXP
12h 40m1 stop
$544British Airways
Find Deal
Tue, May 20 - Tue, May 27
British Airways Logo
7:50 am - 3:55 pmNAP-ORD
15h 05m1 stop
British Airways Logo
8:30 pm - 10:00 pmORD-NAP
18h 30m1 stop
$546British Airways
Find Deal
Fri, May 16 - Sun, Jun 1
United Airlines Logo
9:45 am - 1:10 pmFCO-ORD
10h 25mnonstop
United Airlines Logo
6:30 pm - 10:15 amORD-FCO
32h 45m1 stop
$548United Airlines
Find Deal
Sat, May 24 - Sat, May 24
ITA Airways Logo
9:25 am - 1:10 pmFCO-ORD
10h 45mnonstop
ITA Airways Logo
3:00 pm - 7:25 amORD-FCO
9h 25mnonstop
$581ITA Airways
Find Deal
Fri, Jun 13 - Sun, Jun 29
ITA Airways Logo
9:25 am - 1:10 pmFCO-ORD
10h 45mnonstop
ITA Airways Logo
3:00 pm - 7:25 amORD-FCO
9h 25mnonstop
$582ITA Airways
Find Deal
Fri, Jun 13 - Sun, Jun 29
United Airlines Logo
9:45 am - 1:10 pmFCO-ORD
10h 25mnonstop
United Airlines Logo
4:00 pm - 9:15 amORD-FCO
34h 15m2 stops
$598United Airlines
Find Deal
Sat, May 24 - Sat, May 24
Lufthansa Logo
6:30 am - 2:00 pmVCE-ORD
14h 30m1 stop
Lufthansa Logo
6:00 pm - 7:30 pmORD-VCE
18h 30m1 stop
$668Lufthansa
Find Deal
Fri, May 30 - Thu, Jun 26
Lufthansa Logo
6:00 am - 11:00 amVCE-ORD
12h 00m1 stop
Lufthansa Logo
10:30 pm - 10:30 pmORD-VCE
17h 00m2 stops
$712Lufthansa
Find Deal
Mon, Jul 14 - Wed, Jul 30
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KAYAK's insights & trends for flights to Chicago

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 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 February, where tickets cost $578 on average for return flights. On the other hand, the most expensive months are August and July, where the average cost of tickets from Italy is $817 and $742 respectively. For one-way flights, the best month to travel is January with an average price of $484.

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 $664 round-trip, from Milan Malpensa Airport $847 round-trip, from Naples $952 round-trip.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price, you should book around 4 weeks before departure. For the absolute cheapest price, our data suggests you should book 19 weeks 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 Greater Rockford Airport (RFD), with an average flight price of $137.


Good to know

Low seasonJanuary
High seasonAugust
Cheapest flight$307
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 11% increase in price.
Flight from Naples to Chicago

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 $859. The cheapest price found on KAYAK in the last 2 weeks cost $542 and departed from Rome Fiumicino Airport.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Thursday where round-trip tickets can be as cheap as $790. On the other hand, the most expensive day to fly is Friday, where round-trip prices are $898 on average.

  • 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.

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

    The cheapest time of day to fly to Chicago is generally in the afternoon, when round-trip flights cost $748 on average. The most expensive time of day to fly to Chicago is generally in the morning, which is peak travel time and where the average cost of a ticket is $838.

  • How many direct flights to Chicago are there each week?

    Each week there are around 10,604 direct flights from within Italy to Chicago. The most common day for departures is Sunday, with 15% of flights taking off on this day.

Top tips for finding cheap flights to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $678 or less one-way and $664 or less round-trip.
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

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
United AirlinesOverall score based on 8696 reviews
7.1Entertainment
7.7Boarding
6.6Food
7.3Comfort
8.1Crew
Airline reviews

So far so good but food and entertainment are not available for this flight

8.0 ExcellentAnonymous, Apr 2025YUL - ORD
Read more United Airlines reviews

So far so good but food and entertainment are not available for this flight

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.

Very modern plane. Good seat spacing. Meals were good. Screens had tons of movies and worked

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

Other than being delayed 5.5 hours and having to get a hotel because I missed my connecting flight, it was an okay flight. No in-flight Wi-Fi or entertainment.

I don't like anything in this flight the food was bad the service was bad the flight was old and not connected to the screen no intertainments at all and it was long trip was bad intertainments the crew not helping

The flight was great. I don’t know about the food because I was asleep and they didn’t leave me any.

The flight was great, smooth and even a little ahead of time.

There wasn't a time for neither food morning entertainment in a short one hour hop over.

Flight on time, flight assistants super nice, business class very comfortable. The whole experience was very good.

Not online or self check in, sent emails in Italian language ,not recommended.

Premium Economy was average for class. Seat comfort was just okay. Crew was attentive. Checkin was fine and moved quickly. Boarding process in Rome was not well organized.

It was horrible the woman next to me was sick and I asked if they would change my seat and they said that they didn’t have any available. I sat next to this women for 9 hour and now I am sick .

We booked and purchase our seats in February for a September flight. We choose seats then also, did the online check in on the app the day before and all was fine. At the airline check in they charged our seats and we were not even sitting together after paying for business class seats. They separated us with no explanation and would not change them back. I was very upset. On the return flight, they tried to put us on standby! When again, we purchased seats in February for this flight. The plane was old and smaller and the business class seats were not comfortable like the flight from NYC. Flight attendants were hard to find once the first meal was served, luckily the flights were smooth.

Crew was good. Very nice staff. Wine was good. Problems- no AC while waiting for takeoff. Long wait so we should have been more comfortable. No water for quite awhile. Food should have been better for an Italian airline. Chicken was pressed rounds of processed meat- not tasty. We had only one hour for our connection- ran through airport- plane waited for us and staff was helpful.

I wish seats were not reclinable. It's so claustrophobic when the person in front of you spends most of a nine hour flight leaned all the way back. The crew was really nice though and the dinner (red Thai curry) was pretty compelling.

Our flights were severely delayed, then canceled and we had to fly out next day with no sleep accommodation help. This led to our baggage being lost and the service reps after baggage couldn’t be bothered to help. They kept sending us to different counters when we were at the right counter to begin with. The only saving grace was the angel woman supervisor with blond hair who helped us put in a missing baggage claim.

The boarding system was all bogus - employees at the boarding gate were not sound like proffesional or may be possibly rational

I got an email in the morning of the flight 1/7, from Kayak, that I was rebooked from UA 906 to LH 430. Nobody at Lufthansa ot United knew about this. I went to both counters. at the airport. Also, Cheap Flights, who I booked the ticket through, did not know. I ended up staying on the United flight. But this was very disturbing, since I got a very late notice that I was rebooked to an earlier flight, I hurried to the airport to find out after a lot of inquiring that this was a mistake. Not a good Kayak experience.

After living in Europe for five years and flying with Lufthansa and KLM airlines, I’ve realized that United Airlines is now a budget carrier. The flight attendant are not friendly. The seats are not comfortable. And everything comes at a cost. I will be flying with KLM and Skyteam like Delta to the US going forward no doubt. United Airlines is not what it once was:

Delayed take off but I think they waited for passengers.

I had to fly United where the flight crew was atrocious

Flight was delayed for no reason and I missed my connection. This added another day of travel and I missed an event I was traveling home for.

I traveled with my sister, however ,we booked a flight separately, and we don't sitting next to each other. The staff on the board where on the top of this unit they find us sitting together. Ty lufthansa team. U are the best

Courtesy of waitress. Could improve on time management and check-in

Boarding is a mess. They never check group # so lots of people crowding in. Comfortable seats this flight. I had an empty seat next to me, very convenient. Food was really not good, but I was starved. The pizza snack thing was horrible. Crew was grand. They really make it enjoyable.

Too much long line at the TSA and Security. Prepare for long walk for baggage claim.

Crew very helpful and friendly. Food is so so. Main meal is not always the best. Did have a choice of a snack part way which was either a cookie, corn snack, or similar. Second kind of meal was basically like a pizza pastry that really wasn’t a favorite but probably a European snack? Screens and selections of movies, tv and such were good. No WI-Fi unless you buy so no free texting or such on the long flight but I think that might be any overseas flight.

The boarding process was quite loud and chaotic. The flight attendants kept barking over the PA system about people needing to only stow large items in the overhead bins. During the one and only service, I was hit by the service cart. At the same time, a passenger was returning from the bathroom and the crew definitely saw him but stopped a few seats short of allowing him to sit down before starting service and made him wait a good 10 minutes before passing his seat and allowing him to sit down, after which he had to ask for his snack and beverage or he would have been passed over. Neither flight attendant thanked passengers as they left; in fact, I did not see them again once the plane door was opened.

Flight Attendant Karen Lynn was an absolute delight. She assisted in every portion of the services provided throughout the flight, aided with any and all concerns expressed by passengers, and even helped comfort an upset child who was one of five of a traveling family. This quality of service is what keeps me coming back to American. Thank you!

The worst, flight cancelled because the aircraft was not full. Heathrow ground crew totally not helpful and arrogant. Lady proposed us flight with 40min layover instead of direct and said it is our problem of course she was unable to do anything as everything was beyond her control she claimed. after calling on hotline another flight was booked. Flight was cancelled last second so we could not take direct from Zurich but we had to stay overnight in London.

The seats in row 31 are terrible and small and uncomfortable. Don't ever sit there. The window seat is so close to the curve of the plane is so annoying. I paid extra for this seat and I hated all 10 hours in it.

Food was terrible , crew were excellent , IFE was dire . Overall comfortable seat and cabin. Nothing special .

If my tv wasn’t broken and I wasn’t in a seat that didn’t allow for sleeping

Delayed flight due to lack of crew caused me to miss my connection

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Chicago

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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