$217 Find Cheap Flights from Chicago to Italy - Compare and Save

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Cheap Flights from Chicago to Italy

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Rome
Rome1 stop$592
Milan
Bergamo2 stops$636
Florence
Florence1 stop$669
Naples
Naples1 stop$612
Palermo
Palermo1 stop$628
Bologna
Bologna1 stop$610
Turin
Turin1 stop$618
Rome
Rome1 stop$592
Milan
Bergamo2 stops$636
Florence
Florence1 stop$669
Naples
Naples1 stop$612
Palermo
Palermo1 stop$628
Bologna
Bologna1 stop$610
Turin
Turin1 stop$618
Booking Insights

Price, demand and travel trends for Chicago to Italy flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

Are flights from Chicago to Italy cheaper or more expensive than last year?

Fares from Chicago to Italy are running about the same as they were around this time last year, averaging $902 round-trip.

What are the cheapest fares from Chicago to Italy right now?

Here are the cheapest round-trip fares from Chicago to Italy on KAYAK in the last week:

• Rome Fiumicino (FCO) from $592
• Bologna Guglielmo Marconi (BLQ) from $610
• Bari Palese (BRI) from $611
• Naples (NAP) from $612
• Venice Marco Polo (VCE) from $617

What’s the cheapest month to fly from Chicago to Italy?

February is the cheapest time of year to fly, with average fares of $635. Prices are highest in June, when average flight costs increase to around $1,071.

When is the best time to book flights from Chicago to Italy?

Book your flights 26 weeks before your trip. KAYAK data collected over the past 12 months shows that booking in this window can save you around 15% compared to booking last-minute (within 2 weeks of departure).

Which airport in Italy is the cheapest to fly to from Chicago?

Based on KAYAK data from the past 12 months, the cheapest airports to fly into Italy are:

• Turin Citta Di Torino (TRN) from $857
• Rome Fiumicino (FCO) from $881
• Milan Linate (LIN) from $896

What’s the cheapest day to fly from Chicago to Italy?

Sunday tends to be the cheapest day to fly from Chicago to Italy, while Friday is the most expensive. Fares run about 11% higher that day, based on the past 12 months of KAYAK data.

What's the cheapest time of day to fly from Chicago to Italy?

Data from the past 12 months shows it's cheapest to fly to Italy during the morning with average prices of $779. The night is the most expensive time to fly, with average prices of $1,083.

Key details for Chicago to Italy flights

Low season

January

Cheapest flight

$217
Beat the crowds with an average 52% drop in travelers.
The most popular month to fly with an average 60% increase in travelers.
One-way flight from Chicago O'Hare Intl Airport to Milan Malpensa Airport

Your Chicago to Italy flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Chicago to Italy?

    Yes. Fares from Chicago to Italy are low right now. As a rule of thumb, a round-trip under $734 (cheaper than most fares this year) is a good deal, so if you spot one at or below that, it's a good time to book.

  • How much should I budget for a flight from Chicago to Italy?

    Over the past 12 months, round-trip fares from Chicago to Italy have ranged from $734 to $1,245.

  • What are the main airports serving Italy?

    Italy has 43 airports. The three busiest are Rome Fiumicino (FCO) (48% of arrivals), Venice Marco Polo (VCE) (11%) and Milan Malpensa (MXP) (10%).

  • What airlines fly nonstop from Chicago to Italy?

    Based on the flight schedule for the next 3 months, 2 airlines offer nonstop flights on this route:

    • United Airlines
    • American Airlines

  • Where in Italy can I fly nonstop from Chicago?

    Based on the flight schedule for the next 3 months, you can fly nonstop from Chicago to two destinations: Rome and Milan.

  • Is it cheaper to fly with a layover from Chicago to Italy?

    Yes. Nonstop flights from Chicago to Italy average $1,038 over the past 12 months, but flights with a layover can cost less. The most affordable connecting airports are:

    • Lisbon Humberto Delgado (LIS) from $650
    • Reykjavik Keflavik Intl (KEF) from $701
    • Kastrup Copenhagen (CPH) from $721

  • How long is a flight from Chicago to Italy?

    Nonstop flights take 8h 58m on average. The fastest scheduled flight takes 8h 40m, from Chicago O'Hare Intl (ORD) to Milan Malpensa (MXP).

  • How often are flights from Chicago to Italy delayed and what's the average delay?

    30% of flights on this route are delayed by at least 15 minutes. The average delay is 2h 37m.

  • Which cabin classes are available on flights from Chicago to Italy?

    On flights from Chicago to Italy you can book Economy Class, Premium Economy Class, Business Class or First Class.

  • What are some popular landmarks in Italy?

    KAYAK travelers' favorite landmarks in Italy include:

    • Piazza Navona
    • Colosseum
    • Pantheon
    • Fontana di Trevi

  • What are the earliest and latest flights from Chicago to Italy?

    The earliest nonstop flight from Chicago to Italy departs at 3:40 pm and the latest departs at 10:35 pm. Nonstop flights take about 8h 58m.

  • If my flight to Italy will be landing at Milan Malpensa Airport (MXP), will I be able to find ground transportation to take me from the airport to downtown Milan?

    One of the quickest and most cost-effective ways to make this trip is aboard the light rail service offered by Malpensa Express. This train makes the trip to downtown Milan in around 37min for a cost of about 13 EUR (15 USD).

  • If I am going to be flying from Chicago to Italy, will I need to get a visa before I travel and do I need a passport?

    Before you hop aboard your flight to Italy, it is important that you bring with you a passport that is valid for at least 90 days from the date you plan to leave Italy. Make sure that the passport has at least two blank pages. If you are heading to Italy on a vacation as a tourist, you will not need to get a visa as long as your stay will be less than 90 days in Italy.

  • If my kids are coming with me on the trip to Italy and we are going to rent a car, what type of seatbelt laws do I need to be aware of before I start driving off from the airport?

    All children riding in vehicles in Italy that are 15 months old or less must ride in a rear-facing car seat. Any child over 15 months but less than four years old must ride in a forward-facing car seat. Once children are more than four years old and up to 12 years old, they must ride in a booster seat. All children riding in vehicles must be in the rear seat of the vehicle.

  • If my flight to Italy is going to be landing at Venice Marco Polo Airport (VCE), will I find any shower services available at the airport?

    The airport provides shower services on a pay-per-use basis. You can find the showers in the Marco Polo Club Lounge, which is located in the airside section of the terminal building on the second floor.

Your guide to booking Chicago to Italy flights

Get tips on when to book, when to fly and what to know before your trip.
  • If you can plan ahead, the sweet spot for booking your flight is 26 weeks before your trip. KAYAK data shows fares in this window are around 15% lower than last-minute bookings (made within 2 weeks of departure). Not ready to commit? Set a Price Alert and we'll let you know when prices change.
  • If your travel dates are flexible, book your trip for February when flights are typically cheapest and avoid June when prices are at their highest.
  • Flying on Sunday is usually the cheapest. Flights on Friday cost about 11% more on average, so being flexible with your travel dates could help you save.
  • If arriving on time matters more than price, consider flying with one of the most punctual airlines on this route: ITA Airways, American Airlines and United Airlines.
  • If you're looking to save, Turin Citta Di Torino (TRN) is the cheapest airport to fly into from Chicago. If you have onward travel, don't forget to factor in the cost of your journey by train, bus or domestic flight.
  • Start your trip in Rome, which is the most popular destination in Italy. From there, it's easy to continue on to other popular destinations such as Milan, Venice and Florence.
  • If you want the shortest trip, choose the nonstop route from Chicago O'Hare Intl Airport to Italy. If you'd rather save money, the route from Chicago Midway Airport via Lisbon Humberto Delgado (LIS) is usually the cheapest.
  • When looking for a convenient way to get to either of the Chicago area airports from downtown Chicago, a good choice is to take the light rail services aboard the Chicago Transit Authority. For example, you can travel to Chicago O' Hare International Airport (ORD) in about 42min for a cost of around $3.50.
  • If you will be parking your own car at Chicago Midway Airport (MDW) and you will be away for more than 30 days, it is important to let the Parking Garage Office know this as they may tow your car if they are not notified of the length of your stay.
  • For nursing mothers that are traveling from Chicago Midway Airport, there is a mother's room in Concourse C at the airport. The room offers comfortable seating as well as a sink and wash area.
  • If you are flying out of Chicago O' Hare International Airport, you will be glad to know that there are airline lounges provided by United Airlines, Swiss Airlines, and SAS, which is very convenient since all of these airlines offer one-stop flights to Italy from the airport.
  • If someone will be dropping you off at Chicago O' Hare International Airport before your flight to Italy, the airport recommends that you use the Kiss 'n' Fly Lot. Here you can say your goodbyes and then hop aboard the convenient shuttle service that will take you directly to the terminal.

Reviews of the top 5 airlines serving from Chicago to Italy

 
Need help choosing which airline to fly with from Chicago to Italy? 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
Turkish AirlinesOverall score based on 4461 reviews
7.3Comfort
7.5Entertainment
7.3Boarding
7.8Crew
7.5Food
Airline reviews

I always travel on Turkish Airlines but seriously I am I am considering to change because this is not the first time that the flight attendant are rude and they dont help. I asked for cold water with ice 5 times and I got water with no ice and this is not the first time to ask for something and you dont get it. Also I noticed this behavior only towards people who are not turkish.

6.0 GoodRana, Aug 2026
Read more Turkish Airlines reviews

I always travel on Turkish Airlines but seriously I am I am considering to change because this is not the first time that the flight attendant are rude and they dont help. I asked for cold water with ice 5 times and I got water with no ice and this is not the first time to ask for something and you dont get it. Also I noticed this behavior only towards people who are not turkish.

Istanbul to Lahore flight was less than standard for international business class cabins. Seat did not were not flat and it did not operate easily. I had to push buttons hard repeatedly to operate the seat. I was in 5A seat

My, Syed Zawar Hussein Shirazi frequently flyer membership number was not included on my boarding pass from O’Hare to Istanbul despite my reminder to the attendant at check in. Further she forgot to give me my boarding pass form Istanbul to Lahore and she needs to improve her customer service, please 🙏

Chicago to Istanbul was a much better experience than I expected since I’m more accustomed to Qatar Airways business class. The business lounge in the Istanbul airport was amazing - loved the lockers and phone charging stations, and the bathroom was a spa experience in itself. The onward leg from Istanbul to Karachi was utterly disappointing. Terrible plane, and I felt like I was in economy - the seats don’t come near to lying flat and the food was mediocre. What a sad downgrade - it isn’t as though the ticket on that leg was cheaper. So, on that front, there’s no contest with Qatar airways.

Second leg of Turkish Airline with Indigo is disaster for following reason. 1) You have to carry your cabin bags through ladder to boeing 777 because it was parked somewhere in parking lot and was not given a gate to board passengers and this seems to be people traveling to and fro from those flights and is not issue with flight itself. 2) I choose non vegetarian food on Turkish portal way ahead of checkin to entire trip, However the Indigo flight gave me random veg food saying they code veg food code from Turkish. 3) Indigo did not served any alcoholic beverages stating some weird reason which is non nonsensical. 4)Indigo have TV screens in front of you but it displays nothing except "Welcome Onboard" with annoying white black ground in dark flight. This is the most stupidest and annoying part because you are held hostage for 7 hours and only thing you could do is stare back at white screen which does not have entertainment package or even flight tracker. Such a shame.

During mid flight, try to get a flight attendant to help I couldn’t find one Otherwise, everything was perfect

The 2 agents on the check in counter were super nice , helpful and very polite. Boarding was like a 1 2 3, I would recommend Turkish airlines for your next trip.

7 stars hospitality and an excellent service by the Turkish Airline entire team. Somehow, our membership numbers for mileage points were not indicated on our boarding passes issued at O’Hare Airport by the Turkish Airlines check in desk. During transit in Istanbul, I brought to attention of customer service Turkish Airlines. Please have our mileage points posted to our membership account from O’Hare Chicago to Lahore for both my wife Kaukab Shirazi Thank you

Terrible boarding process, no proper line maintained even for business class, crews are not very attentive, business class food quality / variety / quantity have gone down, everything has become cheap.

Food quality and the overall service of the staff and significantly decreased. The flight was delayed at the Istanbul airport and the passengers were kept onboard for more than 3 hours. The staff didn’t kept the passengers informed and everyone was upset.

I WAS CANCELLED ! I thought entire flight was canceled but it was still ongoing and I was only canceled as a passenger and one day before my flight with really poor "choice" of next flights that completely ruined my family event. Absolutely disappointed by SAS. Will be avoiding this airline now

The flight was pleasant with landing and take off being very smooth. Toilets were a bit busy at times but crew was very accommodating. Food service was quick and hot. The connecting short flight was full and there was not room for hand luggage.

No crying babies the whole flight would be nice. Impossible to sleep. No free snacks , only the main meal

They lost my luggage and can’t find it. My trip is ruined. Online tracking of lost luggage doesn’t work

Seat was lumpier than I’ve ever remembered it to be although comfortable when tilted back. I don’t recall being that hungry after being served food from SAS before. Flight attendant on the second flight to Aalborg seemed to be having a bad day.

They charge for bottles of water which is crazy period we hit turbulent weather and it's in a good job period

On this shorter leg and with an older plane, just mediocre. On the connecting long haul (Chicago to Copenhagen) everything was great.

My outbound flight was incredible... Milan to Chicago. The crew worked so well together. Each passenger felt spoiled and incredibly valued. The crew on this flight was fine. Nothing to complain specifically about but could not give top rating only because of the superior crew, hospitality, warmth we felt on the first flight. Unfortunately. You managed to lose my luggage ..my only piece checked in. Lost in Copenhagen so I had the added stress, time wasted to file the report. To make things worse, Italian rail decided to strike that Sunday so I could not take the train as planned back to Switzerland. Horrible waiting time and poor communication for boarding substitution bus. The substition bus to the town of Stabio did not run on time and was late about 40 minutes.

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

The flight was cancelled early on and messed up the whole vacation and hard to get a refund from Kayak as they owned the ticket and of course they did not believe that SAS cancelled the ticket. Definite bad side to third party. SAS had rescheduled but overlapped the connecting flights. That did not work. Flight was cancelled long ago but Kayak still has it. Like it was taken? Bad IT ? Or all assumptions and no follow up which is the whole IT world. It needs to wake up and be more efficient. Especially as the world is going, there will be no freedom to do anything. And we will be living like the Middle Ages. Yeah, go read up on that while you still can.

The guy in front of me was talking constantly, even when the pilot was making announcements. I found this very disrespectful to the pilot and to others.

We left 1.5 hours late due to a “maintenance” issue. Very poor communication as to when we would board & depart. The crew in First Class was uncharacteristically not friendly). Delay into Brussels cost me my connection to Rome so lost the entire first day of vacation ( had a 10:30am flight to Rome - ended up on a 6:55pm flight).

Everything was OK except the meals, that was overpriced chicken meat.

Miss My connection I had to take a flight from Indianapolis to Denver , then to san fransisco , sleep in sans fransisco en the flight to Los Cabos the next morning

The TVs on the plane were all broken and inoperable. No snacks or food were served. Plane was very old and uncomfortable.

Takeoff delayed 2 hrs. Boarded on time to find we were missing part of the flight crew. Then informed that they had loaded too much fuel. Spent 1 1/2 hrs sitting there burning off the excess, which included a couple of laps around the runway until we were light enough to fly! Ridiculous!

I especially enjoyed having a lightly packed flight which enabled me and my wife to occupy a three seat area with nobody in the middle seat.

The seats are very small, that is all the staff did a good job.

It was great. The staff is always helpful and polite. The app is great and makes the whole trip and process so easy. They even offer a step to step guide to your correct terminal. And they keep all the information you'll need updated. Anything you can think of! Great experience.

Perfect. On time and the weather was perfect so we came in a few minutes early.

Other than the toilets it was great. One was broken and another wasn’t flushing by the end of the flight

Premium economy was very comfortable with excellent service and legroom. On Kayak I was able to find a very affordable discounted fare

Overall seamless flight from SFO to FCO. I chose economy to have more money to spend while in Italy. The seats bottoms are a bit on the thin side but they give you a pillow and blanket so Inl used the blanket to thicken up the seat bottom. You have to have a physical boarding pass (at least for my flight) so that was interesting. Crew was nice, food was good and over pretty down the middle.

1 1/2 hours delayed boarding at JFK caused us to almost miss connecting flight in Rome. Only 30 minutes of time to run from one end of FCO to the other for connecting flight. Not very easy to do for older travelers.

Staff was nice but seat is not what I expected

Flew Premium Economy. The seats were comfortable and tilted back far enough to sleep. Food was okay and service friendly and efficient. We bought tickets through Kayak partner Underpricer and the price was good.

ITA has these new Airbus A330 Neo that hates economy class passengers. The seats have absolutely no cushion to a point where it hits your spine constantly and reminds you to fork out for premium economy or don’t travel next time. The food was absolutely horrible, ETA mentioned 3 meals for 12 hour flight but it was mostly 1 meal and 2 light snacks. I am vegetarian, so my 2’d food was 1 slice of tomato, 1 cucumber on a dry cold bun. The other 2 meals were disgusting. My young one threw up the entire time. Flight attendants were the cherry on top - plain bad. They would skip servicing drinks to some passengers completely and if you call for an attendant, they will come and stop the button on top without even asking you what you need. I would avoid ITA by all means - there are plenty of options including SAS for same routes with better seats and humane treatment.

The boarding process was organized and efficient, and the crew was friendly and attentive throughout the flight. Food and drinks were typical economy class, but good. The aircraft was old, and the restroom was not very clean. However, we arrived on time, so overall the experience was good.

It was fine. I wish there were more or better selections for entertainment.

The worst part about the trip was the seat. It looked old, with a sagging cushion and crumbs on it before I sat down. When I sat down I saw that the back of the seat was broken and it would only stay in one (reclined) position. I had purposefully paid extra ($65) for that seat because a) I can only sleep on translatlantic flights if I am next to the window and b) I wanted to be close to the front because I had a tight connecting flight in Rome. One flight attendant didn't care about the problem while another offered me a middle seat in the back of the plane. Of course he did not mention a refund for the fee I had paid for this seat. The food was mediocre, not even close to the good food in Alitalia, back in the day. The entertainment system did not work when I tried to "follow the flight". English of announcements was often impossible to understand (spoke poorly and too fast).

The flight and staff were perfect. No notes. Amazing experience overall.

It was a safe and smooth flight. Members of the crew at the second level, business could have been more polite and engaging.

I was booked to travel from Dallas to Nairobi via Chicago and Brussels and had been issued boarding passes for all three segments of my journey. At the boarding gate in Dallas, I was required to check my carry-on luggage due to limited cabin space. Despite my attempts to explain that I was traveling internationally and would not have access to the bag during transit, my concerns were not considered. I also informed the staff that I did not have a padlock to secure the luggage, but this was disregarded. Consequently, I had to hastily transfer essential items from my carry-on into my handbag. Unfortunately, the onboard experience on the Chicago to Brussels flight further reinforced my dissatisfaction. The cabin crew appeared disengaged, indifferent, and lacking in attentiveness, resulting in a service experience that fell well below my expectations.

Flight was on time and got us to destination quicker than scheduled.

I have very bad experience with United because Vince two weeks that I did not receive my luggage yet

It was okay. Mothers with rowdy children should be invited to sit in front of them.

Good food, overall very comfy. The flight was full so obviously not optimal, but it is what it is.

Flight was delayed by several hours and then cancelled due to weather. But Staff was very helpful getting me on a different flight. United should offer food coupons and tooth brush and paste for stranded passengers

I had a good comfortable seat. There was nearly an hour delay. There was an accident with the champagne, but I was well compensated. These things happen sometimes.

We missed our flight. There was not enough time built into the layover to get through immigration, customs, bagclaim, bag rechecking, and the long trip to another terminal and gate. Kayak really screwed up. We took the bus up to Wisconsin and then were picked up in Brookfield by private car. It was lucky we didnt miss the last bus out.

More options for your flight from Chicago to Italy

Complete your trip to Italy with a hotel stay or car rental