$261 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
Milan
Bergamo2 stops$605
Florence
Florence1 stop$589
Naples
Naples1 stop$608
Palermo
Palermo2 stops$606
Bologna
Bologna1 stop$589
Turin
Turin1 stop$666
Milan
Bergamo2 stops$605
Florence
Florence1 stop$589
Naples
Naples1 stop$608
Palermo
Palermo2 stops$606
Bologna
Bologna1 stop$589
Turin
Turin1 stop$666
Booking Insights

KAYAK's insights & trends for Chicago to Italy flights

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

What is the cheapest Chicago to Italy flight route?

The cheapest ticket to Italy from Chicago found in the last 5 days was to Rome, at $745 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Rome Fiumicino Airport (FCO), and the cheapest round-trip airline ticket found on this route in the last 5 days was $745.

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

The cheapest time of day to fly to Italy is generally in the evening, when round-trip flights cost $985 on average. Morning departures are around 100% cheaper than evening flights, on average. The most expensive time of day to fly to Italy is generally in the evening, which is peak travel time and where the average cost of a ticket is $985.

Can I save money by flying with a layover from Chicago to Italy?

No, with an average price for the route of $806, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago to Italy?

The cheapest month for flights from Chicago to Italy is February, when tickets cost $610 (return) on average. On the other hand, the most expensive months are June and July, when the average cost of round-trip tickets is $1,064 and $1,012 respectively.

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

If you are looking for a flight deal from Chicago to Italy, look for departures on Sundays and avoid leaving on a Friday, as it's usually the priciest day. When flying back from Italy, Thursday is the cheapest day to fly and Tuesday is the most expensive.

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

To get a below average price on the flight from Chicago to Italy, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.

Good to know

Low season

February

Cheapest flight

$261
Best time to beat the crowds with an average 30% drop in price.
Most popular time to fly with an average 42% increase in price.
Flight from Chicago O'Hare Airport to Florence

FAQs - booking Italy flights

  • 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.

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

    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 from Chicago to Italy.

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

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

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

    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 from Chicago to Italy 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 from Chicago to Italy?

    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 from Chicago to Italy up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Italy

  • 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 4475 reviews
7.3Boarding
7.3Comfort
7.8Crew
7.5Entertainment
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.

The layover was very long. Other than that, great trip so far

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.

Boarding the plane outside in the rain was a pain. Very safe flight

Terrible service - they don’t want to be there and bad food. Entertainment system in economy from the 2000s

No drink service but there was no N/A as an option to choose. Seats were extremely tight. I am under 5.5 and I bumped my knees have no idea how taller people could manage.

Flight delayed, last seat on the plane, no arrival Gate available due to the plane departing late

Kayak booked this flight with only 1h 20min layover in Chicago. This made it impossible for me and several other passengers to reach this flight. Moreover, the gate closed boarding in spite of several passengers still on their way without waiting even one more minute. However, the plane departed with 20min (!) delay, i.e., there would have been at least 15 min time to let the delayed passengers board without causing any delays. I complained and as a "thank you" the attendent booked us on the last (!) flight to Indianapolis ~7h later! Thankfully, I caught the spitefulness and the United customer line rebooked the flight to an earlier flight. Although I can't grade this particular flight since I never had a chance to take it, Kayak made the mistake of a too short layover and the crew at the gate was awful.

Flight did not have wifi service. It was experiencing technical difficulties. Definitely and old plane that needs updating.

This flight has a history of leaving late, however, I was pleasantly surprised that it was not delayed this day. The flight went smooth, except I was in a window seat and the wall and my feet were freezing. I found it difficult to sleep due to being so cold, I also was using 2 provided UAL blankets and could not get my feet warm. This was annoying, but I still made it there on time and safe.

Old 757 with poor entertainment system. United no longer partners with United for free text and email. O'Hara an absolute disaster! Limited gates clauses two hour delay. Unfortunately this appears to be the norm.

It was a good experience, unfortunately my checked baggages were come late and not arrived on time.

Very stressful to locate United Airline boarding area, delayed flight, changing boarding area again to another location with all tiredness 😩. But flying was fine.

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

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.

I tried both on line and by calling the Customer Service line to arrange for a special meal as i have food intolerances. I was under the impression from your service representative that I was successful. I was not. I cannot eat spicy foods and get very ill if i eat bell peppers. I could not eat either menu choice and no special meal was actually ordered. ( your representative tried to order it for a flight that did not have meal service!!! - found this out later). Your wonderful cabin crew managed to put together a fruit, salad, roll and cheese tray for me so I had something to eat. WHY WOULD YOU SERVE SPICY FOOD, WITH NO MILDER OPTION,ON AN INTERNATIONAL FLIGHT???

I liked Quiet people around me. Crew could have helped people with overhead luggage so they aren't moving other peoples bags around and causing problems for people that had there bags there first

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.

Nice flight. Uneventful, very good crew, comfortable seats. Pleasant experience.

ITA cancelled fligh rebooked with Lufthansa. Flight good, but 2hour connection in Frankfurt was HORRIBLE, took 1.9 hours to get through scanner, customs, another security, got to gate after running all the way, so caught it but stressful and terrible start to trip.

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.

In Prem Econ, safe and timely flight, good amount of space, mostly comfortable seats. Little irritants: When lying down, seat kept shifting on me...as a short person w/light weight, my seat often reverted to semi-upright. Footrest was broken. TV screen didn't work, after I asked a few times a FA rebooted it to work again. And food was marginal. I don't expect much from airplane food...surprisingly, ITA didn't even meet expectations.

Flight was canceled. Rebooked on Lufthansa Also Canceled. Had to pay 3000 more per person and fly Alaska to EWR and fly emirates to Athens.

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).

More options for your flight from Chicago to Italy

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