$220 Find Cheap Flights from Chicago to Italy

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Italy departing on 2/23. 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
1 adult, Economy, 0 bags

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Cheap Flights from Chicago to Italy

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Milan
Bergamo2 stops$471
Florence
Florence2 stops$468
Naples
Naples1 stop$501
Palermo
Palermo2 stops$491
Bologna
Bologna2 stops$436
Turin
Turin1 stop$483
Milan
Bergamo2 stops$471
Florence
Florence2 stops$468
Naples
Naples1 stop$501
Palermo
Palermo2 stops$491
Bologna
Bologna2 stops$436
Turin
Turin1 stop$483

Book Cheap Chicago to Italy Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Italy 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Italy

Thu, Jan 15 - Sat, Jan 24
Icelandair Logo
6:30 pm - 2:00 pm
ORD
-
FCO
12h 30m1 stop
Icelandair Logo
11:25 am - 5:20 pm
FCO
-
ORD
12h 55m1 stop
$399Icelandair
Thu, Jan 22 - Sat, Jan 31
Icelandair Logo
6:30 pm - 2:00 pm
ORD
-
FCO
12h 30m1 stop
Icelandair Logo
11:25 am - 5:20 pm
FCO
-
ORD
12h 55m1 stop
$401Icelandair
Fri, Jan 23 - Fri, Jan 30
Scandinavian Airlines Logo
6:25 pm - 10:15 am
ORD
-
VCE
32h 50m2 stops
Scandinavian Airlines Logo
11:20 am - 4:55 pm
VCE
-
ORD
12h 35m1 stop
$401Scandinavian Airlines
Fri, Jan 9 - Sat, Jan 24
Icelandair Logo
6:30 pm - 2:00 pm
ORD
-
FCO
12h 30m1 stop
Icelandair Logo
11:25 am - 5:20 pm
FCO
-
ORD
12h 55m1 stop
$403Icelandair
Sun, Feb 1 - Sun, Feb 8
Scandinavian Airlines Logo
6:25 pm - 10:30 am
ORD
-
VCE
33h 05m2 stops
Scandinavian Airlines Logo
11:05 am - 4:55 pm
VCE
-
ORD
12h 50m1 stop
$406Scandinavian Airlines
Sun, Jan 11 - Wed, Jan 21
TAP AIR PORTUGAL Logo
8:25 pm - 12:05 am
ORD
-
FCO
20h 40m1 stop
TAP AIR PORTUGAL Logo
6:00 am - 3:00 pm
FCO
-
ORD
16h 00m1 stop
$422TAP AIR PORTUGAL
Sun, Jan 11 - Tue, Jan 27
TAP AIR PORTUGAL Logo
8:25 pm - 12:05 am
ORD
-
FCO
20h 40m1 stop
TAP AIR PORTUGAL Logo
4:40 pm - 3:00 pm
FCO
-
ORD
29h 20m1 stop
$423TAP AIR PORTUGAL
Thu, Apr 23 - Mon, May 4
Turkish Airlines Logo
11:25 am - 2:50 pm
ORD
-
NAP
20h 25m1 stop
Turkish Airlines Logo
9:25 am - 6:15 pm
NAP
-
ORD
15h 50m1 stop
$515Turkish Airlines
Thu, Jan 29 - Mon, Feb 2
Turkish Airlines Logo
8:20 pm - 6:25 pm
ORD
-
NAP
15h 05m1 stop
Turkish Airlines Logo
9:15 am - 6:25 pm
NAP
-
ORD
16h 10m1 stop
$519Turkish Airlines
Tue, Jan 20 - Thu, Feb 5
Lufthansa Logo
6:00 pm - 12:30 pm
ORD
-
NAP
11h 30m1 stop
Lufthansa Logo
6:15 pm - 12:45 pm
NAP
-
ORD
25h 30m2 stops
$537Lufthansa
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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Italy from Chicago found in the last 72 hours was to Rome, at $522 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 72 hours was $522.

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

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $813, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Italy, 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 from Chicago to Italy is November, when tickets cost $570 (return) on average. On the other hand, the most expensive months are June and July, when the average cost of round-trip tickets is $1,134 and $950 respectively.

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

The average price of all round-trip flights from Chicago to Italy clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Chicago to Italy, look for departures on Mondays and avoid leaving on a Thursday, 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 calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Italy, 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 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 25 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$220
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Chicago O'Hare Airport to Milan Malpensa Airport

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.

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

    The cheapest time of day to fly to Italy is generally at night, when round-trip flights cost $686 on average. Morning departures are around 16% 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 $962.

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
Scandinavian AirlinesOverall score based on 1605 reviews
7.6Boarding
8.0Crew
6.7Food
7.3Comfort
6.7Entertainment
Airline reviews

Excellent service throughout. Airport process is quick and easy. Very courteous staff. Great service in the plane! Just outstanding punctuality and service overall!!

10.0 ExcellentSunderesh, Dec 2025
EWR - ARN
Read more Scandinavian Airlines reviews

Excellent service throughout. Airport process is quick and easy. Very courteous staff. Great service in the plane! Just outstanding punctuality and service overall!!

I have paid for extra legroom on my flight. My seat was broken and did not recline. The crew could not fix it and refused to provide me with another seat

Over all experience was good. However the connection time was too short at CPG. We missed our connecting flight to AMS as the passport control line was too long and by the time we got our passport control done it was too late I wish there were some SAS staff to help us out at the passport control center Though they put us in a KLM flight from CPG to AMS, That flight was also delayed by over two hours

No vegetarian option was provided for the regular meal or the pre-landing snack.

The Scandinavian flight was excellent, however the second flight was partnered with TAP Portugal which was not so good. crowded gate area with no chairs, delayed flight, bad boarding process, no entertainment system onboard, and the baggage didn’t get to the carousel until well over an hour which caused our taxi that was waiting to leave. Love SAS, hate TAP.

Great logistics and timeliness as we arrived quite early. Flight smooth and fast. Excellent entertainment. Plane itself was a bit tired and the crew mostly indifferent. Baggage took forever but that’s on CPH. Would use SAS again for sure.

Will not recommend SAS for business travel. Food was so-so. Service was very good. First leg was very good. Second leg from Copenhagen to Barcelona was terrible. We paid a LOT for business class and to have seats worse than most coach seats with no entertainment and no charging available for 1/3rd of the whole trip was not acceptable. Very disappointing. I thought they were coming back in the U.S. with style, NOT YET.

I do not have a problem with the airline but both my two suitcases that were supposed to go from Hawaii to Copenhagen didn’t get on the plane in Seattle. I arrive on Monday the 21st at 10:30 in the morning. I did not get my two suitcases before Friday late afternoon that is unacceptable.

No choice of food. Needed to pay more even for a can of coke!!!

The seats were really close together and hard to get comfortable. The food was okay. The cheese was amazing! I loved the cold towels they gave us.

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Seats in waiting area and on plane hard as rock. Fast internet on the flight was great! Crew was kind.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

My wife and I love to travel, so we fly a lot. We've already logged 381,075 miles and with practically every major airline. But this flight was very disappointing. It started off well, with no delays and a new plane. But when lunchtime approached, all that good impression was ruined. Instead of white tablecloths, we were offered small, dark placemats, which, as it turned out, were perfectly adequate for the food. All the food offered—and my wife and I only took fish, and the meat—was not just bad, it was downright disgusting and not heated enough. The same applies to the appetizers. This was the first time in many years of traveling that we've been offered such disgusting food.

Lost luggage stuck no clothes and no word after 2 days leaving on cruise no stuff or clothes

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

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

The plane was delayed by two hours in Chicago which led to us missing the next flight. Lufthansa rebooked the flight and booked us a hotel for the night in Frankfurt. The level of customer service and getting us taken care of was superb. The flight crew and the service on the ground was superb.

Boarding and flight update was fantastic as I experienced about a 10-15 delayed for both flights. The food served onboard was great; the service of the flight attendants was excellent.

The row of seats were so cramped it was difficult to get in and out of your seat. I even upgraded. A long flight and sad accommodations 😵‍💫 the shorter flight was very comfortable and the seating was spacious

Complete mess. Our reservation was mistakenly cancelled. After almost missing the connection and walking all over the Munich airport, the Service desk got involved and we were run to our flight. Not all 4 of us in Business and not seated together as originally booked. This was the worst treatment I have ever had. And I travel a lot. 1K million miler.

I have flown with many airlines. My first time was several years ago. Now I remember why I avoided them for so long. Lufthanza is the only airline who has ever raised a size/weight issue with my modest standard size carry on. I had to repack three times to meet their carry-on weight criteria. (Apparently the rules of physics apply differently on Lufthansa flight than on other airlines.) In the meantime their staff was quite rude, repeating meaningless phrases like "Rules are Rules." And ignoring the additional fact that weight is also weight, whether it is in found in your carry on or in your suitcase. They eventually acknowledged that customer service and satisfaction is, for them, a low priority. Never choosing Lufthansa again.

They are professional. Nice crew. Still flying Boeing 747. Thank you for that. I love this airplane. Traditional.

There is more space in this economy seat. It felt like a better layout, not so cramped.

Connecting from Germany with not enough time to go thru TSA and security so many times. Kayak or whomever doesn’t leave you enough time between flights. I made it with 5 min before my zone was called. Too stressful

The seats were extremely uncomfortable. I spent €25 on internet and never gained access to it. A flight attendant told me she would file a complaint/report on my behalf but it put me in a very difficult situation.

The check in process is chaotic. It says partially checked-in. Never heard of such a thing. Then lost our reserved seats when we finally checked in at the airport. The seats don’t recline. Then we had to get mew boarding passes at the connection. Last, my companion lost her baggage and up to now there’s no update. We’re already half-way through our vacation and still no news what happened to the luggage.

Wonderful! Everyone very helpful and kind. Returning flight was cancelled but rebooking was easy.

Pretty normal flight was delayed due to traffic could have missed connecting flight to Venice but crew kept us well informed so we made it

Flight was on time and pretty standard. No Hiccups. I have no complaints, which is a lot to say about a 12 hour flight.

-The seats could be roomier -The entertainment in English could be more current! The moves were very old!!! -They served too many carbs! What happened to fruit and yogurt!!!!

We upgraded to premium economy and it made a difference in a 12 hr flight. I didn’t like that we had to deplane in the tarmac with our carryon luggage. Other than that, it was ok.

Everything was much better than I had expected, since I hadn’t heard of your airline before. I hope to take advantage of your excellent service again.

Staff were nice, we left on time and arrived early, food was good. Unfortunately, they lost one of our bags and have been unable to find it. So we are in Italy for a week for my husband‘s birthday and he does not have any of his clothing.

They gave us sandwiches as a meal twice. Snacks mid flight with cookies and a tuna panini. Then just the same tuna panini for dinner. That was it.

Top notch re cleanliness, comfort, operational. Attendants attentive, cheerful, courteous and professional. An unusually high-grade experience all around.

Everything you need to know for your flight from Chicago to Italy

Cabin class types available on flights to Italy

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