$174 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 10/12. 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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1 adult, Economy

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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
Milan2 stops$418
Florence
Florence1 stop$442
Naples
Naples2 stops$420
Palermo
Palermo1 stop$492
Bologna
Bologna1 stop$484
Turin
Turin1 stop$520
Milan
Milan2 stops$418
Florence
Florence1 stop$442
Naples
Naples2 stops$420
Palermo
Palermo1 stop$492
Bologna
Bologna1 stop$484
Turin
Turin1 stop$520

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

Fri, Nov 14 - Thu, Nov 20
TAP AIR PORTUGAL Logo
8:15 pm - 6:45 pmORD-FCO
15h 30m1 stop
TAP AIR PORTUGAL Logo
4:40 pm - 3:15 pmFCO-ORD
29h 35m1 stop
$334TAP AIR PORTUGAL
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Mon, Aug 11 - Thu, Aug 28
TAP AIR PORTUGAL Logo
6:10 pm - 7:00 pmORD-FCO
17h 50m1 stop
TAP AIR PORTUGAL Logo
5:55 am - 12:50 pmFCO-ORD
13h 55m1 stop
$335TAP AIR PORTUGAL
Find Deal
Tue, Nov 25 - Fri, Dec 5
United Airlines Logo
3:45 pm - 7:45 amORD-FCO
9h 00mnonstop
United Airlines Logo
12:50 pm - 1:09 pmFCO-ORD
31h 19m2 stops
$372United Airlines
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Tue, Nov 25 - Fri, Dec 5
United Airlines Logo
10:00 am - 11:05 amORD-FCO
18h 05m1 stop
United Airlines Logo
12:50 pm - 1:09 pmFCO-ORD
31h 19m2 stops
$379United Airlines
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Sun, Nov 23 - Fri, Dec 5
Lufthansa Logo
9:50 pm - 6:20 pmORD-FCO
13h 30m1 stop
Lufthansa Logo
9:45 am - 1:10 pmFCO-ORD
10h 25mnonstop
$421Lufthansa
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Sun, Oct 26 - Sun, Nov 9
Lufthansa Logo
10:50 pm - 5:25 pmORD-NAP
12h 35m1 stop
Lufthansa Logo
6:15 pm - 6:25 pmNAP-ORD
31h 10m1 stop
$508Lufthansa
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Sun, Aug 10 - Tue, Aug 26
American Airlines Logo
9:50 am - 10:00 amORD-NAP
17h 10m1 stop
American Airlines Logo
3:00 pm - 6:50 pmNAP-ORD
10h 50mnonstop
$518American Airlines
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Sun, Aug 10 - Tue, Aug 26
American Airlines Logo
9:50 am - 10:00 amORD-NAP
17h 10m1 stop
American Airlines Logo
12:00 pm - 10:49 pmNAP-ORD
17h 49m1 stop
$524American Airlines
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Mon, Aug 18 - Wed, Aug 27
ITA Airways Logo
3:00 pm - 2:30 pmORD-FLR
16h 30m1 stop
ITA Airways Logo
6:25 am - 1:10 pmFLR-ORD
13h 45m1 stop
$680ITA Airways
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Wed, Aug 13 - Tue, Aug 26
ITA Airways Logo
3:00 pm - 10:10 amORD-LIN
12h 10m1 stop
ITA Airways Logo
7:00 pm - 1:10 pmLIN-ORD
25h 10m1 stop
$685ITA Airways
Find Deal
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 price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to Italy.

The cheapest ticket to Italy from Chicago found in the last 72 hours was to Rome, at $537 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 $537.

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $2,202 on average.

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 February, when tickets cost $546 (return) on average. On the other hand, the most expensive months are June and July, when the average cost of round-trip tickets is $1,105 and $941 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 Tuesdays 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 Sunday 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 2 weeks before departure, which saves you about 12% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.


Good to know

Low seasonJanuary
Cheapest flight$174
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Chicago O'Hare Airport to Rome Fiumicino 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 15% 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 $946.

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
United AirlinesOverall score based on 8896 reviews
7.3Comfort
6.6Food
8.1Crew
7.7Boarding
7.1Entertainment
Airline reviews

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

10.0 ExcellentAnita, Jul 2025ORD - CMH
Read more United Airlines reviews

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

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

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

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 staff was not at pleasant as those on the first leg of our trip.

Boarding was easy and well organized, Breakfast was not very good.

Better consideration for families traveling with a disabled person. They insisted each person hold their own boarding pass on their own devices and gave us a hard time accepting eight boarding passes on a single device.

Two of my four flights had issues with toilets either NOT fully operational or completely out of order. Boarding was a joke because they have NOT established who is running the show. In the end, she did a terrible job. The seats 💺 were loose goose and the drinks and snacks were limiting in choices. Also, following Alitalia as an inspiration was strange since they went out of business.

We had a 3 hour delay and then a long taxi to take off. It would have been helpful for the pilot to have communicated more about what was going on. There was no A/C during the wait, and the cabin must have been more than 85 to 90 degrees. The crew gave water to the people in the front but by the time they go to the back of the plane they stopped giving out water. Eventually I went back and asked for some in the rear of the plane (for a second time). The food was close to inedible. I thought on an Italian flight that the pasta would be better than the chick, but honestly, a Swanson's TV dinner would have been better. I had a bite or two to keep my blood sugar up, but basically I couldn't eat it.

Boarding was chaotic. Service was poor. Attendant was slow and rude. In business class, I was not offered a drink until 1.5 hrs,after takeoff. Food was inedible.

Terrible. They canceled 2 flights and then sent everyone by BUS from Rome. They should make amends by offering some sort of compensation.

We ordered a gluten free meal and never got it!

The company tries shamelessly to squeeze every dollar)Euro out of its passengers. During the check-in the force you to go through the seat selection, you can skip it. They will assign you the worst seat available, then show you the other available seats on the map, for a fee. But they won't show you the fee until you click on it. And once you do click, there's no way to unselect it!! You will get stuck and forced to pay for that seat. Cheaters!!

Seats weren’t comfortable. Both of our seat backs were either almost straight vertical or laying back into the laps of the people behind us, which is a weird angle to try to get some sleep even on a plane. No in between. Also, neither seat would spring forward like they should.

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.

Old tired plane, Uncomfortable business class seat. Breakfast dreadful and meagre. At least flight was on time!

Boarding market okay just because of the delay we had, but not related to the crew in any way…

Safe arrival. Improvement on Time efficiency Effective Communication will be great.

The crew is very friendly and helpful. The food is good for airplane food. The flight is long and hard to sleep. The leg space is great. The plane arrived in plenty of time.

A good flight back to Tampa and thankfully although we had a 90 minute delay because of thunder storms from Charlotte to bottom iof Florida, it was a prudent to avoid these for a comfortable flight as opposed to being tossed around with turbulence.

They removed our booking without telling us. Cost us thousands to book last minute

Enjoyable flight, helpful crew everything was organized to accommodate passengers.

Captain sick. Unable to get replacement so delayed me 30 hours, many others delayed 54 hours. TOTALLY DESTROYED ALL MY PLANS, including lost my rental car which would now cost over 5 times what I paid so stuck with buses n trains... lost hotel reservations.... HORRIBLE!!!

The international flight from PHL to Lisbon was one of the worst I’ve experienced, ever. What was really disappointing was the entire experience of comfort and service in the coach cabin after takeoff. The food was inedible and the wine served with dinner was such low quality - it tasted of petrol. I couldn’t eat more than a bite or two of the chicken entree, being worried it would make me ill. The service took so long to reach the entire coach cabin, I ended up having the lights turned off on me as though I had to rush though dinner (though as I mentioned, it wasn’t as if I ate much - only the salad). Most of the attendants seemed generally annoyed and were not friendly or polite. While there was some turbulence, it wasn’t too uncomfortable and I know that is just a chance. The temperature of the cabin was so warm, even a friend a row or two up and on the other side of the plane felt like this. To top it all off, the seat was so uncomfortable and flattened/overused, I had back pains for DAYS afterward.

They’ve lost my bag and I have no way of really getting in touch with anyone and have received no updates.

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.

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