$126 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 6/15. 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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Best Italy Flight Deals from Chicago

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Milan
Milan1 stop$393
Florence
Florence1 stop$470
Naples
Naples2 stops$532
Palermo
Palermo1 stop$666
Bologna
Bologna1 stop$521
Turin
Turin2 stops$897
Milan
Milan1 stop$393
Florence
Florence1 stop$470
Naples
Naples2 stops$532
Palermo
Palermo1 stop$666
Bologna
Bologna1 stop$521
Turin
Turin2 stops$897

Cheap Flight Deals from Chicago to Italy (CHI-IT0)

 
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.

Recent round-trip flight deals from Chicago to Italy

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Chicago to Italy.
Discover the best prices for you by selecting your travel dates on KAYAK.
Scandinavian Airlines Logo
7:15 pm - 10:00 amORD-VCE
31h 45m1 stop
Scandinavian Airlines Logo
7:55 pm - 4:10 pmVCE-ORD
27h 15m1 stop
$390Scandinavian Airlines
Find Deal
Sun, Sep 28 - Sun, Oct 5
Scandinavian Airlines Logo
7:15 pm - 8:35 amORD-MXP
30h 20m1 stop
Scandinavian Airlines Logo
9:15 am - 4:10 pmMXP-ORD
13h 55m1 stop
$393Scandinavian Airlines
Find Deal
Tue, Sep 30 - Thu, Oct 16
United Airlines Logo
8:40 am - 9:15 amORD-FCO
17h 35m1 stop
United Airlines Logo
9:45 am - 1:10 pmFCO-ORD
10h 25mnonstop
$560United Airlines
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Tue, Oct 14 - Tue, Nov 4
United Airlines Logo
2:08 pm - 9:15 amORD-FCO
12h 07m1 stop
United Airlines Logo
9:45 am - 1:10 pmFCO-ORD
10h 25mnonstop
$610United Airlines
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Mon, Oct 20 - Mon, Nov 3
British Airways Logo
5:25 pm - 5:45 pmORD-NAP
18h 20m2 stops
British Airways Logo
6:55 pm - 1:55 pmNAP-ORD
26h 00m1 stop
$610British Airways
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Sun, Oct 26 - Sun, Nov 9
ITA Airways Logo
3:00 pm - 6:15 pmORD-FLR
20h 15m1 stop
ITA Airways Logo
6:25 am - 1:10 pmFLR-ORD
13h 45m1 stop
$690ITA Airways
Find Deal
Wed, May 14 - Fri, May 23
British Airways Logo
5:25 pm - 5:45 pmORD-NAP
18h 20m2 stops
British Airways Logo
6:55 pm - 3:25 pmNAP-ORD
27h 30m1 stop
$690British Airways
Find Deal
Sun, Oct 26 - Sun, Nov 9
ITA Airways Logo
3:00 pm - 2:45 pmORD-FLR
16h 45m1 stop
ITA Airways Logo
11:25 am - 1:10 pmFLR-ORD
32h 45m1 stop
$739ITA Airways
Find Deal
Wed, Sep 17 - Tue, Sep 23
Lufthansa Logo
10:30 pm - 8:15 pmORD-FLR
14h 45m2 stops
Lufthansa Logo
8:15 am - 9:17 pmFLR-ORD
20h 02m2 stops
$873Lufthansa
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Thu, May 15 - Tue, May 20
Lufthansa Logo
10:30 pm - 8:15 pmORD-FLR
14h 45m2 stops
Lufthansa Logo
9:45 am - 7:55 pmFLR-ORD
17h 10m2 stops
$887Lufthansa
Find Deal
Thu, May 15 - Fri, May 23
Useful Info

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 $623 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 $623.

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 1 stop layover the cheapest option at $1,993 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 $552 (return) on average. On the other hand, the most expensive months are June and May, when the average cost of round-trip tickets is $1,147 and $966 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 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.


Good to know

Low seasonJanuary
High seasonSeptember
Cheapest flight$126
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly and prices are also 8% lower on average.
Flight from Chicago O'Hare Airport to Rome Fiumicino Airport

Flights from Chicago to Italy: the best tips from KAYAK users

Insights shared by verified travelers who flew the route from Chicago to Italy 
FrancescaFlew with IberiaORD-FCOJun 2024
Expect small seats, narrow spaces for luggage and in aisles, but very nice flight attendants
MikeFlew with British AirwaysORD-FCOJun 2024
Make sure you check the plane type and economy seating space.
Verified travelerFlew with British AirwaysORD-FCOJun 2024
Get on an early flight and do not fly American

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 10% 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 $938.

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.

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 8696 reviews
6.6Food
7.7Boarding
8.1Crew
7.3Comfort
7.1Entertainment
Airline reviews

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

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

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.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

I believe it was short flight in plane I understand not that much compared to other airlines but weighting for checkin was too long need extra person for checkin or Atleast someone to let the customer knows don’t worry someone will be here shortly.

Noted in last review. Good to know, though air Lingus on European flights does not offer any food or drink, even though we were on the plane for 3 1/2 hours from Naples to Dublin everything you had to purchase even water.

Boarding seemed a bit chaotic and we had to walk outside across the tarmac. Passengers of all ages had to drag carry on luggage up the outside stairway into the aircraft. There was no WiFi. Very uncomfortable crammed seats. Glad in-air time was only an hour!

Booked through Kayak, couldnt take flight, Kayak punted to Orbiz, Orbiz punted to Aer Lingus, Aer Lingus said sorry about your luck, try Kayak/Orbiz. Terrible customer service collecting air fares and not even offering a voucher when customers cant take flight

There was no flight. I booked a flight from Toronto to Bordeaux with a stopover in Dublin. I arrived in Dublin and the flight number I had didn't exist and the flight going to Bordeaux I wasn't on. I had to book a new flight with a different airline for later in the day and pay out of pocket.

Gate agents kind of serious. Had to wait til arriving at gate to choose seats. Thankfully they did give us seats together! And grateful the honored our age, giving us seats at the front.

Very polite and helpful staff. Jet blue…ok, but not as helpful!..

Seat was very uncomfortable. The worst in all of my travels. It sagged in the middle, worse than anything any airline can offer. Not flying aer lingus again.

This flight was delayed and caused me to miss my connecting flight from New York to Boston. I had to rent a car and drive myself home to avoid waiting another 5 hours in the airport.

Flight was cancelled. There were no Aer Lingus reps to help. I had to rebook my flight and find a hotel. Still had nothing from the airline.

We ordered a gluten free meal and never got it!

The seats are horribly uncomfortable. We were in premium economy and paid a premium price yet, the seats were the worst! You could feel every structural bar in the seat, there was no padding, no amenities kit, and the leg rests were broken. Duct tape was holding another seat together. When we arrived at our final destination, Venice, my suitcase was ripped open, and my clothes were about to fall out of the bag. I would’ve been more comfortable if I flew a paper airplane across the Atlantic.

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.

It is the worst ever airline. All employees I spoke with over the phone were pompous asses.

The gate information was never populated on the Delta app or the airport displays or the desk at the Delta lounge. We found at the last minute that we had to switch terminals and just made it to our flight. Even this we found accidentally by asking an employee at another gate. On board service was poor. Seats were very poor. All in all a poor experience. At best like a Premium Economy on other airlines

No online or self check in. Sent emails in Italian language. In general, not recommended airline company.

You idiots…ITA cancelled our flights one month out and we had to buy new tickets at a much higher price. You stiffed us by not refunding the cost of the insurance. I’ll never buy through Kayak again.

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.

Sitting in a hotel in Chicago because I was rebooked due to a missed connection. Very frustrating.

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

The flight from Seattle was delayed, which made me miss my connection to Florence. I was re-booked NINE HOURS LATER!!! That’s basically a vacation day lost. British Airways needs to partner with other airlines when possible to get a more realistic travel time, if delays occur. I realize there aren’t many flights to Florence from London, so I would book differently were I to return. The actual flight from Seattle was very comfortable and the crew was great, no faults there. I enjoy British Airways, this was an anomaly.

The crew could not have been more helpful, my meal was excellent, I slept peacefully until right before landing, and the BA lounge was a godsend. The only negative I encountered was the coffee both on the plane and in the lounge. Not to my taste but that’s a personal preference.

I don’t understand why a reputable airline like BA would delegate their London flights to AA. Makes no sense to me, as most domestic carriers do such a poor job these days. Terminal 3 at LHR is a total dump

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

Cancelled flight minutes before boarding. Rescheduled flight was two days later

The flight attendants were EXTREMELY personable and appreciated the service, lights going off after dinner (probably the norm, but I haven’t flown evening overnight flights in a while). Thank you!

Business class seats were very dated on my plane. Very little storage, charging ports were not easily accessible, tv screen kept flopping away. Vegetarian food was disappointing: hardly any protein and severely under-seasoned. Crew was lovely.

Very quick boarding. I was surprised we only got a small water and small thing of cookies, everything else was for purchase. No entertainment. Crew was excellent though.

The food was ok, but not great. They delayed boarding in Portland and did not enforce group boarding. But the crew was excellent, went above and beyond.

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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