$213 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 4/26. 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
Milan2 stops$426
Florence
Florence1 stop$381
Naples
Naples1 stop$381
Palermo
Palermo1 stop$490
Bologna
Bologna1 stop$393
Turin
Turin1 stop$530
Milan
Milan2 stops$426
Florence
Florence1 stop$381
Naples
Naples1 stop$381
Palermo
Palermo1 stop$490
Bologna
Bologna1 stop$393
Turin
Turin1 stop$530

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, Apr 10 - Fri, Apr 24
TAP AIR PORTUGAL Logo
6:00 pm - 6:00 pm
ORD
-
FLR
17h 00m
1 stop
TAP AIR PORTUGAL Logo
6:45 pm - 4:15 pm
FLR
-
ORD
28h 30m
1 stop
$381TAP AIR PORTUGAL
Wed, Apr 8 - Thu, Apr 16
TAP AIR PORTUGAL Logo
6:00 pm - 6:25 pm
ORD
-
NAP
17h 25m
1 stop
TAP AIR PORTUGAL Logo
7:15 pm - 4:00 pm
NAP
-
ORD
27h 45m
1 stop
$381TAP AIR PORTUGAL
Wed, Apr 15 - Fri, Apr 24
Scandinavian Airlines Logo
7:15 pm - 7:50 pm
ORD
-
MXP
17h 35m
2 stops
Scandinavian Airlines Logo
3:55 pm - 4:10 pm
MXP
-
ORD
31h 15m
1 stop
$426Scandinavian Airlines
Mon, Apr 6 - Tue, Apr 14
Scandinavian Airlines Logo
7:15 pm - 11:30 am
ORD
-
FLR
33h 15m
1 stop
Scandinavian Airlines Logo
7:55 pm - 4:10 pm
FLR
-
ORD
27h 15m
1 stop
$426Scandinavian Airlines
Fri, Apr 10 - Sun, Apr 19
Icelandair Logo
10:25 pm - 2:35 pm
ORD
-
FCO
33h 10m
1 stop
Icelandair Logo
3:45 pm - 9:25 pm
FCO
-
ORD
12h 40m
1 stop
$486Icelandair
Tue, Feb 24 - Fri, Mar 6
Lufthansa Logo
9:50 pm - 6:15 pm
ORD
-
FCO
13h 25m
1 stop
Lufthansa Logo
1:35 pm - 8:05 pm
FCO
-
ORD
13h 30m
1 stop
$488Lufthansa
Tue, Feb 17 - Thu, Mar 26
Icelandair Logo
6:30 pm - 2:00 pm
ORD
-
FCO
12h 30m
1 stop
Icelandair Logo
11:25 am - 6:20 pm
FCO
-
ORD
12h 55m
1 stop
$489Icelandair
Wed, Feb 11 - Wed, Feb 18
Lufthansa Logo
9:50 pm - 11:00 pm
ORD
-
FCO
18h 10m
1 stop
Lufthansa Logo
12:20 pm - 6:25 pm
FCO
-
ORD
13h 05m
1 stop
$490Lufthansa
Fri, Feb 20 - Wed, Feb 25
Turkish Airlines Logo
8:20 pm - 8:35 am
ORD
-
VCE
29h 15m
1 stop
Turkish Airlines Logo
9:35 am - 6:25 pm
VCE
-
ORD
15h 50m
1 stop
$540Turkish Airlines
Tue, Mar 31 - Thu, Apr 9
Turkish Airlines Logo
8:10 pm - 7:00 pm
ORD
-
VCE
15h 50m
1 stop
Turkish Airlines Logo
9:20 am - 9:40 am
VCE
-
ORD
31h 20m
1 stop
$541Turkish Airlines
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 $571 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 $571.

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 $1,096 and $943 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 seasonFebruary
Cheapest flight$219
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly and prices are also 9% 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 in the evening, when round-trip flights cost $956 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 $956.

  • How many flights are there between Chicago and Italy per day?

    There is a maximum of 1 nonstop flight a day that takes off from Chicago and lands in Italy, with an average flight time of 9h 00m. The most common departure time is 3:00 pm and most flights take off in the afternoon. Each week, there are 7 flights.

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 9206 reviews
7.3Comfort
8.1Crew
7.1Entertainment
7.7Boarding
6.6Food
Airline reviews

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

6.0 GoodPatricia, Jan 2026
ORD - LAS
Read more United Airlines reviews

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Not United Airlines' fault. It's ORL airport's fault.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

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.

Fantastic. The only thing - out of my six luggage one was lost in Copenhagen, however it was delivered Home 3 Days later so all great..

The crew was friendly, the flight was pleasant. Thank you for your service!

Our trip plan from Kayak stated we were flying SAS. That was not true. The first leg was a Delta flight. We wasted 25 minutes before finding out to check in with the correct airline. Then our SAS flight for the second leg arrived 25 minutes late, and our third leg flight with SAS closed the gate knowing the flight delay was SAS’s fault, and that this flight would only be backed up 5 minutes. The final kicker was that between Delta and SAS, they lost all our checked luggage.

Flight was completely full January 9th? I problem i had the stewardess was bumping into me constantly walking by? very annoying.. on Austrian air I dint have this issue at all...

Amazing! Everyone was so nice and the food was so good!!

Terrible customer service. The flight attendants were rude. We experienced significant turbulence for a large portion of the flight and there was very little check in from the flight deck. The space was extremely limited to the point where it felt like torture. Never again

I was surprised how good an American airline can be - I was really impressed.

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

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

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.

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

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.

My seat was broken and ducted taped and my monitor did not work the entire time over 8 hrs sitting. And I had no books or anything with me

my flight from Rome to Boston was on a very old plane. My video and audio did not work.

Good with timing of flights. The crew was exceptionally unfriendly. I heard more than one person say this. And even with the aisle, it seemed more uncomfortable than usual. The movie selection was old and poor, but the dinner was great - the lasagna and tiramisu.

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.

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.