$238 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 5/3. 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
Milan1 stop$465
Florence
Florence1 stop$650
Naples
Naples1 stop$496
Palermo
Palermo1 stop$479
Bologna
Bologna1 stop$497
Turin
Turin1 stop$537
Milan
Milan1 stop$465
Florence
Florence1 stop$650
Naples
Naples1 stop$496
Palermo
Palermo1 stop$479
Bologna
Bologna1 stop$497
Turin
Turin1 stop$537

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

Mon, Apr 27 - Fri, May 8
Scandinavian Airlines Logo
7:15 pm - 10:35 am
ORD
-
MXP
32h 20m
1 stop
Scandinavian Airlines Logo
3:55 pm - 4:10 pm
MXP
-
ORD
31h 15m
1 stop
$465Scandinavian Airlines
Mon, Apr 27 - Sat, May 9
Scandinavian Airlines Logo
7:15 pm - 8:30 am
ORD
-
MXP
30h 15m
1 stop
Scandinavian Airlines Logo
9:20 am - 4:10 pm
MXP
-
ORD
13h 50m
1 stop
$466Scandinavian Airlines
Fri, Apr 10 - Fri, Apr 17
TAP AIR PORTUGAL Logo
6:00 pm - 6:20 pm
ORD
-
NAP
17h 20m
1 stop
TAP AIR PORTUGAL Logo
12:35 pm - 4:05 pm
NAP
-
ORD
34h 30m
1 stop
$496TAP AIR PORTUGAL
Sat, Apr 18 - Fri, May 1
TAP AIR PORTUGAL Logo
6:05 pm - 4:55 pm
ORD
-
BLQ
15h 50m
1 stop
TAP AIR PORTUGAL Logo
12:05 pm - 4:05 pm
BLQ
-
ORD
35h 00m
1 stop
$497TAP AIR PORTUGAL
Tue, Apr 7 - Tue, Apr 14
Turkish Airlines Logo
11:25 am - 6:20 pm
ORD
-
BLQ
23h 55m
1 stop
Turkish Airlines Logo
2:55 pm - 9:40 am
BLQ
-
ORD
25h 45m
1 stop
$517Turkish Airlines
Sun, Apr 12 - Wed, Apr 22
Aer Lingus Logo
3:45 pm - 10:40 am
ORD
-
NAP
11h 55m
1 stop
Aer Lingus Logo
11:40 am - 7:15 pm
NAP
-
ORD
14h 35m
1 stop
$523Aer Lingus
Tue, Apr 7 - Wed, Apr 15
Turkish Airlines Logo
11:25 am - 1:55 pm
ORD
-
BLQ
19h 30m
1 stop
Turkish Airlines Logo
7:20 pm - 9:40 am
BLQ
-
ORD
21h 20m
1 stop
$526Turkish Airlines
Mon, May 11 - Wed, May 20
Aer Lingus Logo
10:25 pm - 7:55 pm
ORD
-
FCO
14h 30m
1 stop
Aer Lingus Logo
11:10 am - 7:15 pm
FCO
-
ORD
15h 05m
1 stop
$564Aer Lingus
Mon, Aug 10 - Wed, Aug 26
Delta Logo
10:35 am - 10:50 am
MDW
-
FCO
17h 15m
1 stop
Delta Logo
9:45 am - 9:46 pm
FCO
-
MDW
19h 01m
1 stop
$658Delta
Tue, Aug 18 - Tue, Aug 25
Delta Logo
1:05 pm - 11:00 am
MDW
-
FCO
14h 55m
2 stops
Delta Logo
6:30 am - 6:05 pm
FCO
-
MDW
18h 35m
2 stops
$661Delta
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 $593 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 $593.

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

The average price for all round-trip flights from Chicago to Italy depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Italy is generally in the evening, when round-trip flights cost $942 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 $942.

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 $545 (return) on average. On the other hand, the most expensive months are June and July, when the average cost of round-trip tickets is $960 and $926 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 24 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$238
Best time to beat the crowds with an average 33% drop in price.
Most popular time to fly and prices are also 9% 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.

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 9426 reviews
7.3Comfort
8.1Crew
7.1Entertainment
7.7Boarding
6.6Food
Airline reviews

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

4.0 OkayDr. Joseph, Feb 2026
ORD - IAH
Read more United Airlines reviews

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

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. :/

IAH to Istanbul was outstanding across the board. The flight from Istanbul to Male was good, not great.

the cabin was kept too hot. couldn't sleep as a result

It was an amazing experience. Flight crew's service, hospitality, and the food were phenomenal. I don't think I'd want to try any other airline company after this. I would definitely recommend to friends and family. Thank you Turkish Airlines !

Business Class pods are horrible. If you're petite, you might be able to sleep on the uncomfortable seat and bed. Crew and food are fantastic.

I have travelled many times on Turkish, but they always board at least 30-40 minutes past the stated time. If informed properly, passengers can choose to spend more time in the .lounge instead of standing around by the gate waiting to board. The new lounge at DFW was a big disappointment. The aircraft itself was a shock. In the past I have flown this sector with regular business class seating configuration of 1-2-1, The 2-3-2 seating is very disappointing after paying such high prices for tickets. The DFW to Istanbul segment was slightly better, but the Istanbul to Delhi segment was no better than premium economy. I will try to travel more on airlines which give business class passengers more value for their money.

Good overall. Seat spacing a bit tight between IST and ISB.

Excellent staff despite some trying passenger situations. Very impressed with their good attitudes and kindness.

Crew were unfriendly, touch screen for movies didn't work very well, seats were tight and uncomfortable

After arriving in Istanbul, the transit information on the electronic board showed a tight departure time, and the gate changed in the middle, making it difficult to make it on time.

Typically good service onboard but baggage delay in airport was significant

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

I had a good comfortable seat. There was nearly an hour delay. There was an accident with the champagne, but I was well compensated. These things happen sometimes.

We missed our flight. There was not enough time built into the layover to get through immigration, customs, bagclaim, bag rechecking, and the long trip to another terminal and gate. Kayak really screwed up. We took the bus up to Wisconsin and then were picked up in Brookfield by private car. It was lucky we didnt miss the last bus out.

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

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

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.

They lost my checked in bag and have not helped me.

First, ITA lost my bag and the baggage team showed no regard in trying to find it. Second, I had paid for priority boarding as part of a first class ticket and instead they disregarded boarding groups and we all boarded at the same time. Third, wasn't allowed to select my seat in advance even with a first class ticket. When I was assigned bulkhead, I was told I would need to pay to change my seat. Overall, very disappointing experience.

The seats needs to be spruced up , for a long flight very uncomfortable , cushions are worn out but everything else is very good , crew is great.

I guess that was fine with ITA but the Rome airport is so difficult to navigate with so many checkpoints getting new tickets from what was originally given to me

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

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.