$261 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 7/27. 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
Bergamo3 stops$724
Florence
Florence1 stop$587
Naples
Naples2 stops$899
Palermo
Palermo1 stop$744
Bologna
Bologna1 stop$654
Turin
Turin2 stops$863
Milan
Bergamo3 stops$724
Florence
Florence1 stop$587
Naples
Naples2 stops$899
Palermo
Palermo1 stop$744
Bologna
Bologna1 stop$654
Turin
Turin2 stops$863

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

Sun, Oct 4 - Fri, Oct 16
Scandinavian Airlines Logo
7:15 pm - 7:05 pm
ORD
-
FLR
16h 50m
1 stop
Scandinavian Airlines Logo
7:55 pm - 4:10 pm
FLR
-
ORD
27h 15m
1 stop
$587Scandinavian Airlines
Sun, Oct 4 - Mon, Oct 12
Scandinavian Airlines Logo
7:15 pm - 7:05 pm
ORD
-
FLR
16h 50m
1 stop
Scandinavian Airlines Logo
7:55 pm - 4:10 pm
FLR
-
ORD
27h 15m
1 stop
$590Scandinavian Airlines
Fri, Oct 2 - Wed, Oct 14
Scandinavian Airlines Logo
7:15 pm - 6:40 pm
ORD
-
FLR
16h 25m
1 stop
Scandinavian Airlines Logo
7:55 pm - 4:10 pm
FLR
-
ORD
27h 15m
1 stop
$591Scandinavian Airlines
Thu, Nov 12 - Wed, Nov 25
United Airlines Logo
9:35 pm - 1:05 pm
ORD
-
MXP
8h 30mnonstop
United Airlines Logo
11:20 am - 8:05 pm
MXP
-
ORD
15h 45m
1 stop
$779United Airlines
Fri, Aug 14 - Sun, Aug 23
Lufthansa Logo
3:35 pm - 1:00 pm
ORD
-
LIN
14h 25m
1 stop
Lufthansa Logo
6:50 am - 12:55 pm
LIN
-
ORD
13h 05m
1 stop
$780Lufthansa
Sat, Nov 14 - Tue, Nov 24
United Airlines Logo
7:15 am - 10:05 am
ORD
-
MXP
19h 50m
1 stop
United Airlines Logo
11:20 am - 8:05 pm
MXP
-
ORD
15h 45m
1 stop
$783United Airlines
Sat, Aug 15 - Thu, Aug 20
Lufthansa Logo
3:35 pm - 9:10 am
ORD
-
LIN
10h 35m
1 stop
Lufthansa Logo
6:50 am - 12:55 pm
LIN
-
ORD
13h 05m
1 stop
$790Lufthansa
Sat, Oct 31 - Sat, Nov 7
Turkish Airlines Logo
9:15 pm - 8:20 am
ORD
-
NAP
29h 05m
1 stop
Turkish Airlines Logo
7:35 pm - 6:20 pm
NAP
-
ORD
29h 45m
1 stop
$901Turkish Airlines
Fri, Oct 30 - Sat, Nov 7
Turkish Airlines Logo
9:15 pm - 6:35 pm
ORD
-
NAP
15h 20m
1 stop
Turkish Airlines Logo
9:20 am - 7:20 pm
NAP
-
ORD
17h 00m
1 stop
$903Turkish Airlines
Sun, Jun 28 - Tue, Aug 18
ITA Airways Logo
3:00 pm - 6:25 pm
ORD
-
VCE
20h 25m
1 stop
ITA Airways Logo
7:10 pm - 1:10 pm
VCE
-
ORD
25h 00m
1 stop
$977ITA Airways
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 5 days was to Rome, at $739 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 5 days was $739.

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 $948 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 $948.

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 $837, 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 $594 (return) on average. On the other hand, the most expensive months are July and June, when the average cost of round-trip tickets is $1,076 and $1,052 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 Sundays and avoid leaving on a Thursday, as it's usually the priciest day. When flying back from Italy, Saturday 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 4 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$261
Best time to beat the crowds with an average 31% drop in price.
Most popular time to fly with an average 45% increase in price.
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
Turkish AirlinesOverall score based on 4409 reviews
7.5Food
7.8Crew
7.3Comfort
7.5Entertainment
7.3Boarding
Airline reviews

Entertainment system is okay, flight attendants were ok. Leg space very narrow, I couldn’t get what I wanted to eat, dinner nor breakfast.

6.0 GoodAnonymous, Jun 2026
SFO - IST
Read more Turkish Airlines reviews

Entertainment system is okay, flight attendants were ok. Leg space very narrow, I couldn’t get what I wanted to eat, dinner nor breakfast.

Excellent experience with business class area. Staff was attentive and food was amazing. Only one bathroom for business class which was logistically difficult for the staff while preparing meals. Need to offer fluids with meals. I did not get enough water to drink. But overall I rate it 5 star.

On time, great food, good drink selection! Only down was alcohol-free lounge. Lufthansa had a much better offering!

Be honest of what you sell: This was sold as Business Class on all three legs, while the JetBlue plane didn't even have business class seats, and wanted $164 for extra legroom seats.

Seat assignments for family traveling with 2 children. Loud crowd during sleep time

Very good. I was happy that business seats were in a 1-2-1 configuration for the long haul flight. The shorter flight was a 2-2-2 configuration which I do not like as much, but it was a 3 hour flight that I slept through.

It was crowded… the bathrooms dirty and smelly. The seats have been made even smaller.

delayed to take off from detroit by 3 hours lost baggage in istanbul and now in venice without baggage

Seats were very tight with poor legroom - and I am average height. During the 12 hour flight, tiny paper cups of drinks we're only offered during the super and breakfast services, with the crew nowhere to be seen in between. One of the bathrooms was out of order, leading to long lines waiting to use the remaining two available to the economy class passengers.

short flight but we still got a very nice lunch and the crew did an excellent job in taking care of us

Upon departing and landing, the man seating in front of me had his seat leaning back. Taking off nobody told him anything. Landing someone from the crew said something but the passenger ignored him and nobody followed up. Felt a bit unsecured. If this that is some of the basics are missed, what else was overlooked?

On time, reasonably comfortable for economy, decent food. All in all a very good experience.

Every flight got canceled or delayed. Customer service was awful.

They lost my luggage and can’t find it. My trip is ruined. Online tracking of lost luggage doesn’t work

No free Wi-Fi. I have SkyMiles but not a high status, having an account has been enough for Wi-Fi on other flights, but this one was going to charge me to use it. Also turbulence was really bad toward the end, but I didn't count this in my ratings since I know Delta cannot control the weather - it's 2026 and lack of WiFi alone is enough for a poor rating.

The stewardess was incredibly rude. The gave you only one drink with dinner.

Cancelled flight, wasn't refunded paid selected seats. Poor customer service. Called airline and they didn't realize the flight was cancelled until several hours after the email notice was sent.

The worst with the trip was the space in economy, my knees are still hurting. There was no way to control personal air by turning a knob above you, it was way to hot on both rides. During the night flight they allowed 2 people from across the aile which was narrow to sit and talk for 7 hours while also using tablets and the flashlight from their phones pointing into the row where I sat at times. They allowed people with way too large baggage to bring onboard. I paid way too much for the ticket ($1,364} for economy. Kayak misinformed me to get cancellation insurance that was only valid for a very short time (less than 12 hours) and was over one hundred dollars. Hotel booking was incorrect, I had the room booked myself at the hotel, only double or larger rooms available which I paid over 400 dollars for. I will never fly with SAS again unless there is no other alternative.

Crew members were excellent. The seat wasn’t the best as well as a food options.

5 of my 7 pieces of luggage are missing and they cant call to find out where it is. I have to fill out a form and wait for them to mail it to me in several days (if they find it). That does not work for my travel itinerary. I need my full ticket cost refunded please.

Smooth travel. Immediate update prior flight delay so I can arrange myself properly without too rush.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

Never made it to Lufthansa because of Air Canadas negligence.

Good food, overall very comfy. The flight was full so obviously not optimal, but it is what it is.

Flight was delayed by several hours and then cancelled due to weather. But Staff was very helpful getting me on a different flight. United should offer food coupons and tooth brush and paste for stranded passengers

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

ITA has these new Airbus A330 Neo that hates economy class passengers. The seats have absolutely no cushion to a point where it hits your spine constantly and reminds you to fork out for premium economy or don’t travel next time. The food was absolutely horrible, ETA mentioned 3 meals for 12 hour flight but it was mostly 1 meal and 2 light snacks. I am vegetarian, so my 2’d food was 1 slice of tomato, 1 cucumber on a dry cold bun. The other 2 meals were disgusting. My young one threw up the entire time. Flight attendants were the cherry on top - plain bad. They would skip servicing drinks to some passengers completely and if you call for an attendant, they will come and stop the button on top without even asking you what you need. I would avoid ITA by all means - there are plenty of options including SAS for same routes with better seats and humane treatment.

Nice flight. Uneventful, very good crew, comfortable seats. Pleasant experience.

Stews were nice. Plane was very old. Some of the mechanics for travelers outdated. Not enough bathrooms. Hideous food.

Our flight was changed to a day we could not travel so we cancelled it. Will never use kayak again

Comfortable flight Attendants are professional Had a luggage delay at one destination but was delivered the next day

ITA cancelled fligh rebooked with Lufthansa. Flight good, but 2hour connection in Frankfurt was HORRIBLE, took 1.9 hours to get through scanner, customs, another security, got to gate after running all the way, so caught it but stressful and terrible start to trip.

The boarding process was organized and efficient, and the crew was friendly and attentive throughout the flight. Food and drinks were typical economy class, but good. The aircraft was old, and the restroom was not very clean. However, we arrived on time, so overall the experience was good.

In Prem Econ, safe and timely flight, good amount of space, mostly comfortable seats. Little irritants: When lying down, seat kept shifting on me...as a short person w/light weight, my seat often reverted to semi-upright. Footrest was broken. TV screen didn't work, after I asked a few times a FA rebooted it to work again. And food was marginal. I don't expect much from airplane food...surprisingly, ITA didn't even meet expectations.

Flight was canceled. Rebooked on Lufthansa Also Canceled. Had to pay 3000 more per person and fly Alaska to EWR and fly emirates to Athens.

Our flight was cancelled the day before our trip and we we put on a Turkish Airline flight that got us in half a day later.

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.