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Find cheap flights from Chicago to Italy from $233

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 9/17. 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
0 bags
sáb 6/15
sáb 6/22

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Best Italy Flight Deals

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

Rome
Romenonstop$723
Milan
Milan1 stop$455
Florence
Florence1 stop$521
Naples
Naples2 stops$708
Palermo
Palermo1 stop$780
Bologna
Bologna1 stop$778
Turin
Turin1 stop$734

Good to know

Low season

January

High season

September

Cheapest flight

$233
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly with an average 2% 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 to Italy from Chicago 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 to Italy with an airline and back to Chicago 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 to Italy from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Italy

  • Morning departure is around 5% cheaper than an evening flight, on average*.
  • 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.
See more tips
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

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 10946 reviews
8.1Crew
6.7Food
7.7Boarding
7.2Comfort
7.1Entertainment
Airline reviews

Energetic crew - flight full of swiftied going to Taylor's opening show in Paris! Long lines for bathroom made out kind of suck though

8.0 ExcellentSusan, May 2024ORD - CDG
Read more about United Airlines reviews

Energetic crew - flight full of swiftied going to Taylor's opening show in Paris! Long lines for bathroom made out kind of suck though

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

Nothing beats ANA customer service on my opinion. Maybe because of their Japanese culture (and food). Arigatō

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

Flight delayed for 2 hours due to a part. The plane sat waiting for boarding for a long time and during final preflight inspection the issue was found. Why not do the preflight inspection sooner if you know the plane is being used?

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

Aircraft has better leg room than any of United's larger planes. We had requested mobility assistance for this and related flights. United's response to all was superb.

It was spectacular. I had basic Economy and was given so much space and their seats lean back so far. Staff was superb, food was superb, everything was superb, Finnair is Fantastic.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

We were delayed bc ground crew gave the flight crew the wrong paperwork. We taxiied to the runway then back to the gate to get the correct paperwork that no one bothered reviewing the first time we pushed back. Boarding was rude and stressful like it always is. Gate agents and flight attendants are all over 55 years of age, embittered by years of underpayment From AA leading to their passive agressive bitchiness for no reason.

Boarding time was easy & quick. Crew was excellent. In-flight entertainment was great/easy. Seats are too small and not enough room between rows: felt like a sardine/very cramped.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Second time I took this flight, and they lost my luggage both times. Waiting for my suitcase now, last time it took two days to get it back.

Disappointed everytime. The app doesn't load the boarding passes. They have lots of agent that seem to be busy doing nothing with a long line waiting to get paper boarding passes. Food choices are poor. Entertainment is less than entertaining.

Horrible experience. Nothing to give to kids to keep them entertained.

Trouble keeps changing the time and I was booked different flight without knowing it was bad experience

Hated every minute of it. Delayed for over 10 hours only to have to cancel rental car, car insurance and hotel. Its taken me 3days to get to my final destination when it should have only taken 12-14 hours. Very unhappy with Lufthansa.

This flight is always a cramped bus. The gate area was inadequate and announcements were hard to hear. The flight was delayed 45 minutes to an hour by a broken aircraft door, making our total delay from Vilnius 5 hours.

didn’t even get to go one of my returning flights cancelled and I wasn’t even in their system, vacation ruined thanks for nothing

You need to reimburse me for my seats purchased and luggage.

Flight delay wasn’t managed well. I was booked for the next flight for 2 days later!

My baggage has been lost for the last 6 days! The problem originated at LAX with Lufthansa, which was a very big disappointment from LAX to Munich. The flight was delayed over an hour, the overhead bins on the window side are too small for most carryon's, the in-seat video screen were very poor as they would not respond to your touch quickly and would stop and start all over again, the earphone jacks are not like most standard ones, the seats still has wrappers and trash in pockets and on the seats. and there was no USB outlet to charge your phone or other devices. The German reputation for quality is bogus with this airline. BUT the responsibility for delivering my luggage became Air Dolomiti's as they were the last leg of the trip. The baggage area was chaos because several flights arrived at once. I took me over an hour to file a claim, the agent entered my info incorrectly, and the contact numbers for Lost and Found at the airport was never answered. I have never been called by Air Dolomiti or the baggage delivery company. I had to do all the calling. AD's live agents gave me two wrong phone numbers for the baggage company. When I finally got the right one on my third call, OF COURSE, no one answers and I still do not have any information on when my bags should arrive. VERY UNPROFESSIONAL operations by Lufthansa and Air Dolomiti. I will make sure I book any other air carriers on the rest of my flights to Italy this year.

- OK plane. Basic accommodations. OK food. The digital window shade wasn't working.

- OK plane. Basic accommodations. OK food. The digital window shade wasn't working. - Expect to be woken up more than an hour before landing when they start dinging the bell and making announcements and turning on all cabin lights to serve a snack. I would prefer they remain quiet and only serve people who want to wake up.

Better food and more space in the seats. Also when doing the web check in both times I was going in to your site the minute you open it and there is not really many seats to choose only to buy!!!

It was ok, not as good as it used to be. The Heathrow connection was a disaster - complete anarchy, unknowledgable and skimpy assistance and signage. Gate crew at next flight was great, held the flight while my wife struggled through security.

It was great! The seats were comfortable, and they fed me during the transatlantic flight, something which I have been missing out on for the past 3 years as I travel to and from school.

This flight was cancelled at the last minute. We were rebooked on another flight but a day later. We lost a day of our vacation and paid for a night in a hotel we couldn’t use. The flights we were rebooked on (both American) messed up our seating on both flights-we didn’t get the seats we had paid for. All in all, a terrible experience.

Lost our bags in Heathrow, We didn’t receive bags in Mallorca for 3 days, out of a 7 day cycling vacation. Really inconvenient and disappointing!

We missed the flight to Barcelona because the flight from Baltimore was delayed. We flew on Vueling VW6653. Our luggage didn’t arrive. Please help us get our luggage. We are staying at Hotel Gran Via in Barcelona

The seats were tiny, being of a fairly petite build, I don’t usually expect to feel crammed and cramped in a seat, but I definitely was on this flight. I couldn’t even bend over to get anything out from under the seat in front and getting up to go to the bathroom at night with the seat backs reclined was nearly impossible. I had to do gymnastics to get over and out. For an airline that does long flights overnight, it’s kind of ridiculous.

Not connecting flights. Missed my flight from Dublin to Liverpool because I arrived at Dublin one hour too late. For this mistake, they offered me a flight from Dublin to Manchester. Thats great and all, but I waste time and money to commute to Liverpool. Be sure to check the time of your connecting flights, because they sure don’t when they sell it to you

It was a short haul trip, so food and entertainment weren’t a big issue

The plane seemed very dated. The entertainment was very limited. There was a school group on our flight and the crew seemed bothered by them. They were not overly friendly or welcoming.

Ok, but no entertainment. Left late, but made up most of the time.

May be it is not an ITA issue, but the bags took long time to go out.

Good. But there food was poor quality and 95% of movies didn't have English subtitles

I thought they had rebranded themselves in every aspect but it was quite the opposite. The food was terrible the service was sub-par. Overall it was not a good experience.

Service from staff was poor, food choices were limited. Air plane was not clean or hygienic and seemed like not cleaned for days. Seats were uncomfortable.

service from stAff was barely there , food choices were limited. AirPlane was not clean and seemed like it was not cleaned for days.. Seats were very uncomfortable.

I paid for premium seats and the last minute they changed the aircraft for a bigger one, they bumped me to another seat which was NOT at all comfortable for an 11 hour flight, will fight for a refund!!

The landing was catastrophic. I was very scared. I thought it were my last lminues. Pilotes should be more experienced

Book cheap flights from Chicago to Italy

Recent round-trip flight deals

10/23qua
1 stopTAP AIR PORTUGAL
23h 35mORD-MXP
11/3dom
1 stopTAP AIR PORTUGAL
16h 10mMXP-ORD
$455
10/18sex
1 stopTAP AIR PORTUGAL
15h 45mORD-MXP
11/2sáb
1 stopTAP AIR PORTUGAL
28h 45mMXP-ORD
$489
8/20ter
1 stopITA Airways
12h 50mORD-FLR
8/27ter
1 stopITA Airways
13h 35mFLR-ORD
$684
11/4seg
2 stopsUnited Airlines
22h 30mORD-LIN
11/11seg
2 stopsUnited Airlines
38h 52mLIN-ORD
$685
9/9seg
1 stopITA Airways
12h 30mORD-VCE
9/23seg
1 stopITA Airways
24h 55mVCE-ORD
$697
11/12ter
1 stopLufthansa
11h 20mORD-LIN
11/29sex
2 stopsLufthansa
19h 01mLIN-ORD
$716
10/6dom
1 stopBritish Airways
31h 40mORD-MXP
10/9qua
1 stopBritish Airways
17h 05mMXP-ORD
$724
7/14dom
1 stopBritish Airways
18h 20mORD-FCO
7/23ter
1 stopBritish Airways
18h 49mFCO-ORD
$772
7/31qua
nonstopUnited Airlines
9h 05mORD-FCO
8/15qui
1 stopUnited Airlines
15h 41mFCO-ORD
$835
8/26seg
1 stopLufthansa
15h 45mORD-FLR
12/14sáb
1 stopLufthansa
16h 55mFLR-ORD
$844

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Recent one-way flight deals

9/17ter
2 stops
22h 51mORD-MXP
$233
9/7sáb
2 stops
42h 52mORD-VCE
$254
7/16ter
nonstopITA Airways
9h 20mORD-FCO
$576
8/13ter
nonstopUnited Airlines
9h 05mORD-FCO
$580
7/17qua
2 stopsUnited Airlines
16h 50mORD-FCO
$584
8/12seg
nonstopITA Airways
9h 20mORD-FCO
$593
7/14dom
nonstopLufthansa
9h 05mORD-FCO
$780
7/1seg
3 stopsLufthansa
30h 25mORD-FCO
$790
6/17seg
nonstopBritish Airways
9h 10mORD-FCO
$858
9/19qui
nonstopBritish Airways
9h 00mORD-VCE
$1,010

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Last minute flights from Chicago to Italy

Last minute flight, train and bus deals

5/21ter
multi-stop
29h 05mORD-FCO
5/25sáb
multi-stop
22h 19mFCO-ORD
$748
5/17sex
nonstopITA Airways
9h 20mORD-FCO
5/21ter
nonstopITA Airways
10h 50mFCO-ORD
$764
5/19dom
multi-stopScandinavian Airlines
17h 10mORD-FCO
5/25sáb
multi-stopScandinavian Airlines
28h 10mFCO-ORD
$771
5/17sex
multi-stopScandinavian Airlines
17h 10mORD-FCO
5/26dom
multi-stopScandinavian Airlines
13h 30mFCO-ORD
$776
5/17sex
multi-stopBritish Airways
12h 05mORD-FCO
5/21ter
nonstopBritish Airways
10h 25mFCO-ORD
$807
5/17sex
multi-stopUnited Airlines
16h 42mORD-FCO
5/21ter
multi-stopUnited Airlines
14h 11mFCO-ORD
$813
5/17sex
multi-stopUnited Airlines
14h 15mORD-FCO
5/24sex
multi-stopUnited Airlines
28h 58mFCO-ORD
$818
5/17sex
multi-stopLufthansa
14h 05mORD-FCO
5/22qua
multi-stopLufthansa
24h 35mFCO-ORD
$929
5/21ter
nonstopLufthansa
9h 10mORD-FCO
5/28ter
nonstopLufthansa
10h 15mFCO-ORD
$1,131
5/21ter
multi-stopBritish Airways
11h 50mORD-FLR
7/3qua
multi-stopBritish Airways
32h 05mFLR-ORD
$1,782

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Flights to Italy

Return flight deals:

Italy - Chicago

Cabin classes:

$3,612
$2,828
$1,494
$645