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Find cheap flights from Chicago to Italy from $258

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 7/9. 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
Sat 6/22
Sat 6/29

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Best Italy Flight Deals

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

Rome
Rome1 stop$520
Milan
Milan2 stops$426
Florence
Florence1 stop$532
Naples
Naples1 stop$589
Palermo
Palermo2 stops$791
Bologna
Bologna1 stop$718
Turin
Turin1 stop$588

Good to know

Low season

January

High season

September

Cheapest flight

$258
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 14% 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 10852 reviews
7.1Entertainment
7.2Comfort
7.7Boarding
8.1Crew
6.7Food
Airline reviews

Standard flight experience, but there is only power at the seat to row 20 on the aircraft, on my initial check in it did not say that was the case

6.0 Goodmichael, May 2024ORD - YVR
Read more about United Airlines reviews

Standard flight experience, but there is only power at the seat to row 20 on the aircraft, on my initial check in it did not say that was the case

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

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.

Staff disappeared after dinner service until breakfast, no help with beds, no help running to our gate to catch connection cause flight was late, our luggage didn’t make it, took over 24 hours to get luggage to hotel, no compensation!!

Everything was good except food. I believe there is room for improvement

Houston to Porto flight delayed landing made us miss our connection. Tried to get on standby for the next flight and even though the lady knew we wouldn’t be able to get on it and she sent us down there. We sat there three hours and then we’re told there’s no way you’re getting on this flight. So we had to go to customer service and ended up having to spend the night in Frankfurt and missed a whole day of our vacation in Porto

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.

Wonderful service and very comfy in the bulkhead in Economy Plus! Delicious food.

The BA team at Sky Harbor is deplorable, full of unnecessary attitude and poor communication. It seems like every member of the team was looking at another to solve the problem, instead of taking agency to do so themselves. I saw no less than 6 altercations with the same gate agent where he threatened to revoke the passengers boarding pass for asking a wildly reasonable question, something as simple as where the cue to board was. I’ve complained to BA before but it seems this isn’t an issue for them, which is very disappointing

Boarding poor in London,ok in Chicago. Don’t like Heatrow/terminal5

It was very good. We got a late start by about an hour and a half. However I worked rather have that than crash. It was purely mechanical. They had our tickets ready when we came off the plane in London for the next leg. The only mishap was when we got to Lisbon my husbands luggage made or bit mine didn't. All was not lost because I did finally get it 2 days later. I was really pleased that they c made the effort.

Leg space was not enough. The meal was not satisfactory.

Liked that my American Airlines status seamlessly transferred to BA so luggage check was free. Flights were on time, boarding quick. Wish they didn’t assign connecting gate so late at Heathrow.

The entire process was flawless and as expected flying first class. The only thing that I have a complaint on...when first boarding, the plane was EXTREMELY cold; then when we were trying to sleep, it was way too hot - just better regulating (especially trying to sleep) would have made it perfect.

- 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 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

11/10Sun
2 stopsScandinavian Airlines
32h 55mORD-LIN
11/19Tue
2 stopsScandinavian Airlines
60h 10mLIN-ORD
$426
11/12Tue
1 stopDelta
12h 50mMDW-FCO
11/22Fri
2 stopsDelta
18h 45mFCO-MDW
$520
11/10Sun
1 stopBritish Airways
13h 10mORD-LIN
11/19Tue
1 stopBritish Airways
18h 15mLIN-ORD
$661
8/12Mon
1 stopITA Airways
20h 45mORD-FLR
8/19Mon
1 stopITA Airways
28h 45mFLR-ORD
$673
10/30Wed
1 stopUnited Airlines
12h 05mORD-FLR
11/8Fri
1 stopUnited Airlines
14h 40mFLR-ORD
$676
8/14Wed
1 stopITA Airways
15h 10mORD-LIN
8/25Sun
1 stopITA Airways
26h 10mLIN-ORD
$688
11/1Fri
1 stopUnited Airlines
15h 30mORD-FLR
11/8Fri
1 stopUnited Airlines
14h 40mFLR-ORD
$726
8/16Fri
1 stopBritish Airways
29h 30mORD-FCO
8/25Sun
nonstopBritish Airways
10h 25mFCO-ORD
$745
11/1Fri
1 stopLufthansa
12h 40mORD-FLR
11/10Sun
1 stopLufthansa
12h 45mFLR-ORD
$776
9/7Sat
1 stopLufthansa
12h 10mORD-FLR
12/6Fri
1 stopLufthansa
12h 45mFLR-ORD
$854

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Recent one-way flight deals

7/9Tue
2 stops
34h 21mORD-MXP
$258
9/7Sat
2 stops
42h 17mORD-NAP
$270
6/18Tue
nonstopITA Airways
9h 20mORD-FCO
$522
7/21Sun
nonstopITA Airways
9h 20mORD-FCO
$576
8/13Tue
nonstopUnited Airlines
9h 05mORD-FCO
$580
7/24Wed
2 stopsUnited Airlines
16h 50mORD-FCO
$584
9/3Tue
1 stopBritish Airways
18h 00mORD-MXP
$615
7/1Mon
1 stopLufthansa
14h 10mORD-VCE
$625
9/3Tue
1 stopBritish Airways
16h 20mORD-NAP
$658
7/14Sun
2 stopsLufthansa
18h 55mORD-FCO
$727

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Last minute flights from Chicago to Italy

Last minute flight, train and bus deals

5/27Mon
multi-stop
13h 35mORD-FCO
6/4Tue
multi-stop
20h 05mFCO-ORD
$910
5/27Mon
multi-stop
47h 05mORD-FCO
6/10Mon
multi-stop
22h 19mFCO-ORD
$914
5/26Sun
nonstopITA Airways
9h 20mORD-FCO
6/5Wed
nonstopITA Airways
10h 50mFCO-ORD
$974
5/28Tue
nonstopITA Airways
9h 20mORD-FCO
6/5Wed
nonstopITA Airways
10h 50mFCO-ORD
$976
5/28Tue
multi-stopUnited Airlines
12h 10mORD-FCO
6/9Sun
nonstopUnited Airlines
10h 15mFCO-ORD
$1,146
5/28Tue
multi-stopLufthansa
11h 00mORD-MXP
6/8Sat
nonstopLufthansa
9h 45mMXP-ORD
$2,072
5/24Fri
multi-stopBritish Airways
30h 20mORD-FLR
6/29Sat
multi-stopBritish Airways
26h 55mFLR-ORD
$2,122
5/25Sat
multi-stopLufthansa
11h 00mORD-MXP
6/15Sat
nonstopLufthansa
9h 45mMXP-ORD
$2,135
5/28Tue
nonstopUnited Airlines
8h 45mORD-MXP
6/8Sat
nonstopUnited Airlines
9h 45mMXP-ORD
$2,232
5/24Fri
multi-stopBritish Airways
31h 20mORD-FLR
7/20Sat
multi-stopBritish Airways
32h 25mFLR-ORD
$2,277

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Flights to Italy

Return flight deals:

Italy - Chicago

Cabin classes:

$3,612
$2,395
$1,446
$644