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Find cheap flights from Chicago to Italy from $237

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 9/11. 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
Tue 7/2
Tue 7/9

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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$490
Milan
Milan1 stop$490
Florence
Florence2 stops$551
Naples
Naples1 stop$553
Palermo
Palermo1 stop$589
Bologna
Bologna1 stop$581
Turin
Turin1 stop$604

Good to know

Low season

January

High season

September

Cheapest flight

$237
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 Midway 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 7% more expensive 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 10755 reviews
8.1Crew
7.1Entertainment
7.7Boarding
7.2Comfort
6.7Food
Airline reviews

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

8.0 ExcellentBob, Jun 2024ORD - LAX
Read more about United Airlines reviews

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

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?

My husband and I pre-ordered our food, but they did not have my husband’s order, and my cheese plate was very average. I asked for a blanket and was told they don’t carry blankets on domestic routs. The flight was on time and smooth!

Original flight delayed several times and finally canceled at 2:30 in the morning. Staff at the gate was not very helpful in resolving problems or communicating why there were delays. I spent 34 hours at the airport before I could leave, they couldn't book me on another early flight even after canceling my original flight. Next flight available after my original flight was canceled was 22 hours later. I will never fly American Airlines again.

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.

Poor, we had 1 hour to grab our checked luggage, go through customs, recheck bags and run across terminals to make our United flight. Poorly planned connections.

Check in in Albuquerque was awful. The people were great but they were over loaded. The procedures were terrible. We got through fine but it took 90+ minutes.

Will try to not fly with them again. Delays because of weather but got redirected to an airport where I could not make connection.

Staff didn’t care in business class. Closed the door on my mom while she was on the jetbridge and flight attendant told me she would make it from the connecting flight. They lied. My luggage was damaged on arrival. No success in filing damage claim.

Boston Logan is a crummy airport - signage is terrible or lacking in areas. Boarding seemed to be a free for all and with all the different airlines speaking, you couldn't tell who was supposed to be where and when. Plain and simple, airlines should board from the back of the plane to the front. Also someone was sitting in my seat. By the time that was figured out, I had to place my overhead behind me which made de-planing more difficult. Logan is not Lufthansa's fault so that is not on them, Boarding is on them! Still, overall it was a Good Experience flying with Lufthansa. This is not my first flight with them...

Overall, the flight was comfortable without any serious issues. Transit through Frankfurt airport was a little confusing, but not too difficult if you follow the signs

There was a screaming child behind our seats. This prevented us from getting any sleep during the night.

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

Boarding was as fast and efficient as possible. The flight crew were amazing and extremely friendly. We enjoyed our flight.

Very bed boarding, there was overbooked and make a lot of problems and noises

There was a problem in the luggage because there were not porters

On my way from Chicago to London, I was seated next to a quite heavy passenger. I could barely move. BA should have ensured that overweight customers are placed in comfortable seats and not to penalize also other passengers because BA is not willing to accommodate these passengers and their needs. No respect at all.

The flight as far as timings go was excellent. Unfortunately we ended up sat with someone on a night flight who had been drinking alcohol before boarding and BA staff were happily serving him more alcohol. He was very drunk which made our flight uncomfortable and awkward. My partner had this person lying on him whilst asleep. Alcohol should be served minimally. If there had been an emergency this person would not have been in a fit state to act accordingly.

First time flying with BA and I will do it again. Staff at airport and on board were very nice and helpful

they are improving. The crew from Charlotte to Tampa was outstanding. SMILING and trying to be helpful with the customers.

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

AMS FCO in their full flat business. Amazing sear and food experience.

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!!

Book cheap flights from Chicago to Italy

Recent round-trip flight deals

10/21Mon
1 stopTAP AIR PORTUGAL
23h 35mORD-MXP
10/30Wed
1 stopTAP AIR PORTUGAL
16h 10mMXP-ORD
$490
11/12Tue
1 stopDelta
15h 30mMDW-FCO
11/22Fri
2 stopsDelta
17h 43mFCO-MDW
$490
10/29Tue
2 stopsUnited Airlines
35h 40mORD-NAP
11/12Tue
1 stopUnited Airlines
13h 00mNAP-ORD
$622
8/7Wed
1 stopITA Airways
20h 25mORD-VCE
8/20Tue
1 stopITA Airways
25h 00mVCE-ORD
$636
11/7Thu
1 stopUnited Airlines
12h 05mORD-FLR
11/14Thu
2 stopsUnited Airlines
21h 57mFLR-ORD
$652
8/18Sun
1 stopITA Airways
16h 20mORD-NAP
8/27Tue
1 stopITA Airways
24h 25mNAP-ORD
$652
9/3Tue
1 stopBritish Airways
17h 35mORD-MXP
11/20Wed
1 stopBritish Airways
14h 18mMXP-ORD
$697
11/2Sat
2 stopsBritish Airways
35h 05mORD-VCE
11/11Mon
1 stopBritish Airways
31h 50mVCE-ORD
$697
9/7Sat
1 stopLufthansa
15h 45mORD-FLR
12/5Thu
2 stopsLufthansa
18h 30mFLR-ORD
$814
7/14Sun
nonstopLufthansa
9h 05mORD-FCO
7/21Sun
nonstopLufthansa
10h 15mFCO-ORD
$839

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Recent one-way flight deals

9/11Wed
2 stops
43h 57mMDW-MXP
$237
9/11Wed
2 stops
18h 26mORD-MXP
$245
7/15Mon
nonstopITA Airways
9h 20mORD-FCO
$435
7/31Wed
nonstopITA Airways
9h 20mORD-FCO
$446
7/31Wed
nonstopLufthansa
9h 05mORD-FCO
$473
7/14Sun
2 stopsUnited Airlines
15h 05mORD-FCO
$507
8/28Wed
1 stopBritish Airways
13h 40mORD-MXP
$626
8/28Wed
1 stopBritish Airways
16h 30mORD-LIN
$626
7/2Tue
nonstopLufthansa
9h 05mORD-FCO
$723
6/10Mon
2 stopsUnited Airlines
15h 05mORD-FCO
$771

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Last minute flights from Chicago to Italy

Last minute flight, train and bus deals

6/7Fri
multi-stopTAP AIR PORTUGAL
27h 35mORD-FCO
6/21Fri
multi-stopTAP AIR PORTUGAL
34h 00mFCO-ORD
$799
6/7Fri
multi-stopTAP AIR PORTUGAL
31h 30mORD-FCO
6/20Thu
multi-stopTAP AIR PORTUGAL
17h 15mFCO-ORD
$803
6/3Mon
multi-stopUnited Airlines
24h 50mORD-FLR
6/17Mon
multi-stopUnited Airlines
32h 35mFLR-ORD
$860
6/3Mon
multi-stopUnited Airlines
19h 21mORD-FLR
6/10Mon
multi-stopUnited Airlines
32h 35mFLR-ORD
$862
6/3Mon
multi-stopBritish Airways
13h 45mORD-FCO
6/11Tue
nonstopBritish Airways
10h 25mFCO-ORD
$902
6/4Tue
multi-stopBritish Airways
12h 35mORD-FCO
6/11Tue
nonstopBritish Airways
10h 25mFCO-ORD
$908
6/6Thu
multi-stopLufthansa
15h 45mORD-FLR
6/13Thu
multi-stopLufthansa
18h 35mFLR-ORD
$965
6/4Tue
nonstopLufthansa
9h 05mORD-FCO
6/19Wed
nonstopLufthansa
10h 15mFCO-ORD
$967
6/3Mon
nonstopITA Airways
9h 20mORD-FCO
6/15Sat
nonstopITA Airways
10h 50mFCO-ORD
$1,172
6/3Mon
nonstopITA Airways
9h 20mORD-FCO
6/11Tue
nonstopITA Airways
10h 50mFCO-ORD
$1,183

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Flights to Italy

Return flight deals:

Italy - Chicago

Cabin classes:

$6,263
$2,395
$1,445
$629