$295 Find Cheap Flights from Italy to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 1/30. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
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Everything you should know

Cheapest round-trip
$465
Typical prices: $607-$910
TAP AIR PORTUGAL
Sat 11/22Fri 12/5
VCE - ORD • 1 stop
Cheapest non-stop
$634
Lufthansa
Tue 11/11Tue 11/18
MXP - ORD • Non-stop
Top airlines
United Airlines
Most flights • 14 per week
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
February
Cheapest • 14% price drop
August
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Italy to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Italy to Chicago 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 Italy to Chicago

Sat, Nov 22 - Fri, Dec 5
TAP AIR PORTUGAL Logo
5:50 pm - 2:45 pmVCE-ORD
27h 55m1 stop
TAP AIR PORTUGAL Logo
8:15 pm - 5:00 pmORD-VCE
13h 45m1 stop
$465TAP AIR PORTUGAL
Find Deal
Fri, Apr 17 - Sat, Apr 25
TAP AIR PORTUGAL Logo
7:05 pm - 4:15 pmVCE-ORD
28h 10m1 stop
TAP AIR PORTUGAL Logo
6:15 pm - 6:15 pmORD-VCE
17h 00m1 stop
$478TAP AIR PORTUGAL
Find Deal
Thu, Mar 19 - Tue, Apr 14
ITA Airways Logo
7:15 pm - 6:28 pmVCE-ORD
29h 13m2 stops
ITA Airways Logo
11:15 am - 10:30 amORD-VCE
16h 15m2 stops
$601ITA Airways
Find Deal
Tue, Apr 28 - Tue, May 5
ITA Airways Logo
9:00 pm - 1:10 pmLIN-ORD
23h 10m1 stop
ITA Airways Logo
10:40 am - 11:40 amORD-LIN
18h 00m2 stops
$606ITA Airways
Find Deal
Thu, Nov 27 - Thu, Dec 4
Lufthansa Logo
6:55 am - 8:05 pmVCE-ORD
20h 10m1 stop
Lufthansa Logo
10:35 pm - 10:55 pmORD-VCE
17h 20m1 stop
$609Lufthansa
Find Deal
Wed, Nov 12 - Thu, Nov 27
Lufthansa Logo
7:05 am - 8:05 pmFCO-ORD
20h 00m1 stop
Lufthansa Logo
9:50 pm - 11:00 pmORD-FCO
18h 10m1 stop
$611Lufthansa
Find Deal
Sat, Nov 22 - Fri, Dec 5
United Airlines Logo
6:45 am - 8:00 pmVCE-ORD
20h 15m2 stops
United Airlines Logo
1:46 pm - 8:55 amORD-VCE
12h 09m1 stop
$620United Airlines
Find Deal
Thu, Nov 13 - Sat, Jan 24
United Airlines Logo
6:55 am - 3:20 pmVCE-ORD
15h 25m1 stop
United Airlines Logo
6:50 pm - 2:10 pmORD-VCE
12h 20m1 stop
$621United Airlines
Find Deal
Mon, Dec 15 - Wed, Jan 14
British Airways Logo
11:00 am - 3:44 pmFCO-ORD
35h 44m1 stop
British Airways Logo
9:45 pm - 4:55 pmORD-FCO
12h 10m1 stop
$639British Airways
Find Deal
Sun, Dec 14 - Sun, Jan 18
British Airways Logo
1:10 pm - 10:19 pmFCO-ORD
16h 09m1 stop
British Airways Logo
3:27 pm - 4:55 pmORD-FCO
18h 28m2 stops
$644British Airways
Find Deal
Booking Insights

KAYAK's insights & trends for flights to Chicago

Get data-powered insights and trends for flights to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights to Chicago, 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 to Chicago is January, where tickets cost $566 on average for one-way flights. On the other hand, the most expensive months are November and July, where the average cost of tickets from Italy is $1,012 and $779 respectively. For return trips, the best month to travel is February with an average price of $591.

What is a good deal for flights to Chicago?

If you’re looking for cheap airfare to Chicago, 25% of our users found tickets to Chicago for the following prices or less: From Rome Fiumicino Airport $560 one-way - $781 round-trip, from Naples $655 one-way - $757 round-trip, from Milan Malpensa Airport $706 one-way - $752 round-trip.

How far in advance should I book a flight to Chicago?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights to Chicago, 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, you should book around 0 weeks before departure. For the absolute cheapest price, our data suggests you should book 72 days before departure.

Which is the cheapest airport to fly into in Chicago?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Chicago is Chicago Greater Rockford Airport, with an average flight price of $153.

Good to know

Low seasonJanuary
Cheapest flight$295
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 3% increase in price.
Flight from Milan Malpensa Airport to Chicago O'Hare Airport

FAQs - booking Chicago flights

  • Which Chicago airport is closest to central Chicago?

    Chicago is served by 3 major airports. Chicago Midway Airport (9 miles) is the closest to the center of Chicago. Chicago O'Hare Airport is 16 miles from the center and Chicago Greater Rockford is 79 miles away from the center.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $835. The cheapest price found on KAYAK in the last 2 weeks cost $415 and departed from Rome Fiumicino Airport.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Wednesday where tickets can be as cheap as $772. On the other hand, the most expensive day to fly is Monday, where prices are $956 on average.

  • How does KAYAK find such low prices on flights to Chicago?

    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 to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to 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 to Chicago?

    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 Chicago 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 to Chicago?

    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 Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Chicago?

    The cheapest time of day to fly to Chicago is generally in the afternoon, when flights cost $748 on average. The most expensive time of day to fly to Chicago is generally in the morning, which is peak travel time and where the average cost of a ticket is $775.

Top tips for finding cheap flights to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $640 or less one-way and $825 or less round-trip.
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Reviews of the top 5 airlines serving from Italy to Chicago

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Italy to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with to Chicago? 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 8998 reviews
8.1Crew
7.3Comfort
6.6Food
7.1Entertainment
7.7Boarding
Airline reviews

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

10.0 ExcellentDr. Joseph, Oct 2025STL - ORD
Read more United Airlines reviews

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Excellent all round, first time flying United. App is very helpful.

Efficient all round, very good crew. Short flight so the food, of course, was just snacks

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Flight, food and crew were all good, friendly and very satisfactory.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Premium economy seat was decent. As always poor headphones, poor food and beverage, crew is not overly friendly

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

The flight was on time and crew were nice, seats were tight and there was entertainment available

The seat space seemed small especially when the person ahead reclined but other than that, very good.

Luggage transfer in Chicago was not performed in time. I received my luggage at my destination two days later.

Food was poor quality and the screens for entertainment didn’t work properly

It was a short flight, everything was good with it.

I darted through the Frankfurt airport to make my connecting flight. I asked if it was a possibility to upgrade and the agent did. This was the kindest gesture and it made up for the previous delayed flight and distress/anxiety of anticipating that Zi was going to miss my Frankfurt-Chicago connection. I cannot express my gratitude for the upgrade.. I am 5feet 10 inches do the leg space was amazing.

I meant this flight was not good, the one from Tirana to Frankfurt was better!

I was very grateful for Lufthansa's role in organizing mobility support. The touchscreen on my seat was faulty: slow, stained (I couldn't get it clean), and glitchy. This made selecting movies extremely time consuming, and twice I had to start all over from the beginning.

The crew was the best I’ve ever encountered. Business class was spacious, immaculate, and very modern.

I wish seats were not reclinable. It's so claustrophobic when the person in front of you spends most of a nine hour flight leaned all the way back. The crew was really nice though and the dinner (red Thai curry) was pretty compelling.

Our flights were severely delayed, then canceled and we had to fly out next day with no sleep accommodation help. This led to our baggage being lost and the service reps after baggage couldn’t be bothered to help. They kept sending us to different counters when we were at the right counter to begin with. The only saving grace was the angel woman supervisor with blond hair who helped us put in a missing baggage claim.

Wonderful! Everyone very helpful and kind. Returning flight was cancelled but rebooking was easy.

The seats are very tight and uncomfortable. The recline position did not work.

Flight was on time, there were no issues. It was also direct to SFO. For an international flight, I call that a win.

Flight was on time and pretty standard. No Hiccups. I have no complaints, which is a lot to say about a 12 hour flight.

On both sides of my itinerary, the planes were old, the seats did not work, the seats were filthy, and the crew were unfriendly

A lady with a smelly dog sat next to me

It was bad experience . I was about to lose my flight . The airline announced the gate very late , an hour before the flight , and you need to rush to find the gate in a big airport . The flight is a long flight and the food is poor . I difintelely not taking this airplane again

It was Ok for Business class considering we paid almost $10K for two seats. Disappointing part was the $640 (RT) to reserve the seats prior to departure unlike other airlines that is complementary when buying business class seats. Would I use ITA to go to Europe on my next trip -NO.

Top notch re cleanliness, comfort, operational. Attendants attentive, cheerful, courteous and professional. An unusually high-grade experience all around.

The staff was very good, the only thing was the air conditioning wasn't working during the boarding process so it was very hot inside the plane until we got airborne. The food wasn't great, the chicken was dry and hard to cut, the ravioli was ok and the little pizza pocket thing was pretty bad. Other than that is was a good flight all around

Not my definition of first class. No leg room and barely any recline. The food was good. The crew was great. The comfort for the price I paid for London to Cairo was highway robbery. The Wi-Fi didn't work for me either.

There might be more food options for people who can't eat so much starch/sugar/bread/rice. Meat, cheese, walnuts/pecans for snack, maybe jerky or other kinds of meat-based snacks would be better than bread and rice and sweets. I had an extra chardonnay, which was fine. The entertainment was great.

Unfortunately, my flight was cancelled because of some sort of emergency over the Atlantic and had to return to London. While I think British Airways made every effort to mitigate the situation, I must say it was still pretty unpleasant. I do appreciate the fact, however, that British Airways put my safety first…and I think the effort to correct a bad situation was very sincere. But I think the process might be handled better in future.

Crew service was poor and very little difference between premium economy and economy. Disappointed.

My bags never made it on the flight and I now have to wait for them to arrive hopefully tomorrow. You can’t even track your bags in the app to see where they are since they didn’t arrive. You have to file a claim and then wait for them to inform you when you will receive your bag. We were already delayed for an hour due to baggage so I don’t understand how my bag didn’t make the flight.

One of the worst experience given the middle seat even asked for the change no one honored,boarded at the end and overall one of the worst experience

It was good although our flight to the UK was cancelled and rescheduled for two days later. This was after we were already seated on the plane. We missed the first leg of our trip. BA did put us up at a hotel and paid for our meals but we lost our hotel costs in Glasgow.

The crew was very nice and pleasant. We were very reluctant to book our flight with British Airlines because we had bad experience with their flight attendants on the previous trips, they were rude and not helpful.

I am a 25+ years American Airlines member. British Airways is simply above and beyond in every customer satisfaction category.

The seat pads are past there sell by date now and are uncomfotable. Also, with screens in the back of the seat, the seats shouldnt be able to recline as this puts rhe screen in your face.

Traveling to a place near Chicago?

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Everything you need to know for your flight to Chicago

Cabin class types available on flights to Chicago

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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