$293 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 11/18. 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

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

Wed, Sep 17 - Mon, Sep 29
TAP AIR PORTUGAL Logo
11:50 am - 10:55 amMXP-ORD
30h 05m1 stop
TAP AIR PORTUGAL Logo
6:10 pm - 7:15 pmORD-MXP
18h 05m1 stop
$443TAP AIR PORTUGAL
Find Deal
Wed, Sep 17 - Sun, Sep 21
TAP AIR PORTUGAL Logo
8:15 pm - 10:55 amMXP-ORD
21h 40m1 stop
TAP AIR PORTUGAL Logo
6:00 pm - 12:45 amORD-MXP
23h 45m1 stop
$448TAP AIR PORTUGAL
Find Deal
Thu, Sep 18 - Wed, Oct 15
United Airlines Logo
6:40 am - 2:55 pmNAP-ORD
15h 15m1 stop
United Airlines Logo
10:40 am - 7:00 amORD-NAP
13h 20m1 stop
$509United Airlines
Find Deal
Fri, Sep 12 - Fri, Sep 19
United Airlines Logo
6:40 am - 2:55 pmNAP-ORD
15h 15m1 stop
United Airlines Logo
8:15 pm - 7:00 amORD-NAP
27h 45m1 stop
$527United Airlines
Find Deal
Wed, Aug 20 - Sun, Aug 31
British Airways Logo
12:00 pm - 8:11 pmNAP-ORD
15h 11m1 stop
British Airways Logo
9:15 pm - 7:25 pmORD-NAP
15h 10m1 stop
$536British Airways
Find Deal
Wed, Aug 20 - Sun, Aug 31
British Airways Logo
12:00 pm - 3:45 pmNAP-ORD
34h 45m1 stop
British Airways Logo
8:35 pm - 10:00 pmORD-NAP
18h 25m1 stop
$538British Airways
Find Deal
Wed, Sep 17 - Sun, Sep 21
ITA Airways Logo
7:00 am - 1:10 pmLIN-ORD
13h 10m1 stop
ITA Airways Logo
3:00 pm - 11:10 amORD-LIN
13h 10m1 stop
$566ITA Airways
Find Deal
Fri, Sep 12 - Fri, Sep 19
ITA Airways Logo
6:15 am - 1:10 pmVCE-ORD
13h 55m1 stop
ITA Airways Logo
3:00 pm - 10:30 amORD-VCE
12h 30m1 stop
$571ITA Airways
Find Deal
Thu, Sep 11 - Sat, Sep 27
Lufthansa Logo
9:10 am - 2:55 pmMXP-ORD
12h 45m1 stop
Lufthansa Logo
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
$576Lufthansa
Find Deal
Fri, Aug 22 - Sun, Sep 21
Lufthansa Logo
8:00 am - 2:00 pmFCO-ORD
13h 00m1 stop
Lufthansa Logo
3:45 pm - 7:55 amORD-FCO
9h 10mnonstop
$579Lufthansa
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 February, where tickets cost $597 on average for return flights. On the other hand, the most expensive months are August and June, where the average cost of tickets from Italy is $807 and $780 respectively. For one-way flights, the best month to travel is January with an average price of $566.

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 $644 round-trip, from Naples $718 round-trip, from Milan Malpensa Airport $748 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 4 weeks before departure, which saves you about 28% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 11 weeks 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 (RFD), with an average flight price of $108.


Good to know

Low seasonJanuary
Cheapest flight$293
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 8% increase in price.
Flight from Rome Fiumicino 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 $861. The cheapest price found on KAYAK in the last 2 weeks cost $606 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 Thursday where round-trip tickets can be as cheap as $807. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $882 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 round-trip 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 $795.

  • How many direct flights to Chicago are there each week?

    Each week there are around 11,085 direct flights from within Italy to Chicago. The most common day for departures is Sunday, with 15% of flights taking off on this day.

Top tips for finding cheap flights to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $753 or less one-way and $780 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 8896 reviews
7.3Comfort
8.1Crew
7.7Boarding
6.6Food
7.1Entertainment
Airline reviews

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

4.0 OkayGary, Jul 2025PIA - ORD
Read more United Airlines reviews

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

All flight attendants could benefit by taking an international flight on Qantas Airline. Qantas attendants are much more hospitable in every way. Much superior than and attendants on any US airline.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

So far so good but food and entertainment are not available for this flight

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

We booked a flight from FCO(Rome) with a stop over at DUB(Dublin) going to JFK. Boarding from Rome was kind of chaotic since the airport I guess is very small and we needed to shuttle to the airplane. The gate agent just let everyone and anyone go without using the sections so that took a lot longer than usual boarding. From drinking to JFk boarding was good and organized. Amazingly the flights was very smooth sailing and we’ve flown American big airplane to small companies before. The aircraft’s itself is on the older side, can’t complain tho because the plane ride wa smooth. For a 3 hour plane ride, nothing was complimentary. But for the longer leg of the plane complimentary snacks, meals and drinks were provided which was great. The food wasn’t bad either. I would fly with them again, great price and good service.

I wish Aer Lingus offered free wifi and had power outlets at the seats. Overall, the flight was good. Seat back entertainment had some interesting options. Food and snack options were mediocre at best. I enjoyed the canned red wine.

This was the most expensive economy flight per minute of flight time ever. But the quality was lacking. Extremely Aer Lingus rude staff at LHR said that the flight from London to Dublin (Ireland) was “NOT international.” Horrified at the colonial and imperial perspective. Seats were dirty with trash in seat pockets. Airline doesn’t clean or care about hygiene and safety.

When I booked the flight, I wasn't aware that this was a "no frills" flight. No wifi, no reclining seat, no complimentary soft drinks.

In business class overhead bins were minuscule. Had to use cabin staff to find a place for my carry-on bag. Boarding process was shambolic, as “passengers who needed assistance in boarding” absorbed an excessive amount of time and attention that Aer Lingus was apparently unprepared for.

Aer Lingus was fabulous.nhowever, Aiirfare Assist who Kayak routes me to to purchase tickets for m was awful. They messed up my reservation so bad that after about six hours on the phone with them over the week before departure, I had been choice but to show up at the airport. The Aer Lingus staff were amazing and got it sorted out but I would recommend not using Airfare Assist.

Dublin to Boston was decent. Food and entertainment was included and that was expected for the rate paid.

The Nice airport was a horrible boarding experience. I have never experienced the kind of compressed mob (in the B12-B17 gate area) of people all unclear what was happening and no airport staff to assist. There was no signage and 1000’s of people waiting for any info for 2 hours.

Flight was on time. Boarding was quick and efficient. Seats were comfortable. Food was fine.

I like Aer Lingus so that is why I’m writing this critique so they can become better. The boarding gate was too small to board properly. Our seats were toward the back of the plane knowing we would be boarding after business class, we moved to that area after business class boarded. An Aer Lingus employee told us we couldn’t stand there. We explained we were the next group to board and wouldn’t even be able to hear when our boarding was called. She didn’t care and was not very professional. The cabin was freezing. I wouldn’t feed my dog the food. We were over an hour late coming into chicago because of weather which can’t be avoided. I asked the crew if they could make an annoucement for before whose final destination is chicago to wait and allow the people with connecting to deplane first. He said there are a lot of people with connecting flights. He said, it doesn’t matter. Well, yes it does. He could have been more considerate of his passengers.

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.

The boarding system was all bogus - employees at the boarding gate were not sound like proffesional or may be possibly rational

I got an email in the morning of the flight 1/7, from Kayak, that I was rebooked from UA 906 to LH 430. Nobody at Lufthansa ot United knew about this. I went to both counters. at the airport. Also, Cheap Flights, who I booked the ticket through, did not know. I ended up staying on the United flight. But this was very disturbing, since I got a very late notice that I was rebooked to an earlier flight, I hurried to the airport to find out after a lot of inquiring that this was a mistake. Not a good Kayak experience.

After living in Europe for five years and flying with Lufthansa and KLM airlines, I’ve realized that United Airlines is now a budget carrier. The flight attendant are not friendly. The seats are not comfortable. And everything comes at a cost. I will be flying with KLM and Skyteam like Delta to the US going forward no doubt. United Airlines is not what it once was:

Delayed take off but I think they waited for passengers.

The crew were great and constantly cleaning bathrooms and taking care of passengers. Flight was on time and arrived on time. Boarding was easy and hassle free. Food could have been better but decent selection. Overall recommend and will fly again.

Everything was good except the bathrooms were usually dirty and the trash bins in the bathrooms were full.

Better consideration for families traveling with a disabled person. They insisted each person hold their own boarding pass on their own devices and gave us a hard time accepting eight boarding passes on a single device.

At least it was a direct flight, however the boarding process was a nightmare. 2+ hours in line to check my bag. Then told it was overbooked and I have to go standby even though I bought my ticket months ago. Then sent to another line to get on standby - another long wait and finally started yelling that my flight was boarding. They sent me somewhere else. In the end I did make the flight - among the last group to board, even though I arrived 4 hours early at the airport. Worst check in process I've ever experienced in 50 years off flying.

Great crew, newer plane, boarding was very disorganized, I still don’t understand why airline keep boarding front to back for coach instead of back to front

Paid for a seat I didn’t get. Flight attendant said they would “report “ the problem. Food terrible. No service unless requested. Plane filthy. Seats falling apart. Broken footrest. Bathroom toilet held in place with tape. No gate announcements though delayed 2 hours. Is that enough?

I don't like anything in this flight the food was bad the service was bad the flight was old and not connected to the screen no intertainments at all and it was long trip was bad intertainments the crew not helping

The flight was great. I don’t know about the food because I was asleep and they didn’t leave me any.

The flight was great, smooth and even a little ahead of time.

There wasn't a time for neither food morning entertainment in a short one hour hop over.

Excellent everywhere but Philly, the most rotten airport in the world.

Check in was not the greatest as had to talk to an agent to clarify things and then he transferred us to another agent who had difficulty processing my credit card as there was a system glitch and not a card error.

I was put into business class. Wow! My flight attendant was great! The food amazing’

The gate at London Gatwick had confusing signs for the different zones and the staff seemed harried because people didn't know when it was their turn to come to the desk. Plus, with there were too many carry-on bag travelers, myself included. The charge scheme for checking bags is frustrating. If you travel light, you want the freedom to leave as soon as you deplane. When you are forced to gate-check your bag simply because the flight is fully booked, you lose whatever time you'd hoped to save because you're still stuck waiting for your bag to come off the conveyor belt.

Safe arrival. Improvement on Time efficiency Effective Communication will be great.

Not so good with their baggage handling as they damaged one of my check in luggage

A good flight back to Tampa and thankfully although we had a 90 minute delay because of thunder storms from Charlotte to bottom iof Florida, it was a prudent to avoid these for a comfortable flight as opposed to being tossed around with turbulence.

All went well on the flight, not happy of course with having to pay for a seat and in hold luggage of £50

They removed our booking without telling us. Cost us thousands to book last minute

The decided to just remove our booking without telling us. It ended up costing us thousands

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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