$352 Find Cheap Flights from Italy to Chicago - Compare and Save

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Cheap Flights from Italy to Chicago

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Italy to Chicago

Tue, Apr 20 - Sun, Apr 25
Scandinavian Airlines Logo
7:55 pm - 4:10 pmFLR  Florence Peretola-ORD Chicago O'Hare Intl
27h 15m1 stop Kastrup Copenhagen
Scandinavian Airlines Logo
7:15 pm - 11:30 amORD  Chicago O'Hare Intl-FLR Florence Peretola
33h 15m1 stop Kastrup Copenhagen
$587Scandinavian Airlines
Thu, Apr 15 - Mon, Apr 26
Scandinavian Airlines Logo
9:20 am - 4:10 pmMXP  Milan Malpensa-ORD Chicago O'Hare Intl
13h 50m1 stop Kastrup Copenhagen
Scandinavian Airlines Logo
7:15 pm - 8:30 amORD  Chicago O'Hare Intl-MXP Milan Malpensa
30h 15m1 stop Kastrup Copenhagen
$595Scandinavian Airlines
Sun, Nov 22 - Thu, Nov 26
Scandinavian Airlines Logo
11:20 am - 4:45 pmMXP  Milan Malpensa-ORD Chicago O'Hare Intl
12h 25m1 stop Kastrup Copenhagen
Scandinavian Airlines Logo
7:10 pm - 10:30 amORD  Chicago O'Hare Intl-MXP Milan Malpensa
32h 20m1 stop Kastrup Copenhagen
$597Scandinavian Airlines
Thu, Dec 3 - Mon, Dec 7
American Airlines Logo
6:00 am - 2:55 pmNAP  Naples-ORD Chicago O'Hare Intl
15h 55m1 stop Madrid Barajas
American Airlines Logo
5:40 pm - 2:20 pmORD  Chicago O'Hare Intl-NAP Naples
13h 40m1 stop Madrid Barajas
$647American Airlines
Sat, Nov 21 - Thu, Dec 3
American Airlines Logo
7:30 am - 2:55 pmFCO  Rome Fiumicino-ORD Chicago O'Hare Intl
14h 25m1 stop Madrid Barajas
American Airlines Logo
8:30 pm - 12:30 pmORD  Chicago O'Hare Intl-FCO Rome Fiumicino
33h 00m1 stop London Heathrow
$648American Airlines
Fri, Nov 20 - Thu, Dec 3
American Airlines Logo
7:30 am - 2:55 pmFCO  Rome Fiumicino-ORD Chicago O'Hare Intl
14h 25m1 stop Madrid Barajas
American Airlines Logo
8:30 pm - 12:30 pmORD  Chicago O'Hare Intl-FCO Rome Fiumicino
33h 00m1 stop London Heathrow
$648American Airlines
Sun, Feb 14 - Wed, Feb 24
United Airlines Logo
7:05 am - 3:20 pmFCO  Rome Fiumicino-ORD Chicago O'Hare Intl
15h 15m1 stop Frankfurt am Main
United Airlines Logo
3:40 pm - 7:45 amORD  Chicago O'Hare Intl-FCO Rome Fiumicino
9h 05mnonstop
$666United Airlines
Thu, Feb 18 - Mon, Mar 22
United Airlines Logo
7:05 am - 3:20 pmFCO  Rome Fiumicino-ORD Chicago O'Hare Intl
15h 15m1 stop Frankfurt am Main
United Airlines Logo
4:40 pm - 7:45 amORD  Chicago O'Hare Intl-FCO Rome Fiumicino
9h 05mnonstop
$669United Airlines
Fri, Feb 5 - Sun, Feb 28
Lufthansa Logo
6:15 pm - 2:10 pmBRI  Bari Palese-ORD Chicago O'Hare Intl
26h 55m1 stop Munich Franz Josef Strauss
Lufthansa Logo
3:15 pm - 5:15 pmORD  Chicago O'Hare Intl-BRI Bari Palese
19h 00m1 stop Frankfurt am Main
$673Lufthansa
Thu, Dec 10 - Sat, Dec 26
Lufthansa Logo
7:00 am - 1:10 pmVCE  Venice Marco Polo-ORD Chicago O'Hare Intl
13h 10m1 stop Frankfurt am Main
Lufthansa Logo
6:05 pm - 6:35 pmORD  Chicago O'Hare Intl-VCE Venice Marco Polo
17h 30m2 stops Amsterdam Schiphol Frankfurt am Main
$986Lufthansa
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 day to fly to Chicago?

Based on KAYAK data, the cheapest day to fly to Chicago is Saturday where round-trip tickets can be as cheap as $766. On the other hand, the most expensive day to fly is Wednesday, where round-trip prices are $953 on average.

What is the cheapest month to fly to Chicago?

The cheapest month for flights to Chicago is May, where tickets cost $740 on average for return flights. On the other hand, the most expensive months are July and June, where the average cost of tickets from Italy is $926 and $913 respectively. For one-way flights, the best month to travel is March with an average price of $584.

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

The cheapest time of day to fly to Chicago is generally in the morning, when round-trip flights cost $827 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 $827.

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 $812 round-trip, from Milan Malpensa Airport $842 round-trip, from Naples $1,061 round-trip.

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

To get a below average price, you should book around 3 weeks before departure, which saves you about 36% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 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 $126.

Good to know

Low season

November

Cheapest flight

$352
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 5% increase in price.
Flight from Milan Malpensa Airport to Chicago

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 $950. The cheapest price found on KAYAK in the last 2 weeks cost $540 and departed from Rome Fiumicino Airport.

  • 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.

Top tips for finding cheap flights to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $793 or less one-way and $905 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 4 airlines serving from Italy to Chicago

 
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
Turkish AirlinesOverall score based on 4460 reviews
7.8Crew
7.5Entertainment
7.5Food
7.3Comfort
7.3Boarding
Airline reviews

Bussing in a major flight is idiotic. Cabin was too warm. Food was bland and felt old

4.0 OkayHassan, Aug 2026
Read more Turkish Airlines reviews

Bussing in a major flight is idiotic. Cabin was too warm. Food was bland and felt old

Horrible service at the baggage claim. Stuck on plane for an hour due to taxing and no gate.

I really would like it if they provided at least some limited free wi-fi.

Excellent food and service on my international flight. Most notable is the food provided by Turkish even for coach passengers is very good.

Food is very turkish. No regard for other natinalities taste and preference. The entertainment can be improved- it was the same menu on 10/8/25 and 10/25/25. The boarding is the worst in the airline industry- I suggest you ask your staff to and watch how other airlines do it.

We couldn’t fly to Chicago on our booked flight. The flight was overbooked.

Took forever to board. They made announcements without the loudspeaker and since the waiting room was full of screaming kids, no one could hear what they were saying. The business class sleeper seats were designed for tall skinny people. When partially reclined there was nowhere to rest my feet because they did not reach the footrest. and when fully reclined there wasn't room at my sides for my arms. Definitely one of the worst sleeper seats I have ever had.

About an hour delay but we made it to Chicago. I feel that the smaller connecting flights are the ones that cause the delays on the bigger planes that fly international.

One of the best flights I have been on in a while.

Here's a sample answer: "Honestly, I was really impressed with Turkish Airlines, but if I had to suggest one area for improvement, it would be: - *More efficient boarding process*: I noticed that boarding took a bit longer than expected, which might be frustrating for passengers with tight connections.

Just sat on the run way after we arrived early

The Code Share with Air Canada was not very streamlined. I had to check in at airport (not online) on the outbound and return flights

Stored my cloth purse under seat in front off me as instructed. When I retrieved it, half of it was soaked, along with everything inside it. I don’t really know how that could have been prevented because the area did not look wet, but I was not happy about it.

Phx - ORD was nice 737 with starlink and the ORD - grr was ancient bare bones airbus with not even a power port lol

It was easy to board, and the staff was friendly and helpful. What could have been better is that I shouldn't have to pay extra for a seat that doesn't recline.

Was on the plane sitting longer than the actual flight in air was, boarded at 5:45p and didn't take off until 6:50p flight was only about 30 minutes long. Just was poor experience will booking more with American Airlines.

The couple in front of me were constantly talking over the announcement from the captain and this was annoying me.

Legroom in Economy was fair to good. Seat was omay; I was hit in the shoulder twice by the cart as it was being whisked through the aisle. Overhead space was good for my carryon. Lighting environment was nice

Bad, but r that was because Chicago to stl flight 14 hours late.

Check in, boarding processes were fine. Crew was great; pleasant and helpful. The food was absolutely terrible. One expects decent food, especially in Business class. The evening meal was edible. The before landing " meal" was inedible. Don't serve food that doesn't do well after hours of refrigeration ( frozen?), like a chicken burger (soggy bun, rubbery chicken)and fries (cold and hard).

We would fly ITA again. The planes had relatively comfortable seating. The crew was fine. The inflight entertainment was very good. The food was meh. But overall we got what we paid for.

I paid for extra Comfort Seats that turned out to be regular ones and have asked for a refund. The bathrooms were filthy the entertainment screen didn't work the Wi-Fi didn't work the food was mediocre at best and the seat I was in was terribly cramped especially when the person in front of me put their seat back. You couldn't even open the tray table. The staff was inattentive. I do not intend to take ITA ever again

Flight late but they were nice and food is pretty decent. The seats could use updating.

ITA does not allow free seat selection even in business class, if you don't want to pay extra for the seat they assign it to you during check in. For me it was seat #8 in both ways. It's last seat in business class with smaller space, close to kitchen, toilets and closets for supplies. WiFi didn't work at all. ITA is lower coaster, better to buy premium economy in regular company (AirFrance, Delta, Lufthansa, United, etc) than business in ITA Airways. ITA - never again

The flight attendants weren’t friendly. They gave us yucky food.

No complaints. Everything was fine. Very glad I was in premium economy

Overall flight was fine as was price. FCO leaves a lot to be desired. Not enough agents to check people in quickly, confusing security location and extremely, ridiculously long lines to get through multiple security checks. It was the least to say it was a hot sticky nightmare. Dulles is not better although arrival was fine, traffic to the arrival area was a nightmare where I finally gave up, parked the rental and met my wife with the luggage in the parking lot. I will avoid Dulles in the future.

Crew was very friendly and accommodating. Main enter was good but snack could be better. Perhaps adding fruit would be an excellent option.

The cleanliness of the Business class continues to disappoint. There was food on the floor when I boarded.

Flight bumpy and aircraft old with tape over seats , it seems there is a lack of maintenance, air pipe blow off in the middle of the flight, flight attendant seemed not to be worried about it. Food got very bad over time , not only for the quality but for the quantity . Seats are very uncomfortable , entertainment not working properly.

I'm a nervous, autistic adult. The staff were very friendly and answered my questions and came by at regular intervals to check everyone's comfort. They even resolved a fight between two couples in front of me!

roomiest flight in economy I've taken in years. Excellent experience!

I was booked to travel from Dallas to Nairobi via Chicago and Brussels and had been issued boarding passes for all three segments of my journey. At the boarding gate in Dallas, I was required to check my carry-on luggage due to limited cabin space. Despite my attempts to explain that I was traveling internationally and would not have access to the bag during transit, my concerns were not considered. I also informed the staff that I did not have a padlock to secure the luggage, but this was disregarded. Consequently, I had to hastily transfer essential items from my carry-on into my handbag. To my surprise, upon arriving at Chicago Airport, I observed numerous international travelers boarding with cabin bags that were significantly larger than mine. This experience left me extremely disappointed and led me to decide against using United Airlines for future international travel, a sentiment I have also shared with friends and family. Unfortunately, the onboard experience on the Chicago to Brussels flight further reinforced my dissatisfaction. The cabin crew appeared disengaged, indifferent, and lacking in attentiveness, resulting in a service experience that fell well below my expectations.

I want to highlight the crew members and their excellent work and professionalism. They work hard to make a long trip the most comfortable as possible, the food and drinks they offer are pretty good. And they are always asking if you need something else. I have had experiences with other airlines where you have to basically beg for a bottle of water. This is not the case. Highly recommended!!!

the blanket was great and pillow helped. really need a toothpick packed with meals

Very comfortable plane. The food was very good (for airplane food). The crew was great

The legroom was lacking and the entertainment system lacked adequate selection of older films. Modern films are generally not very good.

Courtesy of waitress. Could improve on time management and check-in

The flight leaving mxp was late I lost connection in ORD Changing flight was hectic and messy, overnight and meals vouchers very poor

seats in economy are just uncomfortable due to the amount of space this, or any airline provides. Until the government sets minimum standards for comfort this will continue.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
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