$362 Find Cheap Flights from Italy to Chicago - Compare and Save

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 9/18. 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, 0 bags

Save 20% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

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

Fri, Sep 18 - Fri, Oct 2
Icelandair Logo
3:55 pm - 9:25 pm
VCE
-
ORD
12h 30m
1 stop
Icelandair Logo
10:25 pm - 2:45 pm
ORD
-
VCE
33h 20m
1 stop
$509Icelandair
Fri, Aug 28 - Fri, Sep 11
Icelandair Logo
3:55 pm - 9:25 pm
VCE
-
ORD
12h 30m
1 stop
Icelandair Logo
10:25 pm - 2:45 pm
ORD
-
VCE
33h 20m
1 stop
$517Icelandair
Tue, Sep 8 - Sun, Sep 20
ITA Airways Logo
6:35 am - 1:10 pm
NAP
-
ORD
13h 35m
1 stop
ITA Airways Logo
3:00 pm - 2:20 pm
ORD
-
NAP
16h 20m
1 stop
$594ITA Airways
Thu, Sep 10 - Wed, Sep 23
British Airways Logo
1:10 pm - 10:31 pm
FCO
-
ORD
16h 21m
1 stop
British Airways Logo
5:00 pm - 7:20 pm
ORD
-
FCO
19h 20m
1 stop
$668British Airways
Wed, Sep 16 - Sun, Sep 20
American Airlines Logo
7:35 am - 2:25 pm
FCO
-
ORD
13h 50m
1 stop
American Airlines Logo
4:55 pm - 9:10 am
ORD
-
FCO
9h 15mnonstop
$670American Airlines
Wed, Sep 2 - Thu, Oct 15
British Airways Logo
10:00 am - 1:30 pm
FCO
-
ORD
10h 30mnonstop
British Airways Logo
5:10 pm - 9:10 am
ORD
-
FCO
9h 00mnonstop
$671British Airways
Thu, Sep 3 - Thu, Sep 17
American Airlines Logo
10:00 am - 1:30 pm
FCO
-
ORD
10h 30mnonstop
American Airlines Logo
10:13 am - 9:50 am
ORD
-
FCO
16h 37m
1 stop
$671American Airlines
Sat, Sep 5 - Sat, Sep 12
ITA Airways Logo
9:20 am - 1:10 pm
FCO
-
ORD
10h 50mnonstop
ITA Airways Logo
3:00 pm - 7:25 am
ORD
-
FCO
9h 25mnonstop
$673ITA Airways
Tue, Sep 22 - Thu, Oct 8
United Airlines Logo
6:50 am - 12:55 pm
FCO
-
ORD
13h 05m
1 stop
United Airlines Logo
3:50 pm - 7:55 am
ORD
-
FCO
9h 05mnonstop
$803United Airlines
Sun, Aug 23 - Mon, Sep 21
United Airlines Logo
6:50 am - 2:55 pm
FCO
-
ORD
15h 05m
1 stop
United Airlines Logo
12:55 pm - 8:15 am
ORD
-
FCO
12h 20m
1 stop
$803United Airlines
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?

The average price of all round-trip flights to Chicago clicked on KAYAK for each day over the last 12 months.

Based on KAYAK data, the cheapest day to fly to Chicago is Saturday where round-trip tickets can be as cheap as $746. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $1,000 on average.

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 round-trip 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 September, where tickets cost $688 on average for return flights. On the other hand, the most expensive months are June and July, where the average cost of tickets from Italy is $909 and $904 respectively. For one-way flights, the best month to travel is March with an average price of $588.

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

The average price for all round-trip flights to Chicago depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Chicago is generally in the morning, when round-trip flights cost $825 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 $825.

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 $679 round-trip, from Naples $822 round-trip, from Milan Malpensa Airport $910 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 3 weeks before departure, which saves you about 24% 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 $176.

Good to know

Low season

April

Cheapest flight

$362
Best time to beat the crowds but there is an average 19% increase in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from Bergamo 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 $833. The cheapest price found on KAYAK in the last 2 weeks cost $400 and departed from Naples 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 $686 or less one-way and $804 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

 
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
Turkish AirlinesOverall score based on 4457 reviews
7.3Boarding
7.3Comfort
7.5Food
7.8Crew
7.5Entertainment
Airline reviews

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

4.0 OkayDebbie, Jul 2026
IST - ORD
Read more Turkish Airlines reviews

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.

Not worth pay business class and get service economy class

Gluten free snack options and meals that offer both gluten free and dairy free.

Not a bad flight but a long delay boarding and taking off due to the pilot not arriving on time.

I would have preferred a flight voucher and to hop on a different flight. Delayed over 6 hours.

I almost missed my connection in Chicago due to having to wait on a gate to be open I am assuming. Having to run from E terminal to C terminal and I barely made it there before they closed the door. This may not be the actual airline's fault it's crazy how there is so little time between flight especially when they are placed so far apart in the airport.

The Wi-Fi did not work, so you weren't able to watch entertainment on your own device. They did not have wired headphones so you couldn't watch it on the in-seat entertainment screen either. There was plenty of time to do a drink and snag service but the flight attendants chose not to.

Great experience, boarding was fast and efficient, so much so that we arrived to Chicago very early

The flight did not have its customary snacks during the flight. Apparently they were never loaded on the plane.

The seats on this flight weren’t as comfortable as we had expected. Even leaned back these seats left us feeling crappy in our backs. Also we had to use our own tablets for movies, but nothing in the seats in front of us to hold the tablets up.

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).

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.

Perfect airline, super friendly, great service, tasty food. Would fly again.

Everything could have been better. What needed to be wrong with United went wrong

It was good. The seats in economy weren’t bad

Very good. Comfortable and I felt well taken care of from start to finish

We were in premium economy seats that appeared to be locked in plae, No reclining. My aching back.

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.

Sitting at Logan on the taxiway for 90 mins waiting for a gate after an 8 hour flight is unacceptable. Logan and delta need to do better

The flight was long and offered very little comfort. The seats were exceptionally small and quite uncomfortable, making it difficult to rest on a long journey. The onboard meals were below expectations, although the cabin crew was excellent throughout the flight—professional, attentive, and courteous. I understand the commercial pressures airlines face, but maximizing capacity by reducing seat size and comfort has become an industry-wide concern. While many travelers will continue to tolerate these conditions out of necessity, an increasing number of passengers will choose alternative airlines whenever possible in search of a more comfortable travel experience. Investing in passenger comfort is not only appreciated—it is also an important factor in long-term customer loyalty.

Worst airline. Nine hours late. Checkin agent was not helpful at all.

One bathroom wasn’t working and the other bathroom faucet wasn’t working.

Horrible. I was on flight AZ620 from Rome to LA. I paid over $4k for my business class seat and had a horrible experience. The WiFi was not connected for the entire flight and instead of being transparent with the passengers, the staff passed out WiFi vouchers and failed to let us know that the Wifi did not and would not work for the entire flight. Much worse is the terrible treatment from the manager of the flight attendant staff. I got up from my business class seat to use the restroom meant for this section. The flight attendant manager (I didn't catch her name but later learned she was the manager from another employee) started yelling at me that I couldn't use the restroom. I thought maybe it was busy. Then another flight attendant came to my seat and said that her manager thinks I'm not in business class, but I should let her know I am so I can use the restroom. I stood up again and before I reached the restroom, the manager was already yelling at me again to use the restroom in the back! She was judging me based solely on my appearance and assumed I wasn't business class. I had to interrupt her constant yelling to tell her "I am business class." She was racist and rude. I travel constantly for work, but moving forward I am never going to spend my money on an ITA airway flight again. Thanks to this manager, you lost a customer.

I am vegan, and the food was not what I expected it to be One meal was good, but the rest of the things were not very satisfying… I was disappointed in the food The flight itself was very smooth and everybody was very very nice… The boarding was very good

Kayak was an utter disaster. They booked the tickets through a 3rd party and the 3rd party changed the dates of the flight without checking with us. They promised to change it back, but they never did, and I eventually had to dispute the credit card charge to get my money back and had to reserve through another website. NEVER use KAYAK again!

Crazy and confusing check in process for connecting international flights. Extremely uncomfortable seats in economy, bad in flight service with useless attendants, 10 year old movie selection, inedible food + only 1 full meal for 12+ hours long flight - 2nd snack was a cold bun with 1 slice of tomato and 1 slice of cucumber; 3rd was 2 breads - 1 hot and 1 cold. Finally absolute bad information on arrival time - in flight suggested we will reach at 12 AM until last minute, when we landed it was 1:15 PM

The crew was business like and not very friendly. It was very disappointing in that they handed out the meal at the beginning of our journey. Eight hours later, they handed a sandwich and a drink. During their eight hour break all they did was sit in the back, looked at their phone and read. They never came down the aisle during those eight hours and offered another beverage or to See if there was anything they could do for the passengers.

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.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Munster
Schererville
Chesterton
Porter
Monticello
Saint John
Griffith

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.