$372 Find Cheap Flights from Italy to Chicago - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 21% 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

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

Recent round-trip flight deals from Italy to Chicago

Thu, Oct 22 - Wed, Oct 28
Multiple Airlines Logo
8:15 am - 6:15 pmBGY  Bergamo Orio Al Serio-ORD Chicago O'Hare Intl
17h 00m2 stops Gdansk Rebiechowo Reykjavik Keflavik Intl
Multiple Airlines Logo
7:30 pm - 5:00 pmORD  Chicago O'Hare Intl-BGY Bergamo Orio Al Serio
15h 30m2 stops Reykjavik Keflavik Intl Gdansk Rebiechowo
$491Multiple Airlines
Thu, Oct 15 - Wed, Oct 28
Icelandair Logo
3:45 pm - 6:15 pmFCO  Rome Fiumicino-ORD Chicago O'Hare Intl
33h 30m1 stop Reykjavik Keflavik Intl
Icelandair Logo
7:30 pm - 2:00 pmORD  Chicago O'Hare Intl-FCO Rome Fiumicino
12h 30m1 stop Reykjavik Keflavik Intl
$498Icelandair
Sat, Jan 30 - Sat, Feb 13
Icelandair Logo
11:25 am - 5:20 pmFCO  Rome Fiumicino-ORD Chicago O'Hare Intl
12h 55m1 stop Reykjavik Keflavik Intl
Icelandair Logo
6:30 pm - 2:00 pmORD  Chicago O'Hare Intl-FCO Rome Fiumicino
12h 30m1 stop Reykjavik Keflavik Intl
$534Icelandair
Tue, Oct 27 - Thu, Oct 29
United Airlines Logo
3:00 pm - 1:40 pmVCE  Venice Marco Polo-ORD Chicago O'Hare Intl
28h 40m1 stop Zurich
United Airlines Logo
10:05 am - 9:20 amORD  Chicago O'Hare Intl-VCE Venice Marco Polo
17h 15m2 stops New York LaGuardia Montreal Pierre Elliott Trudeau Intl
$552United Airlines
Mon, Dec 14 - Mon, Dec 14
United Airlines Logo
7:05 am - 6:41 pmFCO  Rome Fiumicino-ORD Chicago O'Hare Intl
18h 36m2 stops Frankfurt am Main Newark
United Airlines Logo
9:21 pm - 10:55 amORD  Chicago O'Hare Intl-FCO Rome Fiumicino
30h 34m1 stop Toronto Pearson Intl
$558United Airlines
Thu, Oct 15 - Fri, Oct 23
ITA Airways Logo
7:10 pm - 1:10 pmVCE  Venice Marco Polo-ORD Chicago O'Hare Intl
25h 00m1 stop Rome Fiumicino
ITA Airways Logo
3:00 pm - 10:30 amORD  Chicago O'Hare Intl-VCE Venice Marco Polo
12h 30m1 stop Rome Fiumicino
$564ITA Airways
Tue, Sep 22 - Sun, Oct 4
ITA Airways Logo
9:20 am - 1:10 pmFCO  Rome Fiumicino-ORD Chicago O'Hare Intl
10h 50mnonstop
ITA Airways Logo
3:00 pm - 7:25 amORD  Chicago O'Hare Intl-FCO Rome Fiumicino
9h 25mnonstop
$570ITA Airways
Tue, Sep 22 - Sun, Oct 4
American Airlines Logo
10:00 am - 9:12 pmFCO  Rome Fiumicino-ORD Chicago O'Hare Intl
18h 12m1 stop New York John F Kennedy Intl
American Airlines Logo
11:50 am - 11:20 amORD  Chicago O'Hare Intl-FCO Rome Fiumicino
16h 30m1 stop Charlotte Douglas
$592American Airlines
Wed, Oct 7 - Sun, Oct 18
American Airlines Logo
10:00 am - 1:40 pmFCO  Rome Fiumicino-ORD Chicago O'Hare Intl
10h 40mnonstop
American Airlines Logo
10:30 pm - 7:20 pmORD  Chicago O'Hare Intl-FCO Rome Fiumicino
13h 50m1 stop London Heathrow
$658American Airlines
Fri, Oct 2 - Sat, Oct 10
Lufthansa Logo
6:20 am - 11:00 amMXP  Milan Malpensa-ORD Chicago O'Hare Intl
11h 40m1 stop Frankfurt am Main
Lufthansa Logo
9:40 pm - 4:40 pmORD  Chicago O'Hare Intl-MXP Milan Malpensa
12h 00m1 stop Munich Franz Josef Strauss
$705Lufthansa
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 $738. On the other hand, the most expensive day to fly is Wednesday, where round-trip prices are $935 on average.

What is the cheapest month to fly to Chicago?

The cheapest month for flights to Chicago is September, where tickets cost $694 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 $918 and $904 respectively. For one-way flights, the best month to travel is March with an average price of $587.

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 $816 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 $816.

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 Milan Malpensa Airport $640 round-trip, from Rome Fiumicino Airport $683 round-trip, from Naples $843 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 27% 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 $123.

Good to know

Low season

April

Cheapest flight

$372
Best time to beat the crowds but there is an average 11% increase 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 $850. The cheapest price found on KAYAK in the last 2 weeks cost $546 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 $692 or less one-way and $722 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 4475 reviews
7.5Entertainment
7.5Food
7.3Comfort
7.3Boarding
7.8Crew
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.

Crew was great. Seats are cramped and uncomfortable and I’m a small person.

Awful. Delay after delay. And then again on the tarmac.

Kept changing the takeoff time and the moved it up so arrived when boarding had already started. Then sat waiting to taxi in for a long time

Food was not Good Nuts came very wet & not tasting Good Main course I asked for Steak they got me Chicken because they don’t have more !!!!

It cancelled and we were unable to catch our connecting international flights.

Leaving at 7 when scheduled to leave at 4:20 - you tell me. Understood there was a ground stop. Then having to "reboot" the plane because of a lighting strike, also understood. But basically the flight was a "clusterf#$%".

On boarding crew at the airport called in the boarding numbers too early meaning before the previous line was completed resulting in later numbers getting to board ahead. Also she asked those who boarded from number 3 to have the tags in their carry-on bags and leave it in the jet bridge. Most of the overhead bins were empty though. This is more work for the ground staff in addition to more inconvenience for passengers waiting to get their carry-ons from the jet bridge.

ok, butt flght was delyed for 2,5h from Frankfurt, and next Flight to Columbuse same

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).

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.

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

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.

What occurred during this flight was far beyond an ordinary inconvenience or dissatisfaction with the onboard service. There were multiple failures involving the aircraft’s passenger-seat systems, the ability to summon cabin crew, sanitation, cabin crew responsiveness, food and beverage service, and the overall standard of passenger care. The circumstances were particularly serious because I am diabetic, and during the flight I experienced a situation in which I needed assistance while essential passenger-control functions at our seats were not working. I am requesting that ITA Airways treat this as a formal complaint requiring individual investigation, rather than responding with a generic customer-service apology. 1. All three seats had significant equipment failures Seat 46F: The entertainment screen was completely non-functional for the entire flight. Seats 46G and 46H: The screens themselves displayed content, but the following controls did not function: Cabin-light control Flight-attendant call button Flight-tracker button These were not merely entertainment-system failures. The malfunctioning controls affected our ability to control the lighting at our seats and, more importantly, our ability to summon a flight attendant when assistance was required. I specifically request that ITA investigate the maintenance records for the aircraft and these specific seats and determine whether these defects were known before departure, reported during the flight, or documented by the cabin crew. 2. The defective equipment directly affected my ability to manage my diabetes I am diabetic and require insulin. Because the cabin-light controls at our seats were not functioning, I was unable to properly illuminate my seating area when I needed to administer my insulin during the flight. More seriously, when my blood sugar became low, I was unable to use the attendant-call button to request assistance because the button was not functioning. This transformed what might ordinarily be considered an entertainment-system problem into a much more serious passenger-care issue. I was on a long transatlantic flight, unable to properly illuminate my seating area when necessary and unable to summon a member of the cabin crew through the designated call system. 3. My daughter repeatedly attempted to obtain assistance when my blood sugar was low When my blood sugar became low, I needed juice or another rapidly available source of carbohydrate. Because I could not use the attendant-call button, I sent my daughter to ask the cabin crew for juice. She made multiple attempts to obtain assistance. Despite these repeated attempts, the cabin crew did not appropriately respond to her request. After multiple attempts from my daughter, the curtain was closed. I ultimately had to obtain candy from passengers seated nearby because I could not obtain the assistance I was seeking from the cabin crew. I consider this one of the most serious incidents on the flight. I am not suggesting that cabin crew were required to provide medical treatment. However, when a passenger is seeking assistance because of low blood sugar—particularly when that passenger’s designated call button is not functioning—I believe a reasonable standard of passenger care requires the request to be acknowledged and handled appropriately. I therefore request that ITA investigate this incident specifically, including: Which crew members were assigned to our cabin/section; Whether any crew member observed my daughter requesting assistance; Whether any crew report was made concerning this incident; Whether the crew knew that the attendant-call buttons at our seats were not functioning; and What ITA’s procedures require when a passenger reports that they are experiencing low blood sugar or otherwise needs assistance. 4. The circumstances caused significant distress and interfered with my ability to manage my condition.The combination of the defective lighting controls, inability to use the attendant-call system, and failure to obtain timely assistance caused me significant distress.I was particularly distressed because I was unable to properly manage my medical needs in the manner I normally would during a long flight. My blood sugar subsequently remained elevated for an extended period. I believe the prolonged stress and circumstances surrounding this incident contributed to the difficulty I experienced managing my blood sugar during the flight. I am documenting this because I do not want ITA to reduce this complaint to a complaint about an entertainment screen. The equipment failures directly affected my ability to manage my medical needs and obtain assistance. 5. Unacceptable restroom conditions. One restroom was completely out of service for the entire flight.The remaining restrooms were extremely dirty with visible urine stains and no toilet paper. 6. Unprofessional and dismissive cabin crew behavior. Throughout the flight, the attendants were unpleasant and appeared irritated

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

My son was served a muffin which had broken pieces of glass in it. Thank god he didnt swallow them and spit them out. i did let the crew member know and took pictures but nothing they could do. This could have been a very dangerous situation.

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

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
Hammond
Saint Joseph
Portage
Lansing
Valparaiso
Munster
Schererville
Chesterton
Porter
Monticello
Saint John
Griffith

More options for your flight to Chicago