$328 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 4/16. 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

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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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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, Apr 17 - Mon, Apr 27
Icelandair Logo
3:45 pm - 9:25 pm
FCO
-
ORD
12h 40m
1 stop
Icelandair Logo
7:25 pm - 2:35 pm
ORD
-
FCO
12h 10m
1 stop
$524Icelandair
Tue, Apr 21 - Tue, Apr 28
Icelandair Logo
3:45 pm - 6:15 pm
FCO
-
ORD
33h 30m
1 stop
Icelandair Logo
7:25 pm - 2:35 pm
ORD
-
FCO
12h 10m
1 stop
$527Icelandair
Thu, Apr 16 - Sat, May 2
TAP AIR PORTUGAL Logo
7:15 pm - 4:00 pm
VCE
-
ORD
27h 45m
1 stop
TAP AIR PORTUGAL Logo
6:05 pm - 6:15 pm
ORD
-
VCE
17h 10m
1 stop
$530TAP AIR PORTUGAL
Fri, Apr 17 - Tue, Apr 21
Iberia Logo
7:50 am - 2:25 pm
LIN
-
ORD
13h 35m
1 stop
Iberia Logo
4:55 pm - 1:40 pm
ORD
-
LIN
13h 45m
1 stop
$592Iberia
Mon, Apr 27 - Mon, May 4
ITA Airways Logo
7:00 pm - 6:44 pm
LIN
-
ORD
30h 44m
2 stops
ITA Airways Logo
3:00 pm - 7:10 pm
ORD
-
LIN
21h 10m
1 stop
$606ITA Airways
Mon, Apr 27 - Tue, May 5
ITA Airways Logo
9:00 pm - 6:44 pm
LIN
-
ORD
28h 44m
2 stops
ITA Airways Logo
11:00 am - 11:40 am
ORD
-
LIN
17h 40m
2 stops
$611ITA Airways
Fri, Apr 24 - Fri, May 1
British Airways Logo
12:15 pm - 7:00 pm
VCE
-
ORD
13h 45m
1 stop
British Airways Logo
9:15 pm - 10:15 pm
ORD
-
VCE
18h 00m
1 stop
$624British Airways
Wed, Apr 22 - Fri, May 1
British Airways Logo
7:25 am - 2:55 pm
LIN
-
ORD
14h 30m
1 stop
British Airways Logo
9:15 pm - 4:40 pm
ORD
-
LIN
12h 25m
1 stop
$630British Airways
Wed, Apr 1 - Wed, Apr 8
American Airlines Logo
1:40 pm - 9:18 pm
VCE
-
ORD
14h 38m
1 stop
American Airlines Logo
8:35 pm - 7:25 pm
ORD
-
VCE
15h 50m
1 stop
$637American Airlines
Tue, Apr 14 - Sat, May 2
American Airlines Logo
12:15 pm - 7:00 pm
VCE
-
ORD
13h 45m
1 stop
American Airlines Logo
10:30 pm - 10:35 am
ORD
-
VCE
29h 05m
1 stop
$639American 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 $1,013 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 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 May, where tickets cost $640 on average for return flights. On the other hand, the most expensive months are January and June, where the average cost of tickets from Italy is $810 and $799 respectively. For one-way flights, the best month to travel is May with an average price of $575.

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 $783 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 $783.

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 $681 round-trip, from Rome Fiumicino Airport $740 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 32% 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 $151.

Good to know

Low seasonJanuary
Cheapest flight$328
Most popular time to fly and prices are also 3% 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 $775. The cheapest price found on KAYAK in the last 2 weeks cost $422 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 $626 or less one-way and $768 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 9426 reviews
6.6Food
8.1Crew
7.7Boarding
7.3Comfort
7.1Entertainment
Airline reviews

They never clean the toilet, and the food is worse

4.0 OkayAnonymous, Mar 2026
HND - ORD
Read more United Airlines reviews

They never clean the toilet, and the food is worse

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Chargers didn’t work, no entertainment and we had to wait for taxiing for easily 40 minutes after arriving early. Bags were late too!

No real complaints. The in flight food was much better than I expected. The in flight entertainment was excellent.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

Horrible Flight significantly delayed. Not due to united issue. But trying to rebook connection flight and get information about overnight accommodation was difficult. Agent did not seem to care or have any interest to help.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

This Japanese airline provides great service and very helpful in assisting their passengers.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Extremely bad BAD BAD BAD. NEVER TURKISH AIRLINES EVER AGAIN..PIRATES COMPANY.

Typically great service from Turkish with comfortable seat and amenitie, good food and great attention from staff.

Delicious food, comfortable and clean plane. It's a little cramped in the hall in front of the gate.

Very hot cabin made long flight uncomfortable, even in business class! Food was great. Istanbul business lounge had great food but too few bathrooms and seating . They also need more electric outlets for charging devices. Appreciate the ability to go through fast track lines w business class

The crew on this flight provided exceptional business class service to me.

The staff at the boarding or the rudest uninformative and no English whatsoever they’re very rude as if they are envious of you travelling I don’t understand how could someone would be this rude and this out of touch and cold

You charged me for luggage although the airline does not- you charged me for seat when customers can pick their own seat at checkout in I travel to Europe slot and I will not use kayak again

They oversold the tickets by one which was my ticket so I didn’t have a ticket till last second

Not good. I was supposed to be in Mint but got in economy class

Requested food options were always finished. Supplied food items were good but of course not the desired choices.

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.

I don’t understand how they charge as much as they do for such a poor experience

I wish the plane had pod seating for business class. I had a window seat (8K) and I had to climb over the person sitting on the aisle when I needed to get up. Also there is no partition between the seats for privacy when sleeping. The Asian airlines have much nicer business class seating. Their seats are wider for better comfort when sleeping.

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.

Flight attendant really had bad behavior.. yelled at people when she is trying to defend, to have favor w her people..!

Appreciated being met with a glass of sparkling wine - also the warm cleansing towel offered before the meal. The food was tasty!

First, ITA lost my bag and the baggage team showed no regard in trying to find it. Second, I had paid for priority boarding as part of a first class ticket and instead they disregarded boarding groups and we all boarded at the same time. Third, wasn't allowed to select my seat in advance even with a first class ticket. When I was assigned bulkhead, I was told I would need to pay to change my seat. Overall, very disappointing experience.

Inside plane needs to be updated, the lady sitting behind me was saying the frame from the window fell on her lap right before taking off and seats are very uncomfortable, cushioning is need of repair ASAP.

I did not leave to Italy yet. We had technical problems on flight from SF to Maimi and had to land in Denver and wait for another plane to take us to Miami, so I missed my plane to Italy. I am still waiting for the Agency to fix my flight till today the haven’t done anything and I am paying for my Hotel stay. Everyday they are promising to fix my flight, they are not doing so and they are not even looking for another solution

Overbooked. They left a lot of passengers on the ground

Need better food options. Need warm food both times Stevie was provided. Bathrooms are too small. For an international flights, seats are small and leg room isn’t enough. And for an international flight, serving spirits should be included, not just Italian beer and cheap wine. All the tv/film entertainment is quite old and not updated, but the size of the screen was good.

my flight from Rome to Boston was on a very old plane. My video and audio did not work.

Awful cold sandwich, pizza was bad and coffee was extremely cold I expected better quality in wines on the way to Rome I order red wine and could not drink it ! Bad quality of wine . Being an European airline’s wine are inexpensive so could have better selección of wines . So on the way back a settle for water with is a pity . The crew disappear and didn’t pick up the trays after meals or the garbage of the snacks . Iberia has better service and other airlines

The toilets are very small for a long trip like this. There is no space whatsoever. Totally unusable,

I paid for a very expensive Business Class seat to and from Cairo Egypt from Charleston SC. There was partnership from states to London using American Airlines. That leg was amazing. The British Airlines leg was a joke. They used the standard no leg room 3 by 3 seats. A tray was put on the middle seat. The trip was 5 hours, from London to Cairo, thus my BC purchase. There was no screen proving tv/movie options, only a small device plug. The fold down tray and the bag of peanuts were typical of normal short run flying. The one toilet was located in the galley. We all got to know each other well. This was my first and last trip with British Airlines. I now understand why they would NEVER give me a seat chart so that I could make a selection.prior to departure. It honestly would not have made a difference, there were less than 50% of occupied seats. Apparently everyone got the memo but me. I have never felt so cheated as with that trip, got to so another going back to London, yeah. I will be sending a letter to customer service and asking for a refund. I will be photos comparing the two BC legs. OH, one more thing. The FC ticket holders got bulkhead and exit row seats. I know they had to be thrilled

Late takeoff, but on time landing. Lost bags, 3 days to find them, still in transit to my location. Power outlets broken, Wi-Fi not working, so much for working on the long flight.

Late! Late and late! More than 1hr 30mn. This sucks when it is the last of a 4 flight journey. I missed my dinner! Which is not nice on Valentine’s Day!!! But better than the gate next to us, the poor Chinese people were rebooked to the next day flight. AA had to call security as it became very heated with the passengers! It was a mess at DFW that afternoon/evening. I wish they had some food for the people who travel as part of international journey. Indigo does it in India and it is fantastic.

Good. For a long flight. The comfort of the seat could be better. Also, the food was « normal » plane food. Not indian plane food unfortunately! Everything else was smooth and great.

The seats were comfortable. So many empty seats allowed for stretching out and sleeping. The onboard entertainment was pretty good. The cabin crew were so kind and kept the passengers well- hydrated, and well fed.

We had American Airlines on our return and it was confusing if we were going with Aa or BA I had 2 different flight numbers and didn’t get our gate until it was boarding. So we were a bit nervous as the which it was

Our Jackson, Mississippi to Dallas Fort Worth flight was delayed on 1/19/26.. This was changed to Jackson to Charlotte in the last minute because of this delay. This started some kind of disconnect between American Airlines and British Airways bookings. We could not go past the passport control in London Heathrow. I had to go to the counter and waited for more than 30 minutes to get a new boarding pass. Problems did not end there. Somehow our entire return flight was canceled by someone. I had to make several phone calls over several days to fix the problem – this was not easy from India. Looks like there was some kind of disconnect between two airlines or some agent did not do it right. I’m anxious to know what went wrong.

My touch screen at my seat wasn't working, the films BA advertised on the website for this flight were not available, and the plane was a little dated, food was good and the staff were good, just let down by the aircraft facilities.

Did not like the seating configuration at all with 2+3+2 in business class. Lacking total privacy and comfort

The flight crew was kind, flexible, and accommodating. The seats on the plane were extremely uncomfortable.

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.