$357 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 9/30. 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
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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, Oct 9 - Mon, Oct 12
Icelandair Logo
4:10 pm - 9:25 pm
VCE
-
ORD
12h 15m
1 stop
Icelandair Logo
7:25 pm - 3:00 pm
ORD
-
VCE
12h 35m
1 stop
$520Icelandair
Fri, Sep 4 - Wed, Sep 30
Icelandair Logo
4:10 pm - 9:25 pm
VCE
-
ORD
12h 15m
1 stop
Icelandair Logo
10:25 pm - 3:00 pm
ORD
-
VCE
33h 35m
1 stop
$524Icelandair
Wed, Jun 10 - Sun, Jun 28
ITA Airways Logo
7:10 pm - 1:10 pm
VCE
-
ORD
25h 00m
1 stop
ITA Airways Logo
3:00 pm - 10:30 am
ORD
-
VCE
12h 30m
1 stop
$548ITA Airways
Mon, Jun 1 - Mon, Jun 29
ITA Airways Logo
7:00 am - 1:10 pm
LIN
-
ORD
13h 10m
1 stop
ITA Airways Logo
3:00 pm - 10:10 am
ORD
-
LIN
12h 10m
1 stop
$554ITA Airways
Mon, May 18 - Mon, May 25
Finnair Logo
3:00 pm - 6:55 pm
NAP
-
ORD
10h 55mnonstop
Finnair Logo
5:30 pm - 10:00 am
ORD
-
NAP
9h 30mnonstop
$580Finnair
Mon, May 18 - Mon, May 25
Finnair Logo
3:00 pm - 6:55 pm
NAP
-
ORD
10h 55mnonstop
Finnair Logo
5:30 pm - 10:00 am
ORD
-
NAP
9h 30mnonstop
$581Finnair
Mon, May 18 - Sun, May 24
British Airways Logo
3:00 pm - 6:55 pm
NAP
-
ORD
10h 55mnonstop
British Airways Logo
7:04 pm - 10:00 pm
ORD
-
NAP
19h 56m
2 stops
$611British Airways
Tue, Sep 8 - Wed, Sep 16
British Airways Logo
3:00 pm - 6:50 pm
NAP
-
ORD
10h 50mnonstop
British Airways Logo
7:05 pm - 10:00 pm
ORD
-
NAP
19h 55m
1 stop
$612British Airways
Sat, May 16 - Mon, May 25
American Airlines Logo
7:35 am - 2:25 pm
FCO
-
ORD
13h 50m
1 stop
American Airlines Logo
8:50 pm - 8:05 pm
ORD
-
FCO
16h 15m
1 stop
$642American Airlines
Thu, May 21 - Fri, May 29
American Airlines Logo
7:35 am - 2:25 pm
FCO
-
ORD
13h 50m
1 stop
American Airlines Logo
8:50 pm - 7:20 pm
ORD
-
FCO
15h 30m
1 stop
$643American 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 flight to Chicago?

These are the best round-trip prices found by users searching on KAYAK in the last 72 hours.

In the last 3 days, the cheapest flight deal to Chicago was found on the route from Venice, at $520 return. The most popular connection is from New York to Chicago and KAYAK users have found round-trip deals for as low as $143 in the last 3 days.

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 $755. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $923 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 September, where tickets cost $639 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 $798 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 $800 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 $800.

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 $655 round-trip, from Rome Fiumicino Airport $665 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 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 $152.

Good to know

Low seasonJanuary
Cheapest flight$357
Most popular time to fly and prices are also 3% lower on average.
Flight from Venice to Chicago O'Hare Airport

FAQs - booking Chicago flights

  • What is the cheapest flight to Chicago?

    In the last 3 days, the cheapest flight deal to Chicago was found on the route from Venice, at $520 return. The most popular connection is from New York to Chicago and KAYAK users have found round-trip deals for as low as $143 in the last 3 days.

  • 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 $802. The cheapest price found on KAYAK in the last 2 weeks cost $522 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 $749 or less one-way and $660 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
Turkish AirlinesOverall score based on 4346 reviews
7.8Crew
7.5Food
7.3Comfort
7.5Entertainment
7.3Boarding
Airline reviews

Excellent service. Friendly and attentive flight attendants, can lay back in business class and be pretty comfortable, and delicious food. Flight on time departing and arriving.

10.0 ExcellentMichelle, Apr 2026
IST - BOS
Read more Turkish Airlines reviews

Excellent service. Friendly and attentive flight attendants, can lay back in business class and be pretty comfortable, and delicious food. Flight on time departing and arriving.

I will say the same as my previous comment. Great job over all! From 1-10, ten be the best… I will give 9!

had to wait 1 hour once boarded. so we were 1 hour late arriving.

They are absolutely impossible to get hold of. A death in the family caused us to delay our departure. They are impossible to get through to and after waiting 41/2 hours I was told they would not consider helping us. They cancelled our return flight and have not reimbursed anything. I strongly urge readers to consider a different airline.

A lot of snacks and provided on request by traveller. Preferred meals which were on their menu were not always sufficient for those who wanted them. We were told 2 different items and offer which we asked for were not offered initially. We rejected the 3rd item given as a substitute for our initial choices which we didn't want and so we didn't accept it. Eventually our initial choice was offered. During service of coffee and tea, the crew member didn't offer us and moved back. Luckily neither of us wanted tea at that time. Crew members must avoid behavior that may be suggestive of discrimination

The crew was awesome. My husband fell while traveling to the WC and got a head abrasion. The crew helped him greatly and a physician that was also on the flight checked him out as well. They all get an A+!

Online check in and seat assignments are terrible. All 4 flights

Cabin was kept very hot and it was uncomfortable. Entertainment system did not work at my seat. Crew and service is fantastic

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.

Flight crew was super friendly and helpful. Food was frequent and honestly pretty good. Plenty of on-board entertainment. Economy seats are super cramped for such a long flight, but the crew allowed people to get up and stretch, and kids could wander with their parents, so we all made it work. Overall a very good experience.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Starlink is great Crew was polite Business class didn’t get a welcome drink just water and snacks were ok

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

very average service no complimentary alcoholics drinks unlike other airlines such as Porter airlines No decent seats available during check-in time the day before

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

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.

ITA changed our 9 hr direct flight without giving any reason to 4 stop overs 24 hrs flight without delays.

Poor food choices for AVML. Totally out of the world food. Bad food menu.

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.

A shout-out to the flight attendent, Lauren, who was the main person assisting me. She was amazing - perfect balance of bright, cheerful, engaging, yet formal

1st class seats NOT REALLY 1st class or business class but like premier economy. Should be listed as such or named something else. I have flown 1st class with other airlines and they are nothing like it at all.

The flight from Dallas to madrid was delayed for 2 to 3 hours, the flight back from Dallas to Sacramento was fine , but there were 5 gate changes within the span of 2 hours, last one was in a differny terminal. Flight and crew was okay

I was downgraded from business class to economy class with no compensation. American Airlines is absolutely the worst airline for international travel. They treat their business class customers like dogs.

OK, except for a cabin attendant's lack of attention.

efficient. on time. cabin crew were very professional and very nice to deal with. would definately fly BA again.

It was great overall. A few slight improvements could be made on the onboarding process at the Gates with announcements and clarity of communications (both at the gate and in flight). The movies in the entertainment options could be improved for bollywood, hollywood.

I alrady responded to this request, and expllaned at length that this was the worst flying experience in my 77 years. I will NEVER fly BA again.

Airbus A350 is poorly designed for wheelchair users and reduced mobility passengers. The angle of the pods makes it awkward to transfer. I was able to but I have ab stability. It could be a real challenge for people with more severe mobility impairments. You'd think Airbus would have come up with a solution for this or thought more about us disabled folks more when designing this aircraft.

Check-in in SAN was long. ORD was good. Flight delayed On board crew was ok. No warmth or personality. LHrR barely made connection

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
Chesterton
Schererville
Munster
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.