When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 21 days in advance, which can save you up to 14% on flights from Chicago to Italy compared to booking the week you need them. Waiting 21 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $742. For sooner than that we have options available in the next 3 days from $998.
The best pricing can be found in the month of February. Prices to Italy from Chicago average $873. You can even find prices in February for less than $873, as users have found deals to Italy from as low as $398. The month of June appears to be one of the more expensive times to travel to Italy from Chicago. Flying in the targeted month can save you up to 46%.
When flying from Chicago to Italy, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Fly from
Fly to
Budget
$461 - $560
Route
Depart
Return
Price
Chicago O'Hare IntlMilan Malpensa
ORD - MXP
ORDMXP
Chicago O'Hare Intl
Mon 4/8
1 stop16h 30m
Milan Malpensa
Wed 4/17
1 stop28h 50m
Chicago O'Hare IntlRome Fiumicino
ORD - FCO
ORDFCO
Chicago O'Hare Intl
Tue 5/7
2 stops30h 34m
Rome Fiumicino
Tue 5/14
1 stop22h 19m
Chicago O'Hare IntlRome Fiumicino
ORD - FCO
ORDFCO
Chicago O'Hare Intl
Mon 4/1
1 stop23h 10m
Rome Fiumicino
Tue 4/16
1 stop29h 35m
Chicago O'Hare IntlRome Fiumicino
ORD - FCO
ORDFCO
Chicago O'Hare Intl
Sat 4/13
1 stop12h 00m
Rome Fiumicino
Wed 4/17
1 stop33h 30m
Chicago O'Hare IntlMilan Linate
ORD - LIN
ORDLIN
Chicago O'Hare Intl
Tue 4/23
1 stop11h 55m
Milan Linate
Sat 5/4
1 stop14h 45m
Chicago O'Hare IntlRome Fiumicino
ORD - FCO
ORDFCO
Chicago O'Hare Intl
Tue 4/9
Nonstop9h 20m
Rome Fiumicino
Fri 4/19
Nonstop10h 50m
Chicago O'Hare IntlRome Fiumicino
ORD - FCO
ORDFCO
Chicago O'Hare Intl
Sun 3/31
1 stop13h 43m
Rome Fiumicino
Tue 4/16
1 stop14h 44m
Chicago O'Hare IntlRome Fiumicino
ORD - FCO
ORDFCO
Chicago O'Hare Intl
Sat 3/30
1 stop31h 20m
Rome Fiumicino
Wed 4/17
1 stop32h 36m
Chicago O'Hare IntlRome Fiumicino
ORD - FCO
ORDFCO
Chicago O'Hare Intl
Tue 4/9
1 stop15h 10m
Rome Fiumicino
Thu 4/18
1 stop25h 10m
Food
Boarding
Crew
Entertainment
Comfort
Overall
Reviews
I'm a long time SQ patron. For good reason. Had a similar trip last year and took another airline (at that time, price was the main factor). This time I took SQ as they had really good rates. No comparison. Dependable, reliable service and excellent aircraft. No issue with my special checked in item (a guitar that had to be handled differently) on my way to my destination (not this flight). In the previous mentioned other airline, they misplace my luggage upon arrival. After spending about an hour (with no effective help from that airline's agent), I managed to find it at another belt!
Food
Boarding
Crew
Entertainment
Comfort
Overall
Reviews
I'm a long time SQ patron. For good reason. Had a similar trip last year and took another airline (at that time, price was the main factor). This time I took SQ as they had really good rates. No comparison. Dependable, reliable service and excellent aircraft. No issue with my special checked in item (a guitar that had to be handled differently) on my way to my destination (not this flight). In the previous mentioned other airline, they misplace my luggage upon arrival. After spending about an hour (with no effective help from that airline's agent), I managed to find it at another belt!
Food
Boarding
Crew
Entertainment
Comfort
Overall
Reviews
I'm a long time SQ patron. For good reason. Had a similar trip last year and took another airline (at that time, price was the main factor). This time I took SQ as they had really good rates. No comparison. Dependable, reliable service and excellent aircraft. No issue with my special checked in item (a guitar that had to be handled differently) on my way to my destination (not this flight). In the previous mentioned other airline, they misplace my luggage upon arrival. After spending about an hour (with no effective help from that airline's agent), I managed to find it at another belt!
Food
Boarding
Crew
Entertainment
Comfort
Overall
Reviews
I'm a long time SQ patron. For good reason. Had a similar trip last year and took another airline (at that time, price was the main factor). This time I took SQ as they had really good rates. No comparison. Dependable, reliable service and excellent aircraft. No issue with my special checked in item (a guitar that had to be handled differently) on my way to my destination (not this flight). In the previous mentioned other airline, they misplace my luggage upon arrival. After spending about an hour (with no effective help from that airline's agent), I managed to find it at another belt!
Food
Boarding
Crew
Entertainment
Comfort
Overall
Reviews
I'm a long time SQ patron. For good reason. Had a similar trip last year and took another airline (at that time, price was the main factor). This time I took SQ as they had really good rates. No comparison. Dependable, reliable service and excellent aircraft. No issue with my special checked in item (a guitar that had to be handled differently) on my way to my destination (not this flight). In the previous mentioned other airline, they misplace my luggage upon arrival. After spending about an hour (with no effective help from that airline's agent), I managed to find it at another belt!
Food
Boarding
Crew
Entertainment
Comfort
Overall
Reviews
I'm a long time SQ patron. For good reason. Had a similar trip last year and took another airline (at that time, price was the main factor). This time I took SQ as they had really good rates. No comparison. Dependable, reliable service and excellent aircraft. No issue with my special checked in item (a guitar that had to be handled differently) on my way to my destination (not this flight). In the previous mentioned other airline, they misplace my luggage upon arrival. After spending about an hour (with no effective help from that airline's agent), I managed to find it at another belt!
0%of flight departures | Early morningMidnight to 6 am |
---|---|
0%of flight departures | Morning6 am to noon |
100%of flight departures | AfternoonNoon to 6 pm |
0%of flight departures | Evening6 pm to midnight |
Deals for Chicago to Italy flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.
Millions of users choose and trust Cheapflights to book the best flight deals from Chicago to Italy for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.
Yes, we can. To see specific flights from Chicago to Italy with no change fees, users can toggle flexible booking options after using the search form above to find flights.
Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!