When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 38 days in advance, which can save you up to 57% on flights from Italy to Chicago compared to booking the week you need them. Waiting 38 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 $570. For sooner than that we have options available in the next 3 days from $769.
November is one of the best times of the year to fly to Chicago from Italy. Prices for November average $676 per person but you can even find prices for as low as $450. The most expensive prices can be found in the month of July. Opting for a November flight can save you 27% on your journey compared to booking in July
When flying from Italy to Chicago, 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
$428 - $544
Route
Depart
Return
Price
Milan LinateChicago O'Hare Intl
LIN - ORD
LINORD
Milan Linate
Mon 11/4
1 stop13h 10m
Chicago O'Hare Intl
Wed 11/6
1 stop12h 10m
Milan MalpensaChicago O'Hare Intl
MXP - ORD
MXPORD
Milan Malpensa
Sun 9/15
1 stop17h 15m
Chicago O'Hare Intl
Sun 10/13
1 stop23h 35m
Milan MalpensaChicago O'Hare Intl
MXP - ORD
MXPORD
Milan Malpensa
Thu 9/12
1 stop12h 45m
Chicago O'Hare Intl
Sun 10/13
1 stop12h 00m
Venice Marco PoloChicago O'Hare Intl
VCE - ORD
VCEORD
Venice Marco Polo
Mon 7/8
1 stop25h 00m
Chicago O'Hare Intl
Mon 7/22
1 stop20h 25m
Milan MalpensaChicago O'Hare Intl
MXP - ORD
MXPORD
Milan Malpensa
Wed 10/16
1 stop28h 50m
Chicago O'Hare Intl
Sun 10/27
1 stop16h 00m
Milan MalpensaChicago O'Hare Intl
MXP - ORD
MXPORD
Milan Malpensa
Tue 9/10
1 stop16h 01m
Chicago O'Hare Intl
Wed 9/25
1 stop18h 15m
Milan MalpensaChicago O'Hare Intl
MXP - ORD
MXPORD
Milan Malpensa
Mon 6/24
1 stop29h 11m
Chicago O'Hare Intl
Thu 7/4
1 stop11h 30m
Milan LinateChicago O'Hare Intl
LIN - ORD
LINORD
Milan Linate
Mon 10/28
2 stops21h 07m
Chicago O'Hare Intl
Mon 11/11
1 stop11h 20m
Milan MalpensaChicago O'Hare Intl
MXP - ORD
MXPORD
Milan Malpensa
Thu 6/13
2 stops19h 57m
Chicago O'Hare Intl
Wed 6/26
Nonstop8h 45m
No data available for this route at this time. Please check back soon.
Entertainment
Boarding
Crew
Food
Overall
Comfort
Reviews
The staff was super awesome and responsive! One of the best flights we have been on, ever.
Entertainment
Boarding
Crew
Food
Overall
Comfort
Reviews
The staff was super awesome and responsive! One of the best flights we have been on, ever.
Entertainment
Boarding
Crew
Food
Overall
Comfort
Reviews
The staff was super awesome and responsive! One of the best flights we have been on, ever.
Entertainment
Boarding
Crew
Food
Overall
Comfort
Reviews
The staff was super awesome and responsive! One of the best flights we have been on, ever.
Entertainment
Boarding
Crew
Food
Overall
Comfort
Reviews
The staff was super awesome and responsive! One of the best flights we have been on, ever.
5%of flight departures | Early morningMidnight to 6 am |
---|---|
64%of flight departures | Morning6 am to noon |
31%of flight departures | AfternoonNoon to 6 pm |
0%of flight departures | Evening6 pm to midnight |
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Yes, Cheapflights offers price alerts on Italy to Chicago flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.