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Cheap flights from Chicago (CHI) to Italy

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How to find the cheapest flight from
Chicago (CHI) to Italy

How far in advance should I book a flight from Chicago to Italy?

To save on the cost of your flight from Chicago to Italy, book at least 57 days before your planned departure. Booking around this time can save you about 43% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $619 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $731.

Cheap flights from Chicago to Italy in November, December 2020

The best prices found for CHI to Italy flights for November, December
20 Dec - 15 Jan
$398pp
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
MXP
Milan Malpensa
MXP
Milan Malpensa
TAP AIR PORTUGAL
 
1 STOP
ORD
Chicago O'Hare Intl
20 Dec - 15 Jan
$428pp
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
BGY
Milan Orio Al Serio
BGY
Milan Orio Al Serio
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
27 Dec - 15 Jan
$449pp
ORD
Chicago O'Hare Intl
TAP AIR PORTUGAL
 
1 STOP
MXP
Milan Malpensa
MXP
Milan Malpensa
TAP AIR PORTUGAL
 
1 STOP
ORD
Chicago O'Hare Intl

Chicago to Italy 2021 flight deals

Cheap flights to Italy from Chicago found for next year
20 Dec - 15 Jan
$398pp
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
MXP
Milan Malpensa
MXP
Milan Malpensa
TAP AIR PORTUGAL
 
1 STOP
ORD
Chicago O'Hare Intl
20 Dec - 15 Jan
$428pp
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
BGY
Milan Orio Al Serio
BGY
Milan Orio Al Serio
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
27 Dec - 15 Jan
$449pp
ORD
Chicago O'Hare Intl
TAP AIR PORTUGAL
 
1 STOP
MXP
Milan Malpensa
MXP
Milan Malpensa
TAP AIR PORTUGAL
 
1 STOP
ORD
Chicago O'Hare Intl

Non-stop flights to Italy from Chicago

Save time with Chicago to Italy direct flight deals
28 Apr - 12 May
$720pp
ORD
Chicago O'Hare Intl
Finnair
Non-Stop
FCO
Rome Fiumicino
FCO
Rome Fiumicino
Finnair
Non-Stop
ORD
Chicago O'Hare Intl
5 Apr - 19 May
$721pp
ORD
Chicago O'Hare Intl
Finnair
Non-Stop
FCO
Rome Fiumicino
FCO
Rome Fiumicino
Finnair
Non-Stop
ORD
Chicago O'Hare Intl
10 May - 21 May
$760pp
ORD
Chicago O'Hare Intl
Finnair
Non-Stop
FCO
Rome Fiumicino
FCO
Rome Fiumicino
Finnair
Non-Stop
ORD
Chicago O'Hare Intl

Last minute flights from Chicago to Italy

Late deals on round-trip flights to Italy from Chicago, departing today and this week
30 Nov - 15 Jan
$454pp
ORD
Chicago O'Hare Intl
Multiple Airlines
     
3 STOPS
MXP
Milan Malpensa
MXP
Milan Malpensa
TAP AIR PORTUGAL
 
1 STOP
ORD
Chicago O'Hare Intl
2 Dec - 18 Dec
$472pp
ORD
Chicago O'Hare Intl
Multiple Airlines
     
3 STOPS
MXP
Milan Malpensa
MXP
Milan Malpensa
TAP AIR PORTUGAL
 
1 STOP
ORD
Chicago O'Hare Intl
29 Nov - 17 Dec
$477pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
MXP
Milan Malpensa
MXP
Milan Malpensa
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

One-way flights to Italy from Chicago

The cheapest one-way flights from Chicago to Italy
1:20 pm - 8:30 am
Multiple Airlines
1 Stop
12h 10m
ORD - CIA
Multiple Airlines
$213
Kiwi.com
1:20 pm - 10:00 am
TAP AIR PORTUGAL
1 Stop
13h 40m
ORD - FCO
TAP AIR PORTUGAL
$224
mytrip.com
5:25 pm - 8:30 am
Multiple Airlines
2 Stops
32h 05m
ORD - CIA
Multiple Airlines
$219
Kiwi.com

Related info for your journey

Useful info, stats and facts about Chicago to Italy flights.

Flight FAQs

From Chicago to Italy

Are flight prices decreasing from Chicago to Italy due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Chicago and Italy for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

What safety measures are being taken by airlines flying from Chicago to Italy to control the spread of COVID-19?

New policies can now be found on Delta and Alitalia to help keep travelers safe while flying. Airline carriers are regularly disinfecting and sanitizing their aircraft. Masks are provided and are mandatory while on board. Pre-flight testing for symptoms and antibodies, alongside socially distanced seating (for a limited time) will work towards keeping travelers safer while flying from Chicago to Italy. Policies will vary by airline.

Which airlines flying from Chicago to Italy have flexible cancellations due to COVID-19?

Some of the carriers operating flights from Chicago to Italy that may be offering flexible cancellation policies are American Airlines, British Airways, and United Airlines. Our site will let you filter for all airlines offering greater flexibility due to COVID-19.

Can I find flights from Chicago to Italy for under $400 on Cheapflights?

Yes, there are multiple flights from Chicago to Italy for under $400. The cheapest flight booked recently is on Multiple Airlines for just $369, but on average you can expect to pay $408.

Are there nonstop flights from Chicago to Italy for under $800 on Cheapflights?

Cheapflights has at least 20 direct flights from Chicago to Italy under $800. A good price for a nonstop flight from Chicago to Italy is less than $877.

Are there last-minute flights available from Chicago to Italy for under $500?

There are currently 20+ open flights from Chicago to Italy within the next 7 days for less than $500.

What are the most popular airlines that fly from Chicago to Italy?

The most popular airlines flying from Chicago to Italy are Major Airline, American Airlines and Air Canada. Something to consider prior to booking your flight.

What are the most popular routes from Chicago to Italy?

Most travelers choose Chicago O'Hare Intl - Rome Fiumicino, Chicago Midway - Rome Fiumicino or Chicago O'Hare Intl - Rome Ciampino when deciding on the best route from Chicago to Italy.

What are the cheapest Flights from Chicago to Italy?

Looking at all options, your cheapest flight can be booked for $442. While the most popular route (Chicago O'Hare Intl - Rome Fiumicino) can be booked for $369 on average our data indicates $835 when flying from Chicago to Italy

How long is the flight from Chicago to Italy?

For as low as $744, American Airlines can have you in Italy from Chicago in 11h 05m. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

What is the cheapest airline to fly from Chicago to Italy round-trip?

Our cheapest airline available from Chicago to Italy is TAP AIR PORTUGAL. Our recent data shows that you can find tickets from as low as $378 on this airline.

What are the cheapest airlines to fly from Chicago to Italy one-way?

The cheapest airline one-way is TAP AIR PORTUGAL, with whom users have recently found tickets for as low as $224.

Arrival points for flights from Chicago to Italy

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Destination information for Italy

Things to know before you go. Useful info for your trip from Chicago to Italy
Today's exchange rate
$1 = €0.85

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Top 10 airlines from Chicago to Italy

The chart below displays the airlines Cheapflights users traveling from Chicago to Italy choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.

Airline Cheapest Average Flexibility On-time COVID-19 safety
Norwegian
$456 $646 No cancel fee 74%
Turkish Airlines
$410 $746 No cancel fee 77%
Air Italy
$388 $779 No cancel fee N/A

We couldn't confirm the COVID-19 safety measures taken by Air Italy. Please check directly on their website for additional information.

Brussels Airlines
$318 $803 No change fee N/A
Iberia
$330 $837 No change fee 77%
Austrian Airlines
$550 $838 No change fee 78%
Air Canada
$410 $882 No cancel fee 67%
SWISS
$329 $890 No change fee 79%
Air France
$541 $920 No change fee 77%
LOT
$932 $1,077 No change fee 81%
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