Cheap flights from Chicago (CHI) to Italy

CHI — VCE
Sep 27 — Oct 41

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

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 60 days in advance, which can save you up to 10% on flights from Chicago to Italy compared to booking the week you need them. Waiting 60 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 $850. For sooner than that we have options available in the next 3 days from $850.

What is the cheapest month to fly from Chicago to Italy?

The best pricing can be found in the month of November. Prices to Italy from Chicago average $685. You can even find prices in November for less than $685, as users have found deals to Italy from as low as $418. 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 38%.

When is the cheapest time to fly from Chicago to Italy (CHI - IT)?

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.

Cheap flights from Chicago to Italy in September, October 2022

The best prices found for CHI to Italy flights for September, October
Oct 24 - Oct 31
ORD

Chicago O'Hare Intl

MXP

Milan Malpensa

1 stop

14h 30m
MXP

Milan Malpensa

ORD

Chicago O'Hare Intl

1 stop

21h 10m
$363

TAP AIR PORTUGAL

Pick Dates

Deal found 20/9/22

Oct 24 - Oct 31
ORD

Chicago O'Hare Intl

MXP

Milan Malpensa

1 stop

14h 30m
MXP

Milan Malpensa

ORD

Chicago O'Hare Intl

1 stop

15h 55m
$365

TAP AIR PORTUGAL

Pick Dates

Deal found 20/9/22

Oct 24 - Nov 21
ORD

Chicago O'Hare Intl

FCO

Rome Fiumicino

1 stop

19h 00m
FCO

Rome Fiumicino

ORD

Chicago O'Hare Intl

1 stop

15h 25m
$400

TAP AIR PORTUGAL

Pick Dates

Deal found 22/9/22

Chicago to Italy 2022 flight deals

Cheap flights to Italy from Chicago found for this year
Nov 7 - Nov 23
ORD

Chicago O'Hare Intl

FCO

Rome Fiumicino

1 stop

13h 30m
FCO

Rome Fiumicino

ORD

Chicago O'Hare Intl

1 stop

21h 25m
$359

TAP AIR PORTUGAL

Pick Dates

Deal found 22/9/22

Oct 24 - Oct 31
ORD

Chicago O'Hare Intl

MXP

Milan Malpensa

1 stop

14h 30m
MXP

Milan Malpensa

ORD

Chicago O'Hare Intl

1 stop

21h 10m
$363

TAP AIR PORTUGAL

Pick Dates

Deal found 20/9/22

Nov 7 - Nov 16
ORD

Chicago O'Hare Intl

FCO

Rome Fiumicino

1 stop

18h 40m
FCO

Rome Fiumicino

ORD

Chicago O'Hare Intl

1 stop

21h 25m
$364

TAP AIR PORTUGAL

Pick Dates

Deal found 21/9/22

Cheap Turkish Airlines flights from Chicago to Italy

Nov 8 - Nov 16
ORD

Chicago O'Hare Intl

VCE

Venice Marco Polo

1 stop

28h 15m
VCE

Venice Marco Polo

ORD

Chicago O'Hare Intl

1 stop

34h 35m
$624

Turkish Airlines

Pick Dates

Deal found 22/9/22

Nov 1 - Nov 8
ORD

Chicago O'Hare Intl

VCE

Venice Marco Polo

1 stop

19h 00m
VCE

Venice Marco Polo

ORD

Chicago O'Hare Intl

1 stop

15h 20m
$634

Turkish Airlines

Pick Dates

Deal found 20/9/22

Sep 28 - Nov 3
ORD

Chicago O'Hare Intl

FCO

Rome Fiumicino

1 stop

24h 15m
FCO

Rome Fiumicino

ORD

Chicago O'Hare Intl

1 stop

38h 15m
$680

Turkish Airlines

Pick Dates

Deal found 19/9/22

Cheap TAP AIR PORTUGAL flights from Chicago to Italy

Nov 7 - Nov 23
ORD

Chicago O'Hare Intl

FCO

Rome Fiumicino

1 stop

13h 30m
FCO

Rome Fiumicino

ORD

Chicago O'Hare Intl

1 stop

21h 25m
$359

TAP AIR PORTUGAL

Pick Dates

Deal found 22/9/22

Jan 25 - Feb 4
ORD

Chicago O'Hare Intl

MXP

Milan Malpensa

1 stop

11h 40m
MXP

Milan Malpensa

ORD

Chicago O'Hare Intl

1 stop

21h 10m
$361

TAP AIR PORTUGAL

Pick Dates

Deal found 21/9/22

Feb 8 - Feb 15
ORD

Chicago O'Hare Intl

MXP

Milan Malpensa

1 stop

18h 15m
MXP

Milan Malpensa

ORD

Chicago O'Hare Intl

1 stop

15h 55m
$362

TAP AIR PORTUGAL

Pick Dates

Deal found 20/9/22

Non-stop flights to Italy from Chicago

Save time with Chicago to Italy direct flight deals
Oct 11 - Oct 20
ORD

Chicago O'Hare Intl

FCO

Rome Fiumicino

Nonstop

9h 05m
FCO

Rome Fiumicino

ORD

Chicago O'Hare Intl

Nonstop

10h 50m
$545

Iberia

Pick Dates

Deal found 20/9/22

Oct 17 - Oct 27
ORD

Chicago O'Hare Intl

FCO

Rome Fiumicino

Nonstop

9h 05m
FCO

Rome Fiumicino

ORD

Chicago O'Hare Intl

Nonstop

10h 50m
$546

Iberia

Pick Dates

Deal found 20/9/22

Oct 17 - Oct 25
ORD

Chicago O'Hare Intl

FCO

Rome Fiumicino

Nonstop

9h 05m
FCO

Rome Fiumicino

ORD

Chicago O'Hare Intl

Nonstop

10h 50m
$547

Iberia

Pick Dates

Deal found 19/9/22

Last minute flights from Chicago to Italy

Late deals on return flights to Italy from Chicago, departing today and this week
Sep 28 - Nov 1
ORD

Chicago O'Hare Intl

FCO

Rome Fiumicino

1 stop

14h 20m
FCO

Rome Fiumicino

ORD

Chicago O'Hare Intl

1 stop

31h 55m
$607

TAP AIR PORTUGAL

Pick Dates

Deal found 21/9/22

Sep 28 - Oct 31
ORD

Chicago O'Hare Intl

FCO

Rome Fiumicino

1 stop

14h 20m
FCO

Rome Fiumicino

ORD

Chicago O'Hare Intl

1 stop

15h 25m
$626

TAP AIR PORTUGAL

Pick Dates

Deal found 21/9/22

Sep 27 - Oct 20
ORD

Chicago O'Hare Intl

FCO

Rome Fiumicino

1 stop

12h 38m
FCO

Rome Fiumicino

ORD

Chicago O'Hare Intl

Nonstop

10h 25m
$645

British Airways

Pick Dates

Deal found 20/9/22

One-way flights to Italy from Chicago

The cheapest one-way flights from Chicago to Italy
Nov 15
ORD

Chicago O'Hare Intl

VCE

Venice Marco Polo

2 stops

24h 33m
$270

Multiple Airlines

Pick Dates

Deal found 21/9/22

Nov 29
ORD

Chicago O'Hare Intl

VCE

Venice Marco Polo

3 stops

29h 55m
$278

Multiple Airlines

Pick Dates

Deal found 20/9/22

Mar 1
ORD

Chicago O'Hare Intl

FCO

Rome Fiumicino

1 stop

18h 40m
$281

TAP AIR PORTUGAL

Pick Dates

Deal found 19/9/22

Related info for your journey

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

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 United Airlines, Lufthansa, and Iberia. 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 TAP AIR PORTUGAL for just $359, but on average you can expect to pay $367.

Are there nonstop flights from Chicago to Italy for under $600 on Cheapflights?

Cheapflights has at least 20 direct flights from Chicago to Italy under $600. A good price for a nonstop flight from Chicago to Italy is less than $581.

Are there last-minute flights available from Chicago to Italy for under $700?

There are currently 20+ open flights from Chicago to Italy within the next 7 days for less than $700.

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 - Milan Malpensa when deciding on the best route from Chicago to Italy.

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

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

What are the cheapest flights from Chicago to Italy?

Looking at all options, your cheapest flight can be booked for $349. While the most popular route (Chicago O'Hare Intl - Rome Fiumicino) can be booked for $361 on average our data indicates $1,865 when flying from Chicago to Italy.

Top 10 airlines flying 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.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Juneyao AirlinesCheapest$12Average$20FlexibilityNo cancel feeOn-time66%COVID-19 safety
Search Juneyao Airlines flights
TAP AIR PORTUGALCheapest$262Average$631FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search TAP AIR PORTUGAL flights
British AirwaysCheapest$364Average$902FlexibilityNo cancel feeOn-time70%COVID-19 safety
Search British Airways flights
KLMCheapest$371Average$564FlexibilityNo cancel feeOn-time75%COVID-19 safety
Search KLM flights
Scandinavian AirlinesCheapest$387Average$614FlexibilityNo cancel feeOn-time77%COVID-19 safety
Search Scandinavian Airlines flights
Air ItalyCheapest$388Average$779FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Air Italy flights
LufthansaCheapest$408Average$1,029FlexibilityNo cancel feeOn-time76%COVID-19 safety
Search Lufthansa flights
ITA AirwaysCheapest$433Average$652FlexibilityNo cancel feeOn-time81%COVID-19 safety
Search ITA Airways flights
SWISSCheapest$439Average$958FlexibilityNo cancel feeOn-time79%COVID-19 safety
Search SWISS flights
Turkish AirlinesCheapest$450Average$662FlexibilityNo cancel feeOn-time77%COVID-19 safety
Search Turkish Airlines flights

Hourly flight availability from Chicago to Italy

See what time of day planes typically take off from Chicago to Italy
1%of flight departuresEarly morningMidnight to 6 am
0%of flight departuresMorning6 am to noon
87%of flight departuresAfternoonNoon to 6 pm
12%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM