$268 Find Cheap Flights from Chicago to Italy - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Italy departing on 10/17. 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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Cheap Flights from Chicago to Italy

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Milan
Milan1 stop$613
Florence
Florence1 stop$801
Naples
Naples1 stop$598
Palermo
Palermo1 stop$646
Bologna
Bologna1 stop$600
Turin
Turin1 stop$609
Milan
Milan1 stop$613
Florence
Florence1 stop$801
Naples
Naples1 stop$598
Palermo
Palermo1 stop$646
Bologna
Bologna1 stop$600
Turin
Turin1 stop$609

Book Cheap Chicago to Italy Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Italy 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 Chicago to Italy

Thu, Aug 27 - Wed, Sep 9
TAP AIR PORTUGAL Logo
7:45 pm - 6:15 pm
ORD
-
VCE
15h 30m
1 stop
TAP AIR PORTUGAL Logo
7:10 pm - 12:40 pm
VCE
-
ORD
24h 30m
1 stop
$586TAP AIR PORTUGAL
Thu, Aug 27 - Wed, Sep 9
TAP AIR PORTUGAL Logo
7:45 pm - 6:15 pm
ORD
-
VCE
15h 30m
1 stop
TAP AIR PORTUGAL Logo
7:10 pm - 12:40 pm
VCE
-
ORD
24h 30m
1 stop
$587TAP AIR PORTUGAL
Tue, Sep 8 - Tue, Sep 15
Turkish Airlines Logo
8:10 pm - 7:50 pm
ORD
-
NAP
16h 40m
1 stop
Turkish Airlines Logo
8:50 pm - 9:40 am
NAP
-
ORD
19h 50m
1 stop
$606Turkish Airlines
Wed, Sep 9 - Wed, Sep 16
Turkish Airlines Logo
8:10 pm - 7:50 pm
ORD
-
NAP
16h 40m
1 stop
Turkish Airlines Logo
8:50 pm - 9:40 am
NAP
-
ORD
19h 50m
1 stop
$608Turkish Airlines
Wed, Aug 19 - Sun, Aug 30
Icelandair Logo
10:25 pm - 2:45 pm
ORD
-
VCE
33h 20m
1 stop
Icelandair Logo
3:55 pm - 9:25 pm
VCE
-
ORD
12h 30m
1 stop
$639Icelandair
Sun, Aug 23 - Sun, Aug 30
Icelandair Logo
10:25 pm - 2:45 pm
ORD
-
VCE
33h 20m
1 stop
Icelandair Logo
3:55 pm - 9:25 pm
VCE
-
ORD
12h 30m
1 stop
$639Icelandair
Wed, Aug 19 - Wed, Aug 26
ITA Airways Logo
3:00 pm - 10:35 am
ORD
-
NAP
12h 35m
1 stop
ITA Airways Logo
11:00 am - 1:10 pm
NAP
-
ORD
33h 10m
1 stop
$650ITA Airways
Sun, Aug 16 - Tue, Aug 25
ITA Airways Logo
3:00 pm - 10:15 am
ORD
-
NAP
12h 15m
1 stop
ITA Airways Logo
10:55 am - 1:10 pm
NAP
-
ORD
33h 15m
1 stop
$650ITA Airways
Tue, Sep 8 - Tue, Sep 15
Multiple Airlines Logo
11:25 am - 6:55 pm
ORD
-
MXP
24h 30m
2 stops
Multiple Airlines Logo
3:05 pm - 9:40 am
MXP
-
ORD
25h 35m
2 stops
$652Multiple Airlines
Tue, Sep 8 - Tue, Sep 15
Multiple Airlines Logo
11:25 am - 6:55 pm
ORD
-
MXP
24h 30m
2 stops
Multiple Airlines Logo
3:05 pm - 9:40 am
MXP
-
ORD
25h 35m
2 stops
$653Multiple Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Italy flights

Get data-powered insights and trends into flights from Chicago to Italy to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago to Italy flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Italy from Chicago found in the last 5 days was to Rome, at $649 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Rome Fiumicino Airport (FCO), and the cheapest round-trip airline ticket found on this route in the last 5 days was $649.

What is the cheapest time of day to fly to Italy?

The average price for all round-trip flights from Chicago to Italy depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Italy is generally in the evening, when round-trip flights cost $969 on average. Morning departures are around 100% cheaper than evening flights, on average. The most expensive time of day to fly to Italy is generally in the evening, which is peak travel time and where the average cost of a ticket is $969.

Can I save money by flying with a layover from Chicago to Italy?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $806, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Italy, 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 from Chicago to Italy is February, when tickets cost $604 (return) on average. On the other hand, the most expensive months are June and July, when the average cost of round-trip tickets is $1,053 and $1,002 respectively.

What’s the cheapest day of the week to fly from Chicago to Italy?

The average price of all round-trip flights from Chicago to Italy clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Chicago to Italy, look for departures on Sundays and avoid leaving on a Friday, as it's usually the priciest day. When flying back from Italy, Thursday is the cheapest day to fly and Tuesday is the most expensive.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Italy, 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 on the flight from Chicago to Italy, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.

Good to know

Low season

February

Cheapest flight

$268
Best time to beat the crowds with an average 32% drop in price.
Most popular time to fly with an average 43% increase in price.
Flight from Chicago O'Hare Airport to Milan Malpensa Airport

FAQs - booking Italy flights

  • If my flight to Italy will be landing at Milan Malpensa Airport (MXP), will I be able to find ground transportation to take me from the airport to downtown Milan?

    One of the quickest and most cost-effective ways to make this trip is aboard the light rail service offered by Malpensa Express. This train makes the trip to downtown Milan in around 37min for a cost of about 13 EUR (15 USD).

  • If I am going to be flying from Chicago to Italy, will I need to get a visa before I travel and do I need a passport?

    Before you hop aboard your flight to Italy, it is important that you bring with you a passport that is valid for at least 90 days from the date you plan to leave Italy. Make sure that the passport has at least two blank pages. If you are heading to Italy on a vacation as a tourist, you will not need to get a visa as long as your stay will be less than 90 days in Italy.

  • If my kids are coming with me on the trip to Italy and we are going to rent a car, what type of seatbelt laws do I need to be aware of before I start driving off from the airport?

    All children riding in vehicles in Italy that are 15 months old or less must ride in a rear-facing car seat. Any child over 15 months but less than four years old must ride in a forward-facing car seat. Once children are more than four years old and up to 12 years old, they must ride in a booster seat. All children riding in vehicles must be in the rear seat of the vehicle.

  • If my flight to Italy is going to be landing at Venice Marco Polo Airport (VCE), will I find any shower services available at the airport?

    The airport provides shower services on a pay-per-use basis. You can find the showers in the Marco Polo Club Lounge, which is located in the airside section of the terminal building on the second floor.

  • How does KAYAK find such low prices on flights from Chicago to Italy?

    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 from Chicago to Italy.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Italy?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to Italy is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Italy?

    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 from Chicago to Italy 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 from Chicago to Italy?

    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 from Chicago to Italy 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 Italy

  • When looking for a convenient way to get to either of the Chicago area airports from downtown Chicago, a good choice is to take the light rail services aboard the Chicago Transit Authority. For example, you can travel to Chicago O' Hare International Airport (ORD) in about 42min for a cost of around $3.50.
  • If you will be parking your own car at Chicago Midway Airport (MDW) and you will be away for more than 30 days, it is important to let the Parking Garage Office know this as they may tow your car if they are not notified of the length of your stay.
  • For nursing mothers that are traveling from Chicago Midway Airport, there is a mother's room in Concourse C at the airport. The room offers comfortable seating as well as a sink and wash area.
  • If you are flying out of Chicago O' Hare International Airport, you will be glad to know that there are airline lounges provided by United Airlines, Swiss Airlines, and SAS, which is very convenient since all of these airlines offer one-stop flights to Italy from the airport.
  • If someone will be dropping you off at Chicago O' Hare International Airport before your flight to Italy, the airport recommends that you use the Kiss 'n' Fly Lot. Here you can say your goodbyes and then hop aboard the convenient shuttle service that will take you directly to the terminal.

Everything you need to know for your flight from Chicago to Italy

Cabin class types available on flights to Italy

Cabin classes available on flights to Italy. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.