Cheap flights from Chicago to Italy from $249
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Italy departing on 9/23. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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How to get the cheapest flight ticket from Chicago to Italy
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Italy?
The cheapest month to fly to Italy from Chicago is in February. Flight prices, which tend to average around $552, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of February, then book flights to Italy from Chicago during January instead. Flights to Italy in January, while not as cheap as those in February, still average around $562.
What is the cheapest day to depart on your flight to Italy?
According to our data, Tuesday is the cheapest day to fly to Italy from Chicago. The lowest ticket price found for a Tuesday departure recently was $893. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. When flying out on a Friday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Italy for around $1,007.
What is the cheapest time of day to depart on your flight to Italy?
Our data shows that the cheapest Chicago to Italy flights are usually those with departure times in the evening. Our users have found flights to Italy in the evening for as low as $686. In contrast, the most expensive time of day to depart to Italy is in the afternoon when prices are around $938.
What is the cheapest Chicago to Italy flight route?
Fly from Chicago O'Hare Intl to Rome Fiumicino for the best Chicago - Italy flight prices
How far in advance should I book a flight to Italy?
You are more likely to see cheaper flights to Italy from Chicago when booking 11 weeks ahead of your departure date. In general, you can expect to find flights to Italy for around $795 when searching 11 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Italy from Chicago for as low as $734 on momondo.
What cabin class options are available on Chicago to Italy flights?
There are 3 cabin classes available to choose from on Chicago to Italy flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from Chicago to Italy?
TAP AIR PORTUGAL, Air Serbia, and Icelandair are the most popular carriers operating from Chicago to Italy
What airlines fly to Italy?
ITA Airways, United Airlines and American Airlines are the top three most popular airlines that fly to Italy from Chicago according to our data. ITA Airways is the first choice among our users, with 43% of people opting to fly with this airline when traveling to Italy. Keep in mind that there are 20 different airlines that fly to Italy on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago to Italy on average per day?
13 flights are operational daily from Chicago to Italy as of April 2025. The most popular departure time for this route is 3:00PM, with 100% of flights per day taking off in the afternoon.
How many flights depart from Chicago to Italy on average per week?
As of April 2025, there are 96 flights per week flying from Chicago to Italy. The most common day of the week flights depart is Wed, with 17% of flights taking off on this day.
Cheap Chicago to Italy flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Italy
When did momondo last update prices for flights from Chicago to Italy?
Prices for flights from Chicago to Italy refresh daily.
How many operators does momondo search for flights from Chicago to Italy?
As of April 2025, there are 19 operators available to choose from for flights from Chicago to Italy.
How old do you have to be to fly from Chicago to Italy?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Italy.
What documentation or ID do you need to fly to Italy?
The travel and health documents you'll need for your trip to Italy may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Italy. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago to Italy?
Based on momondo bookings for flights between Chicago and Italy, the leading plane model is Boeing 787 Dreamliner, making up 47.23% of the total bookings. Other popular models include Boeing 787-8 Dreamliner with 26.06%, Boeing 787-10 Dreamliner with 16.60%, and Airbus A330 with 8.73%.
Best airlines flying from Chicago to Italy
Compare and see reviews for airlines that fly from Chicago to Italy with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $41 | Free Cancellation | Rating 6.5 39 reviews | |||
| PriceFrom $365 | Free Cancellation | Rating 7.0 478 reviews | |||
| PriceFrom $377 | Free Cancellation | Rating 7.1 1,837 reviews | |||
| PriceFrom $429 | Free Cancellation | Rating 7.3 1,333 reviews | |||
| PriceFrom $484 | Free Cancellation | Rating 7.5 1,575 reviews | |||
| PriceFrom $500 | Free Cancellation | Rating 7.0 9,083 reviews | |||
| PriceFrom $503 | Free Cancellation | Rating 6.7 6,985 reviews | |||
| PriceFrom $506 | Free Cancellation | Rating 7.0 1,060 reviews | |||
| PriceFrom $517 | Free Cancellation | Rating 6.6 6,738 reviews | |||
| PriceFrom $518 | Free Cancellation | Rating 7.3 3,753 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to Italy?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Italy from Chicago.
Can I find flights from Chicago to Italy with flexible booking policies on momondo?
All flight searches from Chicago to Italy on momondo can be filtered to show those which offer flexible booking policies.
How can momondo help me find flights from Chicago to Italy?
momondo provides multiple filters to help you find the best flight to Italy from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from Chicago to Italy right now. Can momondo alert me if prices change?
If you are not ready to book a flight from Chicago to Italy now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Italy and let you know when they change.