Cheap flights from Italy to Chicago from $310
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Italy to Chicago departing on 9/8. 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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TAP AIR PORTUGAL flights from Italy to Chicago
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How to get the cheapest flight ticket from Italy to Chicago
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 Chicago?
The month of February is, on average, the cheapest month to fly to Chicago from Italy, with most prices found around $597. If you’re not able to fly to Chicago in February, then April is your next best option. Flight prices from Italy to Chicago during April average around $611.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $757. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Italy to Chicago for around $944.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from Italy to Chicago during this time can be as low as $748. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $828.
What is the cheapest Italy to Chicago flight route?
Fly from Naples to Chicago O'Hare Intl for the best Italy - Chicago flight prices
How far in advance should I book a flight to Chicago?
You are more likely to see cheaper flights to Chicago from Italy when booking 11 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $745 when searching 11 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Italy for as low as $452 on momondo.
What cabin class options are available on Italy to Chicago flights?
There are 4 cabin classes available to choose from on Italy to Chicago 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 Italy to Chicago?
Icelandair, TAP AIR PORTUGAL, and Air Serbia are the most popular carriers operating from Italy to Chicago
What airlines fly to Chicago?
American Airlines, United Airlines and British Airways are the top three most popular airlines that fly to Chicago from Italy according to our data. American Airlines is the first choice among our users, with 37% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from Italy to Chicago on average per day?
As of June 2025, 18 flights take off from Italy and land in Chicago each day. The most common flight departure time for this route is 9:00AM, with 63% of daily flights taking off at noon.
How many flights depart from Italy to Chicago on average per week?
As of June 2025, 127 flights take off from Italy and land in Chicago each week. The most common flight departure day for this route is Mon, with 15% of weekly flights taking off on this day.
Cheap Italy to Chicago flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Italy to Chicago
When did momondo last update prices for flights from Italy to Chicago?
Prices for flights from Italy to Chicago are updated daily.
How many operators does momondo search for flights from Italy to Chicago?
As of June 2025, there are 7 operators available to choose from for flights from Italy to Chicago.
How old do you have to be to fly from Italy to Chicago?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Italy to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents you'll need for your trip to Chicago 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 Chicago. 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 Italy to Chicago?
Based on momondo bookings for flights between Italy and Chicago, the leading plane model is Boeing 787 Dreamliner, making up 39.09% of the total bookings. Other popular models include Boeing 787-8 Dreamliner with 22.03%, Boeing 787-10 Dreamliner with 10.36%, and Airbus A330 with 7.40%.
Best airlines flying from Italy to Chicago
Compare and see reviews for airlines that fly from Italy to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $525 | Free Cancellation | Rating 6.6 7,008 reviews | |||
| PriceFrom $536 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $537 | Free Cancellation | Rating 7.1 1,885 reviews | |||
| PriceFrom $550 | Free Cancellation | Rating 7.0 2,776 reviews | |||
| PriceFrom $611 | Free Cancellation | Rating 7.4 8,790 reviews | |||
| PriceFrom $639 | Free Cancellation | Rating 6.7 7,136 reviews | |||
| PriceFrom $658 | Free Cancellation | Rating 6.7 990 reviews |
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Italy to Chicago?
Finding the right flight to Chicago from Italy is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.
Can I find flights from Italy to Chicago with flexible booking policies on momondo?
All flight searches from Italy to Chicago on momondo can be filtered to show those which offer flexible booking policies.
How can momondo help me find flights from Italy to Chicago?
Once all potential Italy to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.
I’m not ready to book a flight from Italy to Chicago right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Chicago from Italy. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.