Cheap flights from Chicago to Italy from £344

Q: What is the cheapest flight to Italy from Chicago?

The cheapest flight from Chicago to Italy costs £344. Explore the different prices of flights from Chicago to Italy and find the best option for you.

Q: When is it the cheapest time to fly from Chicago to Italy?

The cheapest month to fly from Chicago to Italy is November. See if any of these flights in November suit you.

Q: What is the cheapest Chicago to Italy flight route?

We've taken a look at the year ahead using our flights calendar. The cheapest flight route from Chicago to Italy is Chicago to Bologna International. You can buy a ticket to fly this route from £344. Take a look at Chicago to Bologna International flights.

Q: How long is the flight from Chicago to Italy?

The average flight time from Chicago to Italy is 9 hours and 7 minutes.

Q: What is the cheapest airline that flies to Italy from Chicago?

Looking at the year ahead, the cheapest airline flying to Italy from Chicago is Scandinavian Airlines. Explore Scandinavian Airlines flight ticket options today. If this airline doesn't suit you, the second cheapest airline is United.

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Where in Italy would you like to go?

There are lots of destinations to choose from when you're planning your trip from Chicago to Italy.

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Flying from Chicago to Italy

The things to know before you go.

Cheapest flight ticket found	£346
Cheapest month to fly	November
Average flight time	9 hrs, 9 mins
Places to go	42
Most popular airline	American Airlines
Average flights per week	298

Cheapest time to fly from Chicago to Italy

Looking for the cheapest ticket prices to Italy from Chicago? We can help you pick the cheapest month to fly.

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Chicago to Italy flight deals

Looking for a cheap flight ticket from Chicago to Italy? Whether you're looking for a direct flight, return flight or one way ticket we've got you.

Bologna.£346 per passenger.Departing Sun, 2 Nov, returning Sun, 9 Nov.Return flight with Scandinavian Airlines.Outbound indirect flight with Scandinavian Airlines, departs from Chicago O'Hare International on Sun, 2 Nov, arriving in Bologna International.Inbound indirect flight with Scandinavian Airlines, departs from Bologna International on Sun, 9 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From £346, select.

Milan.£352 per passenger.Departing Mon, 20 Oct, returning Mon, 27 Oct.Return flight with Scandinavian Airlines.Outbound indirect flight with Scandinavian Airlines, departs from Chicago O'Hare International on Mon, 20 Oct, arriving in Milan Malpensa.Inbound indirect flight with Scandinavian Airlines, departs from Milan Malpensa on Mon, 27 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From £352, select.

Florence.£373 per passenger.Departing Sun, 7 Sep, returning Sun, 14 Sep.Return flight with Scandinavian Airlines.Outbound indirect flight with Scandinavian Airlines, departs from Chicago O'Hare International on Sun, 7 Sep, arriving in Florence.Inbound indirect flight with Scandinavian Airlines, departs from Florence on Sun, 14 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From £373, select.

Rome.£380 per passenger.Departing Sun, 15 Mar, returning Fri, 3 Apr.Return flight with British Airways and Iberia.Outbound indirect flight with British Airways, departs from Chicago O'Hare International on Sun, 15 Mar, arriving in Rome Fiumicino.Inbound indirect flight with Iberia, departs from Rome Fiumicino on Fri, 3 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From £380, select.

Venice.£437 per passenger.Departing Mon, 8 Sep, returning Mon, 15 Sep.Return flight with Scandinavian Airlines.Outbound indirect flight with Scandinavian Airlines, departs from Chicago O'Hare International on Mon, 8 Sep, arriving in Venice Marco Polo.Inbound indirect flight with Scandinavian Airlines, departs from Venice Marco Polo on Mon, 15 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From £437, select.

Naples.£444 per passenger.Departing Tue, 30 Sep, returning Tue, 7 Oct.Return flight with Turkish Airlines.Outbound indirect flight with Turkish Airlines, departs from Chicago O'Hare International on Tue, 30 Sep, arriving in Naples International.Inbound indirect flight with Turkish Airlines, departs from Naples International on Tue, 7 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From £444, select.

Catania.£448 per passenger.Departing Wed, 7 May, returning Wed, 14 May.Return flight with Spirit Airlines and Ryanair.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Wed, 7 May, arriving in Catania Fontanarossa.Inbound indirect flight with Ryanair, departs from Catania Fontanarossa on Wed, 14 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From £448, select.

Bari.£450 per passenger.Departing Sun, 4 May, returning Mon, 12 May.Return flight with Spirit Airlines and Ryanair.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Sun, 4 May, arriving in Bari.Inbound indirect flight with Ryanair, departs from Bari on Mon, 12 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From £450, select.

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Flights from Chicago to Italy FAQs

What is the cheapest flight to Italy from Chicago?

When is it the cheapest time to fly from Chicago to Italy?

What is the cheapest Chicago to Italy flight route?

How long is the flight from Chicago to Italy?

What is the cheapest airline that flies to Italy from Chicago?

Cheapest flights to Italy from Chicago

Chicago to Bologna from £344
Price found 9 Apr 2025, 16:43
Chicago to Milan from £350
Price found 9 Apr 2025, 19:28
Chicago to Florence from £371
Price found 10 Apr 2025, 21:09
Chicago to Rome from £378
Price found 10 Apr 2025, 22:53
Chicago to Venice from £434
Price found 8 Apr 2025, 12:13
Chicago to Naples from £441
Price found 8 Apr 2025, 02:48
Chicago to Catania from £445
Price found 8 Apr 2025, 22:34
Chicago to Bari from £447
Price found 8 Apr 2025, 12:29
Chicago to Pisa from £460
Price found 10 Apr 2025, 18:55
Chicago to Cagliari from £482
Price found 7 Apr 2025, 21:49
Chicago to Verona from £487
Price found 8 Apr 2025, 15:14
Chicago to Turin from £514
Price found 9 Apr 2025, 08:43

How to find cheap flights from Chicago to Italy

Looking for flight tickets from Chicago to Italy? Round-trip tickets start from £344 and one-way flights from Chicago to Italy start from £191

Here are some tips on how to secure the best flight price and make your journey as smooth as possible.

Simply hit "search." From American Airlines to international carriers like Emirates, we've compared flights from all major airlines and online travel agents to find the cheapest Chicago to Italy flights. And with us, there are no hidden fees – what you see is what you pay.
Compare cheap Chicago to Italy flight deals from over 1,000 providers. Then choose the cheapest plane tickets or fastest journeys. Flight tickets to Italy start from £191 one-way.
Flex your dates to secure the best fares for your Chicago to Italy ticket. If your travel dates are flexible, use Skyscanner's "Whole month" tool to find the cheapest month, and even day to fly from Chicago to Italy.
Set up a Price Alert. We price-check with over 1,000 travel companies so you don't have to. You can easily track the price of your airline tickets from Chicago to Italy by creating an alert. Whenever prices go up or down, you'll get an email or push notification to help make sure you get the best possible flight deal.
Look for direct flights. Only interested in direct flights from Chicago to Italy? Make sure to tick "Direct flights only" when performing a search. If there are direct Chicago to Italy flights available, these will appear in the results.
Find the cheapest Business Class flights from Chicago to Italy. Check the difference in price of your plane ticket to Italy from Chicago when traveling in Economy, Premium Economy, Business or First Class. Note that not all cabin classes are available for every destination or airline.
Include nearby airports in your search. Widen your search for Chicago to Italy flight deals by selecting the "add nearby airports" option. This will allow you to see flight prices for all the nearest airports at your departure and destination point and could help you save money.
Search for flights on the go. To get the best flight booking experience on the go, download our app and search for cheap flight tickets from Chicago to Italy when out and about.

Combine your flight from Chicago to Italy with hotels and car rental

Once you've secured your plane ticket, we'll also help you discover the best prices and exclusive rates for hotels in Italy or close by. Lastly, compare hundreds of car rental companies at once so that you get the best car rental deals for your trip.

Compare Chicago to Italy flight tickets with other routes using the everywhere search

Not quite yet set on flying to Italy from Chicago? You can easily browse other destinations by searching flights to "Everywhere" – this will allow you to find the cheapest place to travel to.