Cheap flights from Chicago to Sicily from $301
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 Sicily departing on 5/3. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Discover deals from 900+ travel sites with momondo.
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Find the cheapest flights from Chicago to Sicily
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
Turkish Airlines flights from Chicago to Sicily
Our best Turkish Airlines deals on Chicago to Sicily flight tickets
ITA Airways flights from Chicago to Sicily
Our best ITA Airways deals on Chicago to Sicily flight tickets
See travel insights to Sicily from
How to get the cheapest flight ticket from Chicago to Sicily
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 Sicily?
In general, January is the cheapest month to fly from Chicago to Sicily. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $606. If you don’t want to visit Sicily in January, then you should wait until February to fly from Chicago, when ticket prices are also cheap, with an average price of $620.
What is the cheapest day to depart on your flight to Sicily?
Our data shows that Wednesday is the least expensive day to fly to Sicily. Tickets to fly out on this day can be as low as $781. Flights from Chicago to Sicily on a Thursday will generally be more expensive and average around $1,355. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.
What is the cheapest time of day to depart on your flight to Sicily?
Our data shows that the cheapest Chicago to Sicily flights are usually those with departure times in the morning. Our users have found flights to Sicily in the morning for as low as $839. Flights to Sicily are more costly in the afternoon, with an average ticket price of $1,091. Departure times in the afternoon fall within the peak daily travel times, which is why tickets can be more expensive.
How far in advance should I book a flight to Sicily?
You are more likely to see cheaper flights to Sicily from Chicago when booking 11 weeks ahead of your departure date. In general, you can expect to find flights to Sicily for around $940 when searching 11 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Sicily from Chicago for as low as $752 on momondo.
What is the cheapest airline that flies from Chicago to Sicily?
Scandinavian Airlines, Lufthansa, and TAP AIR PORTUGAL are the most popular carriers operating from Chicago to Sicily
What airlines fly to Sicily?
ITA Airways, Turkish Airlines and SWISS are the top three most popular airlines that fly to Sicily from Chicago according to our data. ITA Airways is the first choice among our users, with 62% of people opting to fly with this airline when traveling to Sicily. Keep in mind that there are 7 different airlines that fly to Sicily on a routine basis, so you have a few additional options to choose from.
Cheap Chicago to Sicily flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Sicily
When did momondo last update prices for flights from Chicago to Sicily?
Prices for flights from Chicago to Sicily were last updated today.
How many operators does momondo search for flights from Chicago to Sicily?
As of April 2025, there are 7 operators available to choose from for flights from Chicago to Sicily.
How old do you have to be to fly from Chicago to Sicily?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Sicily.
What documentation or ID do you need to fly to Sicily?
The required travel and health documents for your Sicily trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Sicily. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
Best airlines flying from Chicago to Sicily
Compare and see reviews for airlines that fly from Chicago to Sicily with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $41 | Free Cancellation | Rating 6.5 39 reviews | |||
| PriceFrom $526 | Free Cancellation | Rating 7.4 8,616 reviews | |||
| PriceFrom $613 | Free Cancellation | Rating 7.3 3,750 reviews | |||
| PriceFrom $661 | Free Cancellation | Rating 6.7 952 reviews | |||
| PriceFrom $813 | Free Cancellation | Rating 8.0 7,897 reviews | |||
| PriceFrom $825 | Free Cancellation | Rating 6.7 6,963 reviews | |||
| PriceFrom $943 | Free Cancellation | Rating 7.5 1,574 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to Sicily?
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 Sicily from Chicago.
Can I find flights from Chicago to Sicily with flexible booking policies on momondo?
Yes. All flights to Sicily from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.
How can momondo help me find flights from Chicago to Sicily?
Once all potential Chicago to Sicily 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 Chicago to Sicily right now. Can momondo alert me if prices change?
If you are not ready to book a flight from Chicago to Sicily now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Sicily and let you know when they change.