Cheap flights from Chicago to Sicily from $603
This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Sicily departing on 5/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Round-trip
1 adult
Economy
0 bags
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Cheap round-trip flights
These are some of the best round-trip flight deals from Chicago to Sicily that have been recently found on momondo from popular airlines, departing in the coming months.
Cheap one-way flights
Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to Sicily.
Cheap last minute flights
Planning a quick getaway from Chicago to Sicily? These are the last-minute flight deals available now.
Cheap direct flights
If you prefer a non-stop journey, check out our latest direct flight deals to Sicily, so you can enjoy a seamless trip without layovers.
Cheap bus & train deals from Chicago to Sicily
Find recent round-trip train or bus tickets from Chicago to Sicily.
All round-trip flight deals to Sicily
The cheapest plane tickets to Sicily found on KAYAK recently.
Turkish Airlines flights from Chicago to Sicily
Our best Turkish Airlines deals on Chicago to Sicily flight tickets
Turkish Airlines![Turkish Airlines]()
May 5![Turkish Airlines]()
May 12
ORD7:50 pmChicago O'Hare Intl
15h 25m
1 stop
CTA6:15 pmCatania Fontanarossa
CTA9:25 amCatania Fontanarossa
31h 25m
1 stop
ORD9:50 amChicago O'Hare Intl
Turkish Airlines![Turkish Airlines]()
Feb 19![Turkish Airlines]()
Feb 26
ORD8:30 pmChicago O'Hare Intl
14h 55m
1 stop
CTA6:25 pmCatania Fontanarossa
CTA9:35 amCatania Fontanarossa
31h 35m
1 stop
ORD10:10 amChicago O'Hare Intl
TAP AIR PORTUGAL flights from Chicago to Sicily
Our best TAP AIR PORTUGAL deals on Chicago to Sicily flight tickets
TAP AIR PORTUGAL![TAP AIR PORTUGAL]()
Mar 5![TAP AIR PORTUGAL]()
Mar 12
ORD7:15 pmChicago O'Hare Intl
36h 20m
2 stops
CTA2:35 pmCatania Fontanarossa
CTA3:20 pmCatania Fontanarossa
55h 10m
2 stops
ORD4:30 pmChicago O'Hare Intl
TAP AIR PORTUGAL![TAP AIR PORTUGAL]()
Jan 22![TAP AIR PORTUGAL]()
Feb 1
ORD7:15 pmChicago O'Hare Intl
36h 15m
2 stops
PMO2:30 pmPalermo Punta Raisi
PMO3:15 pmPalermo Punta Raisi
31h 15m
2 stops
ORD3:30 pmChicago O'Hare Intl
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
Prices
Airlines
What is the cheapest month to fly to Sicily?
In general, February 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 $599. If you don’t want to visit Sicily in February, then you should wait until January to fly from Chicago, when ticket prices are also cheap, with an average price of $695.
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?
The best time to book a flight to Sicily from Chicago is 42 days out, which is when prices tend to be around $960. In the past 72 hours, momondo users found flights from Chicago to Sicily for as low as $679.
What is the cheapest airline that flies from Chicago to Sicily?
Aer Lingus, TAP AIR PORTUGAL, and Turkish Airlines 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 66% of people opting to fly with this airline when traveling to Sicily. Keep in mind that there are 8 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 January 2025, there are 8 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 38 reviews | |||
| PriceFrom $526 | Free Cancellation | Rating 7.4 8,936 reviews | |||
| PriceFrom $603 | Free Cancellation | Rating 7.1 1,860 reviews | |||
| PriceFrom $660 | Free Cancellation | Rating 7.3 3,898 reviews | |||
| PriceFrom $662 | Free Cancellation | Rating 6.6 923 reviews | |||
| PriceFrom $802 | Free Cancellation | Rating 7.5 1,590 reviews | |||
| PriceFrom $806 | Free Cancellation | Rating 6.7 7,077 reviews | |||
| PriceFrom $813 | Free Cancellation | Rating 8.0 8,503 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.
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