When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 11 days in advance, which can save you up to 121% on flights from Chicago Midway Airport to Sicily compared to booking the week you need them. Waiting 11 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $628. For sooner than that we have options available in the next 3 days from $1,393.
Our data shows that January tends to be the cheapest month to fly to Sicily from Chicago Midway Airport. Users have commonly found prices around $1,189 for the month, but tickets can be as low as $680. Due to multiple factors, prepare for potentially higher prices in August.
When flying from Chicago Midway Airport to Sicily, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Fly from
Fly to
Budget
$940 - $1,502
Route
Depart
Return
Price
Chicago MidwayCatania Fontanarossa
MDW - CTA
MDWCTA
Chicago Midway
Wed 10/30
2 stops41h 25m
Catania Fontanarossa
Sun 11/3
2 stops29h 33m
Chicago MidwayCatania Fontanarossa
MDW - CTA
MDWCTA
Chicago Midway
Wed 10/30
2 stops41h 25m
Catania Fontanarossa
Sun 11/3
2 stops34h 14m
Chicago MidwayCatania Fontanarossa
MDW - CTA
MDWCTA
Chicago Midway
Tue 7/2
3 stops19h 55m
Catania Fontanarossa
Tue 7/9
3 stops18h 37m
Chicago MidwayPalermo Punta Raisi
MDW - PMO
MDWPMO
Chicago Midway
Wed 8/14
2 stops15h 45m
Palermo Punta Raisi
Sat 9/14
2 stops16h 43m
Chicago MidwayPalermo Punta Raisi
MDW - PMO
MDWPMO
Chicago Midway
Sat 7/13
2 stops16h 20m
Palermo Punta Raisi
Sat 8/24
2 stops18h 12m
Chicago MidwayCatania Fontanarossa
MDW - CTA
MDWCTA
Chicago Midway
Mon 9/16
2 stops17h 20m
Catania Fontanarossa
Mon 9/23
2 stops16h 03m
Chicago MidwayPalermo Punta Raisi
MDW - PMO
MDWPMO
Chicago Midway
Mon 8/5
2 stops15h 50m
Palermo Punta Raisi
Sat 8/24
2 stops18h 12m
Chicago MidwayPalermo Punta Raisi
MDW - PMO
MDWPMO
Chicago Midway
Mon 6/24
2 stops21h 56m
Palermo Punta Raisi
Wed 7/24
2 stops22h 36m
Chicago MidwayCatania Fontanarossa
MDW - CTA
MDWCTA
Chicago Midway
Tue 7/2
2 stops20h 17m
Catania Fontanarossa
Tue 7/9
2 stops20h 46m
No data available for this route at this time. Please check back soon.
Food
Comfort
Boarding
Crew
Entertainment
Overall
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Food
Comfort
Boarding
Crew
Entertainment
Overall
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Food
Comfort
Boarding
Crew
Entertainment
Overall
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Cheapflights makes it easy to find Midway to Sicily flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.
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