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
$939 - $1,640
Route
Depart
Return
Price
Chicago MidwayCatania Fontanarossa
MDW - CTA
MDWCTA
Chicago Midway
Wed 10/30
2 stops41h 50m
Catania Fontanarossa
Sun 11/3
2 stops29h 33m
Chicago MidwayCatania Fontanarossa
MDW - CTA
MDWCTA
Chicago Midway
Wed 10/30
2 stops44h 35m
Catania Fontanarossa
Sun 11/3
2 stops29h 46m
Chicago MidwayCatania Fontanarossa
MDW - CTA
MDWCTA
Chicago Midway
Wed 9/4
2 stops22h 34m
Catania Fontanarossa
Wed 9/11
2 stops20h 44m
Chicago MidwayCatania Fontanarossa
MDW - CTA
MDWCTA
Chicago Midway
Mon 9/2
2 stops18h 30m
Catania Fontanarossa
Thu 9/12
2 stops21h 44m
Chicago MidwayPalermo Punta Raisi
MDW - PMO
MDWPMO
Chicago Midway
Wed 9/4
2 stops20h 29m
Palermo Punta Raisi
Wed 9/11
2 stops17h 23m
Chicago MidwayPalermo Punta Raisi
MDW - PMO
MDWPMO
Chicago Midway
Mon 9/2
2 stops17h 30m
Palermo Punta Raisi
Tue 9/10
2 stops16h 43m
Chicago MidwayCatania Fontanarossa
MDW - CTA
MDWCTA
Chicago Midway
Fri 10/11
2 stops17h 15m
Catania Fontanarossa
Fri 10/18
2 stops18h 03m
Chicago MidwayLamezia Terme Intl
MDW - SUF
MDWSUF
Chicago Midway
Sat 7/13
3 stops32h 05m
Lamezia Terme Intl
Sat 7/27
3 stops40h 57m
Chicago MidwayPalermo Punta Raisi
MDW - PMO
MDWPMO
Chicago Midway
Fri 6/14
3 stops17h 50m
Palermo Punta Raisi
Fri 6/21
3 stops18h 57m
No data available for this route at this time. Please check back soon.
Food
Boarding
Comfort
Entertainment
Crew
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
Boarding
Comfort
Entertainment
Crew
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
Boarding
Comfort
Entertainment
Crew
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
Boarding
Comfort
Entertainment
Crew
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.
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Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Sicily from Midway today and book when prices fit your budget.