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$545+ Cheap flights from Sicily to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
CTA — MDW
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Sicily to Midway

Keep the following information in mind while searching for Sicily to Midway flight deals. Data was last updated September 16, 2025.

Round-trip from

$960
(Expedia)

One-way from

$545
(Kiwi.com)
From Sicily to Chicago Midway
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One-way flight from Sicily to Chicago Midway
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Find flight deals from Sicily to Midway

Cheapest flights from Sicily to Midway
Explore the most affordable flight options available from Sicily to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This Expedia deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/66:10 amPMO - MDW
2 stops19h 15mAir France
Fri 11/1412:47 pmMDW - PMO
2 stops15h 53mAir France
Deal found 9/15$960

Cheapflights Fare Finder

 
Customize your flight search to find flights from Sicily to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 16, 2025.
Use the filters below to find and compare flights from Sicily to Chicago Midway Airport that are best for you.

Fly from

Sicily

Fly to

Midway

Route

Depart

Return

Price

PalermoChicago

PMO - MDW

PMOMDW

Palermo Punta Raisi

Thu 11/6

6:10 am-6:25 pm

2 stops19h 15m

Chicago Midway

Fri 11/14

12:47 pm-11:40 am

2 stops15h 53m

$960

PalermoChicago

PMO - MDW

PMOMDW

Palermo Punta Raisi

Thu 3/5

6:10 am-4:25 pm

2 stops41h 15m

Chicago Midway

Mon 3/9

1:05 pm-11:00 pm

2 stops27h 55m

$1,174

PalermoChicago

PMO - MDW

PMOMDW

Palermo Punta Raisi

Thu 3/5

10:00 am-9:46 pm

2 stops18h 46m

Chicago Midway

Mon 3/9

5:59 pm-6:20 pm

2 stops42h 21m

$1,175

PalermoChicago

PMO - MDW

PMOMDW

Palermo Punta Raisi

Sat 10/11

8:15 am-9:31 am

3 stops56h 16m

$567

PalermoChicago

PMO - MDW

PMOMDW

Palermo Punta Raisi

Wed 10/29

12:35 pm-11:25 pm

2 stops40h 50m

$755

PalermoChicago

PMO - MDW

PMOMDW

Palermo Punta Raisi

Sat 10/11

4:10 pm-5:43 pm

2 stops32h 33m

$1,565

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Best time to book a flight from Sicily to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Sicily with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Sicily to Chicago Midway Airport
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Sicily to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Sicily to Chicago Midway Airport?

    Departing from Sicily to Chicago Midway Airport will take you 18h 46m. The distance between Sicily and Chicago Midway Airport is about 5002 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • Can I find deals for flights from Sicily to Midway that include hotel bookings?

    Yes. In addition to deals on Sicily to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Sicily to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Sicily to Midway.

  • Can I find deals for business class flights from Sicily to Midway?

    Yes. Cheapflights offers flight deals from Sicily to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Sicily to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Sicily to Chicago Midway Airport (average of $160). Flying from Sicily to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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