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$565+ Cheap flights from Midway (MDW) to Sicily

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 12/31. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CTA
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap flight deals from Midway to Sicily

Cheapest flights from Midway to Sicily
Explore the most affordable flight options available from Midway to Sicily. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

This KLM deal was found by Cheapflights users on 12/16. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/319:50 amMDW - PMO
2 stops17h 35mKLM
Tue 1/66:10 amPMO - MDW
2 stops18h 24mKLM
Deal found 12/16$3,237

Find flight deals from Midway to Sicily

Keep the following information in mind while searching for Midway to Sicily flight deals. Data was last updated December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$769
(KLM)

One-way from

$565
(KLM)

Popular in

June

Cheapest in

February

Average price

$1,057
Provider with most accurate pricing for Chicago (CHI)-Catania Fontanarossa flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Catania Fontanarossa flights.
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From Chicago Midway to Sicily
Search Deals
One-way flight from Chicago Midway to Sicily
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($237 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($39 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Sicily 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 December 18, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Sicily that are best for you.

Fly from

Midway

Fly to

Sicily

Route

Depart

Return

Price

ChicagoPalermo

MDW - PMO

MDWPMO

Chicago Midway

Sat 1/31

10:46 am-2:30 pm

2 stops20h 44m

Palermo Punta Raisi

Sat 2/7

10:00 am-10:22 pm

2 stops19h 22m

$769

ChicagoPalermo

MDW - PMO

MDWPMO

Chicago Midway

Sat 1/17

5:31 pm-2:30 pm

2 stops37h 59m

Palermo Punta Raisi

Fri 1/30

6:10 am-10:22 pm

2 stops23h 12m

$788

ChicagoCatania

MDW - CTA

MDWCTA

Chicago Midway

Fri 1/30

1:49 pm-3:25 pm

2 stops18h 36m

Catania Fontanarossa

Fri 2/6

6:00 am-10:22 pm

2 stops23h 22m

$883

ChicagoCatania

MDW - CTA

MDWCTA

Chicago Midway

Mon 4/27

6:00 am-7:55 am

2 stops18h 55m

Catania Fontanarossa

Wed 5/6

9:55 am-4:25 pm

2 stops37h 30m

$1,058

ChicagoPalermo

MDW - PMO

MDWPMO

Chicago Midway

Fri 1/30

12:48 pm-1:40 pm

2 stops17h 52m

Palermo Punta Raisi

Fri 2/6

6:10 am-10:22 pm

2 stops23h 12m

$1,236

ChicagoPalermo

MDW - PMO

MDWPMO

Chicago Midway

Fri 4/17

1:00 pm-3:25 pm

2 stops19h 25m

Palermo Punta Raisi

Sun 4/26

1:00 pm-4:25 pm

2 stops34h 25m

$1,381

ChicagoCatania

MDW - CTA

MDWCTA

Chicago Midway

Wed 5/20

6:00 am-7:55 am

2 stops18h 55m

Catania Fontanarossa

Fri 5/29

9:55 am-9:45 pm

2 stops18h 50m

$1,798

ChicagoPalermo

MDW - PMO

MDWPMO

Chicago Midway

Wed 12/31

9:50 am-10:25 am

2 stops17h 35m

Palermo Punta Raisi

Tue 1/6

6:10 am-5:34 pm

2 stops18h 24m

$3,237

ChicagoPalermo

MDW - PMO

MDWPMO

Chicago Midway

Wed 12/31

9:50 am-10:25 am

2 stops17h 35m

$565

ChicagoPalermo

MDW - PMO

MDWPMO

Chicago Midway

Tue 4/21

5:25 pm-8:20 am

2 stops31h 55m

$592

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 12 results
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Best time to book a flight from Midway to Sicily

Have a flexible travel schedule? Discover the best time to fly to Sicily from Midway 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 Chicago Midway Airport to Sicily
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 Midway to Sicily. 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 Chicago Midway Airport to Sicily?

    For as low as $1,381, KLM can have you in Sicily from Chicago Midway Airport in 19h 25m. There are 5002 mi between Chicago Midway Airport and Sicily. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the most popular routes from Chicago Midway Airport to Sicily?

    The most popular route from Chicago Midway Airport to Sicily is Chicago Midway - Catania Fontanarossa. You may also consider Chicago Midway - Palermo Punta Raisi or Chicago Midway - Lamezia Terme Intl.

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

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

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

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

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

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

See more FAQs

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Alternative routes for Midway to Sicily

See prices for flight routes from nearby airports that may be better suited for you.
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