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$298+ 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 4/25. Fares are subject to change and may not be available on all flights or dates of travel.
CTA — MDW
Mar 8 — Mar 151
Sun 3/8
Sun 3/15
1 adult, Economy
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Cheap 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 February 6, 2026.

This Trip.com deal was found by Cheapflights users on 2/5. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/317:20 am
PMO
-
MDW
2 stops17h 02m
Multiple Airlines
Tue 4/141:23 pm
MDW
-
PMO
2 stops21h 57m
Multiple Airlines
Deal found 2/5$679
This Trip.com deal was found by Cheapflights users on 2/6. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/82:25 pm
PMO
-
MDW
2 stops35h 06m
Multiple Airlines
Sat 9/195:59 pm
MDW
-
PMO
2 stops14h 51m
Multiple Airlines
Deal found 2/6$688
This Trip.com deal was found by Cheapflights users on 2/6. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/143:10 pm
PMO
-
MDW
2 stops34h 26m
Multiple Airlines
Wed 4/292:12 pm
MDW
-
PMO
2 stops17h 13m
Multiple Airlines
Deal found 2/6$728
This Trip.com deal was found by Cheapflights users on 2/5. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/263:15 pm
PMO
-
MDW
2 stops38h 16m
Air France
Mon 3/212:45 pm
MDW
-
PMO
2 stops27h 50m
Air France
Deal found 2/5$785
This Trip.com deal was found by Cheapflights users on 2/4. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/303:10 pm
PMO
-
MDW
2 stops33h 44m
KLM
Sun 4/52:05 pm
MDW
-
PMO
2 stops21h 15m
KLM
Deal found 2/4$794
This KLM deal was found by Cheapflights users on 2/6. 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.
Mon 3/236:10 am
PMO
-
MDW
2 stops22h 21m
KLM
Mon 3/3010:45 am
MDW
-
PMO
2 stops16h 45m
KLM
Deal found 2/6$2,015
This KLM deal was found by Cheapflights users on 2/5. 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.
Sat 6/2010:05 am
PMO
-
MDW
2 stops18h 40m
KLM
Thu 6/251:00 pm
MDW
-
PMO
2 stops17h 40m
KLM
Deal found 2/5$2,060
This KLM deal was found by Cheapflights users on 2/4. 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.
Sat 3/216:10 am
PMO
-
MDW
2 stops17h 44m
KLM
Sat 3/282:05 pm
MDW
-
PMO
2 stops17h 20m
KLM
Deal found 2/4$2,206

Find flight deals from Sicily to Midway

Keep the following information in mind while searching for Sicily to Midway flight deals. Data was last updated February 6, 2026.

Round-trip from

$679
(Trip.com)

One-way from

$298
(Kiwi.com)
From Sicily to Chicago Midway
Search Deals
One-way flight from Sicily to Chicago Midway
Search Deals

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 February 6, 2026.
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

Tue 3/31

7:20 am-5:22 pm

2 stops17h 02m

Chicago Midway

Tue 4/14

1:23 pm-6:20 pm

2 stops21h 57m

$679

PalermoChicago

PMO - MDW

PMOMDW

Palermo Punta Raisi

Tue 4/14

3:10 pm-6:36 pm

2 stops34h 26m

Chicago Midway

Wed 4/29

2:12 pm-2:25 pm

2 stops17h 13m

$728

PalermoChicago

PMO - MDW

PMOMDW

Palermo Punta Raisi

Thu 2/26

3:15 pm-10:31 pm

2 stops38h 16m

Chicago Midway

Mon 3/2

12:45 pm-11:35 pm

2 stops27h 50m

$785

PalermoChicago

PMO - MDW

PMOMDW

Palermo Punta Raisi

Mon 3/30

3:10 pm-5:54 pm

2 stops33h 44m

Chicago Midway

Sun 4/5

2:05 pm-6:20 pm

2 stops21h 15m

$794

PalermoChicago

PMO - MDW

PMOMDW

Palermo Punta Raisi

Mon 3/23

6:10 am-10:31 pm

2 stops22h 21m

Chicago Midway

Mon 3/30

10:45 am-10:30 am

2 stops16h 45m

$2,015

PalermoChicago

PMO - MDW

PMOMDW

Palermo Punta Raisi

Sat 6/20

10:05 am-9:45 pm

2 stops18h 40m

Chicago Midway

Thu 6/25

1:00 pm-1:40 pm

2 stops17h 40m

$2,060

PalermoChicago

PMO - MDW

PMOMDW

Palermo Punta Raisi

Sat 3/21

6:10 am-5:54 pm

2 stops17h 44m

Chicago Midway

Sat 3/28

2:05 pm-1:25 pm

2 stops17h 20m

$2,206

PalermoChicago

PMO - MDW

PMOMDW

Palermo Punta Raisi

Sat 4/25

10:25 pm-10:05 am

3 stops42h 40m

$298

PalermoChicago

PMO - MDW

PMOMDW

Palermo Punta Raisi

Wed 4/22

5:35 pm-10:05 am

3 stops47h 30m

$304

PalermoChicago

PMO - MDW

PMOMDW

Palermo Punta Raisi

Mon 4/20

6:05 pm-10:05 am

3 stops47h 00m

$307

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/6

Showing 1-10 of 17 results
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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 33h 44m. 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.

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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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