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$260+ 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 9/25. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CTA
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Midway to Sicily

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

Round-trip from

$890
(Expedia)

One-way from

$260
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$901
From Chicago Midway to Sicily
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One-way flight from Chicago Midway to Sicily
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Highest demand for flights based on searches. 15% potential increase in price ($173 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($36 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 16, 2025.

This KLM 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/176:23 pmMDW - CTA
2 stops20h 47mKLM
Mon 10/2011:40 amCTA - MDW
2 stops37h 45mKLM
Deal found 9/15$1,100
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/66:00 amMDW - CTA
2 stops18h 55mDelta
Wed 10/159:55 amCTA - MDW
2 stops19h 19mDelta
Deal found 9/15$1,579
This Mytrip deal was found by Cheapflights users on 9/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/249:35 amMDW - PMO
3 stops21h 50mMultiple Airlines
Fri 10/316:20 amPMO - MDW
3 stops35h 30mMultiple Airlines
Deal found 9/16$1,654
This KLM deal was found by Cheapflights users on 9/14. 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.
Fri 10/171:08 pmMDW - PMO
2 stops26h 22mKLM
Tue 10/216:10 amPMO - MDW
2 stops19h 15mKLM
Deal found 9/14$2,055
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/3011:00 amMDW - SUF
3 stops23h 10mMultiple Airlines
Thu 11/66:10 amSUF - MDW
3 stops34h 55mMultiple Airlines
Deal found 9/15$2,431
This Mytrip deal was found by Cheapflights users on 9/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/279:35 amMDW - SUF
3 stops22h 00mMultiple Airlines
Tue 9/3011:15 amSUF - MDW
3 stops32h 48mMultiple Airlines
Deal found 9/14$3,229
This Mytrip deal was found by Cheapflights users on 9/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/299:35 amMDW - PMO
3 stops18h 55mMultiple Airlines
Thu 10/25:50 amPMO - MDW
3 stops33h 49mMultiple Airlines
Deal found 9/16$3,471
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/165:04 pmMDW - CTA
2 stops17h 26mDelta
Mon 10/208:55 amCTA - MDW
2 stops20h 19mDelta
Deal found 9/15$13,948

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 September 16, 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

ChicagoCatania

MDW - CTA

MDWCTA

Chicago Midway

Fri 10/17

6:23 pm-10:10 pm

2 stops20h 47m

Catania Fontanarossa

Mon 10/20

11:40 am-6:25 pm

2 stops37h 45m

$1,100

ChicagoCatania

MDW - CTA

MDWCTA

Chicago Midway

Mon 10/6

6:00 am-7:55 am

2 stops18h 55m

Catania Fontanarossa

Wed 10/15

9:55 am-10:14 pm

2 stops19h 19m

$1,579

ChicagoPalermo

MDW - PMO

MDWPMO

Chicago Midway

Fri 10/24

9:35 am-2:25 pm

3 stops21h 50m

Palermo Punta Raisi

Fri 10/31

6:20 am-11:50 am

3 stops35h 30m

$1,654

ChicagoPalermo

MDW - PMO

MDWPMO

Chicago Midway

Fri 10/17

1:08 pm-10:30 pm

2 stops26h 22m

Palermo Punta Raisi

Tue 10/21

6:10 am-6:25 pm

2 stops19h 15m

$2,055

ChicagoLamezia Terme

MDW - SUF

MDWSUF

Chicago Midway

Thu 10/30

11:00 am-4:10 pm

3 stops23h 10m

Lamezia Terme Intl

Thu 11/6

6:10 am-10:05 am

3 stops34h 55m

$2,431

ChicagoLamezia Terme

MDW - SUF

MDWSUF

Chicago Midway

Sat 9/27

9:35 am-2:35 pm

3 stops22h 00m

Lamezia Terme Intl

Tue 9/30

11:15 am-1:03 pm

3 stops32h 48m

$3,229

ChicagoPalermo

MDW - PMO

MDWPMO

Chicago Midway

Mon 9/29

9:35 am-11:30 am

3 stops18h 55m

Palermo Punta Raisi

Thu 10/2

5:50 am-8:39 am

3 stops33h 49m

$3,471

ChicagoCatania

MDW - CTA

MDWCTA

Chicago Midway

Thu 10/16

5:04 pm-5:30 pm

2 stops17h 26m

Catania Fontanarossa

Mon 10/20

8:55 am-10:14 pm

2 stops20h 19m

$13,948

ChicagoPalermo

MDW - PMO

MDWPMO

Chicago Midway

Thu 9/25

4:56 pm-11:15 pm

3 stops47h 19m

$260

ChicagoCatania

MDW - CTA

MDWCTA

Chicago Midway

Thu 10/30

5:56 pm-10:35 am

3 stops58h 39m

$278

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 16 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 $1,579, KLM can have you in Sicily from Chicago Midway Airport in 18h 55m. There are 5116 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 - Lamezia Terme Intl or Chicago Midway - Palermo Punta Raisi.

  • 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.

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

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Sicily (average of $667). Flying from Chicago Midway Airport to Sicily in June is currently the most expensive (average of $1,315). 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

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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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Midway to Palermo flights

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