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$506+ 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 3/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CTA
Dec 2 — Dec 91
Tue 12/2
Tue 12/9
1 adult, Economy
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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 November 2, 2025.

This KLM deal was found by Cheapflights users on 11/1. 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.
Tue 12/21:14 pmMDW - PMO
2 stops15h 26mKLM
Tue 12/166:10 amPMO - MDW
2 stops18h 50mKLM
Deal found 11/1$670
This KLM deal was found by Cheapflights users on 11/1. 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 11/291:15 pmMDW - PMO
2 stops14h 10mKLM
Sun 12/1410:00 amPMO - MDW
2 stops20h 47mKLM
Deal found 11/1$982
This KLM deal was found by Cheapflights users on 11/2. 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 12/1712:50 pmMDW - PMO
2 stops15h 50mMultiple Airlines
Wed 12/246:10 amPMO - MDW
2 stops18h 16mMultiple Airlines
Deal found 11/2$1,012
This Expedia deal was found by Cheapflights users on 11/2. 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.
Wed 12/1712:50 pmMDW - CTA
2 stops24h 55mAir France
Wed 12/246:00 amCTA - MDW
2 stops23h 22mAir France
Deal found 11/2$1,292
This KLM deal was found by Cheapflights users on 11/1. 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 11/85:25 pmMDW - CTA
2 stops18h 40mKLM
Sat 11/154:10 pmCTA - MDW
2 stops32h 58mKLM
Deal found 11/1$1,360
This Expedia deal was found by Cheapflights users on 11/2. 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.
Sun 11/91:05 pmMDW - CTA
2 stops22h 25mKLM
Sat 11/226:00 amCTA - MDW
2 stops19h 08mKLM
Deal found 11/2$1,702
This KLM deal was found by Cheapflights users on 11/1. 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.
Thu 12/253:25 pmMDW - PMO
2 stops16h 05mMultiple Airlines
Fri 1/96:10 amPMO - MDW
2 stops22h 59mMultiple Airlines
Deal found 11/1$2,403
This Air France deal was found by Cheapflights users on 11/1. 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/253:25 pmMDW - PMO
2 stops16h 05mAir France
Thu 1/86:10 amPMO - MDW
2 stops22h 59mAir France
Deal found 11/1$2,655

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 November 2, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$670
(KLM)

One-way from

$506
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$886
Provider with most accurate pricing for Chicago (CHI)-Catania Fontanarossa flight deals.
Search Deals
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. 18% potential increase in price ($208 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($38 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 2, 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

Tue 12/2

1:14 pm-11:40 am

2 stops15h 26m

Palermo Punta Raisi

Tue 12/16

6:10 am-6:00 pm

2 stops18h 50m

$670

ChicagoPalermo

MDW - PMO

MDWPMO

Chicago Midway

Sat 11/29

1:15 pm-10:25 am

2 stops14h 10m

Palermo Punta Raisi

Sun 12/14

10:00 am-11:47 pm

2 stops20h 47m

$982

ChicagoCatania

MDW - CTA

MDWCTA

Chicago Midway

Sat 3/14

9:30 am-11:55 am

2 stops20h 25m

Catania Fontanarossa

Sun 3/22

12:45 pm-4:25 pm

2 stops33h 40m

$995

ChicagoPalermo

MDW - PMO

MDWPMO

Chicago Midway

Wed 12/17

12:50 pm-11:40 am

2 stops15h 50m

Palermo Punta Raisi

Wed 12/24

6:10 am-5:26 pm

2 stops18h 16m

$1,012

ChicagoCatania

MDW - CTA

MDWCTA

Chicago Midway

Wed 12/17

12:50 pm-8:45 pm

2 stops24h 55m

Catania Fontanarossa

Wed 12/24

6:00 am-10:22 pm

2 stops23h 22m

$1,292

ChicagoLamezia Terme

MDW - SUF

MDWSUF

Chicago Midway

Mon 3/9

5:59 pm-11:00 pm

2 stops47h 01m

Lamezia Terme Intl

Thu 3/12

6:15 am-9:46 pm

2 stops21h 31m

$1,294

ChicagoCatania

MDW - CTA

MDWCTA

Chicago Midway

Mon 3/9

10:35 am-1:20 pm

2 stops20h 45m

Catania Fontanarossa

Wed 3/11

3:25 pm-6:34 pm

2 stops33h 09m

$1,357

ChicagoCatania

MDW - CTA

MDWCTA

Chicago Midway

Thu 4/9

5:59 pm-5:30 pm

2 stops16h 31m

Catania Fontanarossa

Wed 4/22

9:55 am-4:25 pm

2 stops37h 30m

$1,619

ChicagoCatania

MDW - CTA

MDWCTA

Chicago Midway

Tue 3/17

11:00 am-7:00 pm

3 stops26h 00m

Catania Fontanarossa

Tue 3/31

11:50 am-10:05 am

3 stops29h 15m

$2,395

ChicagoPalermo

MDW - PMO

MDWPMO

Chicago Midway

Thu 12/25

3:25 pm-2:30 pm

2 stops16h 05m

Palermo Punta Raisi

Fri 1/9

6:10 am-10:09 pm

2 stops22h 59m

$2,403

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 13 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 $670, KLM can have you in Sicily from Chicago Midway Airport in 15h 26m. 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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