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$379+ 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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CTA
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$1,004
(Delta)

One-way from

$404
(Kiwi.com)

Popular in

March

Cheapest in

January

Average price

$1,321
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. 2% potential increase in price ($21 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($37 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Delta deal was found by Cheapflights users on 6/12. 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 10/135:59 pmMDW - PMO
2 stops37h 26mDelta
Tue 10/216:10 amPMO - MDW
2 stops22h 34mDelta
Deal found 6/12$916
This Mytrip deal was found by Cheapflights users on 6/11. 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.
Wed 6/259:40 amMDW - PMO
3 stops21h 35mMultiple Airlines
Sat 6/287:10 amPMO - MDW
3 stops32h 35mMultiple Airlines
Deal found 6/11$1,113
This Mytrip deal was found by Cheapflights users on 6/10. 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 6/219:40 amMDW - CTA
3 stops28h 05mMultiple Airlines
Sat 6/286:00 amCTA - MDW
3 stops33h 45mMultiple Airlines
Deal found 6/10$1,171
This Delta deal was found by Cheapflights users on 6/12. 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 10/157:05 amCTA - MDW
2 stops21h 39mDelta
Deal found 6/12$1,192
This CheapTickets deal was found by Cheapflights users on 6/10. 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 CheapTickets is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/236:20 pmMDW - CTA
2 stops17h 20mAir France
Wed 7/309:55 amCTA - MDW
2 stops18h 47mAir France
Deal found 6/10$1,417
This Aunt Betty deal was found by Cheapflights users on 6/10. 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 Aunt Betty is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/231:09 pmMDW - CTA
2 stops17h 16mKLM
Wed 7/306:00 amCTA - MDW
2 stops19h 40mKLM
Deal found 6/10$1,652
This Delta deal was found by Cheapflights users on 6/12. 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.
Sun 7/279:25 amMDW - SUF
2 stops22h 10mDelta
Sun 8/36:15 amSUF - MDW
2 stops22h 27mDelta
Deal found 6/12$2,273

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 June 12, 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

Mon 10/13

5:59 pm-2:25 pm

2 stops37h 26m

Palermo Punta Raisi

Tue 10/21

6:10 am-9:44 pm

2 stops22h 34m

$916

ChicagoPalermo

MDW - PMO

MDWPMO

Chicago Midway

Wed 6/25

9:40 am-2:15 pm

3 stops21h 35m

Palermo Punta Raisi

Sat 6/28

7:10 am-8:45 am

3 stops32h 35m

$1,113

ChicagoCatania

MDW - CTA

MDWCTA

Chicago Midway

Sat 6/21

9:40 am-8:45 pm

3 stops28h 05m

Catania Fontanarossa

Sat 6/28

6:00 am-8:45 am

3 stops33h 45m

$1,171

ChicagoCatania

MDW - CTA

MDWCTA

Chicago Midway

Tue 7/22

6:00 am-7:55 am

2 stops18h 55m

Catania Fontanarossa

Tue 7/29

8:05 am-9:42 pm

2 stops20h 37m

$1,412

ChicagoCatania

MDW - CTA

MDWCTA

Chicago Midway

Wed 7/23

6:20 pm-6:40 pm

2 stops17h 20m

Catania Fontanarossa

Wed 7/30

9:55 am-9:42 pm

2 stops18h 47m

$1,417

ChicagoCatania

MDW - CTA

MDWCTA

Chicago Midway

Wed 7/23

1:09 pm-1:25 pm

2 stops17h 16m

Catania Fontanarossa

Wed 7/30

6:00 am-6:40 pm

2 stops19h 40m

$1,652

ChicagoLamezia Terme

MDW - SUF

MDWSUF

Chicago Midway

Sun 7/27

9:25 am-2:35 pm

2 stops22h 10m

Lamezia Terme Intl

Sun 8/3

6:15 am-9:42 pm

2 stops22h 27m

$2,273

ChicagoPalermo

MDW - PMO

MDWPMO

Chicago Midway

Sat 10/4

12:48 pm-9:50 pm

3 stops26h 02m

$379

ChicagoPalermo

MDW - PMO

MDWPMO

Chicago Midway

Wed 7/23

1:46 pm-3:00 pm

2 stops18h 14m

$598

ChicagoPalermo

MDW - PMO

MDWPMO

Chicago Midway

Fri 7/25

6:20 pm-3:25 pm

2 stops14h 05m

$654

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 12 results
1
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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

Rainfall in Sicily by month

Plan your trip to Sicily by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Sicily ranges from 0.2 - 3.9 inches per month. October is typically the wettest month, when rainfall can reach 3.9 in. July is typically the driest time to visit Sicily when rainfall is around 0.2 in.

Temperature in Sicily by month

Plan your trip to Sicily by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Sicily, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 78.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 55.4 F).

Reviews of airlines servicing Sicily

Get insights into the airlines that provide service to Sicily. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Sicily. Reviews last updated June 12, 2025.
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,950 reviews
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
KLM
7.8
Good
1,358 reviews
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Air France
7.5
Good
1,463 reviews
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Sicily one-way?

    For one-way options, check prices for Delta. According to our data, you can fly for as low as $598. Users have also found prices from $654 and $660 on Air France and KLM, respectively.

  • 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 - Palermo Punta Raisi. You may also consider Chicago Midway - Catania Fontanarossa 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.

  • 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 $1,318). 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 Bologna flights
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O'Hare Intl to Turin flights
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Midway to Turin flights
Midway to Genoa flights
O'Hare Intl to Ancona flights
Midway to Pisa flights

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