$543 Cheap Flights from Chicago (MDW) to Palermo (PMO)

View $543 flight on Tue, Dec 2, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Punta Raisi Airport (PMO)

Cheap Flights from Chicago to Palermo (MDW-PMO)

Prices were available within the past 7 days and start at $543 for one-way flights and $722 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air France
Wed, Dec 3 - Wed, Dec 10
MDW
Chicago
PMO
Palermo
$722 Roundtrip, found 1 day ago
$722
Roundtrip
found 1 day ago
Select Air France flight, departing Wed, Dec 3 from Chicago to Palermo, returning Wed, Dec 10, priced at $722 found 1 day ago
KLM
Wed, Dec 3 - Wed, Dec 10
MDW
Chicago
PMO
Palermo
$722 Roundtrip, found 1 day ago
$722
Roundtrip
found 1 day ago
Select KLM flight, departing Wed, Dec 3 from Chicago to Palermo, returning Wed, Dec 10, priced at $722 found 1 day ago
Air France
Wed, Dec 3 - Wed, Dec 10
MDW
Chicago
PMO
Palermo
$722 Roundtrip, found 1 day ago
$722
Roundtrip
found 1 day ago
Select Air France flight, departing Wed, Dec 3 from Chicago to Palermo, returning Wed, Dec 10, priced at $722 found 1 day ago
KLM
Mon, Feb 9 - Thu, Feb 26
MDW
Chicago
PMO
Palermo
$731 Roundtrip, found 3 days ago
$731
Roundtrip
found 3 days ago
Select KLM flight, departing Mon, Feb 9 from Chicago to Palermo, returning Thu, Feb 26, priced at $731 found 3 days ago
KLM
Mon, Dec 1 - Tue, Dec 16
MDW
Chicago
PMO
Palermo
$731 Roundtrip, found 1 day ago
$731
Roundtrip
found 1 day ago
Select KLM flight, departing Mon, Dec 1 from Chicago to Palermo, returning Tue, Dec 16, priced at $731 found 1 day ago
Delta
Wed, Dec 3 - Wed, Dec 10
MDW
Chicago
PMO
Palermo
$772 Roundtrip, found 1 day ago
$772
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Dec 3 from Chicago to Palermo, returning Wed, Dec 10, priced at $772 found 1 day ago
KLM
Sun, Dec 7 - Fri, Dec 19
MDW
Chicago
PMO
Palermo
$775 Roundtrip, found 1 day ago
$775
Roundtrip
found 1 day ago
Select KLM flight, departing Sun, Dec 7 from Chicago to Palermo, returning Fri, Dec 19, priced at $775 found 1 day ago
KLM
Mon, Dec 1 - Sun, Dec 21
MDW
Chicago
PMO
Palermo
$781 Roundtrip, found 1 day ago
$781
Roundtrip
found 1 day ago
Select KLM flight, departing Mon, Dec 1 from Chicago to Palermo, returning Sun, Dec 21, priced at $781 found 1 day ago
KLM
Mon, Dec 1 - Fri, Dec 19
MDW
Chicago
PMO
Palermo
$784 Roundtrip, found 1 day ago
$784
Roundtrip
found 1 day ago
Select KLM flight, departing Mon, Dec 1 from Chicago to Palermo, returning Fri, Dec 19, priced at $784 found 1 day ago
Air France
Sat, Nov 15 - Tue, Nov 25
MDW
Chicago
PMO
Palermo
$812 Roundtrip, found 3 days ago
$812
Roundtrip
found 3 days ago
Select Air France flight, departing Sat, Nov 15 from Chicago to Palermo, returning Tue, Nov 25, priced at $812 found 3 days ago

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Punta Raisi Airport (PMO) cost?
Lock in a cheap one-way flight from $543 or cheap return flight from $722 from Midway Intl. Airport (MDW) to Punta Raisi Airport (PMO) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Punta Raisi Airport (PMO)?
December is the least expensive month to fly from MDW to PMO. Traveling during quieter months is often the key to scoring lower fares.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Punta Raisi Airport (PMO)?
To find the cheapest airline flying from MDW to PMO, use Expedia's filter tool. Tailor your search based on what matters most to you, such as preferred carriers and number of stops. You can then sort your results by "Price (lowest to highest)" to see the cheapest fares upfront.
How many flights per day from Midway Intl. Airport (MDW) to Punta Raisi Airport (PMO)?
Direct flights from Midway Intl. Airport (MDW) to Punta Raisi Airport (PMO) aren't available daily, so you'll need to take a flight with a layover. Explore your options with Expedia's filters. Enter your dates and click on either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDW to PMO?
Usually you'll find the most flight options available on a Friday. Tuesdays are often the quietest.* But this can vary depending on the time of year, airline and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Punta Raisi Airport (PMO)?
Book a flight from Midway Intl. Airport (MDW) to Punta Raisi Airport (PMO) that leaves before 3 PM to reduce the likelihood of delays and cancellations. Later departures have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Punta Raisi Airport (PMO) last-minute?
Last-minute bookings from MDW to PMO are usually more expensive. To secure the lowest prices, start looking for flights as soon as possible. That being said, if you can play around with your travel dates, it's possible to score a cheap fare right before your journey.
Is it cheaper to book a MDW to PMO flight and hotel package?
Compared with arranging flights and hotels separately, booking a MDW to PMO flight and hotel package with Expedia could result in significant savings. Better still, having everything in one easy place will take the stress out of travel planning. Just pick your flights and select from our extensive range of stays, then customize your trip with other add-ons like activities and car rentals.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Punta Raisi Airport (PMO)?
Typically, you can reschedule or cancel your MDW to PMO flight. However, there may be additional fees, especially if you made your booking over 24 hours ago. Double-check your itinerary for the airline's rules and fees on flight changes, or if you'd like more details, go to our Customer Service portal.

Travel information

Travel information

Origin airport
Midway Intl.
Destination airport
Punta Raisi
Airlines serving
Air France, KLM
Roundtrip price
$722
Distance
5004 mi

Book with confidence

Book with confidence

Chicago to Palermo Flights

The cheapest times to fly from Chicago to Palermo

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Palermo are during the month of December. You can find some of the cheapest flights from Chicago to Palermo with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Palermo

Sunday is one of the best days to book for cheap flights from Chicago to Palermo: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Palermo

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Palermo in 2025. You can also book with separate airlines for your outbound and return journeys, from $543 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Palermo flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Palermo airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Palermo Flights

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*Available to One Key members.