$503 Cheap Flights from Chicago (ORD) to Palermo (PMO)

View $503 flight on Wed, Nov 12, 2025Opens in a new window

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Find available prices by choosing your travel dates.

Cheap Flights from Chicago to Palermo (ORD-PMO)

Prices were available within the past 7 days and start at $503 for one-way flights and $568 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Scandinavian Airlines
Mon, Sep 29 - Sat, Oct 18
ORD
Chicago
PMO
Palermo
$568 Roundtrip, found 1 day ago
$568
Roundtrip
found 1 day ago
Select Scandinavian Airlines flight, departing Mon, Sep 29 from Chicago to Palermo, returning Sat, Oct 18, priced at $568 found 1 day ago
Scandinavian Airlines
Mon, Oct 6 - Sat, Oct 11
ORD
Chicago
PMO
Palermo
$618 Roundtrip, found 1 day ago
$618
Roundtrip
found 1 day ago
Select Scandinavian Airlines flight, departing Mon, Oct 6 from Chicago to Palermo, returning Sat, Oct 11, priced at $618 found 1 day ago
Turkish Airlines
Wed, Oct 22 - Wed, Nov 5
ORD
Chicago
PMO
Palermo
$674 Roundtrip, found 1 day ago
$674
Roundtrip
found 1 day ago
Select Turkish Airlines flight, departing Wed, Oct 22 from Chicago to Palermo, returning Wed, Nov 5, priced at $674 found 1 day ago
Delta
Tue, May 13 - Thu, May 22
ORD
Chicago
PMO
Palermo
$683 Roundtrip, found 3 days ago
$683
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, May 13 from Chicago to Palermo, returning Thu, May 22, priced at $683 found 3 days ago
Turkish Airlines
Wed, Oct 15 - Wed, Oct 22
ORD
Chicago
PMO
Palermo
$686 Roundtrip, found 18 hours ago
$686
Roundtrip
found 18 hours ago
Select Turkish Airlines flight, departing Wed, Oct 15 from Chicago to Palermo, returning Wed, Oct 22, priced at $686 found 18 hours ago
Delta
Tue, Jul 29 - Tue, Jan 27
ORD
Chicago
PMO
Palermo
$692 Roundtrip, found 2 days ago
$692
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Jul 29 from Chicago to Palermo, returning Tue, Jan 27, priced at $692 found 2 days ago
ITA Airways
Sun, Jul 20 - Fri, Aug 29
ORD
Chicago
PMO
Palermo
$710 Roundtrip, found 2 days ago
$710
Roundtrip
found 2 days ago
Select ITA Airways flight, departing Sun, Jul 20 from Chicago to Palermo, returning Fri, Aug 29, priced at $710 found 2 days ago
British Airways
Mon, Nov 3 - Thu, Nov 13
ORD
Chicago
PMO
Palermo
$716 Roundtrip, found 1 day ago
$716
Roundtrip
found 1 day ago
Select British Airways flight, departing Mon, Nov 3 from Chicago to Palermo, returning Thu, Nov 13, priced at $716 found 1 day ago
KLM
Mon, Aug 11 - Thu, Aug 28
ORD
Chicago
PMO
Palermo
$727 Roundtrip, found 3 days ago
$727
Roundtrip
found 3 days ago
Select KLM flight, departing Mon, Aug 11 from Chicago to Palermo, returning Thu, Aug 28, priced at $727 found 3 days ago
TAP Portugal
Mon, Sep 22 - Wed, Oct 22
ORD
Chicago
PMO
Palermo
$738 Roundtrip, found 11 hours ago
$738
Roundtrip
found 11 hours ago
Select TAP Portugal flight, departing Mon, Sep 22 from Chicago to Palermo, returning Wed, Oct 22, priced at $738 found 11 hours ago
Flights from Chicago (ORD) to Palermo (PMO)
Origin airport
O'Hare Intl.
Destination airport
Punta Raisi
Airlines serving
Air Canada, Air France, American Airlines, Austrian Airlines, British Airways, Brussels Airlines, Delta, ITA Airways, Iberia, KLM, Lufthansa, Scandinavian Airlines, Swiss International Air Lines, TAP Portugal, Turkish Airlines, United
Roundtrip price
$568
Distance
5004 mi

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 September. 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 $503 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.

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Punta Raisi Airport (PMO) cost?
Discover the latest flight deals from ORD to PMO by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from ORD to PMO?
The cheapest flights from ORD to PMO are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from ORD to PMO?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from ORD to PMO. Sort your results by “Price (lowest to highest)” to snap up a great deal.
How many flights per day from O'Hare Intl. Airport (ORD) to Punta Raisi Airport (PMO)?
There are no daily nonstop flights departing from O’Hare Intl. Airport (ORD) to Punta Raisi Airport (PMO). But you can choose flights with layovers. Filter your search on Expedia to include one or more stops, and you’ll be soaring above the clouds in no time.
What day of the week has the most flights from ORD to PMO?
Typically you’ll find the greatest selection of flight options on a Friday. Tuesdays tend to be the quietest.* However, this can vary based on the season, 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 O'Hare Intl. Airport (ORD) to Punta Raisi Airport (PMO)?
Opt for a flight from O’Hare Intl. Airport (ORD) to Punta Raisi Airport (PMO) that takes off before 3 PM to reduce the likelihood of delays and cancellations. Departures after this hour are on average 22% more likely to be canceled.**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 O'Hare Intl. Airport (ORD) to Punta Raisi Airport (PMO) last-minute?
Booking your ticket from ORD to PMO right before your journey is usually more expensive. But if there’s some wiggle room with your itinerary, you could grab a cheap last-minute fare.
Is it cheaper to book an ORD to PMO flight and hotel package?
Booking an ORD to PMO flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Pick from our extensive range of stays and then add car rentals, flights and activities to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Punta Raisi Airport (PMO)?
It’s usually possible to cancel or reschedule your ORD to PMO flight. However, for bookings made more than 24 hours ago, additional charges may apply. Refer to your airline’s policies in your itinerary to see what changes are allowed and whether any costs are involved. You’ll also find more details on our Customer Service portal.

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*Available to One Key members.