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$407+ Cheap flights from Palermo (PMO) to Chicago (CHI)

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 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
PMO — CHI
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Palermo to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Palermo (PMO) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 16, 2025.

Round-trip from

$558
(British Airways)

One-way from

$407
(Kiwi.com)

Popular in

August

Cheapest in

March

Average price

$591
From Palermo Punta Raisi to Chicago (CHI)
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One-way flight from Palermo Punta Raisi to Chicago (CHI)
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Highest demand for flights based on searches. 2% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($19 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 Palermo to Chicago

Cheapest flights from Palermo to Chicago
Explore the most affordable flight options available from Palermo to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

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 11/67:25 amPMO - ORD
2 stops16h 55mMultiple Airlines
Fri 11/146:30 pmORD - PMO
2 stops21h 55mMultiple Airlines
Deal found 9/15$566
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/63:05 pmPMO - ORD
1 stop32h 55mAmerican Airlines
Tue 11/118:40 pmORD - PMO
1 stop32h 55mAmerican Airlines
Deal found 9/14$596
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/63:05 pmPMO - ORD
1 stop31h 20mAmerican Airlines
Fri 11/146:35 pmORD - PMO
2 stops34h 40mAmerican Airlines
Deal found 9/15$601
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/238:10 pmPMO - ORD
1 stop24h 10mMultiple Airlines
Wed 10/2910:50 pmORD - PMO
1 stop30h 30mMultiple Airlines
Deal found 9/15$603
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/107:15 pmPMO - ORD
2 stops23h 55mMultiple Airlines
Wed 11/194:20 pmORD - PMO
1 stop11h 45mMultiple Airlines
Deal found 9/15$605
This British Airways 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1512:55 pmPMO - ORD
1 stop35h 05mBritish Airways
Wed 10/228:25 pmORD - PMO
2 stops39h 40mBritish Airways
Deal found 9/15$610
This Lufthansa 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 Lufthansa is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2212:10 pmPMO - ORD
1 stop13h 15mMultiple Airlines
Wed 12/36:50 pmORD - PMO
1 stop12h 05mMultiple Airlines
Deal found 9/14$658
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/155:50 amPMO - ORD
2 stops23h 17mMultiple Airlines
Wed 10/2210:40 amORD - PMO
2 stops17h 00mMultiple Airlines
Deal found 9/16$670
This lol.travel 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/237:20 amPMO - ORD
2 stops18h 00mITA Airways
Wed 10/2912:50 pmORD - PMO
2 stops16h 50mITA Airways
Deal found 9/15$684
This Lufthansa 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 Lufthansa is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/712:20 pmPMO - ORD
1 stop14h 45mMultiple Airlines
Sun 3/16:50 pmORD - PMO
1 stop16h 35mMultiple Airlines
Deal found 9/15$693
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/66:10 amPMO - MDW
2 stops19h 15mAir France
Fri 11/1412:47 pmMDW - PMO
2 stops15h 53mAir France
Deal found 9/15$960

Cheapflights Fare Finder

 
Customize your flight search to find flights from Palermo to Chicago 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 Palermo to Chicago that are best for you.

Fly from

Palermo

Fly to

Chicago

Route

Depart

Return

Price

PalermoChicago

PMO - ORD

PMOORD

Palermo Punta Raisi

Thu 11/6

3:05 pm-5:00 pm

1 stop32h 55m

Chicago O'Hare Intl

Fri 11/14

8:40 pm-12:15 pm

1 stop32h 35m

$596

PalermoChicago

PMO - ORD

PMOORD

Palermo Punta Raisi

Thu 11/6

3:05 pm-5:00 pm

1 stop32h 55m

Chicago O'Hare Intl

Tue 11/11

8:40 pm-12:35 pm

1 stop32h 55m

$596

PalermoChicago

PMO - ORD

PMOORD

Palermo Punta Raisi

Mon 11/10

7:15 pm-12:10 pm

2 stops23h 55m

Chicago O'Hare Intl

Wed 11/19

4:20 pm-11:05 am

1 stop11h 45m

$605

PalermoChicago

PMO - ORD

PMOORD

Palermo Punta Raisi

Wed 10/15

12:55 pm-5:00 pm

1 stop35h 05m

Chicago O'Hare Intl

Wed 10/22

8:25 pm-7:05 pm

2 stops39h 40m

$610

PalermoChicago

PMO - ORD

PMOORD

Palermo Punta Raisi

Thu 3/5

2:45 pm-4:20 pm

1 stop32h 35m

Chicago O'Hare Intl

Mon 3/9

7:50 pm-2:30 pm

1 stop12h 40m

$658

PalermoChicago

PMO - ORD

PMOORD

Palermo Punta Raisi

Sat 11/22

12:10 pm-6:25 pm

1 stop13h 15m

Chicago O'Hare Intl

Wed 12/3

6:50 pm-1:55 pm

1 stop12h 05m

$658

PalermoChicago

PMO - ORD

PMOORD

Palermo Punta Raisi

Wed 10/15

5:50 am-10:07 pm

2 stops23h 17m

Chicago O'Hare Intl

Wed 10/22

10:40 am-10:40 am

2 stops17h 00m

$670

PalermoChicago

PMO - ORD

PMOORD

Palermo Punta Raisi

Fri 11/7

12:20 pm-8:05 pm

1 stop14h 45m

Chicago O'Hare Intl

Sun 3/1

6:50 pm-6:25 pm

1 stop16h 35m

$693

PalermoChicago

PMO - MDW

PMOMDW

Palermo Punta Raisi

Thu 11/6

6:10 am-6:25 pm

2 stops19h 15m

Chicago Midway

Fri 11/14

12:47 pm-11:40 am

2 stops15h 53m

$960

PalermoChicago

PMO - MDW

PMOMDW

Palermo Punta Raisi

Thu 3/5

6:10 am-4:25 pm

2 stops41h 15m

Chicago Midway

Mon 3/9

1:05 pm-11:00 pm

2 stops27h 55m

$1,174

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 19 results
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Best time to book a flight from Palermo to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Palermo 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 Palermo to Chicago

What is the cheapest time of day to fly from PMO to CHI?

Find hourly flight availability from Palermo to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 16, 2025.

When flying from Palermo to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

How much does it cost to fly round-trip from Palermo to Chicago?

Related info for your journey

Find useful and relevant information for your journey from Palermo to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Palermo to Chicago?

    Palermo Punta Raisi (PMO), located 15.2 mi from the city center, is the airport you fly out of when you book flights from Palermo to Chicago. 0 airlines have flights from Punta Raisi to Chicago on a regular basis. Booking flights from Palermo Punta Raisi to Chicago should not be difficult; the airport handles an average of 0 outbound flights to Chicago per day.

  • How long is the flight from Palermo to Chicago?

    American Airlines, British Airways, and Air France can get you from Palermo to Chicago in just under 19h 15m. Your travel time can differ by up to 15h 50m. There are 5002 mi between Palermo and Chicago. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • Can I find deals for flights from Palermo to Chicago that include hotel bookings?

    Yes. In addition to deals on Palermo to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Palermo to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Palermo to Chicago.

  • Can I find deals for business class flights from Palermo to Chicago?

    Yes. Cheapflights offers flight deals from Palermo to Chicago 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 Palermo to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Palermo to Chicago (average of $245). Flying from Palermo to Chicago in March is currently the most expensive (average of $321). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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