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Cheap flights from Chicago Midway Airport to Palermo from $409

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Palermo departing on 11/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Chicago Midway Airport to Palermo

Cheap round-trip flights

Enter your travel dates to find the best prices.
KLM Logo
10:35 am - 2:20 pmMDW  Chicago Midway-PMO Palermo Punta Raisi
20h 45m2 stops Atlanta Hartsfield-Jackson Rome Fiumicino
KLM Logo
6:10 am - 10:10 pmPMO  Palermo Punta Raisi-MDW Chicago Midway
23h 00m2 stops Rome Fiumicino Atlanta Hartsfield-Jackson
$836KLM
Wed, Jan 20 - Wed, Jan 27
KLM Logo
1:22 pm - 2:20 pmMDW  Chicago Midway-PMO Palermo Punta Raisi
17h 58m2 stops Detroit Metropolitan Wayne County Rome Fiumicino
KLM Logo
10:05 am - 10:10 pmPMO  Palermo Punta Raisi-MDW Chicago Midway
19h 05m2 stops Rome Fiumicino Atlanta Hartsfield-Jackson
$916KLM
Sun, Dec 13 - Thu, Jan 7
KLM Logo
1:22 pm - 2:20 pmMDW  Chicago Midway-PMO Palermo Punta Raisi
17h 58m2 stops Detroit Metropolitan Wayne County Rome Fiumicino
KLM Logo
10:05 am - 10:10 pmPMO  Palermo Punta Raisi-MDW Chicago Midway
19h 05m2 stops Rome Fiumicino Atlanta Hartsfield-Jackson
$966KLM
Sat, Dec 12 - Thu, Jan 7
KLM Logo
1:00 pm - 2:20 pmMDW  Chicago Midway-PMO Palermo Punta Raisi
18h 20m2 stops Atlanta Hartsfield-Jackson Rome Fiumicino
KLM Logo
10:05 am - 10:10 pmPMO  Palermo Punta Raisi-MDW Chicago Midway
19h 05m2 stops Rome Fiumicino Atlanta Hartsfield-Jackson
$966KLM
Fri, Dec 11 - Thu, Jan 7
KLM Logo
1:19 pm - 1:40 pmMDW  Chicago Midway-PMO Palermo Punta Raisi
17h 21m2 stops Detroit Metropolitan Wayne County Rome Fiumicino
KLM Logo
6:10 am - 6:00 pmPMO  Palermo Punta Raisi-MDW Chicago Midway
18h 50m2 stops Rome Fiumicino Detroit Metropolitan Wayne County
$1,085KLM
Mon, Sep 21 - Tue, Oct 20
KLM Logo
1:19 pm - 1:40 pmMDW  Chicago Midway-PMO Palermo Punta Raisi
17h 21m2 stops Detroit Metropolitan Wayne County Rome Fiumicino
KLM Logo
6:10 am - 6:00 pmPMO  Palermo Punta Raisi-MDW Chicago Midway
18h 50m2 stops Rome Fiumicino Detroit Metropolitan Wayne County
$1,128KLM
Mon, Oct 5 - Tue, Oct 20
Multiple Airlines Logo
11:45 am - 11:10 pmMDW  Chicago Midway-PMO Palermo Punta Raisi
28h 25m3 stops Toronto Island Montreal Pierre Elliott Trudeau Intl Paris Orly
Multiple Airlines Logo
6:30 am - 2:35 pmPMO  Palermo Punta Raisi-MDW Chicago Midway
39h 05m3 stops Paris Orly Montreal Pierre Elliott Trudeau Intl Toronto Island
$1,133Multiple Airlines
Wed, Sep 2 - Wed, Sep 16
KLM Logo
1:27 pm - 1:40 pmMDW  Chicago Midway-PMO Palermo Punta Raisi
17h 13m2 stops Detroit Metropolitan Wayne County Rome Fiumicino
KLM Logo
12:15 pm - 10:33 pmPMO  Palermo Punta Raisi-MDW Chicago Midway
17h 18m2 stops Rome Fiumicino Atlanta Hartsfield-Jackson
$1,135KLM
Wed, Oct 7 - Thu, Oct 15
KLM Logo
1:27 pm - 1:40 pmMDW  Chicago Midway-PMO Palermo Punta Raisi
17h 13m2 stops Detroit Metropolitan Wayne County Rome Fiumicino
KLM Logo
6:10 am - 6:00 pmPMO  Palermo Punta Raisi-MDW Chicago Midway
18h 50m2 stops Rome Fiumicino Detroit Metropolitan Wayne County
$1,225KLM
Wed, Oct 7 - Fri, Oct 16

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Delta flights from Chicago Midway Airport to Palermo

Our best Delta deals on Chicago Midway Airport to Palermo flight tickets
Delta
Aug 15
MDW1:25 pmChicago Midway
18h 35m
2 stops
PMO3:00 pmPalermo Punta Raisi
Aug 24
PMO3:45 pmPalermo Punta Raisi
31h 30m
2 stops
MDW4:15 pmChicago Midway
$1,077
Delta
Oct 2
MDW1:19 pmChicago Midway
19h 31m
2 stops
PMO3:50 pmPalermo Punta Raisi
Oct 11
PMO4:45 pmPalermo Punta Raisi
31h 02m
2 stops
MDW4:47 pmChicago Midway
$1,253
Delta
Oct 2
MDW1:19 pmChicago Midway
19h 31m
2 stops
PMO3:50 pmPalermo Punta Raisi
Oct 11
PMO4:45 pmPalermo Punta Raisi
31h 02m
2 stops
MDW4:47 pmChicago Midway
$1,383

KLM flights from Chicago Midway Airport to Palermo

Our best KLM deals on Chicago Midway Airport to Palermo flight tickets
KLM
Jan 20
MDW10:35 amChicago Midway
20h 45m
2 stops
PMO2:20 pmPalermo Punta Raisi
Jan 27
PMO6:10 amPalermo Punta Raisi
23h 00m
2 stops
MDW10:10 pmChicago Midway
$836
KLM
Dec 13
MDW1:22 pmChicago Midway
17h 58m
2 stops
PMO2:20 pmPalermo Punta Raisi
Jan 7
PMO10:05 amPalermo Punta Raisi
19h 05m
2 stops
MDW10:10 pmChicago Midway
$916
KLM
Dec 11
MDW1:00 pmChicago Midway
18h 20m
2 stops
PMO2:20 pmPalermo Punta Raisi
Jan 7
PMO10:05 amPalermo Punta Raisi
19h 05m
2 stops
MDW10:10 pmChicago Midway
$966

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Palermo 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, momondo users made 832,500 searches. Data last updated August 11, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Palermo that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoPalermo

MDW Chicago Midway - PMO Palermo Punta Raisi

MDWPMO

Chicago Midway

Wed 1/20

10:35 am-2:20 pm

2 stops20h 45m

Palermo Punta Raisi

Wed 1/27

6:10 am-10:10 pm

2 stops23h 00m

$836

ChicagoPalermo

MDW Chicago Midway - PMO Palermo Punta Raisi

MDWPMO

Chicago Midway

Sun 12/13

1:22 pm-2:20 pm

2 stops17h 58m

Palermo Punta Raisi

Thu 1/7

10:05 am-10:10 pm

2 stops19h 05m

$916

ChicagoPalermo

MDW Chicago Midway - PMO Palermo Punta Raisi

MDWPMO

Chicago Midway

Sat 12/12

1:22 pm-2:20 pm

2 stops17h 58m

Palermo Punta Raisi

Thu 1/7

10:05 am-10:10 pm

2 stops19h 05m

$966

ChicagoPalermo

MDW Chicago Midway - PMO Palermo Punta Raisi

MDWPMO

Chicago Midway

Fri 12/11

1:00 pm-2:20 pm

2 stops18h 20m

Palermo Punta Raisi

Thu 1/7

10:05 am-10:10 pm

2 stops19h 05m

$966

ChicagoPalermo

MDW Chicago Midway - PMO Palermo Punta Raisi

MDWPMO

Chicago Midway

Mon 9/21

1:19 pm-1:40 pm

2 stops17h 21m

Palermo Punta Raisi

Tue 10/20

6:10 am-6:00 pm

2 stops18h 50m

$1,085

ChicagoPalermo

MDW Chicago Midway - PMO Palermo Punta Raisi

MDWPMO

Chicago Midway

Mon 10/5

1:19 pm-1:40 pm

2 stops17h 21m

Palermo Punta Raisi

Tue 10/20

6:10 am-6:00 pm

2 stops18h 50m

$1,128

ChicagoPalermo

MDW Chicago Midway - PMO Palermo Punta Raisi

MDWPMO

Chicago Midway

Wed 9/2

11:45 am-11:10 pm

3 stops28h 25m

Palermo Punta Raisi

Wed 9/16

6:30 am-2:35 pm

3 stops39h 05m

$1,133
Quickest round-trip

ChicagoPalermo

MDW Chicago Midway - PMO Palermo Punta Raisi

MDWPMO

Chicago Midway

Wed 10/7

1:27 pm-1:40 pm

2 stops17h 13m

Palermo Punta Raisi

Thu 10/15

12:15 pm-10:33 pm

2 stops17h 18m

$1,135

ChicagoPalermo

MDW Chicago Midway - PMO Palermo Punta Raisi

MDWPMO

Chicago Midway

Wed 10/7

1:27 pm-1:40 pm

2 stops17h 13m

Palermo Punta Raisi

Fri 10/16

6:10 am-6:00 pm

2 stops18h 50m

$1,225
Cheapest one-way

ChicagoPalermo

MDW Chicago Midway - PMO Palermo Punta Raisi

MDWPMO

Chicago Midway

Wed 11/25

1:00 pm-2:20 pm

2 stops18h 20m

$409

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 19 resultsSorted by cheapest first
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See travel insights to Palermo from

How to get the cheapest flight ticket from Chicago Midway Airport to Palermo

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Chicago Midway to Palermo Punta Raisi?

KLM and Delta are the most popular carriers operating from Chicago Midway to Palermo Punta Raisi

When to book flights from Chicago Midway Airport to Palermo

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Palermo according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Palermo (MDW to PMO) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Palermo

Fastest flight time

16h 31m

Direct flights

None
The fastest flight from Chicago Midway Airport to Palermo takes 16h 31m
There are no direct flights from Chicago Midway Airport to Palermo. There are no popular flight routes from Chicago Midway Airport to Palermo.
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Frequently asked questions about flying from Chicago Midway Airport to Palermo

  • How far is Chicago Midway to Palermo Punta Raisi by plane?

    A flight from Chicago Midway to Palermo Punta Raisi will travel around 5015.7 mi. In terms of flight time, this usually takes a little over 16h 31m.

  • When did momondo last update prices for flights from Chicago Midway Airport to Palermo Punta Raisi Airport?

    Prices for flights from Chicago Midway Airport to Palermo Punta Raisi Airport are refreshed on a daily basis.

  • How old do you have to be to fly from Chicago Midway Airport to Palermo Punta Raisi Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Palermo Punta Raisi Airport.

  • What documentation or ID do you need to fly to Palermo Punta Raisi Airport?

    The necessary travel and health documents for your Palermo Punta Raisi Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Palermo?

Book flights to Palermo if you plan to visit one of these locations
Cefalù
San Vito Lo Capo
Agrigento
Scopello
Sciacca
Ustica
Castellammare del Golfo
Alcamo

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Palermo?

Finding the right flight to Palermo from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Palermo quick and easy, saving you time and money.

Can I find flights from Chicago to Palermo with flexible booking policies on momondo?

Flights from Chicago to Palermo with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Chicago to Palermo?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Palermo.

I’m not ready to book a flight from Chicago to Palermo right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Chicago to Palermo flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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