$260+ Cheap flights from Chicago (CHI) to Palermo (PMO)
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 8/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PMO
Aug 1 — Aug 81
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Palermo with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Chicago to PalermoExplore the most affordable flight options available from Chicago to Palermo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 2, 2026.
Explore the most affordable flight options available from Chicago to Palermo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:15 pm
ORD
- PMO
1 stop14h 30m
Scandinavian Airlines
Wed 9/236:50 pm
PMO
- ORD
1 stop28h 20m
Scandinavian Airlines
Deal found 6/30![Scandinavian Airlines logo]()
$672
This Scandinavian Airlines deal was found by Cheapflights users on 6/30. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:15 pm
ORD
- PMO
1 stop14h 30m
Scandinavian Airlines
Fri 9/256:50 pm
PMO
- ORD
1 stop28h 20m
Scandinavian Airlines
Deal found 6/30![Scandinavian Airlines logo]()
$701
This Mytrip deal was found by Cheapflights users on 6/29. 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 8/193:00 pm
ORD
- PMO
1 stop18h 40m
Multiple Airlines
Wed 8/269:45 pm
PMO
- ORD
1 stop22h 25m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$705
This lol.travel deal was found by Cheapflights users on 6/27. 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.
Sun 8/93:00 pm
ORD
- PMO
1 stop16h 25m
ITA Airways
Mon 8/248:30 pm
PMO
- ORD
1 stop23h 40m
ITA Airways
Deal found 6/27![ITA Airways logo]()
$706
This Mytrip deal was found by Cheapflights users on 6/30. 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.
Mon 8/1011:05 am
ORD
- PMO
2 stops28h 10m
Multiple Airlines
Tue 8/1810:40 pm
PMO
- ORD
2 stops23h 10m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$707
This Mytrip deal was found by Cheapflights users on 7/1. 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 8/197:25 pm
ORD
- PMO
2 stops20h 20m
Multiple Airlines
Wed 9/99:45 pm
PMO
- ORD
3 stops29h 03m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$709
This oojo deal was found by Cheapflights users on 7/2. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/163:00 pm
ORD
- PMO
1 stop23h 05m
ITA Airways
Thu 8/276:10 am
PMO
- ORD
1 stop14h 00m
ITA Airways
Deal found 7/2![ITA Airways logo]()
$711
This Mytrip deal was found by Cheapflights users on 6/30. 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.
Mon 10/57:15 pm
ORD
- PMO
2 stops21h 35m
Multiple Airlines
Fri 10/167:35 pm
PMO
- ORD
2 stops27h 35m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$712
This oojo deal was found by Cheapflights users on 7/2. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/123:00 pm
ORD
- PMO
1 stop23h 05m
ITA Airways
Wed 8/193:10 pm
PMO
- ORD
1 stop29h 00m
ITA Airways
Deal found 7/2![ITA Airways logo]()
$713
This oojo deal was found by Cheapflights users on 6/28. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/43:00 pm
ORD
- PMO
1 stop24h 40m
ITA Airways
Tue 8/184:40 pm
PMO
- ORD
1 stop27h 30m
ITA Airways
Deal found 6/28![ITA Airways logo]()
$714
This Delta deal was found by Cheapflights users on 6/30. 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 8/101:25 pm
MDW
- PMO
2 stops18h 35m
Delta
Tue 8/183:45 pm
PMO
- MDW
2 stops31h 30m
Delta
Deal found 6/30![Delta logo]()
$834
This KLM deal was found by Cheapflights users on 7/1. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/201:28 pm
MDW
- PMO
2 stops17h 12m
KLM
Tue 11/2410:05 am
PMO
- MDW
2 stops19h 05m
KLM
Deal found 7/1![KLM logo]()
$835
Best flights from Chicago to PalermoDiscover carefully curated flight deals from Chicago to Palermo that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 2, 2026.
Discover carefully curated flight deals from Chicago to Palermo that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 2, 2026.
This ITA Airways deal was found by Cheapflights users on 7/1. 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/43:00 pm
ORD
- PMO
1 stop15h 40m
ITA Airways
Tue 8/188:25 pm
PMO
- ORD
1 stop23h 45m
ITA Airways
Deal found 7/1![ITA Airways logo]()
$722
This Turkish Airlines deal was found by Cheapflights users on 7/1. 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/238:10 pm
ORD
- PMO
1 stop29h 15m
Turkish Airlines
Wed 10/77:35 pm
PMO
- ORD
1 stop21h 05m
Turkish Airlines
Deal found 7/1![Turkish Airlines logo]()
$798
This Delta deal was found by Cheapflights users on 6/30. 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.
Tue 8/411:22 am
ORD
- PMO
2 stops20h 38m
Delta
Tue 8/183:45 pm
PMO
- ORD
2 stops31h 32m
Delta
Deal found 6/30![Delta logo]()
$833
This KLM deal was found by Cheapflights users on 7/1. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/201:28 pm
MDW
- PMO
2 stops17h 12m
KLM
Tue 11/2410:05 am
PMO
- MDW
2 stops19h 05m
KLM
Deal found 7/1![KLM logo]()
$835
This Air France deal was found by Cheapflights users on 7/1. 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 France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/21:18 pm
MDW
- PMO
2 stops18h 07m
Multiple Airlines
Mon 8/246:10 am
PMO
- MDW
2 stops23h 26m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$885
This TAP AIR PORTUGAL deal was found by Cheapflights users on 7/2. 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 TAP AIR PORTUGAL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:45 pm
ORD
- PMO
2 stops39h 35m
TAP AIR PORTUGAL
Thu 9/177:20 am
PMO
- ORD
2 stops39h 40m
TAP AIR PORTUGAL
Deal found 7/2![TAP AIR PORTUGAL logo]()
$908
This ITA Airways deal was found by Cheapflights users on 6/29. 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/133:00 pm
ORD
- PMO
1 stop15h 40m
ITA Airways
Thu 8/206:10 am
PMO
- ORD
1 stop14h 00m
ITA Airways
Deal found 6/29![ITA Airways logo]()
$764
This Turkish Airlines deal was found by Cheapflights users on 6/30. 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/218:10 pm
ORD
- PMO
1 stop15h 25m
Turkish Airlines
Tue 10/207:35 pm
PMO
- ORD
1 stop29h 40m
Turkish Airlines
Deal found 6/30![Turkish Airlines logo]()
$798
This Delta deal was found by Cheapflights users on 6/30. 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 8/101:25 pm
MDW
- PMO
2 stops18h 35m
Delta
Tue 8/183:45 pm
PMO
- MDW
2 stops31h 30m
Delta
Deal found 6/30![Delta logo]()
$834
This TAP AIR PORTUGAL deal was found by Cheapflights users on 6/29. 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 TAP AIR PORTUGAL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/206:00 pm
ORD
- PMO
2 stops22h 05m
TAP AIR PORTUGAL
Tue 10/204:10 pm
PMO
- ORD
2 stops30h 50m
TAP AIR PORTUGAL
Deal found 6/29![TAP AIR PORTUGAL logo]()
$932
This Turkish Airlines deal was found by Cheapflights users on 6/30. 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/98:10 pm
ORD
- PMO
1 stop29h 15m
Turkish Airlines
Tue 9/157:35 pm
PMO
- ORD
1 stop21h 05m
Turkish Airlines
Deal found 6/30![Turkish Airlines logo]()
$873
This KLM deal was found by Cheapflights users on 6/27. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/151:28 pm
MDW
- PMO
2 stops17h 12m
KLM
Tue 10/206:10 am
PMO
- MDW
2 stops18h 55m
KLM
Deal found 6/27![KLM logo]()
$965
This Delta deal was found by Cheapflights users on 6/29. 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.
Thu 8/139:24 am
MDW
- PMO
2 stops22h 36m
Delta
Thu 8/203:45 pm
PMO
- MDW
2 stops33h 48m
Delta
Deal found 6/29![Delta logo]()
$883
This KLM deal was found by Cheapflights users on 7/1. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/281:55 pm
ORD
- PMO
2 stops17h 30m
KLM
Thu 10/810:15 am
PMO
- ORD
2 stops17h 15m
KLM
Deal found 7/1![KLM logo]()
$990
This ITA Airways deal was found by Cheapflights users on 7/1. 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/123:00 pm
ORD
- PMO
1 stop15h 40m
ITA Airways
Sun 7/198:30 pm
PMO
- ORD
1 stop23h 40m
ITA Airways
Deal found 7/1![ITA Airways logo]()
$996
This TAP AIR PORTUGAL deal was found by Cheapflights users on 6/29. 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 TAP AIR PORTUGAL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:00 pm
ORD
- PMO
2 stops21h 30m
TAP AIR PORTUGAL
Sat 9/267:20 am
PMO
- ORD
2 stops39h 40m
TAP AIR PORTUGAL
Deal found 6/29![TAP AIR PORTUGAL logo]()
$1,032
This Delta deal was found by Cheapflights users on 7/1. 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.
Sat 8/151:25 pm
MDW
- PMO
2 stops15h 50m
Delta
Sat 8/224:00 pm
PMO
- MDW
2 stops33h 33m
Delta
Deal found 7/1![Delta logo]()
$1,088
This KLM deal was found by Cheapflights users on 6/28. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/171:19 pm
MDW
- PMO
2 stops17h 21m
KLM
Mon 9/286:10 am
PMO
- MDW
2 stops19h 23m
KLM
Deal found 6/28![KLM logo]()
$1,166
This Delta deal was found by Cheapflights users on 6/27. 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.
Fri 10/21:19 pm
MDW
- PMO
2 stops19h 31m
Delta
Sun 10/114:45 pm
PMO
- MDW
2 stops30h 54m
Delta
Deal found 6/27![Delta logo]()
$1,112
This Delta deal was found by Cheapflights users on 6/30. 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 8/101:25 pm
MDW
- PMO
2 stops18h 35m
Delta
Mon 8/173:45 pm
PMO
- MDW
2 stops31h 30m
Delta
Deal found 6/30![Delta logo]()
$1,169
This KLM deal was found by Cheapflights users on 6/30. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/241:19 pm
MDW
- PMO
2 stops17h 21m
KLM
Mon 10/126:10 am
PMO
- MDW
2 stops18h 55m
KLM
Deal found 6/30![KLM logo]()
$1,331
This Delta deal was found by Cheapflights users on 6/29. 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.
Wed 8/199:24 am
MDW
- PMO
2 stops22h 36m
Delta
Wed 8/263:45 pm
PMO
- MDW
2 stops31h 30m
Delta
Deal found 6/29![Delta logo]()
$1,228
This Delta deal was found by Cheapflights users on 7/2. 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.
Wed 7/221:18 pm
MDW
- PMO
2 stops18h 42m
Delta
Tue 8/43:45 pm
PMO
- MDW
2 stops31h 30m
Delta
Deal found 7/2![Delta logo]()
$1,239
Last-minute flights from Chicago to PalermoDiscover last-minute flight deals from Chicago to Palermo. Data last updated July 2, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Palermo. Data last updated July 2, 2026 and is based on user searches.
This oojo deal was found by Cheapflights users on 6/27. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/123:00 pm
ORD
- PMO
1 stop21h 45m
ITA Airways
Sun 7/196:10 am
PMO
- ORD
1 stop14h 00m
ITA Airways
Deal found 6/27![ITA Airways logo]()
$896
This Air France deal was found by Cheapflights users on 6/30. 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 France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/125:10 pm
ORD
- PMO
1 stop14h 50m
Multiple Airlines
Sun 7/196:10 am
PMO
- ORD
2 stops17h 13m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$1,222
This Air France deal was found by Cheapflights users on 7/1. 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 France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/21:18 pm
MDW
- PMO
2 stops18h 07m
Multiple Airlines
Mon 8/246:10 am
PMO
- MDW
2 stops23h 26m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$885
This Aunt Betty deal was found by Cheapflights users on 6/30. 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.
Sun 8/910:54 am
MDW
- PMO
2 stops17h 26m
Multiple Airlines
Mon 8/249:50 am
PMO
- MDW
2 stops19h 46m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$913
This Delta deal was found by Cheapflights users on 6/30. 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 8/101:25 pm
MDW
- PMO
2 stops18h 35m
Delta
Tue 8/183:45 pm
PMO
- MDW
2 stops31h 30m
Delta
Deal found 6/30![Delta logo]()
$834
This Delta deal was found by Cheapflights users on 6/30. 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 8/101:25 pm
MDW
- PMO
2 stops18h 35m
Delta
Mon 8/173:45 pm
PMO
- MDW
2 stops31h 30m
Delta
Deal found 6/30![Delta logo]()
$1,169
This Delta deal was found by Cheapflights users on 6/29. 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.
Thu 8/139:24 am
MDW
- PMO
2 stops22h 36m
Delta
Thu 8/203:45 pm
PMO
- MDW
2 stops33h 48m
Delta
Deal found 6/29![Delta logo]()
$883
This Trip.com deal was found by Cheapflights users on 6/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/141:25 pm
MDW
- PMO
2 stops18h 50m
Air France
Fri 8/216:10 am
PMO
- MDW
2 stops23h 26m
Air France
Deal found 6/30![Air France logo]()
$920
This Delta deal was found by Cheapflights users on 7/2. 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.
Sat 8/151:25 pm
MDW
- PMO
2 stops18h 35m
Delta
Mon 8/243:45 pm
PMO
- MDW
2 stops31h 30m
Delta
Deal found 7/2![Delta logo]()
$952
This Delta deal was found by Cheapflights users on 7/1. 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.
Sat 8/151:25 pm
MDW
- PMO
2 stops15h 50m
Delta
Sat 8/224:00 pm
PMO
- MDW
2 stops33h 33m
Delta
Deal found 7/1![Delta logo]()
$1,088
This BYOjet deal was found by Cheapflights users on 7/2. 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 BYOjet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/1612:46 pm
MDW
- PMO
2 stops18h 29m
KLM
Sun 8/2310:15 pm
PMO
- MDW
2 stops25h 00m
KLM
Deal found 7/2![KLM logo]()
$907
This Delta deal was found by Cheapflights users on 6/29. 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.
Wed 8/199:24 am
MDW
- PMO
2 stops22h 36m
Delta
Wed 8/263:45 pm
PMO
- MDW
2 stops31h 30m
Delta
Deal found 6/29![Delta logo]()
$1,228
One-way flights from Chicago to PalermoSearch for one-way flight options from Chicago to Palermo. Find affordable one-way fares based on user searches. Data last updated July 2, 2026.
Search for one-way flight options from Chicago to Palermo. Find affordable one-way fares based on user searches. Data last updated July 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:25 pm
ORD
- PMO
3 stops40h 35m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 6/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/307:25 pm
ORD
- PMO
3 stops34h 30m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$270
This Kiwi.com deal was found by Cheapflights users on 6/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/317:25 pm
ORD
- PMO
3 stops46h 00m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$272
This Kiwi.com deal was found by Cheapflights users on 6/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/117:25 pm
ORD
- PMO
2 stops16h 05m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$312
This Kiwi.com deal was found by Cheapflights users on 6/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/310:25 pm
ORD
- PMO
2 stops43h 35m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 6/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/107:25 pm
ORD
- PMO
2 stops30h 40m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$318
This Kiwi.com deal was found by Cheapflights users on 6/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/57:25 pm
ORD
- PMO
2 stops22h 40m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 6/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/127:25 pm
ORD
- PMO
2 stops17h 20m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 6/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/27:25 pm
ORD
- PMO
2 stops20h 15m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$326
This Kiwi.com deal was found by Cheapflights users on 6/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2510:25 am
MDW
- PMO
3 stops27h 55m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$388
This Kiwi.com deal was found by Cheapflights users on 6/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2610:25 am
MDW
- PMO
3 stops26h 15m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$415
This Kiwi.com deal was found by Cheapflights users on 6/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/912:36 pm
MDW
- PMO
3 stops45h 34m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$416
Find flight deals from Chicago to Palermo
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Palermo (PMO). 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 July 2, 2026.
Most accurate provider | Ovago 3 stars |
|---|---|
Most trusted provider | Ovago 3 stars |
Round-trip from | $672 (Kiwi.com) |
One-way from | $260 (Kiwi.com) |
Popular in | December |
Cheapest in | August |
Average price | $1,062 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago 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, Cheapflights users made 2,558,603 searches. Data last updated July 2, 2026.
Use the filters below to find and compare flights from Chicago to Palermo that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoPalermo
ORD - PMO
ORDPMO
Chicago O'Hare Intl
Tue 8/4
3:00 pm-1:40 pm
1 stop15h 40m
Palermo Punta Raisi
Tue 8/18
8:25 pm-1:10 pm
1 stop23h 45m
$722
Quickest round-trip
ChicagoPalermo
ORD - PMO
ORDPMO
Chicago O'Hare Intl
Thu 8/13
3:00 pm-1:40 pm
1 stop15h 40m
Palermo Punta Raisi
Thu 8/20
6:10 am-1:10 pm
1 stop14h 00m
$764
ChicagoPalermo
ORD - PMO
ORDPMO
Chicago O'Hare Intl
Wed 9/23
8:10 pm-8:25 am
1 stop29h 15m
Palermo Punta Raisi
Wed 10/7
7:35 pm-9:40 am
1 stop21h 05m
$798
ChicagoPalermo
ORD - PMO
ORDPMO
Chicago O'Hare Intl
Mon 9/21
8:10 pm-6:35 pm
1 stop15h 25m
Palermo Punta Raisi
Tue 10/20
7:35 pm-6:15 pm
1 stop29h 40m
$798
ChicagoPalermo
ORD - PMO
ORDPMO
Chicago O'Hare Intl
Tue 8/4
11:22 am-3:00 pm
2 stops20h 38m
Palermo Punta Raisi
Tue 8/18
3:45 pm-4:17 pm
2 stops31h 32m
$833
ChicagoPalermo
MDW - PMO
MDWPMO
Chicago Midway
Mon 8/10
1:25 pm-3:00 pm
2 stops18h 35m
Palermo Punta Raisi
Tue 8/18
3:45 pm-4:15 pm
2 stops31h 30m
$834
ChicagoPalermo
MDW - PMO
MDWPMO
Chicago Midway
Tue 10/20
1:28 pm-1:40 pm
2 stops17h 12m
Palermo Punta Raisi
Tue 11/24
10:05 am-10:10 pm
2 stops19h 05m
$835
ChicagoPalermo
ORD - PMO
ORDPMO
Chicago O'Hare Intl
Wed 9/9
8:10 pm-8:25 am
1 stop29h 15m
Palermo Punta Raisi
Tue 9/15
7:35 pm-9:40 am
1 stop21h 05m
$873
ChicagoPalermo
MDW - PMO
MDWPMO
Chicago Midway
Thu 8/13
9:24 am-3:00 pm
2 stops22h 36m
Palermo Punta Raisi
Thu 8/20
3:45 pm-6:33 pm
2 stops33h 48m
$883
ChicagoPalermo
MDW - PMO
MDWPMO
Chicago Midway
Sun 8/2
1:18 pm-2:25 pm
2 stops18h 07m
Palermo Punta Raisi
Mon 8/24
6:10 am-10:36 pm
2 stops23h 26m
$885
Showing 1-10 of 41 resultsSorted by cheapest first
Compare providers for flights from Chicago to Palermo
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Palermo in July.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Palermo flights, users find the pricing of Ovago to be most consistent on Cheapflights vs. Ovago Users can find the same prices on Chicago-Palermo flight deals on Cheapflights vs. Ovago >95% of the time. Price accuracy is based on data collected from Chicago-Palermo flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Palermo flights, Cheapflights users trust Ovago the most. Ovago has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Palermo flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Chicago to Palermo
Have a flexible travel schedule? Discover the best time to fly to Palermo from Chicago with our price prediction graph.
CHI-PMO
ORD-PMO
MDW-PMO
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 to Palermo
CHI-PMO
ORD-PMO
MDW-PMO
What is the cheapest month to book a flight from Chicago to Palermo?
Currently, August is the cheapest month in which you can book a flight from Chicago to Palermo (average of $56). Flying from Chicago to Palermo in May is currently the most expensive (average of $674). 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.
How much does it cost to fly round-trip from Chicago to Palermo?
How far ahead should I book a flight from Chicago to Palermo?
The price you pay for your flight from Chicago to Palermo may vary depending on when you book. For the best chance of a lower fare, look to book 55 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Reviews of airlines servicing Palermo
Get insights into the airlines that provide service to Palermo. 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 Palermo. Reviews last updated July 2, 2026.
Read through reviews of airlines operating flights from Chicago to Palermo, such as SWISS,Turkish Airlines, andLufthansa. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Food
7.1
Entertainment
6.8
Crew
8.3
Boarding
7.7
Comfort
7.4
Overall
7.5
Reviews
1 / 20
6.0
GoodCFJ,Mar 2026
ZRH - VCE
Food
7.1
Entertainment
6.8
Crew
8.3
Boarding
7.7
Comfort
7.4
Overall
7.5
Reviews
1 / 20
6.0
GoodCFJ,Mar 2026
ZRH - VCE
Food
7.1
Entertainment
6.8
Crew
8.3
Boarding
7.7
Comfort
7.4
Overall
7.5
Reviews
1 / 20
6.0
GoodCFJ,Mar 2026
ZRH - VCE
Food
7.1
Entertainment
6.8
Crew
8.3
Boarding
7.7
Comfort
7.4
Overall
7.5
Reviews
1 / 20
6.0
GoodCFJ,Mar 2026
ZRH - VCE
Food
7.1
Entertainment
6.8
Crew
8.3
Boarding
7.7
Comfort
7.4
Overall
7.5
Reviews
1 / 20
6.0
GoodCFJ,Mar 2026
ZRH - VCE
Related info for your journey
Find useful and relevant information for your journey from Chicago to Palermo. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Palermo?
Book flights to Palermo if you plan to visit one of these locationsAgrigento
Cefalù
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Chicago and Palermo flights
Browse other Chicago and Palermo flight options. Last updated on July 2, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on July 2, 2026.
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Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from Chicago to Palermo
Discover the top 4 airlines that operate flights from Chicago to Palermo. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$533 | Average$740 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$596 | Average$932 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$683 | Average$1,053 | FlexibilityNo cancel fee | On-time81% | |
| Cheapest$778 | Average$1,284 | FlexibilityNo cancel fee | On-time76% |