$382 Cheap flight deals from Chicago (CHI) to Palermo (PMO)

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This Weekend's Flight Deals from Chicago to Palermo

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Aug 16 - Fri, Aug 21
ORD
O'Hare Intl.
PMO
Punta Raisi
$1,263 Roundtrip, found 1 day ago
$1,263
Roundtrip
found 1 day ago
Select Iberia flight, departing Sun, Aug 16 from O'Hare Intl. to Punta Raisi, returning Fri, Aug 21, priced at $1,263 found 1 day ago

Airfares from $382 One Way, $747 Round Trip from Chicago to Palermo

Prices starting at $747 for return flights and $382 for one-way flights to Palermo were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon, Oct 5 - Tue, Oct 20
ORD
Chicago
PMO
Palermo
$747 Roundtrip, found 1 day ago
$747
Roundtrip
found 1 day ago
Select Turkish Airlines flight, departing Mon, Oct 5 from Chicago to Palermo, returning Tue, Oct 20, priced at $747 found 1 day ago
Mon, Aug 17 - Fri, Aug 28
ORD
Chicago
PMO
Palermo
$805 Roundtrip, found 5 days ago
$805
Roundtrip
found 5 days ago
Select Swiss International Air Lines flight, departing Mon, Aug 17 from Chicago to Palermo, returning Fri, Aug 28, priced at $805 found 5 days ago
Wed, Aug 19 - Tue, Aug 25
ORD
Chicago
PMO
Palermo
$814 Roundtrip, found 6 days ago
$814
Roundtrip
found 6 days ago
Select Lufthansa flight, departing Wed, Aug 19 from Chicago to Palermo, returning Tue, Aug 25, priced at $814 found 6 days ago
Wed, Aug 26 - Wed, Sep 2
ORD
Chicago
PMO
Palermo
$833 Roundtrip, found 7 hours ago
$833
Roundtrip
found 7 hours ago
Select ITA Airways flight, departing Wed, Aug 26 from Chicago to Palermo, returning Wed, Sep 2, priced at $833 found 7 hours ago
Wed, Nov 25 - Sat, Dec 5
ORD
Chicago
PMO
Palermo
$849 Roundtrip, found 1 day ago
$849
Roundtrip
found 1 day ago
Select TAP Portugal flight, departing Wed, Nov 25 from Chicago to Palermo, returning Sat, Dec 5, priced at $849 found 1 day ago

Palermo economy flight packages

Price found within the past 48 hours. Click for updated prices.
CDSHotels Terrasini - Città del Mare
4.0-star property

CDSHotels Terrasini - Città del Mare

6.8/10 (286 reviews)

Sep 25 - Sep 30

5 night stay

Chicago (CHI) to Palermo (PMO)

ITA Airways • Non-stop roundtrip • Coach
Price was $1,438, price is now $1,290 per person
$1,290
per person
found 9 hours ago
Great views, and plenty of pools. Food is less than ideal. Gym is from the 1900's. Everything is super rusty. It's 'open air' and open 4 hours daily only: 10am to12pm and 4pm to 6pm. Considering its super hot, its not ideal. Staff - hit and miss. Some really nice and some are very unhelpful. For example when i asked for a taxi to go to the next town which is an 8 minute ride away, I was only given one option which was to book a car through the Hotel at 73 Euros. Was told I could try and book my own taxi if i managed to get one - ie was discouraged nor given any help. The day after, I found out I could have taken the bus at Eur1.50 Fully inclusive means b'fast, lunch and dinner only essentially . The only other snacks are just croissants and available only in certain places , and doughy pizza at 6pm. There is no food shop close by - so can only buy extra food from property or be stuck with food of the restaurant. They offer 3 other restaurants - but its a mission to book them and to be accepted. Water - for some reason they do not like guests filling own bottle, instead have to waste paper cups each time.

Reviewed on Aug 11, 2026

The Signature Level at Grand Palladium Sicilia Resort & Spa
5.0-star property

The Signature Level at Grand Palladium Sicilia Resort & Spa

9.2/10 Wonderful! (28 reviews)

Sep 25 - Sep 30

5 night stay

Chicago (CHI) to Palermo (PMO)

ITA Airways • Non-stop roundtrip • Coach
Price was $2,677, price is now $2,225 per person
$2,225
per person
found 9 hours ago
We enjoyed our all inclusive holiday at Grand Palladium Sicily. We stayed at signature level, but I don't think it's really worth it to pay extra - there is a separate pool for signature level, but we couldn't get a sunbed there due to guests reserving them with towels early in the morning. There is a separate restaurant for breakfast and lunch for signature level, but the main buffet is bigger. I could not fault the setting, cleanliness, and staff, but there are a few negatives to mention: More vegetarian options are needed at all the restaurants, it was quite lacking. There should be dedicated smoking areas instead of smokers allowed to smoke anywhere, as someone stinking out the outside bar with a cigar ruins the enjoyment and atmosphere of those areas. The in-room entertainment is very poor .. only news channels, or paying €7 for a film, and finally the app also doesn't work half the time, which is frustrating as it's needed for looking at menus and making reservations. So, mostly great, but a few things which could be improved. The beach was nice although stoney (but we knew this when booking). The hotel should enforce evicting people from sunbeds left unattended with a towel on for 30 mins so that everyone can have a chance to sit by the pool. There are signs up that say this will happen, but no one is actually doing it.

Reviewed on Jul 20, 2026

Grand Palladium Sicilia Resort & Spa
5.0-star property

Grand Palladium Sicilia Resort & Spa

8.8/10 Excellent! (184 reviews)

Sep 25 - Sep 30

5 night stay

Chicago (CHI) to Palermo (PMO)

ITA Airways • Non-stop roundtrip • Coach
Price was $2,343, price is now $1,982 per person
$1,982
per person
found 9 hours ago
Really nice stay at the Grand Palladium Sicilia. I will say that some of areas of room could do with updating. Some of the wardrobes had stains on. The food was excellent! A la carte restaurants were all fantastic and there was such a vast amount of choice and variety in the buffet with a different themed cuisine each night. Everyone was exceptionally helpful and the animation team did a brilliant job throughout the day and night. Would highly recommend!

Reviewed on Aug 3, 2026

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More About Flying To Palermo from Chicago

Route Information for Flights from Chicago to Palermo

Origin Airport IATA Code
CHI
Destination Airport IATA Code
PMO
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Palermo

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.