$334 Cheap flight deals from Chicago (CHI) to Thessaloniki (SKG)

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This Weekend's Flight Deals from Chicago to Thessaloniki

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, Sep 13 - Mon, Sep 28
ORD
O'Hare Intl.
SKG
Macedonia
$1,237 Roundtrip, found 6 days ago
$1,237
Roundtrip
found 6 days ago
Select Swiss International Air Lines flight, departing Sun, Sep 13 from O'Hare Intl. to Macedonia, returning Mon, Sep 28, priced at $1,237 found 6 days ago

Airfares from $334 One Way, $716 Round Trip from Chicago to Thessaloniki

Prices starting at $716 for return flights and $334 for one-way flights to Thessaloniki were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Feb 21 - Thu, Mar 4
ORD
Chicago
SKG
Thessaloniki
$716 Roundtrip, found 2 days ago
$716
Roundtrip
found 2 days ago
Select Swiss International Air Lines flight, departing Sun, Feb 21 from Chicago to Thessaloniki, returning Thu, Mar 4, priced at $716 found 2 days ago
Tue, Nov 3 - Fri, Nov 13
ORD
Chicago
SKG
Thessaloniki
$741 Roundtrip, found 4 days ago
$741
Roundtrip
found 4 days ago
Select Turkish Airlines flight, departing Tue, Nov 3 from Chicago to Thessaloniki, returning Fri, Nov 13, priced at $741 found 4 days ago
Wed, Oct 14 - Thu, Nov 26
ORD
Chicago
SKG
Thessaloniki
$743 Roundtrip, found 5 days ago
$743
Roundtrip
found 5 days ago
Select Air Serbia flight, departing Wed, Oct 14 from Chicago to Thessaloniki, returning Thu, Nov 26, priced at $743 found 5 days ago
Tue, Oct 20 - Thu, Nov 5
ORD
Chicago
SKG
Thessaloniki
$821 Roundtrip, found 1 day ago
$821
Roundtrip
found 1 day ago
Select Austrian Airlines flight, departing Tue, Oct 20 from Chicago to Thessaloniki, returning Thu, Nov 5, priced at $821 found 1 day ago
Wed, Oct 7 - Mon, Oct 12
ORD
Chicago
SKG
Thessaloniki
$860 Roundtrip, found 18 hours ago
$860
Roundtrip
found 18 hours ago
Select LOT-Polish Airlines flight, departing Wed, Oct 7 from Chicago to Thessaloniki, returning Mon, Oct 12, priced at $860 found 18 hours ago

Thessaloniki economy flight packages

Price found within the past 48 hours. Click for updated prices.
Domes Noruz Kassandra - Adults Only, Halkidiki
5.0-star property

Domes Noruz Kassandra - Adults Only, Halkidiki

9.4/10 Exceptional! (151 reviews)

Oct 18 - Oct 24

6 night stay

Chicago (CHI) to Thessaloniki (SKG)

Turkish Airlines • Non-stop roundtrip • Coach
Price was $1,511, price is now $1,259 per person
$1,259
per person
found 11 hours ago
A beautiful resort, with both, an amazing pool adjoining a beautiful seaside. Plenty of lounge area everywhere. Staff was ridiculously attentive and concerned about your stay. If I have to put anything adverse comments, its minor..... the gym is small, but theres one inside and outside (but only idiots like me work out on vacation); room safe had no instructions (but they came and programmed it for me); shower didn't have a shelf for amenities (but they came and installed it immediately)... did I mention the staff was attentive? lol. So there's really nothing at all to complain about. Perfect place to stay and have an amazing time in Cassandra. The city center is a mere 5 minute walk away. I will stay there again, no doubt.

Reviewed on Aug 5, 2026

MERAVIA Leonardo Limited Edition - Adult Only
5.0-star property

MERAVIA Leonardo Limited Edition - Adult Only

8.6/10 Excellent! (74 reviews)

Oct 18 - Oct 24

6 night stay

Chicago (CHI) to Thessaloniki (SKG)

Turkish Airlines • Non-stop roundtrip • Coach
Price was $1,969, price is now $1,644 per person
$1,644
per person
found 11 hours ago
Very good staff

Reviewed on Sep 3, 2026

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More About Flying To Thessaloniki from Chicago

Route Information for Flights from Chicago to Thessaloniki

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

Chicago to Thessaloniki

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If value is what you are after, let Orbitz take care of you. Your low cost Chicago to Thessaloniki flights along with our great bargains on hotels and car rentals will make your trip all the more memorable.

Frequently asked questions

What is the shortest flight from Chicago to Thessaloniki?
The fastest flight time is 10 hours and 35 minutes, so take some precautions to avoid jet lag on your Chicago to Thessaloniki trip. Make sure you wander around the cabin, get some sleep and drink water.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won't keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

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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.