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Skopje

$231+ Cheap flights from Chicago (CHI) to Skopje (SKP)

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 3/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SKP
Feb 15 — Feb 221
Sun 2/15
Sun 2/22
1 adult, Economy
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Cheap flight deals from Chicago to Skopje

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Skopje (SKP). 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 January 16, 2026.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$504
(Mytrip)

One-way from

$231
(Gotogate)

Popular in

May

Cheapest in

November

Average price

$556
Provider with most accurate pricing for Chicago (CHI)-Skopje flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Skopje flights.
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From Chicago (CHI) to Skopje
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One-way flight from Chicago (CHI) to Skopje
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Highest demand for flights based on searches. 21% potential increase in price ($207 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($36 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find flight deals from Chicago to Skopje

Cheapest flights from Chicago to Skopje
Explore the most affordable flight options available from Chicago to Skopje. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 16, 2026.

This Mytrip deal was found by Cheapflights users on 1/15. 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.
Sun 4/122:00 pm
ORD
-
SKP
2 stops23h 05m
Multiple Airlines
Thu 4/304:25 am
SKP
-
ORD
2 stops22h 30m
Multiple Airlines
Deal found 1/15$504
This FlightHub deal was found by Cheapflights users on 1/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/46:50 pm
ORD
-
SKP
1 stop18h 35m
Multiple Airlines
Tue 2/104:30 am
SKP
-
ORD
2 stops15h 55m
Multiple Airlines
Deal found 1/14$506
This Mytrip deal was found by Cheapflights users on 1/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/188:00 am
ORD
-
SKP
2 stops30h 25m
Multiple Airlines
Tue 4/712:35 pm
SKP
-
ORD
2 stops31h 20m
Multiple Airlines
Deal found 1/14$508
This Mytrip deal was found by Cheapflights users on 1/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/287:15 am
ORD
-
SKP
2 stops30h 10m
Multiple Airlines
Thu 3/512:30 pm
SKP
-
ORD
2 stops31h 55m
Multiple Airlines
Deal found 1/14$509
This FlightHub deal was found by Cheapflights users on 1/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/117:15 am
ORD
-
SKP
2 stops30h 10m
Multiple Airlines
Tue 2/174:30 am
SKP
-
ORD
1 stop16h 30m
Multiple Airlines
Deal found 1/13$510
This Gurufare deal was found by Cheapflights users on 1/15. 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 Gurufare is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/69:55 pm
ORD
-
SKP
1 stop12h 00m
LOT
Thu 3/191:35 pm
SKP
-
ORD
1 stop13h 25m
LOT
Deal found 1/15$511
This Ovago deal was found by Cheapflights users on 1/15. 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 Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/83:55 pm
ORD
-
SKP
2 stops17h 30m
Multiple Airlines
Mon 3/168:45 pm
SKP
-
ORD
1 stop26h 35m
Multiple Airlines
Deal found 1/15$512
This CrystalTravel deal was found by Cheapflights users on 1/15. 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 CrystalTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/107:05 pm
ORD
-
SKP
1 stop18h 00m
SWISS
Wed 10/218:30 pm
SKP
-
ORD
1 stop23h 05m
SWISS
Deal found 1/15$513
This oojo deal was found by Cheapflights users on 1/14. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/2211:50 am
ORD
-
SKP
1 stop24h 55m
Turkish Airlines
Mon 3/28:35 pm
SKP
-
ORD
1 stop20h 30m
Turkish Airlines
Deal found 1/14$514
This FlightHub deal was found by Cheapflights users on 1/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/178:40 pm
ORD
-
SKP
2 stops40h 45m
Multiple Airlines
Tue 3/2412:30 pm
SKP
-
ORD
1 stop32h 30m
Multiple Airlines
Deal found 1/14$515
This KAYAK deal was found by Cheapflights users on 1/15. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/69:55 pm
ORD
-
SKP
1 stop12h 00m
LOT
Mon 3/165:35 pm
SKP
-
ORD
1 stop33h 25m
LOT
Deal found 1/15$516
This Mytrip deal was found by Cheapflights users on 1/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/319:50 pm
ORD
-
SKP
2 stops30h 55m
Multiple Airlines
Fri 2/138:55 am
SKP
-
ORD
2 stops17h 50m
Multiple Airlines
Deal found 1/14$517

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Skopje 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 January 16, 2026.
Use the filters below to find and compare flights from Chicago to Skopje that are best for you.

Fly from

Chicago

Fly to

Skopje

Route

Depart

Return

Price

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Wed 4/8

4:05 pm-2:55 pm

1 stop15h 50m

Skopje

Fri 4/17

4:25 am-12:55 pm

2 stops15h 30m

$516

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Mon 3/9

2:30 pm-12:15 am

2 stops27h 45m

Skopje

Wed 3/18

12:30 pm-6:51 pm

2 stops36h 21m

$540

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Tue 3/10

2:30 pm-11:45 am

2 stops15h 15m

Skopje

Wed 3/18

4:30 am-8:15 pm

2 stops21h 45m

$540

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Tue 3/17

1:06 pm-11:45 am

2 stops16h 39m

Skopje

Mon 3/23

4:30 am-3:00 pm

1 stop16h 30m

$542

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Fri 3/6

4:20 pm-11:45 am

1 stop12h 25m

Skopje

Wed 3/18

4:30 am-8:15 pm

2 stops21h 45m

$548

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Tue 3/10

1:06 pm-11:45 am

2 stops16h 39m

Skopje

Mon 3/16

4:30 am-11:44 pm

2 stops25h 14m

$552

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Fri 3/6

4:20 pm-11:45 am

1 stop12h 25m

Skopje

Mon 3/16

4:30 am-11:44 pm

2 stops25h 14m

$559

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Mon 5/11

6:00 am-11:50 am

2 stops22h 50m

Skopje

Thu 10/22

4:25 am-1:20 pm

1 stop15h 55m

$560

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Tue 5/12

10:40 am-11:50 am

2 stops18h 10m

Skopje

Tue 10/20

4:25 am-1:20 pm

1 stop15h 55m

$560

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Sun 5/10

4:20 pm-11:50 am

1 stop12h 30m

Skopje

Fri 10/23

4:25 am-9:05 pm

2 stops23h 40m

$566

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/14

Showing 1-10 of 19 results
1
2

Compare providers for flights from Chicago to Skopje

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 Skopje in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*2 stars
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
JustAirTicketPrice Accuracy-Trust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Skopje flights, users find the pricing of Justfly.com to be most consistent on Cheapflights vs. Justfly.com Users can find the same prices on Chicago-Skopje flight deals on Cheapflights vs. Justfly.com >95% of the time. Price accuracy is based on data collected from Chicago-Skopje flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Skopje flights, Cheapflights users trust Justfly.com the most. Justfly.com 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-Skopje 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 Skopje

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

How far ahead should I book a flight from Chicago to Skopje?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Skopje. Price data was last updated on January 9, 2026.

The price you pay for your flight from Chicago to Skopje may vary depending on when you book. For the best chance of a lower fare, look to book 75 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Chicago to Skopje?

Currently, November is the cheapest month in which you can book a flight from Chicago to Skopje (average of $489). Flying from Chicago to Skopje in June is currently the most expensive (average of $792). 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 Skopje?

What’s the top layover airport for flights from Chicago to Skopje?

Share of 1-stop round-trip flights from Chicago to Skopje chosen by Cheapflights users in the past 12 months, using the same layover each way.

Vienna (VIE) – chosen by Cheapflights users on 51% of 1-stop itineraries from Chicago to Skopje on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to Skopje?

Average round-trip fare for 1-stop flights from Chicago to Skopje, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Zurich (ZRH) is the most affordable 1-stop option, with an average round-trip price of $515.

What’s the fastest layover option from Chicago to Skopje?

Shortest average travel time for 1-stop one-way flights from Chicago to Skopje, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Vienna (VIE) have the shortest average one-way travel time for 1-stop routes: 12h 27m.

Which airport typically offers the quickest layover for flights from Chicago to Skopje?

Average layover duration for 1-stop one-way flights from Chicago to Skopje, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Istanbul (IST) offer the fastest connection on this route, with an average layover time of 2h 42m.

Reviews of airlines servicing Skopje

Get insights into the airlines that provide service to Skopje. 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 Skopje. Reviews last updated January 16, 2026.
See what other customers who have flown with Austrian Airlines, LOT, and Turkish Airlines from Chicago to Skopje have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Austrian Airlines
7.6
Good
894 reviews

Entertainment

6.8

Food

6.8

Overall

7.6

Comfort

7.3

Crew

8.1

Boarding

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Dec 2025

VIE - DXB

Awful . Flight was overbooked. The boarding cards could not be printed, you had to wait more than one hour in a line that only two kiosks were working, staff was leaving and inside the plane they had the same seats in 3 cases at least winter twice!! I’ve never experienced such a disorganization! Awful
Austrian Airlines
7.6
Good
894 reviews
Austrian Airlines
7.6
Good
894 reviews

Entertainment

6.8

Food

6.8

Overall

7.6

Comfort

7.3

Crew

8.1

Boarding

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Dec 2025

VIE - DXB

Awful . Flight was overbooked. The boarding cards could not be printed, you had to wait more than one hour in a line that only two kiosks were working, staff was leaving and inside the plane they had the same seats in 3 cases at least winter twice!! I’ve never experienced such a disorganization! Awful
LOT
7.5
Good
1,174 reviews
Austrian Airlines
7.6
Good
894 reviews

Entertainment

6.8

Food

6.8

Overall

7.6

Comfort

7.3

Crew

8.1

Boarding

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Dec 2025

VIE - DXB

Awful . Flight was overbooked. The boarding cards could not be printed, you had to wait more than one hour in a line that only two kiosks were working, staff was leaving and inside the plane they had the same seats in 3 cases at least winter twice!! I’ve never experienced such a disorganization! Awful
Turkish Airlines
7.3
Good
4,180 reviews
Austrian Airlines
7.6
Good
894 reviews

Entertainment

6.8

Food

6.8

Overall

7.6

Comfort

7.3

Crew

8.1

Boarding

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Dec 2025

VIE - DXB

Awful . Flight was overbooked. The boarding cards could not be printed, you had to wait more than one hour in a line that only two kiosks were working, staff was leaving and inside the plane they had the same seats in 3 cases at least winter twice!! I’ve never experienced such a disorganization! Awful
Lufthansa
6.8
Okay
7,719 reviews
Austrian Airlines
7.6
Good
894 reviews

Entertainment

6.8

Food

6.8

Overall

7.6

Comfort

7.3

Crew

8.1

Boarding

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Dec 2025

VIE - DXB

Awful . Flight was overbooked. The boarding cards could not be printed, you had to wait more than one hour in a line that only two kiosks were working, staff was leaving and inside the plane they had the same seats in 3 cases at least winter twice!! I’ve never experienced such a disorganization! Awful
Air Serbia
6.1
Okay
213 reviews
Austrian Airlines
7.6
Good
894 reviews

Entertainment

6.8

Food

6.8

Overall

7.6

Comfort

7.3

Crew

8.1

Boarding

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Dec 2025

VIE - DXB

Awful . Flight was overbooked. The boarding cards could not be printed, you had to wait more than one hour in a line that only two kiosks were working, staff was leaving and inside the plane they had the same seats in 3 cases at least winter twice!! I’ve never experienced such a disorganization! Awful

Related info for your journey

Find useful and relevant information for your journey from Chicago to Skopje. 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 into for flights to Skopje from Chicago?

    For a flight from Chicago to Skopje, you will be flying into Skopje. Skopje (SKP) is just 9.2 mi from the center of the city. Skopje is the only Skopje airport and it handles 0 inbound flights from Chicago per day. 7 airlines have flights to Skopje from Chicago on a regular basis.

  • How long is the flight from Chicago to Skopje?

    Departing from Chicago to Skopje will take you 15h 15m. The distance from Chicago to Skopje is about 5163 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Chicago to Skopje round-trip?

    According to our current data, SWISS ($513), Turkish Airlines ($521), and United Airlines ($549) offers the cheapest pricing from Chicago to Skopje. SWISS is priced at 31% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Chicago to Skopje one-way?

    For one-way options, check prices for Turkish Airlines. According to our data, you can fly for as low as $284. Users have also found prices from $333 and $421 on Air Serbia and Lufthansa, respectively.

  • Where are the most common layover locations when flying from Chicago to Skopje?

    Flights departing from Chicago and landing in Skopje layover in Istanbul most frequently. Vienna follows Istanbul in terms of the most common layover location on Chicago to Skopje flights. Frankfurt am Main comes in third as the most popular layover location on Chicago to Skopje flights.

  • What are some popular things to do or see while on a layover in Istanbul?

    Taksim Square, Laleli Camii, and Beyazit Meydani are currently the most popular points of interest in Istanbul at the moment. Those on a layover in Istanbul interested in visiting Taksim Square, Laleli Camii, or Beyazit Meydani can do so by traveling 20.8 mi, 21.5 mi, and 21.7 mi, respectively from Istanbul. Those landing in Istanbul looking to spend some time exploring during their layover can rent a car for about $33 per day.

  • What are some popular points of interest to see during a layover in Vienna?

    Musikverein, Cathedral of Vienna, and Austria Center Vienna are the most popular attractions in Vienna if you're in need of something to do during your layover. Musikverein, Cathedral of Vienna and Austria Center Vienna are located about 10.6 mi, 11.0 mi, and 10.8 mi, respectively from Vienna Intl if you are interested in checking them out. Those on a layover in Vienna in need of a rental car can book one at Vienna Intl for about $35.

  • What are points of interest worth seeing during a layover in Frankfurt am Main?

    Frankfurt am Main travelers tend to visit Römerberg, Oper Frankfurt, and Konstablerwache more than any other attractions. Römerberg, Oper Frankfurt, and Konstablerwache are located about 7.4 mi, 7.0 mi, and 7.7 mi, respectively from Frankfurt am Main. Those on a layover in Frankfurt am Main in need of a rental car can book one at Frankfurt am Main for about $46.

  • Where are the least popular layover locations for Chicago to Skopje flights?

    Of the flights from Chicago to Skopje that have layovers, the fewest flights stop in Belgrade. Warsaw follows Belgrade in terms of the least common layover location on Chicago to Skopje flights.

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

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

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

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

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

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

    Currently, November is the cheapest month in which you can book a flight from Chicago to Skopje (average of $489). Flying from Chicago to Skopje in June is currently the most expensive (average of $792). 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

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Alternative routes for Chicago to Skopje

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Skopje flights
St. Louis to Skopje flights

Top 7 airlines flying from Chicago to Skopje

Discover the top 7 airlines that operate flights from Chicago to Skopje. 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 January 16, 2026.
AirlineCheapestAverageFlexibilityOn-time
SWISSCheapest$513Average$884FlexibilityNo cancel feeOn-time79%
Turkish AirlinesCheapest$521Average$925FlexibilityNo cancel feeOn-time77%
United AirlinesCheapest$549Average$915FlexibilityNo cancel feeOn-time69%
Austrian AirlinesCheapest$561Average$960FlexibilityNo cancel feeOn-time78%
LufthansaCheapest$575Average$972FlexibilityNo cancel feeOn-time76%
Air SerbiaCheapest$583Average$893FlexibilityNo cancel feeOn-timeN/A
LOTCheapest$621Average$991FlexibilityNo cancel feeOn-time81%

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