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Skopje

$309+ 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 9/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SKP
oct. 15 — oct. 221
mer. 10/15
mer. 10/22
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Skopje are usually found in January or March, booked 70 days in advance, depart on a Friday or Saturday and return on a Wednesday

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 septembre 15, 2025.

Round-trip from

$582
(LOT)

One-way from

$309
(Kiwi.com)

Popular in

May

Cheapest in

January

Average price

$620
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. 20% potential increase in price ($196 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($35 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 septembre 15, 2025.

This LOT deal was found by Cheapflights users on 9/14. 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 LOT is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 10/104:55 pmORD - SKP
1 stop16h 50mLOT
jeu. 10/301:35 pmSKP - ORD
1 stop13h 25mLOT
Deal found 9/14$582
This United deal was found by Cheapflights users on 9/13. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 12/2410:35 pmORD - SKP
2 stops18h 40mMultiple Airlines
jeu. 1/154:30 amSKP - ORD
2 stops21h 20mMultiple Airlines
Deal found 9/13$583
This United Airlines deal was found by Cheapflights users on 9/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 10/17:30 amORD - SKP
2 stops21h 20mUnited Airlines
sam. 11/14:30 amSKP - ORD
1 stop16h 30mUnited Airlines
Deal found 9/15$584
This KAYAK deal was found by Cheapflights users on 9/14. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 12/2510:35 pmORD - SKP
2 stops30h 10mLufthansa
sam. 1/175:40 amSKP - ORD
1 stop14h 30mLufthansa
Deal found 9/14$585
This KAYAK deal was found by Cheapflights users on 9/14. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 10/108:01 pmORD - SKP
2 stops35h 14mLufthansa
dim. 11/212:30 pmSKP - ORD
2 stops38h 35mLufthansa
Deal found 9/14$586
This KAYAK deal was found by Cheapflights users on 9/15. 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.
ven. 12/267:55 pmORD - SKP
2 stops36h 40mLufthansa
lun. 1/1912:30 pmSKP - ORD
2 stops31h 40mLufthansa
Deal found 9/15$587
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 9/184:20 pmORD - SKP
1 stop12h 30mAustrian Airlines
mar. 9/234:25 amSKP - ORD
1 stop15h 55mAustrian Airlines
Deal found 9/14$588
This KAYAK deal was found by Cheapflights users on 9/14. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 10/1812:55 pmORD - SKP
2 stops15h 55mAustrian Airlines
mer. 10/294:30 amSKP - ORD
1 stop16h 30mAustrian Airlines
Deal found 9/14$589
This FlightHub deal was found by Cheapflights users on 9/13. 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.
jeu. 10/29:40 pmORD - SKP
1 stop12h 05mLOT
mer. 10/155:30 pmSKP - ORD
1 stop33h 10mLOT
Deal found 9/13$590
This Priceline deal was found by Cheapflights users on 9/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 10/116:20 pmORD - SKP
2 stops42h 45mMultiple Airlines
sam. 10/256:15 amSKP - ORD
2 stops19h 17mMultiple Airlines
Deal found 9/15$591
This FlightHub deal was found by Cheapflights users on 9/14. 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.
jeu. 12/2510:35 pmORD - SKP
2 stops18h 40mMultiple Airlines
dim. 1/188:35 pmSKP - ORD
2 stops29h 55mMultiple Airlines
Deal found 9/14$592

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 septembre 15, 2025.
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

jeu. 10/9

8:50 am-11:50 am

2 stops20h 00m

Skopje

ven. 10/31

4:30 am-3:00 pm

1 stop16h 30m

$584

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

mer. 10/1

11:45 am-11:50 am

2 stops17h 05m

Skopje

sam. 11/1

4:30 am-3:00 pm

1 stop16h 30m

$584

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

ven. 10/3

9:40 pm-4:45 pm

1 stop12h 05m

Skopje

jeu. 10/30

1:35 pm-9:00 pm

1 stop13h 25m

$589

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

dim. 10/19

4:00 pm-11:50 am

2 stops12h 50m

Skopje

jeu. 11/6

4:30 am-1:10 pm

2 stops15h 40m

$594

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

dim. 10/19

10:30 pm-12:15 am

2 stops18h 45m

Skopje

mer. 11/5

4:35 pm-1:10 pm

1 stop27h 35m

$599

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

ven. 9/26

4:20 pm-11:50 am

1 stop12h 30m

Skopje

lun. 10/6

4:25 am-1:20 pm

1 stop15h 55m

$602

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

mer. 10/1

10:30 pm-12:15 am

2 stops18h 45m

Skopje

sam. 11/1

4:30 am-3:00 pm

1 stop16h 30m

$603

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

dim. 9/28

8:45 am-11:50 am

2 stops20h 05m

Skopje

sam. 10/11

12:35 pm-1:20 pm

1 stop31h 45m

$614

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

lun. 9/22

8:49 pm-3:40 pm

3 stops59h 51m

$309

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

jeu. 9/25

5:10 am-3:40 pm

3 stops51h 30m

$333

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 16 results
1
2

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 September 12, 2025.

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 70 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 $579). Flying from Chicago to Skopje in June is currently the most expensive (average of $1,195). 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.

What is the cheapest time of day to fly from CHI to SKP?

Find hourly flight availability from Chicago to Skopje. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated septembre 15, 2025.

One of the essential ways to save on airfare from Chicago to Skopje is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the morning could potentially save you up to 22% on airfare.

What is the cheapest day to fly from Chicago to Skopje?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Skopje. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Skopje flight should consider departing on Tuesday mornings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 50% 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.

Vienna (VIE) is the most affordable 1-stop option, with an average round-trip price of $689.

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 Warsaw (WAW) have the shortest average one-way travel time for 1-stop routes: 12h 26m.

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 55m.

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 septembre 15, 2025.
See what other customers who have flown with LOT, Austrian Airlines, 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.
LOT
7.6
Good
1,114 reviews

Comfort

7.5

Entertainment

7.0

Food

7.2

Overall

7.6

Crew

8.2

Boarding

7.6

Reviews

1 / 20
2.0
Mediocre

Enver,Sep 2025

TGD - WAW

We ware in the plane for two hours before takeoff waiting and one hour after takeoff we landed
LOT
7.6
Good
1,114 reviews
LOT
7.6
Good
1,114 reviews

Comfort

7.5

Entertainment

7.0

Food

7.2

Overall

7.6

Crew

8.2

Boarding

7.6

Reviews

1 / 20
2.0
Mediocre

Enver,Sep 2025

TGD - WAW

We ware in the plane for two hours before takeoff waiting and one hour after takeoff we landed
Austrian Airlines
7.6
Good
850 reviews
LOT
7.6
Good
1,114 reviews

Comfort

7.5

Entertainment

7.0

Food

7.2

Overall

7.6

Crew

8.2

Boarding

7.6

Reviews

1 / 20
2.0
Mediocre

Enver,Sep 2025

TGD - WAW

We ware in the plane for two hours before takeoff waiting and one hour after takeoff we landed
Turkish Airlines
7.3
Good
3,968 reviews
LOT
7.6
Good
1,114 reviews

Comfort

7.5

Entertainment

7.0

Food

7.2

Overall

7.6

Crew

8.2

Boarding

7.6

Reviews

1 / 20
2.0
Mediocre

Enver,Sep 2025

TGD - WAW

We ware in the plane for two hours before takeoff waiting and one hour after takeoff we landed
Lufthansa
6.8
Okay
7,407 reviews
LOT
7.6
Good
1,114 reviews

Comfort

7.5

Entertainment

7.0

Food

7.2

Overall

7.6

Crew

8.2

Boarding

7.6

Reviews

1 / 20
2.0
Mediocre

Enver,Sep 2025

TGD - WAW

We ware in the plane for two hours before takeoff waiting and one hour after takeoff we landed
Air Serbia
6.3
Okay
200 reviews
LOT
7.6
Good
1,114 reviews

Comfort

7.5

Entertainment

7.0

Food

7.2

Overall

7.6

Crew

8.2

Boarding

7.6

Reviews

1 / 20
2.0
Mediocre

Enver,Sep 2025

TGD - WAW

We ware in the plane for two hours before takeoff waiting and one hour after takeoff we landed

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 12h 05m. 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, Turkish Airlines ($509), United Airlines ($521), and Austrian Airlines ($567) offers the cheapest pricing from Chicago to Skopje. Turkish Airlines is priced at 32% lower than the current average price of a flight leaving 3 months from now.

  • 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.

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

    Taksim Square, Beyazit Meydani, and Laleli Camii are currently the most popular points of interest in Istanbul at the moment. Those on a layover in Istanbul interested in visiting Taksim Square, Beyazit Meydani, or Laleli Camii can do so by traveling 20.8 mi, 21.7 mi, and 21.5 mi, respectively from Istanbul. Those landing in Istanbul looking to spend some time exploring during their layover can rent a car for about $42 per day.

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

    Musikverein, Stephansplatz, and Austria Center Vienna are the most popular attractions in Vienna if you're in need of something to do during your layover. Musikverein, Stephansplatz 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 $40.

  • 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 Warsaw. Frankfurt am Main follows Warsaw 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 $579). Flying from Chicago to Skopje in June is currently the most expensive (average of $1,195). 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 septembre 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Turkish AirlinesCheapest$509Average$920FlexibilityNo cancel feeOn-time77%
United AirlinesCheapest$521Average$906FlexibilityNo cancel feeOn-time69%
Austrian AirlinesCheapest$567Average$992FlexibilityNo cancel feeOn-time78%
LufthansaCheapest$571Average$990FlexibilityNo cancel feeOn-time76%
Air SerbiaCheapest$580Average$960FlexibilityNo cancel feeOn-timeN/A
LOTCheapest$623Average$973FlexibilityNo cancel feeOn-time81%
SWISSCheapest$640Average$893FlexibilityNo cancel feeOn-time79%

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