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North Macedonia

$292+ Cheap flights from Chicago (CHI) to North Macedonia

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 5/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SKP
Mar 23 — Mar 301
Mon 3/23
Mon 3/30
1 adult, Economy
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Cheap flight deals from Chicago to North Macedonia

Cheapest flights from Chicago to North Macedonia
Explore the most affordable flight options available from Chicago to North Macedonia. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 21, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/18. 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 2/274:20 pm
ORD
-
SKP
1 stop15h 00m
Austrian Airlines
Mon 3/94:30 am
SKP
-
ORD
2 stops20h 21m
Austrian Airlines
Deal found 2/18$498
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 2/256:50 pm
ORD
-
SKP
1 stop18h 35m
Multiple Airlines
Tue 3/34:30 am
SKP
-
ORD
1 stop16h 30m
Multiple Airlines
Deal found 2/19$499
This FlightHub deal was found by Cheapflights users on 2/21. 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 3/311:50 am
ORD
-
SKP
1 stop24h 55m
Turkish Airlines
Wed 3/118:35 pm
SKP
-
ORD
1 stop20h 30m
Turkish Airlines
Deal found 2/21$500
This Kiwi.com deal was found by Cheapflights users on 2/18. 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 3/16:50 pm
ORD
-
SKP
1 stop18h 05m
Multiple Airlines
Wed 3/114:30 am
SKP
-
ORD
1 stop16h 30m
Multiple Airlines
Deal found 2/18$501
This Kiwi.com deal was found by Cheapflights users on 2/18. 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 2/234:20 pm
ORD
-
SKP
1 stop14h 45m
Austrian Airlines
Sun 3/14:30 am
SKP
-
ORD
1 stop16h 30m
Austrian Airlines
Deal found 2/18$504
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 2/234:20 pm
ORD
-
SKP
1 stop14h 45m
Multiple Airlines
Mon 3/28:45 pm
SKP
-
ORD
1 stop26h 35m
Multiple Airlines
Deal found 2/19$505
This Kiwi.com deal was found by Cheapflights users on 2/18. 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 3/110:35 pm
ORD
-
SKP
2 stops30h 10m
Multiple Airlines
Sun 3/88:45 pm
SKP
-
ORD
1 stop26h 35m
Multiple Airlines
Deal found 2/18$508
This FlightHub deal was found by Cheapflights users on 2/17. 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 2/258:20 pm
ORD
-
SKP
1 stop16h 25m
Turkish Airlines
Mon 3/168:35 pm
SKP
-
ORD
1 stop20h 30m
Turkish Airlines
Deal found 2/17$509
This FlightHub deal was found by Cheapflights users on 2/18. 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 3/1012:50 pm
ORD
-
SKP
1 stop24h 55m
Turkish Airlines
Wed 4/228:15 pm
SKP
-
ORD
1 stop20h 25m
Turkish Airlines
Deal found 2/18$510
This FlightHub deal was found by Cheapflights users on 2/20. 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.
Sat 4/188:10 pm
ORD
-
SKP
1 stop16h 15m
Turkish Airlines
Fri 5/18:45 am
SKP
-
ORD
1 stop31h 55m
Turkish Airlines
Deal found 2/20$512
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 2/254:20 pm
ORD
-
SKP
1 stop12h 25m
Multiple Airlines
Mon 3/168:45 pm
SKP
-
ORD
1 stop26h 35m
Multiple Airlines
Deal found 2/20$514

Find flight deals from Chicago to North Macedonia

Keep the following information in mind while searching for Chicago to North Macedonia flight deals. Data was last updated February 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$500
(FlightHub)

One-way from

$292
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$564
Provider with most accurate pricing for Chicago (CHI)-Skopje flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Skopje flights.
Search Deals
From Chicago (CHI) to North Macedonia
Search Deals
One-way flight from Chicago (CHI) to North Macedonia
Search Deals
Highest demand for flights based on searches. 28% potential increase in price ($281 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($31 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to North Macedonia 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 February 21, 2026.
Use the filters below to find and compare flights from Chicago to North Macedonia that are best for you.

Fly from

Chicago

Fly to

North Macedonia

Route

Depart

Return

Price

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Tue 3/3

8:20 pm-8:25 am

1 stop29h 05m

Skopje

Sat 3/7

8:35 pm-6:25 pm

1 stop28h 50m

$636

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Mon 7/6

4:20 pm-12:15 am

1 stop24h 55m

Skopje

Tue 12/15

4:30 am-2:00 pm

1 stop16h 30m

$670

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Thu 3/19

8:50 am-11:45 am

2 stops20h 55m

Skopje

Mon 3/30

4:25 am-11:20 am

2 stops37h 55m

$754

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Tue 3/10

8:55 am-11:45 am

2 stops20h 50m

Skopje

Sat 8/22

4:25 am-12:58 am

2 stops27h 33m

$762

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Tue 6/9

7:40 pm-11:50 am

2 stops57h 10m

Skopje

Fri 6/26

4:25 am-1:20 pm

1 stop15h 55m

$815

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Sat 6/6

9:40 pm-11:50 am

2 stops31h 10m

Skopje

Wed 6/24

4:25 am-9:32 pm

2 stops24h 07m

$819

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Wed 6/17

8:25 pm-7:55 pm

2 stops40h 30m

Skopje

Wed 7/22

12:35 pm-1:20 pm

1 stop31h 45m

$856

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Thu 8/6

4:20 pm-11:50 am

1 stop12h 30m

Skopje

Sun 8/9

4:25 am-4:51 am

2 stops31h 26m

$857

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Tue 8/4

4:20 pm-11:50 am

1 stop12h 30m

Skopje

Sun 8/9

4:25 am-5:46 am

2 stops32h 21m

$857

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Mon 8/3

10:53 pm-11:50 am

2 stops53h 57m

Skopje

Sun 8/9

4:25 am-6:32 am

2 stops33h 07m

$867

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 17 results
1
2

Best time to book a flight from Chicago to North Macedonia

Have a flexible travel schedule? Discover the best time to fly to North Macedonia 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 North Macedonia

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

Currently, November is the cheapest month in which you can book a flight from Chicago to North Macedonia (average of $489). Flying from Chicago to North Macedonia 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.

Reviews of airlines servicing North Macedonia

Get insights into the airlines that provide service to North Macedonia. 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 North Macedonia. Reviews last updated February 21, 2026.
Peruse reviews from past customers who have flown with LOT, Austrian Airlines, and Turkish Airlines from Chicago to North Macedonia to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
LOT
7.5
Good
1,181 reviews

Boarding

7.6

Comfort

7.4

Crew

8.2

Entertainment

6.9

Food

7.1

Overall

7.5

Reviews

1 / 20
4.0
Okay

Kevin,Dec 2025

WAW - JFK

The only thing that I could say I really liked was the speed of travel. I think the flight time was significantly reduced, but I only think happened because there were delays in our departure time. We wound up arriving about 1 hour later than originally planned. A few things that could have improved was the entertainment available on board and also the ability to view the flight details in real time. I was just the lucky passenger to get a busted screen so I couldn't watch any entertainment. The passenger sitting next to me was kind enough to switch seats with me once his move was done. The choices for movies and shows were ok, nothing great, but I was grateful some ok movies were available to pass the time. I was not very happy with the absence of flight details. There was a timer that showed how much time was left in the flight, but no other details. Other airlines I've been with offered interactive maps that showed you where the plane was traveling like a normal GPS app would do on your phone which is super nice to have. Flight attendants were nice and helpful. The clarity of the announcements was terrible. Even in English, I could hardly make out what the person was saying. Please make improvements.
LOT
7.5
Good
1,181 reviews
LOT
7.5
Good
1,181 reviews

Boarding

7.6

Comfort

7.4

Crew

8.2

Entertainment

6.9

Food

7.1

Overall

7.5

Reviews

1 / 20
4.0
Okay

Kevin,Dec 2025

WAW - JFK

The only thing that I could say I really liked was the speed of travel. I think the flight time was significantly reduced, but I only think happened because there were delays in our departure time. We wound up arriving about 1 hour later than originally planned. A few things that could have improved was the entertainment available on board and also the ability to view the flight details in real time. I was just the lucky passenger to get a busted screen so I couldn't watch any entertainment. The passenger sitting next to me was kind enough to switch seats with me once his move was done. The choices for movies and shows were ok, nothing great, but I was grateful some ok movies were available to pass the time. I was not very happy with the absence of flight details. There was a timer that showed how much time was left in the flight, but no other details. Other airlines I've been with offered interactive maps that showed you where the plane was traveling like a normal GPS app would do on your phone which is super nice to have. Flight attendants were nice and helpful. The clarity of the announcements was terrible. Even in English, I could hardly make out what the person was saying. Please make improvements.
Austrian Airlines
7.5
Good
899 reviews
LOT
7.5
Good
1,181 reviews

Boarding

7.6

Comfort

7.4

Crew

8.2

Entertainment

6.9

Food

7.1

Overall

7.5

Reviews

1 / 20
4.0
Okay

Kevin,Dec 2025

WAW - JFK

The only thing that I could say I really liked was the speed of travel. I think the flight time was significantly reduced, but I only think happened because there were delays in our departure time. We wound up arriving about 1 hour later than originally planned. A few things that could have improved was the entertainment available on board and also the ability to view the flight details in real time. I was just the lucky passenger to get a busted screen so I couldn't watch any entertainment. The passenger sitting next to me was kind enough to switch seats with me once his move was done. The choices for movies and shows were ok, nothing great, but I was grateful some ok movies were available to pass the time. I was not very happy with the absence of flight details. There was a timer that showed how much time was left in the flight, but no other details. Other airlines I've been with offered interactive maps that showed you where the plane was traveling like a normal GPS app would do on your phone which is super nice to have. Flight attendants were nice and helpful. The clarity of the announcements was terrible. Even in English, I could hardly make out what the person was saying. Please make improvements.
Turkish Airlines
7.3
Good
4,224 reviews
LOT
7.5
Good
1,181 reviews

Boarding

7.6

Comfort

7.4

Crew

8.2

Entertainment

6.9

Food

7.1

Overall

7.5

Reviews

1 / 20
4.0
Okay

Kevin,Dec 2025

WAW - JFK

The only thing that I could say I really liked was the speed of travel. I think the flight time was significantly reduced, but I only think happened because there were delays in our departure time. We wound up arriving about 1 hour later than originally planned. A few things that could have improved was the entertainment available on board and also the ability to view the flight details in real time. I was just the lucky passenger to get a busted screen so I couldn't watch any entertainment. The passenger sitting next to me was kind enough to switch seats with me once his move was done. The choices for movies and shows were ok, nothing great, but I was grateful some ok movies were available to pass the time. I was not very happy with the absence of flight details. There was a timer that showed how much time was left in the flight, but no other details. Other airlines I've been with offered interactive maps that showed you where the plane was traveling like a normal GPS app would do on your phone which is super nice to have. Flight attendants were nice and helpful. The clarity of the announcements was terrible. Even in English, I could hardly make out what the person was saying. Please make improvements.
Lufthansa
6.8
Okay
7,794 reviews
LOT
7.5
Good
1,181 reviews

Boarding

7.6

Comfort

7.4

Crew

8.2

Entertainment

6.9

Food

7.1

Overall

7.5

Reviews

1 / 20
4.0
Okay

Kevin,Dec 2025

WAW - JFK

The only thing that I could say I really liked was the speed of travel. I think the flight time was significantly reduced, but I only think happened because there were delays in our departure time. We wound up arriving about 1 hour later than originally planned. A few things that could have improved was the entertainment available on board and also the ability to view the flight details in real time. I was just the lucky passenger to get a busted screen so I couldn't watch any entertainment. The passenger sitting next to me was kind enough to switch seats with me once his move was done. The choices for movies and shows were ok, nothing great, but I was grateful some ok movies were available to pass the time. I was not very happy with the absence of flight details. There was a timer that showed how much time was left in the flight, but no other details. Other airlines I've been with offered interactive maps that showed you where the plane was traveling like a normal GPS app would do on your phone which is super nice to have. Flight attendants were nice and helpful. The clarity of the announcements was terrible. Even in English, I could hardly make out what the person was saying. Please make improvements.
Air Serbia
6.1
Okay
215 reviews
LOT
7.5
Good
1,181 reviews

Boarding

7.6

Comfort

7.4

Crew

8.2

Entertainment

6.9

Food

7.1

Overall

7.5

Reviews

1 / 20
4.0
Okay

Kevin,Dec 2025

WAW - JFK

The only thing that I could say I really liked was the speed of travel. I think the flight time was significantly reduced, but I only think happened because there were delays in our departure time. We wound up arriving about 1 hour later than originally planned. A few things that could have improved was the entertainment available on board and also the ability to view the flight details in real time. I was just the lucky passenger to get a busted screen so I couldn't watch any entertainment. The passenger sitting next to me was kind enough to switch seats with me once his move was done. The choices for movies and shows were ok, nothing great, but I was grateful some ok movies were available to pass the time. I was not very happy with the absence of flight details. There was a timer that showed how much time was left in the flight, but no other details. Other airlines I've been with offered interactive maps that showed you where the plane was traveling like a normal GPS app would do on your phone which is super nice to have. Flight attendants were nice and helpful. The clarity of the announcements was terrible. Even in English, I could hardly make out what the person was saying. Please make improvements.

Related info for your journey

Find useful and relevant information for your journey from Chicago to North Macedonia. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to North Macedonia?

    For as low as $501, Turkish Airlines can have you in North Macedonia from Chicago in 18h 35m. Chicago and North Macedonia are separated by a distance of 5163 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    One-way options have recently been found by users for as low as $88 on American Airlines. Other airlines that offer cheap prices include United Airlines from $108 and Southwest from $118 one-way.

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

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

  • How can I find direct flights from Chicago to North Macedonia?

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

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

    Yes. Cheapflights offers flight deals from Chicago to North Macedonia 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 North Macedonia?

    Currently, November is the cheapest month in which you can book a flight from Chicago to North Macedonia (average of $489). Flying from Chicago to North Macedonia 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 North Macedonia

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Chicago to North Macedonia

Discover the top 7 airlines that operate flights from Chicago to North Macedonia. 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 February 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
SWISSCheapest$512Average$1,040FlexibilityNo cancel feeOn-time79%
Turkish AirlinesCheapest$520Average$1,191FlexibilityNo cancel feeOn-time77%
LufthansaCheapest$528Average$950FlexibilityNo cancel feeOn-time76%
Austrian AirlinesCheapest$546Average$895FlexibilityNo cancel feeOn-time78%
Air SerbiaCheapest$547Average$856FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$549Average$880FlexibilityNo cancel feeOn-time69%
LOTCheapest$552Average$984FlexibilityNo cancel feeOn-time81%

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