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$270+ 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 8/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SKP
Aug 17 — Aug 241
Mon 8/17
Mon 8/24
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 July 18, 2026.

This KAYAK deal was found by Cheapflights users on 7/15. 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.
Thu 11/199:50 pm
ORD
-
SKP
2 stops19h 25m
Lufthansa
Tue 12/294:30 am
SKP
-
ORD
2 stops15h 40m
Lufthansa
Deal found 7/15$879
This United Airlines deal was found by Cheapflights users on 7/16. 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.
Sun 11/229:40 pm
ORD
-
SKP
2 stops31h 05m
United Airlines
Sun 12/274:30 am
SKP
-
ORD
1 stop16h 30m
United Airlines
Deal found 7/16$880
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/128:10 pm
ORD
-
SKP
1 stop16h 15m
Multiple Airlines
Thu 9/247:05 pm
SKP
-
ORD
2 stops29h 45m
Multiple Airlines
Deal found 7/17$881
This Mytrip deal was found by Cheapflights users on 7/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/17:25 pm
ORD
-
SKP
2 stops21h 45m
Multiple Airlines
Thu 9/246:00 pm
SKP
-
ORD
2 stops27h 00m
Multiple Airlines
Deal found 7/17$882
This Mytrip deal was found by Cheapflights users on 7/15. 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.
Sat 8/2910:25 pm
ORD
-
SKP
3 stops33h 10m
Multiple Airlines
Fri 9/43:50 am
SKP
-
ORD
3 stops24h 35m
Multiple Airlines
Deal found 7/15$883
This United Airlines deal was found by Cheapflights users on 7/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/129:39 pm
ORD
-
SKP
2 stops31h 11m
United Airlines
Tue 9/224:25 am
SKP
-
ORD
2 stops19h 35m
United Airlines
Deal found 7/17$884
This Gotogate deal was found by Cheapflights users on 7/16. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2011:05 am
ORD
-
SKP
2 stops25h 50m
Multiple Airlines
Tue 9/154:25 am
SKP
-
ORD
2 stops15h 30m
Multiple Airlines
Deal found 7/16$885
This Cheapflightsfares deal was found by Cheapflights users on 7/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/265:10 pm
ORD
-
SKP
2 stops36h 45m
LOT
Wed 8/265:30 pm
SKP
-
ORD
2 stops28h 35m
LOT
Deal found 7/14$886
This oojo deal was found by Cheapflights users on 7/17. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/169:40 pm
ORD
-
SKP
2 stops19h 35m
Lufthansa
Sun 9/1312:35 pm
SKP
-
ORD
2 stops31h 00m
Lufthansa
Deal found 7/17$887
This LOT deal was found by Cheapflights users on 7/13. 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 LOT is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:10 pm
ORD
-
SKP
2 stops40h 35m
LOT
Sat 9/125:30 pm
SKP
-
ORD
1 stop33h 20m
LOT
Deal found 7/13$888
This Turkish Airlines deal was found by Cheapflights users on 7/14. 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/148:10 pm
ORD
-
SKP
1 stop28h 45m
Turkish Airlines
Sat 9/198:45 am
SKP
-
ORD
1 stop31h 55m
Turkish Airlines
Deal found 7/14$889
This oojo deal was found by Cheapflights users on 7/16. 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 7/305:10 pm
ORD
-
SKP
1 stop16h 35m
LOT
Thu 9/31:35 pm
SKP
-
ORD
1 stop13h 15m
LOT
Deal found 7/16$890

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 July 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$879
(KAYAK)

One-way from

$270
(Kiwi.com)

Popular in

July

Cheapest in

November

Average price

$1,217
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. 27% potential increase in price ($291 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($43 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 18, 2026.
Use the filters below to find and compare flights from Chicago to North Macedonia that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Sun 9/13

8:10 pm-7:55 am

1 stop28h 45m

Skopje

Sat 9/19

8:15 pm-9:40 am

1 stop20h 25m

$889

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Tue 9/15

8:10 pm-7:55 am

1 stop28h 45m

Skopje

Sat 9/19

8:15 pm-9:40 am

1 stop20h 25m

$889

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Sat 8/22

11:20 pm-2:10 am

1 stop19h 50m

Skopje

Sun 9/13

3:10 pm-2:30 pm

1 stop30h 20m

$896

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Sat 8/15

8:10 pm-7:55 am

1 stop28h 45m

Skopje

Tue 9/15

8:45 am-9:40 am

1 stop31h 55m

$899

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Wed 9/16

12:55 pm-11:50 am

2 stops15h 55m

Skopje

Wed 9/23

4:25 am-7:00 pm

2 stops21h 35m

$909

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Thu 11/19

4:20 pm-11:45 am

1 stop12h 25m

Skopje

Fri 12/25

4:30 am-11:22 pm

2 stops25h 52m

$924

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Sat 8/22

8:10 pm-7:55 am

1 stop28h 45m

Skopje

Thu 9/10

8:45 am-9:40 am

1 stop31h 55m

$928

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Sat 8/22

11:20 pm-2:35 pm

1 stop32h 15m

Skopje

Tue 9/8

3:10 pm-2:30 pm

1 stop30h 20m

$946

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Sat 11/21

4:20 pm-11:45 am

1 stop12h 25m

Skopje

Sun 12/27

12:30 pm-2:00 pm

1 stop32h 30m

$954

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Tue 9/15

8:10 pm-7:25 pm

1 stop16h 15m

Skopje

Fri 9/18

8:45 am-9:40 am

1 stop31h 55m

$958

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/15

Showing 1-10 of 20 resultsSorted by cheapest first
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, January is the cheapest month in which you can book a flight from Chicago to North Macedonia (average of $550). Flying from Chicago to North Macedonia in June is currently the most expensive (average of $1,100). 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 far ahead should I book a flight from Chicago to North Macedonia?

To ensure you get the cheapest price possible for a flight from Chicago to North Macedonia, you should look to book at least 86 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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 July 18, 2026.
Peruse reviews from past customers who have flown with Austrian Airlines,LOT, andSWISS 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.
Austrian Airlines
7.6
Good
947 reviews

Crew

8.1

Overall

7.6

Food

6.8

Comfort

7.3

Entertainment

6.8

Boarding

7.6

Reviews

1 / 20
2.0
Mediocre

Nate,Dec 2025

IAD - GSP

Again, I missed this flight because of the first leg of my journey being delayed by three hours. I hope the people on the flight had a nice flight.
Austrian Airlines
7.6
Good
947 reviews
Austrian Airlines
7.6
Good
947 reviews

Crew

8.1

Overall

7.6

Food

6.8

Comfort

7.3

Entertainment

6.8

Boarding

7.6

Reviews

1 / 20
2.0
Mediocre

Nate,Dec 2025

IAD - GSP

Again, I missed this flight because of the first leg of my journey being delayed by three hours. I hope the people on the flight had a nice flight.
LOT
7.5
Good
1,212 reviews
Austrian Airlines
7.6
Good
947 reviews

Crew

8.1

Overall

7.6

Food

6.8

Comfort

7.3

Entertainment

6.8

Boarding

7.6

Reviews

1 / 20
2.0
Mediocre

Nate,Dec 2025

IAD - GSP

Again, I missed this flight because of the first leg of my journey being delayed by three hours. I hope the people on the flight had a nice flight.
SWISS
7.5
Good
2,010 reviews
Austrian Airlines
7.6
Good
947 reviews

Crew

8.1

Overall

7.6

Food

6.8

Comfort

7.3

Entertainment

6.8

Boarding

7.6

Reviews

1 / 20
2.0
Mediocre

Nate,Dec 2025

IAD - GSP

Again, I missed this flight because of the first leg of my journey being delayed by three hours. I hope the people on the flight had a nice flight.
Turkish Airlines
7.4
Good
4,447 reviews
Austrian Airlines
7.6
Good
947 reviews

Crew

8.1

Overall

7.6

Food

6.8

Comfort

7.3

Entertainment

6.8

Boarding

7.6

Reviews

1 / 20
2.0
Mediocre

Nate,Dec 2025

IAD - GSP

Again, I missed this flight because of the first leg of my journey being delayed by three hours. I hope the people on the flight had a nice flight.
Air Serbia
6.1
Okay
231 reviews
Austrian Airlines
7.6
Good
947 reviews

Crew

8.1

Overall

7.6

Food

6.8

Comfort

7.3

Entertainment

6.8

Boarding

7.6

Reviews

1 / 20
2.0
Mediocre

Nate,Dec 2025

IAD - GSP

Again, I missed this flight because of the first leg of my journey being delayed by three hours. I hope the people on the flight had a nice flight.

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 $909, Turkish Airlines can have you in North Macedonia from Chicago in 15h 55m. 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 $114 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, January is the cheapest month in which you can book a flight from Chicago to North Macedonia (average of $550). Flying from Chicago to North Macedonia in June is currently the most expensive (average of $1,100). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 July 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
SWISSCheapest$505Average$943FlexibilityNo cancel feeOn-time79%
Turkish AirlinesCheapest$517Average$999FlexibilityNo cancel feeOn-time77%
LufthansaCheapest$525Average$959FlexibilityNo cancel feeOn-time76%
Austrian AirlinesCheapest$549Average$888FlexibilityNo cancel feeOn-time78%
United AirlinesCheapest$549Average$911FlexibilityNo cancel feeOn-time69%
LOTCheapest$552Average$1,086FlexibilityNo cancel feeOn-time81%
Air SerbiaCheapest$755Average$895FlexibilityNo cancel feeOn-timeN/A

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