North Macedonia

$281+ Cheap flights from Chicago (CHI) to North Macedonia

CHI — SKP
Dec 5 — Dec 121
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1. Tell us where you want to go

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Cheap flight deals from Chicago to North Macedonia

Cheapest flights from Chicago to North Macedonia

Tue 12/18:15 pm -
1 stop16h 45m
Wed 12/98:50 pm -
1 stop20h 10m
Deal found 11/2$699
Wed 12/308:15 pm -
1 stop16h 45m
Wed 2/108:50 am -
1 stop16h 30m
Deal found 11/1$706
Tue 12/18:15 pm -
1 stop16h 45m
Tue 3/168:50 am -
1 stop32h 10m
Deal found 11/4$709
Tue 12/2911:45 am -
1 stop25h 15m
Tue 2/98:50 am -
1 stop16h 30m
Deal found 11/1$716
Sat 12/267:30 pm -
1 stop12h 05m
Tue 4/133:05 pm -
1 stop30h 25m
Deal found 11/1$723
Mon 11/911:45 am -
1 stop13h 10m
Wed 11/188:50 pm -
1 stop20h 10m
Deal found 10/31$724
Sat 11/285:20 pm -
1 stop14h 15m
Wed 4/144:00 am -
1 stop17h 30m
Deal found 11/3$725
Sat 11/285:20 pm -
1 stop14h 15m
Tue 4/133:05 pm -
1 stop30h 25m
Deal found 11/3$740
Tue 12/2911:45 am -
1 stop25h 15m
Wed 3/178:50 am -
1 stop16h 30m
Deal found 11/2$749
Sat 11/78:15 pm -
1 stop16h 45m
Sat 11/148:45 am -
1 stop16h 35m
Deal found 11/1$752
Fri 11/2711:45 am -
1 stop25h 15m
Wed 12/28:50 pm -
1 stop20h 10m
Deal found 11/4$753
Thu 12/311:45 am -
1 stop13h 15m
Thu 1/288:50 pm -
1 stop28h 30m
Deal found 11/1$754

Find flight deals from Chicago to North Macedonia

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$699
(Justfly.com)

One-way from

$281
(Kiwi.com)

Popular in

July

Cheapest in

February

Average price

$759
Provider with most accurate pricing for Chicago (CHI)-Skopje flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Skopje flights.
From Chicago (CHI) to North Macedonia
One-way flight from Chicago (CHI) to North Macedonia
Highest demand for flights based on searches. 25% potential increase in price ($280 potential increase over avg. RT price).
Cheapest flight prices on average. 4% potential price decrease ($37 potential savings vs. average RT price).
Average for round-trip flights in November 2026

Cheapflights Fare Finder

 
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 Chicago O'Hare Intl - SKP Skopje

ORDSKP

Chicago O'Hare Intl

Sun 11/29

8:10 pm-6:45 pm

2 stops39h 35m

Skopje

Wed 12/31

12:00 am-5:00 pm

Nonstop0h 00m

$281

ChicagoSkopje

ORD Chicago O'Hare Intl - SKP Skopje

ORDSKP

Chicago O'Hare Intl

Sun 11/15

8:10 pm-11:25 am

3 stops32h 15m

Skopje

Wed 12/31

12:00 am-5:00 pm

Nonstop0h 00m

$320

ChicagoSkopje

ORD Chicago O'Hare Intl - SKP Skopje

ORDSKP

Chicago O'Hare Intl

Sun 3/21

10:50 pm-11:45 am

2 stops54h 55m

Skopje

Wed 12/31

12:00 am-5:00 pm

Nonstop0h 00m

$361

ChicagoSkopje

ORD Chicago O'Hare Intl - SKP Skopje

ORDSKP

Chicago O'Hare Intl

Mon 3/15

10:50 pm-11:45 am

2 stops54h 55m

Skopje

Wed 12/31

12:00 am-5:00 pm

Nonstop0h 00m

$361

ChicagoSkopje

ORD Chicago O'Hare Intl - SKP Skopje

ORDSKP

Chicago O'Hare Intl

Mon 3/22

4:45 pm-11:45 am

2 stops37h 00m

Skopje

Wed 12/31

12:00 am-5:00 pm

Nonstop0h 00m

$361

ChicagoSkopje

ORD Chicago O'Hare Intl - SKP Skopje

ORDSKP

Chicago O'Hare Intl

Mon 3/22

5:20 pm-11:45 am

1 stop12h 25m

Skopje

Wed 12/31

12:00 am-5:00 pm

Nonstop0h 00m

$362

ChicagoSkopje

ORD Chicago O'Hare Intl - SKP Skopje

ORDSKP

Chicago O'Hare Intl

Tue 3/23

7:10 am-11:45 am

2 stops22h 35m

Skopje

Wed 12/31

12:00 am-5:00 pm

Nonstop0h 00m

$367

ChicagoSkopje

ORD Chicago O'Hare Intl - SKP Skopje

ORDSKP

Chicago O'Hare Intl

Sun 12/13

6:30 pm-11:55 pm

2 stops22h 25m

Skopje

Wed 12/31

12:00 am-5:00 pm

Nonstop0h 00m

$378
Quickest round-trip

ChicagoSkopje

ORD Chicago O'Hare Intl - SKP Skopje

ORDSKP

Chicago O'Hare Intl

Sat 3/27

5:20 pm-10:50 am

1 stop11h 30m

Skopje

Wed 12/31

12:00 am-5:00 pm

Nonstop0h 00m

$412

ChicagoSkopje

ORD Chicago O'Hare Intl - SKP Skopje

ORDSKP

Chicago O'Hare Intl

Sat 3/13

4:20 pm-11:45 am

1 stop12h 25m

Skopje

Wed 12/31

12:00 am-5:00 pm

Nonstop0h 00m

$412

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

Showing 1-10 of 32 resultsSorted by cheapest first
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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

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, February is the cheapest month in which you can book a flight from Chicago to North Macedonia (average of $555). Flying from Chicago to North Macedonia in June is currently the most expensive (average of $1,138). 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

Peruse reviews from past customers who have flown with LOT,Austrian Airlines, 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.

Entertainment

6.9

Overall

7.5

Comfort

7.4

Crew

8.2

Food

7.2

Boarding

7.6

Reviews

1 / 20
10.0
Excellent

Rami,Sep 2025

LAX - WAW

The second leg. Very tight seats No WiFi on both flights

Entertainment

6.9

Overall

7.5

Comfort

7.4

Crew

8.2

Food

7.2

Boarding

7.6

Reviews

1 / 20
10.0
Excellent

Rami,Sep 2025

LAX - WAW

The second leg. Very tight seats No WiFi on both flights

Entertainment

6.9

Overall

7.5

Comfort

7.4

Crew

8.2

Food

7.2

Boarding

7.6

Reviews

1 / 20
10.0
Excellent

Rami,Sep 2025

LAX - WAW

The second leg. Very tight seats No WiFi on both flights

Entertainment

6.9

Overall

7.5

Comfort

7.4

Crew

8.2

Food

7.2

Boarding

7.6

Reviews

1 / 20
10.0
Excellent

Rami,Sep 2025

LAX - WAW

The second leg. Very tight seats No WiFi on both flights

Entertainment

6.9

Overall

7.5

Comfort

7.4

Crew

8.2

Food

7.2

Boarding

7.6

Reviews

1 / 20
10.0
Excellent

Rami,Sep 2025

LAX - WAW

The second leg. Very tight seats No WiFi on both flights

Entertainment

6.9

Overall

7.5

Comfort

7.4

Crew

8.2

Food

7.2

Boarding

7.6

Reviews

1 / 20
10.0
Excellent

Rami,Sep 2025

LAX - WAW

The second leg. Very tight seats No WiFi on both flights

Related info for your journey

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

    For as low as $766, Turkish Airlines can have you in North Macedonia from Chicago in 12h 30m. 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 $315 on Air Serbia. Other airlines that offer cheap prices include Austrian Airlines from $329 and Lufthansa from $371 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, February is the cheapest month in which you can book a flight from Chicago to North Macedonia (average of $555). Flying from Chicago to North Macedonia in June is currently the most expensive (average of $1,138). 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

Top 7 airlines flying from Chicago to North Macedonia

AirlineCheapestAverageFlexibilityOn-time
LufthansaCheapest$504Average$976FlexibilityNo cancel feeOn-time76%
SWISSCheapest$505Average$932FlexibilityNo cancel feeOn-time79%
Turkish AirlinesCheapest$515Average$1,029FlexibilityNo cancel feeOn-time77%
United AirlinesCheapest$549Average$997FlexibilityNo cancel feeOn-time69%
Austrian AirlinesCheapest$552Average$951FlexibilityNo cancel feeOn-time78%
LOTCheapest$599Average$1,083FlexibilityNo cancel feeOn-time81%
Air SerbiaCheapest$787Average$984FlexibilityNo cancel feeOn-timeN/A

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