Which layover airport has the shortest connection time from Chicago to Skopje?

Warsaw (WAW) has the shortest average layover time for this route: 3h 03m.

Which airport is the most popular layover for flights between Chicago and Skopje?

Vienna (VIE) was the most common stop: 35% of momondo users choosing 1-stop flights on this route connected there.

What airlines fly to Skopje?

Turkish Airlines, Austrian Airlines and Lufthansa are the top three most popular airlines that fly to Skopje from Chicago according to our data. Turkish Airlines is the first choice among our users, with 37% of people opting to fly with this airline when traveling to Skopje. Keep in mind that there are 7 different airlines that fly to Skopje on a routine basis, so you have a few additional options to choose from.

Which layover airport offers the lowest fares from Chicago to Skopje?

Flights via Frankfurt am Main (FRA) offer the lowest average round-trip price of $625.

Which layover airport has the shortest travel time from Chicago to Skopje?

Flights connecting via Vienna (VIE) have the shortest average one-way travel time: 12h 37m.

When did momondo last update prices for flights from Chicago to Skopje Airport?

Prices for flights from Chicago to Skopje Airport refresh daily.

How many operators does momondo search for flights from Chicago to Skopje Airport?

As of August 2026, there are 7 operators available to choose from for flights from Chicago to Skopje Airport.

How old do you have to be to fly from Chicago to Skopje Airport?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Skopje Airport.

What documentation or ID do you need to fly to Skopje Airport?

The travel and health documents required for your trip to Skopje Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Skopje Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$334 Cheap Flights from Chicago to Skopje in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Skopje

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:30 pm - 2:35 pmORD Chicago O'Hare Intl-SKP Skopje

12h 05m1 stop Belgrade Nikola Tesla

3:10 pm - 9:20 pmSKP Skopje-ORD Chicago O'Hare Intl

13h 10m1 stop Belgrade Nikola Tesla

$818Air Serbia

Sat, Dec 26 - Wed, Jan 6

11:55 pm - 2:05 amORD Chicago O'Hare Intl-SKP Skopje

19h 10m1 stop Belgrade Nikola Tesla

3:10 pm - 9:20 pmSKP Skopje-ORD Chicago O'Hare Intl

13h 10m1 stop Belgrade Nikola Tesla

$818Air Serbia

Wed, Dec 23 - Wed, Jan 6

3:45 pm - 11:45 amORD Chicago O'Hare Intl-SKP Skopje

37h 00m2 stops Montreal Pierre Elliott Trudeau Intl Vienna Intl

8:55 am - 11:07 amSKP Skopje-ORD Chicago O'Hare Intl

33h 12m2 stops Zurich Montreal Pierre Elliott Trudeau Intl

$818Multiple Airlines

Fri, Dec 25 - Fri, Feb 12

10:35 pm - 12:15 amORD Chicago O'Hare Intl-SKP Skopje

18h 40m2 stops Frankfurt am Main Vienna Intl

12:30 pm - 2:00 pmSKP Skopje-ORD Chicago O'Hare Intl

32h 30m1 stop Vienna Intl

$818Multiple Airlines

Wed, Dec 23 - Thu, Jan 7

5:10 pm - 4:45 pmORD Chicago O'Hare Intl-SKP Skopje

16h 35m1 stop Warsaw Frederic Chopin

5:30 pm - 7:50 pmSKP Skopje-ORD Chicago O'Hare Intl

33h 20m1 stop Warsaw Frederic Chopin

$819LOT

Thu, Sep 3 - Fri, Oct 23

9:50 pm - 11:45 amORD Chicago O'Hare Intl-SKP Skopje

30h 55m2 stops Munich Franz Josef Strauss Vienna Intl

12:30 pm - 1:10 pmSKP Skopje-ORD Chicago O'Hare Intl

55h 40m2 stops Vienna Intl Frankfurt am Main

$819Lufthansa

Sun, Nov 8 - Sun, Nov 22

9:50 pm - 11:45 amORD Chicago O'Hare Intl-SKP Skopje

30h 55m2 stops Munich Franz Josef Strauss Vienna Intl

12:30 pm - 1:10 pmSKP Skopje-ORD Chicago O'Hare Intl

55h 40m2 stops Vienna Intl Frankfurt am Main

$819Lufthansa

Tue, Nov 10 - Sun, Nov 22

11:15 am - 11:45 amORD Chicago O'Hare Intl-SKP Skopje

17h 30m2 stops Washington, D.C. Dulles Intl Vienna Intl

4:30 am - 10:15 pmSKP Skopje-ORD Chicago O'Hare Intl

24h 45m3 stops Vienna Intl Boston Logan Intl Newark

$819United Airlines

Mon, Dec 14 - Thu, Dec 24

5:10 pm - 12:55 pmORD Chicago O'Hare Intl-SKP Skopje

12h 45m1 stop Warsaw Frederic Chopin

5:30 pm - 3:10 pmSKP Skopje-ORD Chicago O'Hare Intl

28h 40m1 stop Warsaw Frederic Chopin

$820LOT

Mon, Sep 7 - Mon, Sep 14

4:30 pm - 11:45 amORD Chicago O'Hare Intl-SKP Skopje

36h 15m2 stops Newark Vienna Intl

4:30 am - 2:00 pmSKP Skopje-ORD Chicago O'Hare Intl

16h 30m1 stop Vienna Intl

$820United Airlines

Sat, Nov 14 - Tue, Dec 1

Cheap last minute flights

Enter your travel dates to find the best prices.

2:20 pm - 8:00 pmORD Chicago O'Hare Intl-SKP Skopje

22h 40m1 stop Zurich

8:45 pm - 3:55 pmSKP Skopje-ORD Chicago O'Hare Intl

26h 10m1 stop Zurich

$910SWISS

Sun, Aug 16 - Mon, Aug 24

2:20 pm - 8:00 pmORD Chicago O'Hare Intl-SKP Skopje

22h 40m1 stop Zurich

12:35 pm - 1:20 pmSKP Skopje-ORD Chicago O'Hare Intl

31h 45m1 stop Vienna Intl

$927Multiple Airlines

Sun, Aug 16 - Mon, Aug 31

10:30 pm - 12:15 amORD Chicago O'Hare Intl-SKP Skopje

18h 45m2 stops Frankfurt am Main Vienna Intl

4:25 am - 12:55 pmSKP Skopje-ORD Chicago O'Hare Intl

15h 30m2 stops Vienna Intl Frankfurt am Main

$933Lufthansa

Wed, Aug 12 - Wed, Aug 26

2:20 pm - 8:00 pmORD Chicago O'Hare Intl-SKP Skopje

22h 40m1 stop Zurich

8:45 pm - 3:55 pmSKP Skopje-ORD Chicago O'Hare Intl

26h 10m1 stop Zurich

$940SWISS

Sun, Aug 16 - Wed, Aug 26

12:56 pm - 11:50 amORD Chicago O'Hare Intl-SKP Skopje

15h 54m2 stops Washington, D.C. Dulles Intl Vienna Intl

8:45 pm - 12:35 pmSKP Skopje-ORD Chicago O'Hare Intl

22h 50m1 stop Zurich

$952Multiple Airlines

Wed, Aug 12 - Wed, Aug 26

4:05 pm - 12:15 amORD Chicago O'Hare Intl-SKP Skopje

25h 10m2 stops Frankfurt am Main Vienna Intl

4:25 am - 12:55 pmSKP Skopje-ORD Chicago O'Hare Intl

15h 30m2 stops Vienna Intl Frankfurt am Main

$956Lufthansa

Sun, Aug 16 - Tue, Aug 25

6:03 am - 11:50 amORD Chicago O'Hare Intl-SKP Skopje

46h 47m2 stops Los Angeles Vienna Intl

4:25 am - 1:20 pmSKP Skopje-ORD Chicago O'Hare Intl

15h 55m1 stop Vienna Intl

$976United Airlines

Wed, Aug 12 - Thu, Aug 27

7:00 am - 11:50 amORD Chicago O'Hare Intl-SKP Skopje

21h 50m2 stops Washington, D.C. Reagan-National Vienna Intl

4:25 am - 9:30 pmSKP Skopje-ORD Chicago O'Hare Intl

24h 05m2 stops Vienna Intl Los Angeles

$986United Airlines

Wed, Aug 12 - Fri, Aug 28

4:40 pm - 2:35 pmORD Chicago O'Hare Intl-SKP Skopje

14h 55m1 stop Belgrade Nikola Tesla

3:50 am - 2:30 pmSKP Skopje-ORD Chicago O'Hare Intl

17h 40m1 stop Belgrade Nikola Tesla

$993Air Serbia

Wed, Aug 12 - Tue, Aug 25

4:40 pm - 2:10 amORD Chicago O'Hare Intl-SKP Skopje

26h 30m1 stop Belgrade Nikola Tesla

3:10 pm - 2:30 pmSKP Skopje-ORD Chicago O'Hare Intl

30h 20m1 stop Belgrade Nikola Tesla

$996Air Serbia

Wed, Aug 12 - Tue, Aug 25

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Air Serbia flights from Chicago to Skopje

Our best Air Serbia deals on Chicago to Skopje flight tickets

Air Serbia

Dec 23

ORD11:55 pmChicago O'Hare Intl

19h 10m

1 stop

SKP2:05 amSkopje

Jan 6

SKP3:10 pmSkopje

13h 10m

1 stop

ORD9:20 pmChicago O'Hare Intl

$818

Air Serbia

Aug 22

ORD11:20 pmChicago O'Hare Intl

32h 00m

1 stop

SKP2:20 pmSkopje

Sep 15

SKP3:10 pmSkopje

30h 20m

1 stop

ORD2:30 pmChicago O'Hare Intl

$893

Air Serbia

Aug 24

ORD4:40 pmChicago O'Hare Intl

26h 30m

1 stop

SKP2:10 amSkopje

Sep 26

SKP3:10 pmSkopje

13h 05m

1 stop

ORD9:15 pmChicago O'Hare Intl

$895

Turkish Airlines flights from Chicago to Skopje

Our best Turkish Airlines deals on Chicago to Skopje flight tickets

Turkish Airlines

Sep 16

ORD8:10 pmChicago O'Hare Intl

16h 15m

1 stop

SKP7:25 pmSkopje

Sep 20

SKP8:15 pmSkopje

20h 25m

1 stop

ORD9:40 amChicago O'Hare Intl

$825

Turkish Airlines

Aug 29

ORD8:10 pmChicago O'Hare Intl

16h 15m

1 stop

SKP7:25 pmSkopje

Sep 30

SKP8:15 pmSkopje

20h 25m

1 stop

ORD9:40 amChicago O'Hare Intl

$830

Turkish Airlines

Sep 17

ORD8:10 pmChicago O'Hare Intl

28h 45m

1 stop

SKP7:55 amSkopje

Sep 24

SKP8:45 amSkopje

31h 55m

1 stop

ORD9:40 amChicago O'Hare Intl

$835

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

ChicagoSkopje

ORD Chicago O'Hare Intl - SKP Skopje

ORDSKP

Chicago O'Hare Intl

Sat 12/26

7:30 pm-2:35 pm

1 stop12h 05m

Skopje

Wed 1/6

3:10 pm-9:20 pm

1 stop13h 10m

$818

ChicagoSkopje

ORD Chicago O'Hare Intl - SKP Skopje

ORDSKP

Chicago O'Hare Intl

Wed 12/23

11:55 pm-2:05 am

1 stop19h 10m

Skopje

Wed 1/6

3:10 pm-9:20 pm

1 stop13h 10m

$818

ChicagoSkopje

ORD Chicago O'Hare Intl - SKP Skopje

ORDSKP

Chicago O'Hare Intl

Fri 12/25

3:45 pm-11:45 am

2 stops37h 00m

Skopje

Fri 2/12

8:55 am-11:07 am

2 stops33h 12m

$818

ChicagoSkopje

ORD Chicago O'Hare Intl - SKP Skopje

ORDSKP

Chicago O'Hare Intl

Wed 12/23

10:35 pm-12:15 am

2 stops18h 40m

Skopje

Thu 1/7

12:30 pm-2:00 pm

1 stop32h 30m

$818

ChicagoSkopje

ORD Chicago O'Hare Intl - SKP Skopje

ORDSKP

Chicago O'Hare Intl

Thu 9/3

5:10 pm-4:45 pm

1 stop16h 35m

Skopje

Fri 10/23

5:30 pm-7:50 pm

1 stop33h 20m

$819

ChicagoSkopje

ORD Chicago O'Hare Intl - SKP Skopje

ORDSKP

Chicago O'Hare Intl

Sun 11/8

9:50 pm-11:45 am

2 stops30h 55m

Skopje

Sun 11/22

12:30 pm-1:10 pm

2 stops55h 40m

$819

ChicagoSkopje

ORD Chicago O'Hare Intl - SKP Skopje

ORDSKP

Chicago O'Hare Intl

Tue 11/10

9:50 pm-11:45 am

2 stops30h 55m

Skopje

Sun 11/22

12:30 pm-1:10 pm

2 stops55h 40m

$819

ChicagoSkopje

ORD Chicago O'Hare Intl - SKP Skopje

ORDSKP

Chicago O'Hare Intl

Mon 12/14

11:15 am-11:45 am

2 stops17h 30m

Skopje

Thu 12/24

4:30 am-10:15 pm

3 stops24h 45m

$819

ChicagoSkopje

ORD Chicago O'Hare Intl - SKP Skopje

ORDSKP

Chicago O'Hare Intl

Mon 9/7

5:10 pm-12:55 pm

1 stop12h 45m

Skopje

Mon 9/14

5:30 pm-3:10 pm

1 stop28h 40m

$820

ChicagoSkopje

ORD Chicago O'Hare Intl - SKP Skopje

ORDSKP

Chicago O'Hare Intl

Sat 11/14

4:30 pm-11:45 am

2 stops36h 15m

Skopje

Tue 12/1

4:30 am-2:00 pm

1 stop16h 30m

$820

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago to Skopje

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Layovers

What is the typical price of a round-trip flight between Chicago and Skopje?

Prices are currently typical for flights on this route.

Typical prices usually range from $619 to $1,181.
The lowest price recently found on this route was $818.

What is the cheapest month to fly to Skopje?

The month of January is, on average, the cheapest month to fly to Skopje from Chicago, with most prices found around $550. The month of February is another great option to travel to Skopje, with average flight prices from Chicago averaging around $552.

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

You are more likely to see cheaper flights to Skopje from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Skopje for around $760 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Skopje from Chicago for as low as $794 on momondo.

How have Chicago to Skopje flight prices changed over time?

When to book flights from Chicago to Skopje

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Skopje according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago to Skopje (CHI to SKP) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Skopje

Fastest flight time	12h 25m
Direct flights	None

The fastest flight from Chicago to Skopje takes 12h 25m

There are no direct flights from Chicago to Skopje. There are no popular flight routes from Chicago to Skopje.

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Frequently asked questions about flying from Chicago to Skopje

How far is Chicago to Skopje by plane?
The straight-line distance from Chicago to Skopje is 5149.8 mi. Flights usually cover this in 12h 25m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Chicago to Skopje Airport?
Prices for flights from Chicago to Skopje Airport refresh daily.
How many operators does momondo search for flights from Chicago to Skopje Airport?
As of August 2026, there are 7 operators available to choose from for flights from Chicago to Skopje Airport.
How old do you have to be to fly from Chicago to Skopje Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Skopje Airport.
What documentation or ID do you need to fly to Skopje Airport?
The travel and health documents required for your trip to Skopje Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Skopje Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular airline from Chicago to Skopje?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Chicago to Skopje is Turkish Airlines (27% of total bookings). The next most popular airlines are Austrian Airlines (24%), LOT (18%), and Air Serbia (15%).

Best airlines flying from Chicago to Skopje

Compare and see reviews for airlines that fly from Chicago to Skopje with momondo

Airline	Rating	Free Cancellation	Price
SWISS	PriceFrom $497	Free Cancellation	Rating 7.5 2,034 reviews	Search SWISS flights
Turkish Airlines	PriceFrom $515	Free Cancellation	Rating 7.4 4,480 reviews	Search Turkish Airlines flights
Lufthansa	PriceFrom $520	Free Cancellation	Rating 6.8 8,177 reviews	Search Lufthansa flights
Austrian Airlines	PriceFrom $548	Free Cancellation	Rating 7.6 947 reviews	Search Austrian Airlines flights
United Airlines	PriceFrom $549	Free Cancellation	Rating 7.4 10,101 reviews	Search United Airlines flights
LOT	PriceFrom $561	Free Cancellation	Rating 7.5 1,214 reviews	Search LOT flights
Air Serbia	PriceFrom $755	Free Cancellation	Rating 6.2 234 reviews	Search Air Serbia flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Skopje?

Finding the right flight to Skopje from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Skopje quick and easy, saving you time and money.

Can I find flights from Chicago to Skopje with flexible booking policies on momondo?

Flights from Chicago to Skopje with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Chicago to Skopje?

momondo provides multiple filters to help you find the best flight to Skopje from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to Skopje right now. Can momondo alert me if prices change?

Price alerts on flights to Skopje from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Skopje trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Cheap flights from Chicago to Skopje from $334

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Skopje departing on 1/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Air Serbia flights from Chicago to Skopje

Our best Air Serbia deals on Chicago to Skopje flight tickets

Turkish Airlines flights from Chicago to Skopje

Our best Turkish Airlines deals on Chicago to Skopje flight tickets

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How to get the cheapest flight ticket from Chicago to Skopje

What is the typical price of a round-trip flight between Chicago and Skopje?

What is the cheapest month to fly to Skopje?

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

How have Chicago to Skopje flight prices changed over time?

What airlines fly to Skopje?

Which airport is the most popular layover for flights between Chicago and Skopje?

Which layover airport offers the lowest fares from Chicago to Skopje?

Which layover airport has the shortest travel time from Chicago to Skopje?

Which layover airport has the shortest connection time from Chicago to Skopje?

When to book flights from Chicago to Skopje

Cheap Chicago to Skopje (CHI to SKP) flight deals and tips

Fastest flight time

Direct flights

Frequently asked questions about flying from Chicago to Skopje

Best airlines flying from Chicago to Skopje

Compare and see reviews for airlines that fly from Chicago to Skopje with momondo

Why use momondo?

An easier way to manage your Skopje trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to North Macedonia

Airports servicing North Macedonia

Fly your favorite airline to Skopje

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Skopje

List of cabin classes available on flights landing in Skopje. Availability may vary depending on flight origin and airline.

Popular cities in North Macedonia

Popular flights according to clicks in the last 7 days on momondo

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According to popular flight searches on momondo this year

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