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

Warsaw (WAW) has the shortest average layover time for this route: 3h 08m.

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 38% 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 has the shortest travel time from Chicago to Skopje?

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

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.

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 July 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.

$314 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.

5:10 pm - 12:55 pm

ORD

SKP

12h 45m

1 stop

5:30 pm - 3:10 pm

SKP

ORD

52h 40m

2 stops

$866LOT

Sat, Sep 12 - Sat, Sep 19

8:10 pm - 7:55 am

ORD

SKP

28h 45m

1 stop

8:15 pm - 9:40 am

SKP

ORD

20h 25m

1 stop

$869Turkish Airlines

Fri, Sep 18 - Thu, Oct 15

8:10 pm - 7:55 am

ORD

SKP

28h 45m

1 stop

8:45 am - 9:40 am

SKP

ORD

31h 55m

1 stop

$869Turkish Airlines

Fri, Sep 18 - Sun, Oct 11

8:45 am - 11:45 am

ORD

SKP

20h 00m

2 stops

4:30 am - 8:05 pm

SKP

ORD

22h 35m

2 stops

$869Multiple Airlines

Fri, Dec 11 - Tue, Dec 29

3:35 pm - 12:15 am

ORD

SKP

25h 40m

2 stops

4:25 am - 7:55 pm

SKP

ORD

22h 30m

2 stops

$870Lufthansa

Sun, Sep 6 - Tue, Oct 6

3:35 pm - 12:15 am

ORD

SKP

25h 40m

2 stops

4:25 am - 12:55 pm

SKP

ORD

15h 30m

2 stops

$870Lufthansa

Sun, Sep 6 - Thu, Sep 17

8:10 pm - 7:25 pm

ORD

SKP

16h 15m

1 stop

6:55 pm - 5:50 pm

SKP

ORD

29h 55m

2 stops

$870Multiple Airlines

Sat, Sep 19 - Sat, Oct 10

8:10 pm - 4:45 pm

ORD

SKP

13h 35m

1 stop

1:35 pm - 3:10 pm

SKP

ORD

32h 35m

2 stops

$873LOT

Fri, Aug 28 - Thu, Sep 3

4:00 pm - 11:45 am

ORD

SKP

36h 45m

2 stops

4:30 am - 2:00 pm

SKP

ORD

16h 30m

1 stop

$875United Airlines

Fri, Dec 25 - Tue, Jan 5

3:00 pm - 11:45 am

ORD

SKP

37h 45m

2 stops

4:30 am - 11:15 pm

SKP

ORD

25h 45m

2 stops

$879United Airlines

Fri, Dec 25 - Tue, Jan 5

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Air Serbia flights from Chicago to Skopje

Our best Air Serbia deals on Chicago to Skopje flight tickets

Air Serbia

Aug 26

ORD4:40 pmChicago O'Hare Intl

26h 30m

1 stop

SKP2:10 amSkopje

Sep 8

SKP3:50 amSkopje

17h 40m

1 stop

ORD2:30 pmChicago O'Hare Intl

$895

Air Serbia

Aug 19

ORD4:40 pmChicago O'Hare Intl

26h 30m

1 stop

SKP2:10 amSkopje

Sep 18

SKP3:50 amSkopje

24h 25m

1 stop

ORD9:15 pmChicago O'Hare Intl

$897

Air Serbia

Aug 10

ORD4:40 pmChicago O'Hare Intl

26h 30m

1 stop

SKP2:10 amSkopje

Sep 12

SKP3:10 pmSkopje

13h 05m

1 stop

ORD9:15 pmChicago O'Hare Intl

$947

United Airlines flights from Chicago to Skopje

Our best United Airlines deals on Chicago to Skopje flight tickets

United Airlines

Dec 25

ORD4:00 pmChicago O'Hare Intl

36h 45m

2 stops

SKP11:45 amSkopje

Jan 5

SKP4:30 amSkopje

16h 30m

1 stop

ORD2:00 pmChicago O'Hare Intl

$875

United Airlines

Aug 25

ORD7:45 amChicago O'Hare Intl

21h 05m

2 stops

SKP11:50 amSkopje

Oct 14

SKP4:25 amSkopje

19h 55m

2 stops

ORD5:20 pmChicago O'Hare Intl

$884

United Airlines

Sep 5

ORD9:39 pmChicago O'Hare Intl

31h 11m

2 stops

SKP11:50 amSkopje

Sep 17

SKP4:25 amSkopje

15h 55m

1 stop

ORD1:20 pmChicago O'Hare Intl

$885

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Sat 9/12

5:10 pm-12:55 pm

1 stop12h 45m

Skopje

Sat 9/19

5:30 pm-3:10 pm

2 stops52h 40m

$866

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Fri 9/18

8:10 pm-7:55 am

1 stop28h 45m

Skopje

Thu 10/15

8:15 pm-9:40 am

1 stop20h 25m

$869

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Fri 9/18

8:10 pm-7:55 am

1 stop28h 45m

Skopje

Sun 10/11

8:45 am-9:40 am

1 stop31h 55m

$869

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Fri 12/11

8:45 am-11:45 am

2 stops20h 00m

Skopje

Tue 12/29

4:30 am-8:05 pm

2 stops22h 35m

$869

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Sun 9/6

3:35 pm-12:15 am

2 stops25h 40m

Skopje

Tue 10/6

4:25 am-7:55 pm

2 stops22h 30m

$870

Quickest round-trip

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Sun 9/6

3:35 pm-12:15 am

2 stops25h 40m

Skopje

Thu 9/17

4:25 am-12:55 pm

2 stops15h 30m

$870

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Sat 9/19

8:10 pm-7:25 pm

1 stop16h 15m

Skopje

Sat 10/10

6:55 pm-5:50 pm

2 stops29h 55m

$870

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Fri 8/28

8:10 pm-4:45 pm

1 stop13h 35m

Skopje

Thu 9/3

1:35 pm-3:10 pm

2 stops32h 35m

$873

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Fri 12/25

4:00 pm-11:45 am

2 stops36h 45m

Skopje

Tue 1/5

4:30 am-2:00 pm

1 stop16h 30m

$875

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Fri 12/25

3:00 pm-11:45 am

2 stops37h 45m

Skopje

Tue 1/5

4:30 am-11:15 pm

2 stops25h 45m

$879

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 $866.

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 week ahead of your departure date. In general, you can expect to find flights to Skopje for around $755 when searching week 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 $771 on momondo.

Can stopping save me money on Chicago to Skopje flights?

You could potentially save up to 22% on your flight if you consider stops on a Chicago to Skopje flight.

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 July 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 (28% of total bookings). The next most popular airlines are Austrian Airlines (24%), LOT (17%), 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 2,019 reviews	Search SWISS flights
Turkish Airlines	PriceFrom $516	Free Cancellation	Rating 7.4 4,456 reviews	Search Turkish Airlines flights
Lufthansa	PriceFrom $517	Free Cancellation	Rating 6.8 8,163 reviews	Search Lufthansa flights
Austrian Airlines	PriceFrom $548	Free Cancellation	Rating 7.6 950 reviews	Search Austrian Airlines flights
United Airlines	PriceFrom $549	Free Cancellation	Rating 7.4 10,051 reviews	Search United Airlines flights
LOT	PriceFrom $555	Free Cancellation	Rating 7.6 1,212 reviews	Search LOT flights
Air Serbia	PriceFrom $755	Free Cancellation	Rating 6.2 233 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 $314

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 8/25. 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

United Airlines flights from Chicago to Skopje

Our best United 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?

Can stopping save me money on Chicago to Skopje flights?

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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