HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Skopje

$343+ Cheap flights from Chicago (CHI) to Skopje (SKP)

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 9/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SKP
May 21 — May 281
Thu 5/21
Thu 5/28
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Skopje with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Chicago to Skopje

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

This FlightHub deal was found by Cheapflights users on 4/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/268:10 pm
ORD
-
SKP
1 stop16h 15m
Turkish Airlines
Thu 10/18:45 am
SKP
-
ORD
1 stop31h 55m
Turkish Airlines
Deal found 4/19$654
This KAYAK deal was found by Cheapflights users on 4/19. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/138:10 pm
ORD
-
SKP
1 stop16h 15m
Turkish Airlines
Sat 9/198:15 pm
SKP
-
ORD
1 stop20h 25m
Turkish Airlines
Deal found 4/19$655
This Kiwi.com deal was found by Cheapflights users on 4/20. 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.
Tue 9/158:10 pm
ORD
-
SKP
1 stop16h 15m
Turkish Airlines
Mon 9/218:15 pm
SKP
-
ORD
1 stop20h 25m
Turkish Airlines
Deal found 4/20$673
This FlightHub deal was found by Cheapflights users on 4/20. 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.
Tue 12/111:50 am
ORD
-
SKP
1 stop13h 35m
Turkish Airlines
Sun 1/249:15 am
SKP
-
ORD
1 stop16h 10m
Turkish Airlines
Deal found 4/20$674
This KAYAK deal was found by Cheapflights users on 4/20. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/138:10 pm
ORD
-
SKP
1 stop16h 15m
Turkish Airlines
Thu 9/248:15 pm
SKP
-
ORD
1 stop20h 25m
Turkish Airlines
Deal found 4/20$675
This Kiwi.com deal was found by Cheapflights users on 4/20. 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.
Fri 9/118:10 pm
ORD
-
SKP
1 stop16h 15m
Turkish Airlines
Tue 9/228:15 pm
SKP
-
ORD
1 stop20h 25m
Turkish Airlines
Deal found 4/20$679
This Turkish Airlines deal was found by Cheapflights users on 4/20. 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/168:10 pm
ORD
-
SKP
1 stop16h 15m
Turkish Airlines
Tue 9/228:15 pm
SKP
-
ORD
1 stop20h 25m
Turkish Airlines
Deal found 4/20$680
This FlightHub deal was found by Cheapflights users on 4/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:10 pm
ORD
-
SKP
1 stop16h 15m
Turkish Airlines
Thu 9/38:15 pm
SKP
-
ORD
1 stop20h 25m
Turkish Airlines
Deal found 4/19$691
This Kiwi.com deal was found by Cheapflights users on 4/20. 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.
Tue 9/158:10 pm
ORD
-
SKP
1 stop16h 15m
Turkish Airlines
Sat 9/198:15 pm
SKP
-
ORD
1 stop20h 25m
Turkish Airlines
Deal found 4/20$693
This FlightHub deal was found by Cheapflights users on 4/17. 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.
Fri 7/3111:25 am
ORD
-
SKP
1 stop13h 30m
Turkish Airlines
Sat 9/268:45 am
SKP
-
ORD
1 stop31h 55m
Turkish Airlines
Deal found 4/17$705
This oojo deal was found by Cheapflights users on 4/20. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/198:10 pm
ORD
-
SKP
1 stop16h 15m
Turkish Airlines
Sat 10/319:15 am
SKP
-
ORD
1 stop32h 50m
Turkish Airlines
Deal found 4/20$710
This KAYAK deal was found by Cheapflights users on 4/20. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1111:25 am
ORD
-
SKP
1 stop25h 00m
Turkish Airlines
Thu 9/248:15 pm
SKP
-
ORD
1 stop20h 25m
Turkish Airlines
Deal found 4/20$715

Find flight deals from Chicago to Skopje

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Skopje (SKP). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated April 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$654
(FlightHub)

One-way from

$343
(Mytrip)

Popular in

June

Cheapest in

January

Average price

$673
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 Skopje
Search Deals
One-way flight from Chicago (CHI) to Skopje
Search Deals
Highest demand for flights based on searches. 27% potential increase in price ($269 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($28 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals

Cheapflights Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Fri 5/8

9:30 pm-11:50 am

2 stops31h 20m

Skopje

Tue 5/19

4:25 am-6:03 am

2 stops32h 38m

$1,045

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Fri 7/10

12:11 pm-11:50 am

2 stops16h 39m

Skopje

Wed 8/12

4:25 am-10:19 pm

2 stops24h 54m

$1,062

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Tue 6/30

11:03 am-11:50 am

2 stops17h 47m

Skopje

Mon 8/3

4:25 am-11:26 pm

2 stops26h 01m

$1,163

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Sat 7/18

4:20 pm-11:50 am

1 stop12h 30m

Skopje

Tue 7/28

4:25 am-11:26 pm

2 stops26h 01m

$1,184

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Tue 6/16

3:10 pm-2:30 pm

1 stop16h 20m

Skopje

Tue 7/28

4:25 am-11:26 pm

2 stops26h 01m

$1,184

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Fri 6/26

6:30 pm-2:45 pm

1 stop13h 15m

Skopje

Fri 7/17

4:25 am-11:58 am

2 stops38h 33m

$1,232

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Wed 6/10

4:40 pm-2:10 am

1 stop26h 30m

Skopje

Wed 6/24

4:00 am-2:30 pm

1 stop17h 30m

$1,234
Quickest round-trip

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Sun 6/21

9:00 am-11:50 am

2 stops19h 50m

Skopje

Thu 9/3

4:25 am-1:20 pm

1 stop15h 55m

$1,252

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Tue 6/23

1:18 pm-2:30 pm

2 stops18h 12m

Skopje

Mon 8/3

4:25 am-11:26 pm

2 stops26h 01m

$1,259

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Mon 6/22

7:10 am-2:30 pm

2 stops24h 20m

Skopje

Thu 8/27

4:25 am-6:37 pm

2 stops21h 12m

$1,263

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/20

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

Compare providers for flights from Chicago to Skopje

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Skopje in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
CheapflightsfaresPrice Accuracy2 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Skopje flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Skopje flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Skopje flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Skopje flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Skopje flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Skopje

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

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

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Skopje. Price data was last updated on April 17, 2026.

The price you pay for your flight from Chicago to Skopje may vary depending on when you book. For the best chance of a lower fare, look to book 75 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, May is the cheapest month in which you can book a flight from Chicago to Skopje (average of $353). Flying from Chicago to Skopje in June is currently the most expensive (average of $970). 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 much does it cost to fly round-trip from Chicago to Skopje?

What’s the top layover airport for flights from Chicago to Skopje?

Share of 1-stop round-trip flights from Chicago to Skopje chosen by Cheapflights users in the past 12 months, using the same layover each way.

Vienna (VIE) – chosen by Cheapflights users on 52% of 1-stop itineraries from Chicago to Skopje on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to Skopje?

Average round-trip fare for 1-stop flights from Chicago to Skopje, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Zurich (ZRH) is the most affordable 1-stop option, with an average round-trip price of $569.

What’s the fastest layover option from Chicago to Skopje?

Shortest average travel time for 1-stop one-way flights from Chicago to Skopje, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Vienna (VIE) have the shortest average one-way travel time for 1-stop routes: 12h 27m.

Which airport typically offers the quickest layover for flights from Chicago to Skopje?

Average layover duration for 1-stop one-way flights from Chicago to Skopje, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Istanbul (IST) offer the fastest connection on this route, with an average layover time of 2h 40m.

Reviews of airlines servicing Skopje

Get insights into the airlines that provide service to Skopje. 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 Skopje. Reviews last updated April 21, 2026.
See what other customers who have flown with Austrian Airlines,LOT, andTurkish Airlines from Chicago to Skopje have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Austrian Airlines
7.6
Good
905 reviews

Entertainment

6.8

Comfort

7.3

Overall

7.6

Food

6.8

Boarding

7.6

Crew

8.1

Reviews

1 / 20
10.0
Excellent

KENNETH,Mar 2026

VIE - EWR

Everything was great, took off on time, arrived on time, boarding was smooth, food and movies were great.
Austrian Airlines
7.6
Good
905 reviews
Austrian Airlines
7.6
Good
905 reviews

Entertainment

6.8

Comfort

7.3

Overall

7.6

Food

6.8

Boarding

7.6

Crew

8.1

Reviews

1 / 20
10.0
Excellent

KENNETH,Mar 2026

VIE - EWR

Everything was great, took off on time, arrived on time, boarding was smooth, food and movies were great.
LOT
7.5
Good
1,188 reviews
Austrian Airlines
7.6
Good
905 reviews

Entertainment

6.8

Comfort

7.3

Overall

7.6

Food

6.8

Boarding

7.6

Crew

8.1

Reviews

1 / 20
10.0
Excellent

KENNETH,Mar 2026

VIE - EWR

Everything was great, took off on time, arrived on time, boarding was smooth, food and movies were great.
Turkish Airlines
7.4
Good
4,318 reviews
Austrian Airlines
7.6
Good
905 reviews

Entertainment

6.8

Comfort

7.3

Overall

7.6

Food

6.8

Boarding

7.6

Crew

8.1

Reviews

1 / 20
10.0
Excellent

KENNETH,Mar 2026

VIE - EWR

Everything was great, took off on time, arrived on time, boarding was smooth, food and movies were great.
Lufthansa
6.8
Okay
7,937 reviews
Austrian Airlines
7.6
Good
905 reviews

Entertainment

6.8

Comfort

7.3

Overall

7.6

Food

6.8

Boarding

7.6

Crew

8.1

Reviews

1 / 20
10.0
Excellent

KENNETH,Mar 2026

VIE - EWR

Everything was great, took off on time, arrived on time, boarding was smooth, food and movies were great.
Air Serbia
6.1
Okay
218 reviews
Austrian Airlines
7.6
Good
905 reviews

Entertainment

6.8

Comfort

7.3

Overall

7.6

Food

6.8

Boarding

7.6

Crew

8.1

Reviews

1 / 20
10.0
Excellent

KENNETH,Mar 2026

VIE - EWR

Everything was great, took off on time, arrived on time, boarding was smooth, food and movies were great.

Related info for your journey

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

  • What airport do you fly into for flights to Skopje from Chicago?

    For a flight from Chicago to Skopje, you will be flying into Skopje. Skopje (SKP) is just 9.2 mi from the center of the city. Skopje is the only Skopje airport and it handles 0 inbound flights from Chicago per day. 7 airlines have flights to Skopje from Chicago on a regular basis.

  • How long is the flight from Chicago to Skopje?

    Departing from Chicago to Skopje will take you 31h 20m. The distance from Chicago to Skopje is about 5163 mi.

  • What are the cheapest airlines flying from Chicago to Skopje round-trip?

    According to our current data, SWISS ($512), Turkish Airlines ($514), and Lufthansa ($528) offers the cheapest pricing from Chicago to Skopje. SWISS is priced at 28% lower than the current average price of a flight leaving 3 months from now.

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

    For one-way options, check prices for Turkish Airlines. According to our data, you can fly for as low as $284. Users have also found prices from $315 and $331 on Air Serbia and Austrian Airlines, respectively.

  • Where are the most common layover locations when flying from Chicago to Skopje?

    Flights departing from Chicago and landing in Skopje layover in Istanbul most frequently. Vienna follows Istanbul in terms of the most common layover location on Chicago to Skopje flights. Frankfurt am Main comes in third as the most popular layover location on Chicago to Skopje flights.

  • What are some popular things to do or see while on a layover in Istanbul?

    Taksim Square, Laleli Camii, and Beyazit Meydani are currently the most popular points of interest in Istanbul at the moment. Those on a layover in Istanbul interested in visiting Taksim Square, Laleli Camii, or Beyazit Meydani can do so by traveling 20.8 mi, 21.5 mi, and 21.7 mi, respectively from Istanbul. Those landing in Istanbul looking to spend some time exploring during their layover can rent a car for about $39 per day.

  • What are some popular points of interest to see during a layover in Vienna?

    Cathedral of Vienna, Musikverein, and Austria Center Vienna are the most popular attractions in Vienna if you're in need of something to do during your layover. Cathedral of Vienna, Musikverein and Austria Center Vienna are located about 11.0 mi, 10.6 mi, and 10.8 mi, respectively from Vienna Intl if you are interested in checking them out. Those on a layover in Vienna in need of a rental car can book one at Vienna Intl for about $44.

  • What are points of interest worth seeing during a layover in Frankfurt am Main?

    Frankfurt am Main travelers tend to visit Römerberg, Oper Frankfurt, and Festhalle more than any other attractions. Römerberg, Oper Frankfurt, and Festhalle are located about 7.4 mi, 7.0 mi, and 6.5 mi, respectively from Frankfurt am Main. Those on a layover in Frankfurt am Main in need of a rental car can book one at Frankfurt am Main for about $39.

  • Where are the least popular layover locations for Chicago to Skopje flights?

    Of the flights from Chicago to Skopje that have layovers, the fewest flights stop in Belgrade. Warsaw follows Belgrade in terms of the least common layover location on Chicago to Skopje flights.

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

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

  • How can I find direct flights from Chicago to Skopje?

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

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

    Yes. Cheapflights offers flight deals from Chicago to Skopje 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 Skopje?

    Currently, May is the cheapest month in which you can book a flight from Chicago to Skopje (average of $353). Flying from Chicago to Skopje in June is currently the most expensive (average of $970). 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.

Alternative routes for Chicago to Skopje

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Skopje flights
St. Louis to Skopje flights

Top 7 airlines flying from Chicago to Skopje

Discover the top 7 airlines that operate flights from Chicago to Skopje. 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 April 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
SWISSCheapest$512Average$881FlexibilityNo cancel feeOn-time79%
Turkish AirlinesCheapest$514Average$944FlexibilityNo cancel feeOn-time77%
LufthansaCheapest$528Average$1,000FlexibilityNo cancel feeOn-time76%
Austrian AirlinesCheapest$549Average$871FlexibilityNo cancel feeOn-time78%
United AirlinesCheapest$549Average$898FlexibilityNo cancel feeOn-time69%
LOTCheapest$551Average$1,001FlexibilityNo cancel feeOn-time81%
Air SerbiaCheapest$587Average$868FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.