HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Skopje

$268+ 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 8/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SKP
Aug 12 — Aug 191
Wed 8/12
Wed 8/19
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 July 13, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/12. 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.
Sun 7/195:10 pm
ORD
-
SKP
2 stops36h 45m
LOT
Sat 8/295:30 pm
SKP
-
ORD
1 stop28h 40m
LOT
Deal found 7/12$895
This Kiwi.com deal was found by Cheapflights users on 7/8. 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.
Mon 7/275:10 pm
ORD
-
SKP
1 stop12h 45m
LOT
Wed 8/195:30 pm
SKP
-
ORD
1 stop33h 20m
LOT
Deal found 7/8$896
This Air Serbia deal was found by Cheapflights users on 7/9. 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 Air Serbia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1211:20 pm
ORD
-
SKP
1 stop32h 15m
Air Serbia
Tue 9/223:10 pm
SKP
-
ORD
1 stop30h 20m
Air Serbia
Deal found 7/9$897
This Turkish Airlines deal was found by Cheapflights users on 7/8. 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.
Fri 9/188:10 pm
ORD
-
SKP
1 stop16h 15m
Turkish Airlines
Sun 9/208:15 pm
SKP
-
ORD
1 stop20h 25m
Turkish Airlines
Deal found 7/8$898
This United Airlines deal was found by Cheapflights users on 7/9. 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.
Wed 9/2312:55 pm
ORD
-
SKP
2 stops15h 55m
United Airlines
Fri 10/24:25 am
SKP
-
ORD
1 stop15h 55m
United Airlines
Deal found 7/9$899
This Lufthansa deal was found by Cheapflights users on 7/10. 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 Lufthansa is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/129:40 pm
ORD
-
SKP
2 stops19h 35m
Multiple Airlines
Sun 8/304:25 am
SKP
-
ORD
1 stop15h 55m
Multiple Airlines
Deal found 7/10$900
This Kiwi.com deal was found by Cheapflights users on 7/8. 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.
Mon 7/208:10 pm
ORD
-
SKP
1 stop28h 45m
Multiple Airlines
Wed 8/265:50 pm
SKP
-
ORD
2 stops31h 00m
Multiple Airlines
Deal found 7/8$902
This LOT deal was found by Cheapflights users on 7/12. 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.
Fri 7/248:10 pm
ORD
-
SKP
1 stop33h 45m
LOT
Thu 9/171:35 pm
SKP
-
ORD
1 stop13h 15m
LOT
Deal found 7/12$903
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/248:10 pm
ORD
-
SKP
1 stop33h 45m
LOT
Thu 8/131:35 pm
SKP
-
ORD
2 stops32h 35m
LOT
Deal found 7/13$904
This FlightHub deal was found by Cheapflights users on 7/12. 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 7/269:50 pm
ORD
-
SKP
1 stop32h 05m
LOT
Tue 9/151:35 pm
SKP
-
ORD
2 stops32h 35m
LOT
Deal found 7/12$905
This Air Serbia deal was found by Cheapflights users on 7/12. 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 Air Serbia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/111:20 pm
ORD
-
SKP
1 stop19h 50m
Air Serbia
Thu 10/293:10 pm
SKP
-
ORD
1 stop30h 35m
Air Serbia
Deal found 7/12$906
This Mytrip deal was found by Cheapflights users on 7/10. 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.
Mon 8/2410:25 pm
ORD
-
SKP
3 stops33h 10m
Multiple Airlines
Mon 8/315:45 am
SKP
-
ORD
2 stops22h 40m
Multiple Airlines
Deal found 7/10$907

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 July 13, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$895
(Mytrip)

One-way from

$268
(Kiwi.com)

Popular in

July

Cheapest in

November

Average price

$1,224
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. 28% potential increase in price ($303 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 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 July 13, 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

Sat 8/29

11:20 pm-2:35 pm

1 stop32h 15m

Skopje

Sat 9/12

3:10 pm-9:15 pm

1 stop13h 05m

$896

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Thu 10/1

8:10 pm-7:55 am

1 stop28h 45m

Skopje

Fri 10/9

8:45 am-9:40 am

1 stop31h 55m

$908

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Sun 9/20

5:55 am-11:50 am

2 stops46h 55m

Skopje

Wed 9/30

4:25 am-10:55 pm

2 stops25h 30m

$909
Quickest round-trip

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Wed 9/23

7:30 am-11:50 am

2 stops21h 20m

Skopje

Tue 10/6

4:25 am-5:20 pm

2 stops19h 55m

$909

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Sat 8/15

8:10 pm-7:55 am

1 stop28h 45m

Skopje

Sun 8/30

8:15 pm-9:40 am

1 stop20h 25m

$923

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Wed 8/5

4:40 pm-2:10 am

1 stop26h 30m

Skopje

Fri 9/25

3:50 am-9:15 pm

1 stop24h 25m

$947

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Wed 8/5

4:40 pm-2:10 am

1 stop26h 30m

Skopje

Fri 10/2

3:50 am-9:15 pm

1 stop24h 25m

$947

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Wed 9/2

4:40 pm-2:10 am

1 stop26h 30m

Skopje

Sun 9/6

3:50 am-2:30 pm

1 stop17h 40m

$947

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Mon 8/31

4:40 pm-2:35 pm

1 stop14h 55m

Skopje

Tue 9/8

3:10 pm-2:30 pm

1 stop30h 20m

$949

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Sun 11/22

8:15 pm-7:55 am

1 stop28h 40m

Skopje

Mon 12/28

8:45 pm-10:00 am

1 stop20h 15m

$968

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/8

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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy3 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
MytripPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust Score*1 star
AranGrantPrice 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

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 $472). Flying from Chicago to Skopje in July is currently the most expensive (average of $1,221). 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 36% 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 28m.

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 Warsaw (WAW) offer the fastest connection on this route, with an average layover time of 1h 55m.

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

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 86 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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 July 13, 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
943 reviews

Food

6.8

Overall

7.6

Comfort

7.3

Crew

8.1

Boarding

7.6

Entertainment

6.8

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
943 reviews
Austrian Airlines
7.6
Good
943 reviews

Food

6.8

Overall

7.6

Comfort

7.3

Crew

8.1

Boarding

7.6

Entertainment

6.8

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
1,210 reviews
Austrian Airlines
7.6
Good
943 reviews

Food

6.8

Overall

7.6

Comfort

7.3

Crew

8.1

Boarding

7.6

Entertainment

6.8

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
4,442 reviews
Austrian Airlines
7.6
Good
943 reviews

Food

6.8

Overall

7.6

Comfort

7.3

Crew

8.1

Boarding

7.6

Entertainment

6.8

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.
Lufthansa
6.8
Okay
8,131 reviews
Austrian Airlines
7.6
Good
943 reviews

Food

6.8

Overall

7.6

Comfort

7.3

Crew

8.1

Boarding

7.6

Entertainment

6.8

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
943 reviews

Food

6.8

Overall

7.6

Comfort

7.3

Crew

8.1

Boarding

7.6

Entertainment

6.8

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 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 28h 45m. The distance from Chicago to Skopje is about 5163 mi. This flight may include one or multiple stops.

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

    According to our current data, SWISS ($505), Turkish Airlines ($518), and Lufthansa ($527) offers the cheapest pricing from Chicago to Skopje. SWISS is priced at 33% 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 $329 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.

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

    Taksim Square, Laleli Camii, and Sultan Ahmet Camii 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 Sultan Ahmet Camii can do so by traveling 20.8 mi, 21.5 mi, and 22.3 mi, respectively from Istanbul. Those landing in Istanbul looking to spend some time exploring during their layover can rent a car for about $42 per day.

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

    Musikverein, Cathedral of Vienna, and Prater are the most popular attractions in Vienna if you're in need of something to do during your layover. Musikverein, Cathedral of Vienna and Prater are located about 10.6 mi, 11.0 mi, and 10.4 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 $55.

  • 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. Frankfurt am Main 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 $472). Flying from Chicago to Skopje in July is currently the most expensive (average of $1,221). 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 July 13, 2026.
AirlineCheapestAverageFlexibilityOn-time
SWISSCheapest$505Average$922FlexibilityNo cancel feeOn-time79%
Turkish AirlinesCheapest$518Average$994FlexibilityNo cancel feeOn-time77%
LufthansaCheapest$527Average$963FlexibilityNo cancel feeOn-time76%
Austrian AirlinesCheapest$549Average$888FlexibilityNo cancel feeOn-time78%
United AirlinesCheapest$549Average$911FlexibilityNo cancel feeOn-time69%
LOTCheapest$552Average$1,082FlexibilityNo cancel feeOn-time81%
Air SerbiaCheapest$747Average$895FlexibilityNo 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.