HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Skopje

$274+ 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 1/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SKP
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
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.

Cheapflights Tip: The best prices from Chicago to Skopje are usually found in January or March, booked 70 days in advance, depart on a Friday or Saturday and return on a Wednesday

Find 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 November 26, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/24. 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.
Wed 11/266:25 pmORD - SKP
1 stop14h 10mLufthansa
Tue 12/165:40 amSKP - ORD
2 stops19h 45mLufthansa
Deal found 11/24$512
This Kiwi.com deal was found by Cheapflights users on 11/25. 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.
Sat 11/294:10 pmORD - SKP
1 stop20h 25mMultiple Airlines
Fri 1/2312:30 pmSKP - ORD
2 stops29h 30mMultiple Airlines
Deal found 11/25$513
This FlightHub deal was found by Cheapflights users on 11/26. 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.
Sat 11/293:20 pmORD - SKP
1 stop17h 15mMultiple Airlines
Fri 1/168:55 amSKP - ORD
1 stop14h 25mMultiple Airlines
Deal found 11/26$514
This KAYAK deal was found by Cheapflights users on 11/25. 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.
Wed 11/266:50 pmORD - SKP
1 stop18h 35mSWISS
Sun 12/148:45 pmSKP - ORD
1 stop26h 35mSWISS
Deal found 11/25$515
This FlightHub deal was found by Cheapflights users on 11/23. 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.
Mon 12/82:40 pmORD - SKP
2 stops17h 55mMultiple Airlines
Fri 1/168:55 amSKP - ORD
1 stop14h 25mMultiple Airlines
Deal found 11/23$516
This CrystalTravel deal was found by Cheapflights users on 11/24. 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 CrystalTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/3010:35 pmORD - SKP
1 stop16h 45mLufthansa
Sat 1/245:40 amSKP - ORD
2 stops19h 53mLufthansa
Deal found 11/24$517
This Kiwi.com deal was found by Cheapflights users on 11/24. 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.
Wed 11/264:20 pmORD - SKP
1 stop12h 25mMultiple Airlines
Tue 12/165:40 amSKP - ORD
2 stops19h 45mMultiple Airlines
Deal found 11/24$518
This FlightHub deal was found by Cheapflights users on 11/26. 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 12/59:05 pmORD - SKP
2 stops31h 40mMultiple Airlines
Sun 12/148:45 pmSKP - ORD
1 stop26h 35mMultiple Airlines
Deal found 11/26$521
This KAYAK deal was found by Cheapflights users on 11/25. 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 11/285:50 pmORD - SKP
2 stops42h 45mSWISS
Mon 1/268:45 pmSKP - ORD
1 stop23h 00mSWISS
Deal found 11/25$522
This FlightHub deal was found by Cheapflights users on 11/24. 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.
Wed 11/267:05 amORD - SKP
2 stops30h 20mMultiple Airlines
Thu 1/225:40 amSKP - ORD
1 stop16h 40mMultiple Airlines
Deal found 11/24$524

Cheap 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 November 26, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$513
(Kiwi.com)

One-way from

$274
(Kiwi.com)

Popular in

May

Cheapest in

January

Average price

$733
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. 20% potential increase in price ($195 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($35 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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 November 26, 2025.
Use the filters below to find and compare flights from Chicago to Skopje that are best for you.

Fly from

Chicago

Fly to

Skopje

Route

Depart

Return

Price

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Wed 1/28

6:50 pm-8:25 pm

1 stop18h 35m

Skopje

Sun 2/1

8:45 pm-12:45 pm

1 stop23h 00m

$515

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Sat 11/29

6:50 pm-7:35 pm

1 stop17h 45m

Skopje

Thu 1/15

4:30 am-3:20 pm

2 stops17h 50m

$526

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Mon 1/12

3:20 pm-3:35 pm

1 stop17h 15m

Skopje

Sat 1/24

5:40 am-3:20 pm

1 stop16h 40m

$534

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Mon 1/12

6:25 pm-3:35 pm

1 stop14h 10m

Skopje

Thu 1/22

5:40 am-3:20 pm

1 stop16h 40m

$534

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Sun 11/30

10:35 pm-10:20 pm

1 stop16h 45m

Skopje

Sun 1/25

4:30 am-3:20 pm

2 stops17h 50m

$550

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Mon 12/29

9:50 pm-12:15 am

2 stops19h 25m

Skopje

Tue 3/31

12:35 pm-7:55 pm

2 stops38h 20m

$551

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Sun 12/7

9:19 am-11:45 am

2 stops19h 26m

Skopje

Wed 3/18

4:30 am-3:00 pm

1 stop16h 30m

$553

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Wed 1/28

8:45 am-11:45 am

2 stops20h 00m

Skopje

Thu 2/19

4:30 am-2:00 pm

1 stop16h 30m

$553

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Mon 1/19

12:31 pm-7:10 pm

3 stops47h 39m

$274

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Wed 12/3

8:36 am-1:10 am

3 stops33h 34m

$312

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/25

Showing 1-10 of 17 results
1
2

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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star
AranGrantPrice Accuracy2 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
oojoPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*2 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 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 Justfly.com to be most consistent on Cheapflights vs. Justfly.com Users can find the same prices on Chicago-Skopje flight deals on Cheapflights vs. Justfly.com >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 Justfly.com the most. Justfly.com 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 November 21, 2025.

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 70 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, November is the cheapest month in which you can book a flight from Chicago to Skopje (average of $493). Flying from Chicago to Skopje in June is currently the most expensive (average of $789). 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.

What is the cheapest time of day to fly from CHI to SKP?

Find hourly flight availability from Chicago to Skopje. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 26, 2025.

One of the essential ways to save on airfare from Chicago to Skopje is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight at noon could potentially save you up to 24% on airfare.

What is the cheapest day to fly from Chicago to Skopje?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Skopje. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Skopje flight should consider departing on Tuesday mornings when fares are most often at their lowest. Wednesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 46% 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.

Vienna (VIE) is the most affordable 1-stop option, with an average round-trip price of $541.

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 Warsaw (WAW) have the shortest average one-way travel time for 1-stop routes: 12h 24m.

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 42m.

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 November 26, 2025.
See what other customers who have flown with Austrian Airlines, LOT, and Turkish 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
874 reviews

Crew

8.1

Entertainment

6.8

Overall

7.6

Food

6.8

Boarding

7.6

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Andrew,Sep 2025

FLR - VIE

Staff was really nice, they provided water as a beverage. Otherwise you had to purchase beverages or food. A complementary chocolate was provided at the end of the flight.
Austrian Airlines
7.6
Good
874 reviews
Austrian Airlines
7.6
Good
874 reviews

Crew

8.1

Entertainment

6.8

Overall

7.6

Food

6.8

Boarding

7.6

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Andrew,Sep 2025

FLR - VIE

Staff was really nice, they provided water as a beverage. Otherwise you had to purchase beverages or food. A complementary chocolate was provided at the end of the flight.
LOT
7.5
Good
1,140 reviews
Austrian Airlines
7.6
Good
874 reviews

Crew

8.1

Entertainment

6.8

Overall

7.6

Food

6.8

Boarding

7.6

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Andrew,Sep 2025

FLR - VIE

Staff was really nice, they provided water as a beverage. Otherwise you had to purchase beverages or food. A complementary chocolate was provided at the end of the flight.
Turkish Airlines
7.3
Good
4,063 reviews
Austrian Airlines
7.6
Good
874 reviews

Crew

8.1

Entertainment

6.8

Overall

7.6

Food

6.8

Boarding

7.6

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Andrew,Sep 2025

FLR - VIE

Staff was really nice, they provided water as a beverage. Otherwise you had to purchase beverages or food. A complementary chocolate was provided at the end of the flight.
Lufthansa
6.8
Okay
7,594 reviews
Austrian Airlines
7.6
Good
874 reviews

Crew

8.1

Entertainment

6.8

Overall

7.6

Food

6.8

Boarding

7.6

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Andrew,Sep 2025

FLR - VIE

Staff was really nice, they provided water as a beverage. Otherwise you had to purchase beverages or food. A complementary chocolate was provided at the end of the flight.
Air Serbia
6.2
Okay
209 reviews
Austrian Airlines
7.6
Good
874 reviews

Crew

8.1

Entertainment

6.8

Overall

7.6

Food

6.8

Boarding

7.6

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Andrew,Sep 2025

FLR - VIE

Staff was really nice, they provided water as a beverage. Otherwise you had to purchase beverages or food. A complementary chocolate was provided at the end of the 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 18h 35m. 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, Turkish Airlines ($512), SWISS ($512), and Austrian Airlines ($571) offers the cheapest pricing from Chicago to Skopje. Turkish Airlines is priced at 32% lower than the current average price of a flight leaving 3 months from now.

  • 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. Belgrade 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, Beyazit Meydani, and Laleli 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, Beyazit Meydani, or Laleli Camii can do so by traveling 20.8 mi, 21.7 mi, and 21.5 mi, respectively from Istanbul. Those landing in Istanbul looking to spend some time exploring during their layover can rent a car for about $37 per day.

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

    Musikverein, Cathedral of Vienna, and Stephansplatz are the most popular attractions in Vienna if you're in need of something to do during your layover. Musikverein, Cathedral of Vienna and Stephansplatz are located about 10.6 mi, 11.0 mi, and 11.0 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 $38.

  • What are points of interest worth seeing during a layover in Belgrade?

    Belgrade travelers tend to visit Hram Svetog Save, Slavija Square, and Belgrade Zoo more than any other attractions. Hram Svetog Save, Slavija Square, and Belgrade Zoo are located about 8.0 mi, 7.8 mi, and 7.1 mi, respectively from Belgrade Nikola Tesla. Those on a layover in Belgrade in need of a rental car can book one at Belgrade Nikola Tesla for about $18.

  • 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 Warsaw. Frankfurt am Main follows Warsaw 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, November is the cheapest month in which you can book a flight from Chicago to Skopje (average of $493). Flying from Chicago to Skopje in June is currently the most expensive (average of $789). 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 November 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
Turkish AirlinesCheapest$512Average$919FlexibilityNo cancel feeOn-time77%
SWISSCheapest$512Average$891FlexibilityNo cancel feeOn-time79%
Austrian AirlinesCheapest$571Average$1,012FlexibilityNo cancel feeOn-time78%
United AirlinesCheapest$578Average$1,006FlexibilityNo cancel feeOn-time69%
Air SerbiaCheapest$589Average$891FlexibilityNo cancel feeOn-timeN/A
LOTCheapest$613Average$985FlexibilityNo cancel feeOn-time81%
LufthansaCheapest$673Average$1,014FlexibilityNo cancel feeOn-time76%

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.