HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$355+ Cheap flights from Skopje (SKP) to Chicago (CHI)

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 9/16. Fares are subject to change and may not be available on all flights or dates of travel.
SKP — CHI
Aug 18 — Aug 251
Mon 8/18
Mon 8/25
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Skopje to Chicago 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 Skopje to Chicago are usually found in November or February, booked 83 days in advance, depart on a Wednesday or Saturday and return on a Friday

Cheap flight deals from Skopje to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Skopje (SKP) to Chicago (CHI). 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 August 13, 2025.

Round-trip from

$642
(SWISS)

One-way from

$355
(Kiwi.com)

Popular in

August

Cheapest in

November

Average price

$1,170
From Skopje to Chicago (CHI)
Search Deals
One-way flight from Skopje to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($157 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($40 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals

Find flight deals from Skopje to Chicago

Cheapest flights from Skopje to Chicago
Explore the most affordable flight options available from Skopje to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 13, 2025.

This SWISS deal was found by Cheapflights users on 8/12. 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 SWISS is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/288:35 pmSKP - ORD
1 stop26h 45mSWISS
Sat 1/316:50 pmORD - SKP
1 stop17h 55mSWISS
Deal found 8/12$642
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/18:50 pmSKP - ORD
1 stop26h 05mMultiple Airlines
Tue 9/164:20 pmORD - SKP
1 stop12h 30mMultiple Airlines
Deal found 8/13$645
This United Airlines deal was found by Cheapflights users on 8/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/64:25 amSKP - ORD
2 stops35h 14mUnited Airlines
Wed 9/174:00 pmORD - SKP
2 stops36h 50mUnited Airlines
Deal found 8/13$651
This United Airlines deal was found by Cheapflights users on 8/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/94:25 amSKP - ORD
2 stops34h 21mUnited Airlines
Fri 10/109:37 pmORD - SKP
2 stops31h 13mUnited Airlines
Deal found 8/13$652
This Austrian Airlines deal was found by Cheapflights users on 8/13. 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 Austrian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/912:35 pmSKP - ORD
2 stops36h 50mAustrian Airlines
Fri 10/104:00 pmORD - SKP
2 stops36h 50mAustrian Airlines
Deal found 8/13$653
This United Airlines deal was found by Cheapflights users on 8/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/84:25 amSKP - ORD
1 stop15h 55mUnited Airlines
Fri 10/104:20 pmORD - SKP
1 stop12h 30mUnited Airlines
Deal found 8/12$654
This oojo deal was found by Cheapflights users on 8/13. 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.
Wed 9/35:30 pmSKP - ORD
1 stop28h 40mLOT
Fri 9/199:40 pmORD - SKP
1 stop12h 05mLOT
Deal found 8/13$659
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/23:10 pmSKP - ORD
1 stop30h 15mAir Serbia
Sat 9/2011:20 pmORD - SKP
1 stop19h 45mAir Serbia
Deal found 8/13$660
This Gurufare deal was found by Cheapflights users on 8/13. 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 Gurufare is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/108:30 pmSKP - ORD
1 stop26h 25mMultiple Airlines
Wed 10/84:00 pmORD - SKP
1 stop15h 05mMultiple Airlines
Deal found 8/13$663
This Gurufare deal was found by Cheapflights users on 8/12. 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 Gurufare is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/88:50 pmSKP - ORD
1 stop26h 05mMultiple Airlines
Wed 10/84:00 pmORD - SKP
1 stop15h 05mMultiple Airlines
Deal found 8/12$664
This United Airlines deal was found by Cheapflights users on 8/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/34:25 amSKP - ORD
2 stops20h 56mUnited Airlines
Sat 9/206:30 amORD - SKP
2 stops22h 20mUnited Airlines
Deal found 8/13$669

Cheapflights Fare Finder

 
Customize your flight search to find flights from Skopje to Chicago 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 August 13, 2025.
Use the filters below to find and compare flights from Skopje to Chicago that are best for you.

Fly from

Skopje

Fly to

Chicago

Route

Depart

Return

Price

SkopjeChicago

SKP - ORD

SKPORD

Skopje

Sun 12/28

8:35 pm-4:20 pm

1 stop26h 45m

Chicago O'Hare Intl

Sat 1/31

6:50 pm-7:45 pm

1 stop17h 55m

$642

SkopjeChicago

SKP - ORD

SKPORD

Skopje

Sat 9/6

4:25 am-8:39 am

2 stops35h 14m

Chicago O'Hare Intl

Wed 9/17

4:00 pm-11:50 am

2 stops36h 50m

$651

SkopjeChicago

SKP - ORD

SKPORD

Skopje

Tue 9/9

4:25 am-7:46 am

2 stops34h 21m

Chicago O'Hare Intl

Fri 10/10

9:37 pm-11:50 am

2 stops31h 13m

$652

SkopjeChicago

SKP - ORD

SKPORD

Skopje

Tue 9/9

12:35 pm-6:25 pm

2 stops36h 50m

Chicago O'Hare Intl

Fri 10/10

4:00 pm-11:50 am

2 stops36h 50m

$653

SkopjeChicago

SKP - ORD

SKPORD

Skopje

Wed 9/10

4:25 am-6:25 pm

2 stops21h 00m

Chicago O'Hare Intl

Fri 10/10

4:00 pm-11:50 am

2 stops36h 50m

$653

SkopjeChicago

SKP - ORD

SKPORD

Skopje

Sun 12/28

12:30 pm-2:00 pm

1 stop32h 30m

Chicago O'Hare Intl

Sat 1/31

1:12 pm-12:15 am

2 stops28h 03m

$654

SkopjeChicago

SKP - ORD

SKPORD

Skopje

Mon 9/8

4:25 am-1:20 pm

1 stop15h 55m

Chicago O'Hare Intl

Fri 10/10

4:20 pm-11:50 am

1 stop12h 30m

$654

SkopjeChicago

SKP - ORD

SKPORD

Skopje

Wed 9/3

5:30 pm-3:10 pm

1 stop28h 40m

Chicago O'Hare Intl

Fri 9/19

9:40 pm-4:45 pm

1 stop12h 05m

$659

SkopjeChicago

SKP - ORD

SKPORD

Skopje

Tue 9/2

3:10 pm-2:25 pm

1 stop30h 15m

Chicago O'Hare Intl

Sat 9/20

11:20 pm-2:05 am

1 stop19h 45m

$660

SkopjeChicago

SKP - ORD

SKPORD

Skopje

Wed 9/10

8:30 pm-3:55 pm

1 stop26h 25m

Chicago O'Hare Intl

Wed 10/8

4:00 pm-2:05 pm

1 stop15h 05m

$663

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 19 results
1
2

Best time to book a flight from Skopje to Chicago

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

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

Use this chart to determine the optimal time to book a round-trip flight from Skopje to Chicago. Price data was last updated on August 8, 2025.

The price you pay for your flight from Skopje to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 83 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 Skopje to Chicago?

Currently, August is the cheapest month in which you can book a flight from Skopje to Chicago (average of $245). Flying from Skopje to Chicago in March is currently the most expensive (average of $321). 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 SKP to CHI?

Find hourly flight availability from Skopje to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 13, 2025.

When flying from Skopje to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 13% versus a flight in the afternoon.

How much does it cost to fly round-trip from Skopje to Chicago?

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

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

Istanbul (IST) – chosen by Cheapflights users on 42% of 1-stop itineraries from Skopje to Chicago on Cheapflights.

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

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

Frankfurt am Main (FRA) is the most affordable 1-stop option, with an average round-trip price of $546.

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

Shortest average travel time for 1-stop one-way flights from Skopje to Chicago, 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: 13h 05m.

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

Average layover duration for 1-stop one-way flights from Skopje to Chicago, 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 03m.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated August 13, 2025.
See what other customers who have flown with LOT, Austrian Airlines, and Turkish Airlines from Skopje to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
LOT
7.6
Good
1,107 reviews

Entertainment

7.0

Comfort

7.5

Overall

7.6

Boarding

7.6

Crew

8.2

Food

7.2

Reviews

1 / 20
10.0
Excellent

Tomasz,Jan 2025

JFK - WAW

The food this time was delicious. Pasta meal with mushroom sauce, cobb salad, and real metal utensils.
LOT
7.6
Good
1,107 reviews
LOT
7.6
Good
1,107 reviews

Entertainment

7.0

Comfort

7.5

Overall

7.6

Boarding

7.6

Crew

8.2

Food

7.2

Reviews

1 / 20
10.0
Excellent

Tomasz,Jan 2025

JFK - WAW

The food this time was delicious. Pasta meal with mushroom sauce, cobb salad, and real metal utensils.
Austrian Airlines
7.6
Good
826 reviews
LOT
7.6
Good
1,107 reviews

Entertainment

7.0

Comfort

7.5

Overall

7.6

Boarding

7.6

Crew

8.2

Food

7.2

Reviews

1 / 20
10.0
Excellent

Tomasz,Jan 2025

JFK - WAW

The food this time was delicious. Pasta meal with mushroom sauce, cobb salad, and real metal utensils.
Turkish Airlines
7.3
Good
3,942 reviews
LOT
7.6
Good
1,107 reviews

Entertainment

7.0

Comfort

7.5

Overall

7.6

Boarding

7.6

Crew

8.2

Food

7.2

Reviews

1 / 20
10.0
Excellent

Tomasz,Jan 2025

JFK - WAW

The food this time was delicious. Pasta meal with mushroom sauce, cobb salad, and real metal utensils.
Lufthansa
6.8
Okay
7,317 reviews
LOT
7.6
Good
1,107 reviews

Entertainment

7.0

Comfort

7.5

Overall

7.6

Boarding

7.6

Crew

8.2

Food

7.2

Reviews

1 / 20
10.0
Excellent

Tomasz,Jan 2025

JFK - WAW

The food this time was delicious. Pasta meal with mushroom sauce, cobb salad, and real metal utensils.
Air Serbia
6.2
Okay
199 reviews
LOT
7.6
Good
1,107 reviews

Entertainment

7.0

Comfort

7.5

Overall

7.6

Boarding

7.6

Crew

8.2

Food

7.2

Reviews

1 / 20
10.0
Excellent

Tomasz,Jan 2025

JFK - WAW

The food this time was delicious. Pasta meal with mushroom sauce, cobb salad, and real metal utensils.

Related info for your journey

Find useful and relevant information for your journey from Skopje to Chicago. 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 from for flights from Skopje to Chicago?

    Skopje (SKP), located 9.2 mi from the city center, is the airport you fly out of when you book flights from Skopje to Chicago. 6 airlines have flights from Skopje to Chicago on a regular basis. Booking flights from Skopje to Chicago should not be difficult; the airport handles an average of 0 outbound flights to Chicago per day.

  • What is the cheapest airline to fly from Skopje to Chicago round-trip?

    SWISS, at $642, was found to be the cheapest airline from Skopje to Chicago.. SWISS is 13% cheaper than the average price of flights available within the next 90 days to this destination.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Skopje to Chicago (average of $245). Flying from Skopje to Chicago in March is currently the most expensive (average of $321). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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 Skopje to Chicago

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

Top 6 airlines flying from Skopje to Chicago

Discover the top 6 airlines that operate flights from Skopje to Chicago. 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 August 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
Turkish AirlinesCheapest$537Average$685FlexibilityNo cancel feeOn-time77%
LOTCheapest$575Average$644FlexibilityNo cancel feeOn-time81%
Air SerbiaCheapest$579Average$689FlexibilityNo cancel feeOn-timeN/A
LufthansaCheapest$585Average$672FlexibilityNo cancel feeOn-time76%
United AirlinesCheapest$596Average$713FlexibilityNo cancel feeOn-time69%
Austrian AirlinesCheapest$609Average$739FlexibilityNo cancel feeOn-time78%

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.