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Flights from Chicago to Skopje

Find cheap airlines flights from Chicago to Skopje

You can choose from 1 airlines that fly from Chicago to Skopje, including Turkish Airlines, Air Serbia has lowest fares on this route.
Turkish Airlines logo Turkish Airlines
Airlines are determined based on actual purchased flight tickets from Chicago to Skopje according to previous 12 months data from Trip.com.

Find flight deals from Chicago to Skopje for the next 3 months. Book one way flights from $260 or round trip flights from $846.

      • ORD 9:20 PM
        29h 5m
        1 stop
        SKP 8:25 AM
        Chicago - Skopje | Mon, Mar 16 | Turkish Airlines
        SKP 8:35 PM
        20h 30m
        1 stop
        ORD 11:05 AM
        Skopje - Chicago | Wed, Mar 18 | Turkish Airlines
        $846 $1,509
        44% off
        44% off
        $1,509 $846
      • ORD 5:20 PM
        12h 25m
        1 stop
        SKP 11:45 AM
        Chicago - Skopje | Mon, Mar 16 | United Airlines
        SKP 9:15 AM
        16h 10m
        1 stop
        ORD 7:25 PM
        Skopje - Chicago | Wed, Mar 18 | Turkish Airlines
        $1,141 $1,509
        24% off
        24% off
        $1,509 $1,141
      • ORD 5:20 PM
        12h 25m
        1 stop
        SKP 11:45 AM
        Chicago - Skopje | Mon, Mar 16 | Lufthansa
        SKP 9:15 AM
        16h 10m
        1 stop
        ORD 7:25 PM
        Skopje - Chicago | Wed, Mar 18 | Turkish Airlines
        $1,161 $1,509
        23% off
        23% off
        $1,509 $1,161
      • ORD 5:20 PM
        24h 55m
        1 stop
        SKP 12:15 AM
        Chicago - Skopje | Mon, Mar 16 | Austrian Airlines
        SKP 8:35 PM
        20h 30m
        1 stop
        ORD 11:05 AM
        Skopje - Chicago | Wed, Mar 18 | Turkish Airlines
        $1,161
        23% off
        $1,509 $1,161
      • ORD 5:20 PM
        12h 25m
        1 stop
        SKP 11:45 AM
        Chicago - Skopje | Mon, Mar 16 | Swiss Airlines
        SKP 8:55 AM
        14h 25m
        1 stop
        ORD 5:20 PM
        Skopje - Chicago | Fri, Mar 20 | Swiss Airlines
        $1,358
        10% off
        $1,509 $1,358
      • CHI 1:00 PM
        17h 25m
        1 stop
        SKP Invalid Date
        Chicago - Skopje | Wed, Mar 18 | Normal Airline
        SKP 3:00 PM
        6h
        Nonstop
        CHI 4:00 PM
        Skopje - Chicago | Fri, Mar 20 | Normal Airline
        Find more flights
        Find more flights
      • ORD 11:20 PM
        19h 50m
        1 stop
        SKP 2:10 AM
        Chicago - Skopje | Sat, Apr 18 | Air Serbia
        $260 $507
        49% off
        49% off
        $507 $260
      • ORD 4:40 PM
        26h 30m
        1 stop
        SKP 2:10 AM
        Chicago - Skopje | Wed, Apr 8 | Air Serbia
        $264 $507
        48% off
        48% off
        $507 $264
      • ORD 4:40 PM
        14h 55m
        1 stop
        SKP 2:35 PM
        Chicago - Skopje | Wed, Apr 1 | Air Serbia
        $364 $507
        28% off
        28% off
        $507 $364
      • ORD 5:30 PM
        15h 5m
        1 stop
        SKP 2:35 PM
        Chicago - Skopje | Sat, Mar 21 | Air Serbia
        $386
        24% off
        $507 $386
      • ORD 9:35 PM
        30h 45m
        1 stop
        SKP 10:20 AM
        Chicago - Skopje | Tue, Mar 17 | American Airlines
        $389
        23% off
        $507 $389
      • ORD 11:20 PM
        19h 50m
        1 stop
        SKP 2:10 AM
        Chicago - Skopje | Sat, Apr 4 | Air Serbia
        $392
        23% off
        $507 $392
      • ORD 4:20 PM
        12h 30m
        1 stop
        SKP 11:50 AM
        Chicago - Skopje | Sat, Apr 4 | United Airlines
        $449
        11% off
        $507 $449
      • ORD 6:00 PM
        18h 15m
        1 stop
        SKP 7:15 PM
        Chicago - Skopje | Tue, Mar 31 | American Airlines
        $454
        10% off
        $507 $454
      • ORD 11:20 PM
        32h 15m
        1 stop
        SKP 2:35 PM
        Chicago - Skopje | Sat, Apr 11 | Air Serbia
        $454
        10% off
        $507 $454
      • ORD 4:05 PM
        15h 25m
        1 stop
        SKP 2:30 PM
        Chicago - Skopje | Mon, May 11 | United Airlines
        $456
        10% off
        $507 $456
      • CHI 1:00 PM
        17h 25m
        1 stop
        SKP Invalid Date
        Chicago - Skopje | Wed, Mar 18 | Normal Airline
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Displayed flight fares from Chicago to Skopje are based on average prices across airlines for the next 3 months, according to the latest Trip.com database.

Flight Info | Chicago to Skopje

The distance between Chicago and Skopje is approximately 8,307.61 km. Based on Trip.com's data travel demand peaks in January. The off-season for travel is October.

Cheapest one-way flight price$260
Cheapest round-trip ticket price$846
Off-season for travelOctober
Peak season for travelJanuary
Flight distance8,307.61 km
Popular airlineTurkish Airlines
Flight statistics for the Chicago–Skopje route are based on aggregated booking data from Trip.com over the past 12 months.

Frequently Asked Questions

  • What are the cheapest flights from Chicago to Skopje (CHI-SKP)?

    Based on Trip.com data, Air Serbia offers one-way fares as low as $260 on Cheapest nonstop routes (e.g. ORD to SKP on Sat, Apr 18), while Turkish Airlines offers Cheapest nonstop round-trips from $846 departing on Mon, Mar 16 and returning on Wed, Mar 18.
  • At the moment, several airlines serve connecting flights from Chicago to Skopje, including: Turkish Airlines United Airlines Selected airlines are based on historical data collected from flight bookings made by users on Trip.com within the last 90 days.
  • By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Chicago to Skopje is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.
  • To find best deals on flights from Chicago to Skopje, you can use various tools on Trip.com:
    · Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Sat, Apr 18, with one-way flights priced at just $260.
    · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is Air Serbia.
    · Set up price alerts to easily monitor ticket prices without having to check every day.
    · Check Trip.com flight deals and promo codes frequently.
    · Avoid peak season unless you book very early. It seems the peak season for Skopje travel is around January.
    · Get exclusive promo codes for Trip.com app users.
  • The cheapest months to fly from Chicago to Skopje is October, when demand for travel is lower.
  • After crunching the numbers on our March flight calendar, it's currently cheapest to fly from Chicago to Skopje on March 30, 2026 with United Airlines, with prices starting at $544.
  • You can land at any one of the following hubs in Skopje, with O'Hare International Airport to Skopje International Airport (ORD-SKP) is by far the most common option on this route: Skopje International Airport (SKP).
  • The time difference between Skopje and Chicago is 7h.
  • Tickets can only be changed or canceled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.

Trip.com airline insights on flights from Chicago to Skopje

Which airlines offer the cheapest nonstop flights from Chicago to Skopje?

Data is based on the average price of all nonstop flights from Chicago to Skopje on Trip.com in the past 12 months.

Based on Trip.com data from the past 12 months, Lufthansa offers the cheapest nonstop flights from Chicago to Skopje, with an average price of $479.

$199
$479
$760
$1,041
$1,321
Lufthansa
$479
Lufthansa
Air Serbia
$518
Air Serbia
Turkish Airlines
$618
Turkish Airlines
LOT Polish Airlines
$1,055
LOT Polish Airlines
United Airlines
$1,321
United Airlines

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Note: Prices shown on this page are estimated lowest price and include all taxes and fees found in the last 24 hours.

Book with no extra fees

Prices displayed in this page are all-inclusive prices (incl. taxes, fuel surcharge, civil aviation development fund, etc) with all fees confirmed before payment. Fees for luggage, meals, WLAN, or other additional services are also included as shown in the flight cards.

Real-time pricing updates

Prices, availability, and travel information on this page were updated within last 24 hours—even in real-time. The more popular the route, the more precise the data.

Change & Cancellation Policy

Trip.com displays flight cancellation and change policies for each flight ticket during the booking process, including fees and applicable conditions. Please check the following scenarios:
Voluntary cancellation/change:
To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy.
Cancellation/change due to a flight schedule change:
If the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.