Cheap Flights from Chicago to Skopje
Cheap Flights from Chicago to Skopje
Looking for cheap flights from Chicago to Skopje? PointsYeah scans award availability across major airline and bank transfer programs in one place, so travelers can compare the lowest points and cash routes faster. Instead of searching each airline separately, users can see pricing from programs like Chase, Amex, Capital One, Citi, and Bilt side by side.
Award prices from Chicago to Skopje vary by season, cabin, and date, but available award flights can start around 55,000–75,000 points one way, with premium cabins available at higher mileage levels. The live search above allows filtering by cabin, airline, stops, or maximum points to find the best award flights from Chicago to Skopje for specific travel dates.
2026-11-08
ORD - SKP
Premium Economy | 2 Stops | 9+ left
From 55,000 Pts + $42.7
2026-11-10
ORD - SKP
Premium Economy | 2 Stops | 9+ left
From 55,000 Pts + $57.4
2026-11-11
ORD - SKP
Premium Economy | 2 Stops | 9+ left
From 55,000 Pts + $57.4
2026-11-09
ORD - SKP
Premium Economy | 2 Stops | 9+ left
From 55,000 Pts + $60.9
2026-11-10
ORD - SKP
Business | 2 Stops | 3 left
From 75,000 Pts + $102.1
2026-11-09
ORD - SKP
Business | 2 Stops | 3 left
From 75,000 Pts + $107.7
Chicago to Skopje flight facts
Distance
5,174 mi
8,326 km in a straight line
Estimated flight time
about 10h 45m
In the air, for the straight-line distance
Time difference
+7h
Skopje is 7 hours ahead of Chicago.
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Airports in Skopje
SKP · Skopje Alexander the Great
Nearby airport alternatives
Flights Chicago - Podgorica · Podgorica is 124 mi from Skopje
Premium cabin flights from Chicago to Skopje
Premium cabin
2026-11-10
ORD - SKP
Business | 2 Stops | 3 left
From 75,000 Pts + $102.1
Premium cabin
2026-11-09
ORD - SKP
Business | 2 Stops | 3 left
From 75,000 Pts + $107.7
Premium cabin
2026-11-10
ORD - SKP
Business | 2 Stops | 9+ left
From 88,000 Pts + $31.8
Premium cabin
2026-11-11
ORD - SKP
Business | 2 Stops | 9+ left
From 88,000 Pts + $31.8
Premium cabin
2026-11-09
ORD - SKP
Business | 2 Stops | 1 left
From 88,000 Pts + $75.5
Premium cabin
2026-11-08
ORD - SKP
Premium Economy | 2 Stops | 9+ left
From 55,000 Pts + $42.7
Selected hotels for your next stay
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Frequently Asked Questions
The cheapest route from Chicago to Skopje depends on award space, transfer bonuses, and travel dates. PointsYeah compares bank and airline programs in one place so you can find the best points and cash combinations faster.
Yes. Transferable points from Chase, Amex, Capital One, Citi, and Bilt can often be moved to airline partners for flights from Chicago to Skopje.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to Skopje.
Chicago and Skopje are about 5,174 miles (8,326 km) apart in a straight line.
Flying the 5,174-mile straight-line distance takes about 10h 45m in the air, estimated from typical cruising speed. Actual travel time depends on the routing; itineraries with connections take longer.
Skopje is 7 hours ahead of Chicago.
Departures from Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD). Arrivals in Skopje: Skopje Alexander the Great (SKP).
Travelers searching this route also look at other popular routes into Skopje, plus the return trip when we track it. Fares and award space change daily.
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