Cheap Flights from Caracas to Chicago
Cheap Flights from Caracas to Chicago
Looking for cheap flights from Caracas to Chicago? 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 Caracas to Chicago vary by season, cabin, and date, but available award flights can start around 17,500–87,500 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 Caracas to Chicago for specific travel dates.
2026-11-05
CCS - ORD
Economy | 1 Stop | 9+ left
From 17,500 Pts + $115.7
2026-11-05
CCS - ORD
Business | 1 Stop | 1 left
From 35,000 Pts + $115.7
2026-11-16
CCS - ORD
Business | 1 Stop
From 82,500 Pts + $95.7
2026-11-17
CCS - ORD
Business | 1 Stop
From 82,500 Pts + $95.7
2026-11-17
CCS - ORD
First | 2 Stops
From 82,500 Pts + $101.3
2026-11-16
CCS - ORD
First | 2 Stops
From 87,500 Pts + $101.3
Caracas to Chicago flight facts
Distance
2,507 mi
4,035 km in a straight line
Estimated flight time
about 5h 30m
In the air, for the straight-line distance
Time difference
−2h
Chicago is 2 hours behind Caracas.
Airports in Caracas
CCS · Simón Bolívar Intl
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Nearby airport alternatives
Flights Willemstad - Chicago · Willemstad is 173 mi from Caracas
Premium cabin flights from Caracas to Chicago
Premium cabin
2026-11-05
CCS - ORD
First | 2 Stops
From 99,000 Pts + $101.3
Premium cabin
2026-11-05
CCS - ORD
Business | 1 Stop
From 99,000 Pts + $95.7
Premium cabin
2026-11-17
CCS - ORD
First | 2 Stops
From 82,500 Pts + $101.3
Premium cabin
2026-11-16
CCS - ORD
First | 2 Stops
From 87,500 Pts + $101.3
Premium cabin
2026-11-05
CCS - ORD
Business | 1 Stop | 1 left
From 35,000 Pts + $115.7
Premium cabin
2026-11-16
CCS - ORD
Business | 1 Stop
From 82,500 Pts + $95.7
Selected hotels for your next stay
Chicago (United States)
Chicago Athletic Association
From 15,000 Pts or $236
Chicago (USA)
ACME Hotel Chicago, Outset Collection by Hilton
From 28,000 Pts or $75
Chicago, IL (USA)
Waldorf Astoria Chicago
From 95,000 Pts or $407
Frequently Asked Questions
The cheapest route from Caracas to Chicago 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 Caracas to Chicago.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Caracas to Chicago.
Caracas and Chicago are about 2,507 miles (4,035 km) apart in a straight line.
Flying the 2,507-mile straight-line distance takes about 5h 30m in the air, estimated from typical cruising speed. Actual travel time depends on the routing; itineraries with connections take longer.
Chicago is 2 hours behind Caracas.
Departures from Caracas: Simón Bolívar Intl (CCS). Arrivals in Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD).
Travelers searching this route also look at other popular routes into Chicago, plus the return trip when we track it. Fares and award space change daily.
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