Cheap Flights from Chicago to Cali
Cheap Flights from Chicago to Cali
Looking for cheap flights from Chicago to Cali? 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 Cali vary by season, cabin, and date, but available award flights can start around 13,500–50,000 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 Cali for specific travel dates.
2026-12-30
ORD - CLO
Economy | 2 Stops
From 13,500 Pts + $20.6
2026-12-30
ORD - CLO
Economy | 2 Stops | 9+ left
From 17,500 Pts + $40.6
2026-12-30
ORD - CLO
Economy | 2 Stops
From 23,300 Pts + $44
2026-12-30
ORD - CLO
Business | 1 Stop
From 31,500 Pts + $20.6
2026-12-30
ORD - CLO
Business | 1 Stop | 1 left
From 35,000 Pts + $40.6
2026-12-30
ORD - CLO
Business | 2 Stops | 2 left
From 50,000 Pts + $98.4
Chicago to Cali flight facts
Distance
2,745 mi
4,417 km in a straight line
Estimated flight time
about 6h
In the air, for the straight-line distance
Time difference
+1h
Cali is 1 hour ahead of Chicago.
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Airports in Cali
CLO · Alfonso Bonilla Aragon Intl
Nearby airport alternatives
Flights Chicago - Bogota · Bogota is 174 mi from Cali
Premium cabin flights from Chicago to Cali
Premium cabin
2026-12-30
ORD - CLO
Business | 1 Stop | 4 left
From 69,510 Pts + $56.7
Premium cabin
2026-12-30
ORD - CLO
First | 2 Stops
From 119,000 Pts + $20.6
Premium cabin
2026-12-30
ORD - CLO
Business | 1 Stop
From 31,500 Pts + $20.6
Premium cabin
2026-12-30
ORD - CLO
Business | 1 Stop | 1 left
From 35,000 Pts + $40.6
Premium cabin
2026-12-30
ORD - CLO
Business | 2 Stops | 2 left
From 50,000 Pts + $98.4
Premium cabin
2026-12-30
ORD - CLO
Business | 1 Stop
From 68,400 Pts + $44
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Frequently Asked Questions
The cheapest route from Chicago to Cali 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 Cali.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to Cali.
Chicago and Cali are about 2,745 miles (4,417 km) apart in a straight line.
Flying the 2,745-mile straight-line distance takes about 6h in the air, estimated from typical cruising speed. Actual travel time depends on the routing; itineraries with connections take longer.
Cali is 1 hour ahead of Chicago.
Departures from Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD). Arrivals in Cali: Alfonso Bonilla Aragon Intl (CLO).
Travelers searching this route also look at other popular routes into Cali, plus the return trip when we track it. Fares and award space change daily.
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