Cheap Flights from Chicago to Punta Cana
Cheap Flights from Chicago to Punta Cana
Looking for cheap flights from Chicago to Punta Cana? 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 Punta Cana vary by season, cabin, and date, but available award flights can start around 8,500–11,500 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 Chicago to Punta Cana for specific travel dates.
2026-11-24
ORD - PUJ
Economy | 1 Stop | 9+ left
From 8,500 Pts + $55.5
2026-11-27
ORD - PUJ
Economy | 1 Stop | 9+ left
From 9,200 Pts + $55.5
2026-11-26
ORD - PUJ
Economy | 1 Stop | 9+ left
From 9,900 Pts + $55.5
2026-11-14
ORD - PUJ
Economy | 1 Stop
From 11,500 Pts + $55.5
2026-11-15
ORD - PUJ
Economy | 1 Stop
From 11,500 Pts + $55.5
2026-11-16
ORD - PUJ
Economy | 1 Stop
From 11,500 Pts + $55.5
Premium cabin flights from Chicago to Punta Cana
Premium cabin
2026-10-27
ORD - PUJ
First | 1 Stop | 6 left
From 62,000 Pts + $55.5
Premium cabin
2026-10-26
ORD - PUJ
First | 1 Stop | 9+ left
From 120,500 Pts + $55.5
Premium cabin
2026-11-13
ORD - PUJ
Business | 1 Stop
From 25,000 Pts + $55.5
Premium cabin
2026-10-26
ORD - PUJ
Business | 1 Stop
From 26,000 Pts + $55.5
Premium cabin
2026-10-27
ORD - PUJ
Business | Non stop
From 26,000 Pts + $55.5
Premium cabin
2026-10-26
ORD - PUJ
Business | 1 Stop | 2 left
From 28,826 Pts + $132.8
Selected hotels for your next stay
Punta Cana (Dominican Republic)
Dreams Royal Beach Punta Cana
From 15,000 Pts or $230
La Romana (Dominican Republic)
Dreams La Romana Resort & Spa
From 20,000 Pts or $390
La Romana (Dominican Republic)
Secrets La Romana Resort & Spa
From 20,000 Pts or $413
Frequently Asked Questions
The cheapest route from Chicago to Punta Cana 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 Punta Cana.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to Punta Cana.
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