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 11,500–12,500 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.
2026-11-14
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
2026-12-21
ORD - PUJ
Economy | 1 Stop
From 11,500 Pts + $61.1
2026-10-27
ORD - PUJ
Economy | 1 Stop | 9+ left
From 11,700 Pts + $55.5
2026-10-26
ORD - PUJ
Economy | Non stop | 4 left
From 12,500 Pts + $75.5
Premium cabin flights from Chicago to Punta Cana
Premium cabin
2026-10-27
ORD - PUJ
First | 1 Stop | 1 left
From 91,700 Pts + $55.5
Premium cabin
2026-10-26
ORD - PUJ
Business | 1 Stop | 1 left
From 24,970 Pts + $119.2
Premium cabin
2026-10-27
ORD - PUJ
Business | Non stop | 9+ left
From 25,000 Pts + $75.5
Premium cabin
2026-10-29
ORD - PUJ
Business | Non stop | 9+ left
From 25,000 Pts + $75.5
Premium cabin
2026-10-26
ORD - PUJ
Business | Non stop
From 28,000 Pts + $55.5
Premium cabin
2026-10-27
ORD - PUJ
Business | Non stop
From 28,000 Pts + $55.5
Selected hotels for your next stay
Punta Cana (Dominican Republic)
Dreams Royal Beach Punta Cana
From 15,000 Pts or $230
Punta Cana (Dominican Republic)
Dreams Onyx Resort & Spa
From 20,000 Pts or $249
Punta Cana (Dominican Republic)
Dreams Macao Beach Punta Cana
From 20,000 Pts or $246
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.
Our mission is to provide
the simplest and best
points travel planning
experience. Yeah!
Our mission is to provide the simplest and best
points travel planning experience. Yeah!
