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Cheap flights from Chicago to Punta Cana

Cheapest return fare right now: $415Oct 31 – Nov 5 · American Airlines

Direct flights
No
Typical flight time
5 h 35 min
Price range seen
$415 – $880
Cheapest month (next 3 months)
October 2026

Best dates

DatesNightsAirlineStopsFromPrice
Oct 31 – Nov 55American Airlines1Chicago O'Hare$415Book →
Oct 31 – Nov 77American Airlines1Chicago O'Hare$420Book →
Dec 17 – Dec 3014American Airlines1Chicago O'Hare$699Book →
Dec 16 – Jan 116Air Canada1Chicago O'Hare$717Book →
Dec 17 – Jan 115Air Canada1Chicago O'Hare$856Book →
Dec 19 – Jan 114Air Canada2Chicago O'Hare$880Book →

Prices checked on October 12, 2026.

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Airalo → or Yesim

Tours & tickets

Skip-the-line tickets and tours in Punta Cana.

Klook → Tiqets →

Travel insurance

Cover for medical costs, cancellations and lost luggage.

EKTA →

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Rent from local companies, often without a credit card.

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