Cheap flights from Chicago to Punta Cana
Fares from $237 in November 2026. Compare every month below, then book with the site you like.
Search Chicago → Punta Cana flightsCheapest Chicago to Punta Cana fares by month
Lowest price per person found in recent searches. Prices change often and are checked when you book.
- October 2026Oct 31 · one way · Air Canada · 2 stops$245See deal
- November 2026Nov 1 · one way · Air Canada · 1 stop$237See deal
- December 2026Dec 16 · one way · Frontier · 2 stops$323See deal
Chicago to Punta Cana at a glance
- Distance1,983 miles
- Nonstop flight timeabout 4h 45m
- Cheapest monthNovember 2026
- Airport codesCHI → PUJ
Plan your Punta Cana trip
Frequently asked questions
- How much is a flight from Chicago to Punta Cana?
- The cheapest fare we found recently is $237 per person, departing Nov 1 on Air Canada. Prices change daily, so search your dates to see today's fares.
- What is the cheapest month to fly from Chicago to Punta Cana?
- November 2026 is currently the cheapest month, from $237. December 2026 is the most expensive, from $323.
- Are there direct flights from Chicago to Punta Cana?
- The cheapest fares we found recently have at least one stop. Nonstop flights may still exist at a higher price; tick "Direct only" in the search to check.
- Which airlines fly from Chicago to Punta Cana?
- The cheapest recent fares on this route were on Air Canada, Frontier.
- How long is the flight from Chicago to Punta Cana?
- Chicago and Punta Cana are about 1,983 miles apart, so a nonstop flight takes roughly 4h 45m. Flights with a stop take longer, depending on the connection.
- Do I need a passport to fly from Chicago to Punta Cana?
- Yes. Punta Cana is in Dominican Republic, so you need a valid passport, and some countries also ask for a visa or an online travel authorization. Check the entry rules for your nationality before you book.
- How do I find the cheapest flight from Chicago to Punta Cana?
- Search your dates on Gotoesy. We list fares from several booking sites sorted cheapest first, show nearby dates when your day has no saved fare, and send you straight to the seller to book.
More flights from Chicago
- Chicago to New York
- Chicago to Los Angeles
- Chicago to Miami
- Chicago to Orlando
- Chicago to Las Vegas
- Chicago to San Francisco
- Chicago to Washington, D.C.
- Chicago to Boston
- Chicago to Atlanta
- Chicago to Dallas
- Chicago to Houston
- Chicago to Seattle