Today's drop ·
Cheap flights from Chicago Midway to Punta Cana
$400 round trip right now, 38% under the $643 this route usually costs.
How cheap is this?
Telly prices every departure date six months out on this route, for trips of 2 to 14 nights, and measures each fare against what the route usually costs. The cheapest round trip right now is $400 on Delta Air Lines, 1 stop, against a usual $643. 17% under what Delta Air Lines usually charges.
When to go
The cheapest dates fall in Nov–Apr, for trips of 2 to 7 nights. Nov in Punta Cana runs around 82°. The dates come picked because a cheap fare only exists on certain days; the exact ones and the booking link are in the app.
Passport required
Punta Cana is outside the US and Canada, so you need a passport. Every flight on Telly leaves the country; that is the whole filter.
Questions about this route
How much is a flight from Chicago Midway to Punta Cana?+
Right now $400 round trip, on Delta Air Lines. The route usually costs $643, so this fare is 38% under. Checked Nov 4, 2026.
When are the cheapest dates to fly to Punta Cana?+
The cheapest dates Telly found are in Nov–Apr, for trips of 2 to 7 nights. It prices every departure date six months out on this route and keeps only the lowest. The exact dates are in the app.
Do I need a passport to fly from Chicago Midway to Punta Cana?+
Yes. Punta Cana is outside the US and Canada, and every flight on Telly leaves the country, so every one needs a passport.
