Punta Cana (PUJ) to Chicago (MDW) flights
One airline flies nonstop from Punta Cana (PUJ) to Chicago (MDW): Southwest Airlines. The two airports are 1,969 miles (3,168 km) apart. There are also 27 ways to fly it with one stop, through Charlotte, Cincinnati and Indianapolis and more.
Airlines flying nonstop from PUJ to MDW
- Southwest AirlinesNot in an allianceWho books it
PUJ to MDW with one stop
27 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Charlotte (CLT)American Airlines, then Southwest Airlines
- Via Cincinnati (CVG)Frontier Airlines, then Southwest Airlines
- Via Indianapolis (IND)American Airlines, then Southwest Airlines
- Via Raleigh/Durham (RDU)American Airlines and Breeze Airways, then Southwest Airlines
- Via Columbus (CMH)Southwest Airlines the whole way
- Via Atlanta (ATL)Delta Air Lines and Frontier Airlines the whole way
- Via Nashville (BNA)Southwest Airlines the whole way
- Via Orlando (MCO)Southwest Airlines the whole way
- Via Pittsburgh (PIT)American Airlines and Breeze Airways, then Southwest Airlines
- Via Cleveland (CLE)Frontier Airlines, then Southwest Airlines
- Via Fort Lauderdale (FLL)JetBlue Airways, then Southwest Airlines
- Via Detroit (DTW)Delta Air Lines the whole way
- Via Miami (MIA)American Airlines, LATAM Airlines and 1 more, then Southwest Airlines
- Via Tampa (TPA)Breeze Airways, then Southwest Airlines
- Via Milwaukee (MKE)Sun Country Airlines, then Southwest Airlines
PUJ to MDW: common questions
Which airlines fly nonstop from PUJ to MDW?
Southwest Airlines flies nonstop from Punta Cana (PUJ) to Chicago (MDW).
How far is Punta Cana from Chicago by plane?
Punta Cana (PUJ) and Chicago (MDW) are 1,969 miles (3,168 km) apart along the great circle, the shortest path a flight can take. Connections add distance on top.
How many miles does PUJ to MDW cost?
It depends on the program: each prices the route from its own chart or dynamically. The Award Flight Pricer compares 30+ programs for PUJ to MDW with taxes and fees.
Where can I connect between Punta Cana and Chicago?
The most direct connections are through Charlotte (CLT), Cincinnati (CVG), Indianapolis (IND), Raleigh/Durham (RDU) and Columbus (CMH). On 10 of them the same airline flies both flights, for example Southwest Airlines through Columbus.
More routes
Routes are scheduled nonstop flights. The route data is refreshed monthly; this list was last checked November 11, 2026. Seasonal routes and new launches can be missing or end early, so confirm with the airline before you book. Distances are great-circle, the shortest path between the two airports.