Chicago (MDW) to San Juan (SJU) flights
One airline flies nonstop from Chicago (MDW) to San Juan (SJU): Southwest Airlines. The two airports are 2,059 miles (3,313 km) apart. There are also 30 ways to fly it with one stop, through Charlotte, Indianapolis and Raleigh/Durham and more.
Airlines flying nonstop from MDW to SJU
- Southwest AirlinesNot in an allianceWho books it
MDW to SJU with one stop
30 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Charlotte (CLT)Southwest Airlines, then American Airlines and Frontier Airlines
- Via Indianapolis (IND)Southwest Airlines the whole way
- Via Raleigh/Durham (RDU)Southwest Airlines, then Frontier Airlines, JetBlue Airways and 1 more
- Via Columbus (CMH)Southwest Airlines the whole way
- Via Richmond (RIC)Southwest Airlines, then JetBlue Airways
- Via Norfolk (ORF)Southwest Airlines, then JetBlue Airways
- Via Punta Cana (PUJ)Southwest Airlines, then JetBlue Airways, Frontier Airlines and 1 more
- Via Jacksonville (JAX)Southwest Airlines, then Frontier Airlines and JetBlue Airways
- Via Atlanta (ATL)Delta Air Lines and Frontier Airlines the whole way
- Via Cleveland (CLE)Southwest Airlines, then Frontier Airlines
- Via Nashville (BNA)Southwest Airlines the whole way
- Via Washington (DCA)Southwest Airlines, then JetBlue Airways
- Via Detroit (DTW)Delta Air Lines the whole way
- Via Baltimore (BWI)Southwest Airlines the whole way
- Via Orlando (MCO)Southwest Airlines and Frontier Airlines the whole way
MDW to SJU: common questions
Which airlines fly nonstop from MDW to SJU?
Southwest Airlines flies nonstop from Chicago (MDW) to San Juan (SJU).
How far is Chicago from San Juan by plane?
Chicago (MDW) and San Juan (SJU) are 2,059 miles (3,313 km) apart along the great circle, the shortest path a flight can take. Connections add distance on top.
How many miles does MDW to SJU cost?
It depends on the program: each prices the route from its own chart or dynamically. The Award Flight Pricer compares 30+ programs for MDW to SJU with taxes and fees.
Where can I connect between Chicago and San Juan?
The most direct connections are through Charlotte (CLT), Indianapolis (IND), Raleigh/Durham (RDU), Columbus (CMH) and Richmond (RIC). On 14 of them the same airline flies both flights, for example Southwest Airlines through Indianapolis.
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.