A sample of one-way prices for one traveler from Roame’s fare cache. Points, fees, and seats describe the same observation. Availability can change; confirm with the loyalty program before transferring points.
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Did you mean Flights from Chicago to San Juan?
San Juan
Puerto RicoSJU
Luis Munoz Marin International Airport
Chicago
United StatesMDW
Chicago Midway International Airport
Luis Munoz Marin International Airport (SJU) serves San Juan; Chicago Midway International Airport (MDW) serves Chicago.
The airports are 2,059 miles apart by great-circle distance.
Roame's current schedule feed shows nonstop service from SJU to MDW.
Marketing airlines listed in the current schedule, including codeshare sellers, are Southwest Airlines (WN). This list does not identify the operating airline for each flight; check the flight details before booking.
Published schedule dates span Nov 7, 2026 – May 29, 2027.
These are marketing airlines, including codeshare sellers. This list does not identify the operating airline for each flight; check the flight details before booking.
Luis Munoz Marin International Airport (SJU) is the origin airport and Chicago Midway International Airport (MDW) is the destination airport.
SJU and MDW are approximately 2,059 miles apart by great-circle distance.
Yes. Roame's current schedule feed shows nonstop service from SJU to MDW.
Marketing airlines listed in the current schedule, including codeshare sellers, are Southwest Airlines (WN). This list does not identify the operating airline for each flight; check the flight details before booking.
Aircraft listed in the current schedule include Boeing 737-800 Winglets (73H) and Boeing 737 MAX 8 (7M8).