Flights from San Juan to Chicago (SIG to MDW)

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Frequently asked questions

Are there direct flights from San Juan to Chicago? Currently, there are no direct flights from SIG to MDW. You may need to connect through another airport.

Related guides for this route

Sibling pages from across Flightmaps — fares, visa rules, country aggregations, and per-airline routes for San Juan → Chicago.

Try a nearby airport to San Juan

Flights to Chicago (MDW) from other airports within 350 km of San Juan. Often unlocks cheaper fares or better times.

SJU → MDW 10 km from SIG San Juan → Chicago Puerto Rico · 59 destinations STT → MDW 120 km from SIG Saint Thomas → Chicago U.S. Virgin Islands · 24 destinations STX → MDW 161 km from SIG Saint Croix → Chicago U.S. Virgin Islands · 8 destinations EIS → MDW 165 km from SIG Beef Island → Chicago British Virgin Islands · 9 destinations PUJ → MDW 239 km from SIG Punta Cana → Chicago Dominican Republic · 75 destinations

Or try a nearby airport to Chicago

Flights from San Juan (SIG) to other airports within 350 km of Chicago.

SIG → ORD 25 km from MDW San Juan → Chicago USA · 282 destinations SIG → SBN 119 km from MDW San Juan → South Bend USA · 22 destinations SIG → RFD 121 km from MDW San Juan → Rockford USA · 8 destinations SIG → MKE 130 km from MDW San Juan → Milwaukee USA · 34 destinations SIG → BMI 175 km from MDW San Juan → Bloomington USA · 6 destinations

Other flights from San Juan (SIG)

Culebra (CPX) All 1 destinations →

Other flights from Chicago (MDW)

Aguascalientes (AGU) Albany (ALB) Albuquerque (ABQ) Asheville (AVL) Atlanta (ATL) Austin (AUS) Baltimore (BWI) Birmingham (BHM) All 97 destinations →

Flights from San Juan to Chicago (SIG → MDW)