Flights from Chicago to San Juan (MDW to SIG)

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Frequently asked questions

Are there direct flights from Chicago to San Juan? Currently, there are no direct flights from MDW to SIG. 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 Chicago → San Juan.

Try a nearby airport to Chicago

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

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

Or try a nearby airport to San Juan

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

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

Other flights from San Juan (SIG)

Culebra (CPX) All 1 destinations →

Flights from Chicago to San Juan (MDW → SIG)