Direct flights from Chicago to San Juan (MDW → SJU)

Distance 3,313 km (2,059 mi)
Est. duration 3h 54m
MDW
Chicago
Chicago Midway International, USA
SJU
San Juan
Luis Munoz Marin International, Puerto Rico
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Live fares · MDW → SJU

Available flights

Southwest AirlinesNon-stop
from$154
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Frequently asked questions

How far is the flight from Chicago to San Juan? The flight distance from MDW to SJU is approximately 3,313 km (2,059 miles).
How long is the flight from MDW to SJU? The estimated flight time from Chicago to San Juan is approximately 3h 54m.
What airlines fly from MDW to SJU? Airlines operating direct flights from Chicago to San Juan include: WN.

Cheapest fares Chicago → San Juan

Chicago MDW
San Juan SJU
May from $293 June — July from $126 August — September — October —

Related guides for this route

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

Cheap flights from Chicago to San Juan Cheapest month to fly to San Juan Flights from USA Flights to Puerto Rico Visa-free with USA passport All airports in Puerto Rico WN routes & destinations All routes by this carrier

Try a nearby airport to Chicago

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

ORD → SJU 25 km from MDW Chicago → San Juan USA · 282 destinations SBN → SJU 119 km from MDW South Bend → San Juan USA · 22 destinations RFD → SJU 121 km from MDW Rockford → San Juan USA · 8 destinations MKE → SJU 130 km from MDW Milwaukee → San Juan USA · 34 destinations BMI → SJU 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 → STT 110 km from SJU Chicago → Saint Thomas U.S. Virgin Islands · 24 destinations MDW → STX 151 km from SJU Chicago → Saint Croix U.S. Virgin Islands · 8 destinations MDW → EIS 155 km from SJU Chicago → Beef Island British Virgin Islands · 9 destinations MDW → PUJ 249 km from SJU Chicago → Punta Cana Dominican Republic · 75 destinations MDW → LRM 305 km from SJU Chicago → La Romana Dominican Republic · 9 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 (SJU)

Anguilla (AXA) Atlanta (ATL) Austin (AUS) Baltimore (BWI) Beef Island (EIS) Bogota (BOG) Boston (BOS) Buffalo (BUF) All 59 destinations →