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

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

Available flights

Southwest AirlinesNon-stop
from$246
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Frequently asked questions

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

Cheapest fares San Juan → Chicago

San Juan SJU
Chicago MDW
May from $247 June from $126 July from $125 August — September — October from $204

Related guides for this route

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

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

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.

STT → MDW 110 km from SJU Saint Thomas → Chicago U.S. Virgin Islands · 24 destinations STX → MDW 151 km from SJU Saint Croix → Chicago U.S. Virgin Islands · 8 destinations EIS → MDW 155 km from SJU Beef Island → Chicago British Virgin Islands · 9 destinations PUJ → MDW 249 km from SJU Punta Cana → Chicago Dominican Republic · 75 destinations LRM → MDW 305 km from SJU La Romana → Chicago Dominican Republic · 9 destinations

Or try a nearby airport to Chicago

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

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

Other flights from Chicago (MDW)

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