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Direct flights from San Juan to Chicago

Did you mean Flights from Chicago to San Juan?

Flightmap/Flights from SJU/SJU to MDW

San Juan

Puerto Rico

SJU

Luis Munoz Marin International Airport

Chicago

United States

MDW

Chicago Midway International Airport

Route
Nonstop service available
Distance
2,059 miles
Marketing airlines
1 airline
Aircraft
2 aircraft types
Dates
Nov 7, 2026 – Aug 1, 2027

Observed award fares

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.

Departure window: 2026-10-23 – 2026-11-21.

No recent fares appear in this limited preview. This does not mean the route is sold out. Use the search controls to check other dates and routes.

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Explore these airports and cities

  • Flights from SJU
  • Flights to MDW
  • Award flights to Chicago

San Juan to Chicago route overview

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 – Aug 1, 2027.

Marketing airlines on the San Juan to Chicago route

These are marketing airlines, including codeshare sellers. This list does not identify the operating airline for each flight; check the flight details before booking.

Aircraft flying from SJU to MDW

Frequently asked questions

Which airports serve the San Juan to Chicago route?

Luis Munoz Marin International Airport (SJU) is the origin airport and Chicago Midway International Airport (MDW) is the destination airport.

How far is Chicago from San Juan?

SJU and MDW are approximately 2,059 miles apart by great-circle distance.

Are there direct flights from SJU to MDW?

Yes. Roame's current schedule feed shows nonstop service from SJU to MDW.

Which airlines market flights 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.

Which aircraft fly from SJU to MDW?

Aircraft listed in the current schedule include Boeing 737-800 Winglets (73H) and Boeing 737 MAX 8 (7M8).

More routes from San Juan

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  • ATLAtlantaUnited States
  • STTCharlotte AmalieVirgin Islands, U.S.
  • EISRoad TownVirgin Islands, British
  • VQSVieques IslandPuerto Rico
  • PHLPhiladelphiaUnited States
  • EWRNewarkUnited States
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