San JuantoChicagoFlight Time
SJU–MDW · Nonstop
San Juan (Luis Munoz Marin International Airport) to Chicago (Chicago Midway International Airport).
The estimated flight time from San Juan (SJU) to Chicago (MDW) is about 4h 50m, covering 2,059 miles. Southwest Airlines flies the route nonstop with 2×/wk departures, from 05:30 to 16:30 local time.
Plan this routeAt a glance
| Est. flight time | Distance | Route type | Captured freq. | Market |
|---|---|---|---|---|
| ~4h 50m Estimated from great-circle distance — no tracked flights yet. | 2,059 mi | Nonstop | 2×/wk From the current provider sample; confirm live timetables before booking. | Domestic |
Airlines on this route
Nonstop airlines from San Juan to Chicago
Southwest Airlines operates 2×/wk flights from SJU to MDW. Departures leave from Terminal B at SJU.
- First departure
- 05:30
- Last departure
- 16:30
- Cadence
- 2 departures/day
- Scheduled departure times
- 2
| Airline | Captured daily freq. | Aircraft | Departures (local) |
|---|---|---|---|
| Southwest Airlines | 2×/wk | Boeing 737 · Terminal B · Seat map | 05:30 |
Aircraft on this route
Flying the other way?
MDW to SJU flights — 2×/wk on 1 airline →Methodology: airline, aircraft, terminal, and departure-time details come from a full week of published airline schedules for SJU, refreshed on a rolling basis. Frequency uses 2 scheduled departures across 2 observed days; flight time is estimated from flying distance until this route has enough tracked flights for an observed average.
Route FAQ
How long is the flight from San Juan to Chicago?
The estimated flight time from San Juan (SJU) to Chicago (MDW) is about 4h 50m, based on the 2,059-mile flying distance.
How far is San Juan from Chicago?
San Juan (SJU) to Chicago (MDW) is about 2,059 miles by air.
Are there nonstop flights from San Juan to Chicago?
Yes. Southwest Airlines flies nonstop from San Juan (SJU) to Chicago (MDW), with 2×/wk departures.
Which airlines fly from San Juan to Chicago?
Southwest Airlines flies nonstop from San Juan (SJU) to Chicago (MDW).
What aircraft fly from San Juan to Chicago?
The SJU–MDW route is flown with Boeing 737.
Route hubs
Nearby airport options
Near Chicago
- ORD - ChicagoChicago O'Hare International Airport · 15 mi from MDWFlights to ORD
- MKE - MilwaukeeGeneral Mitchell International Airport · 81 mi from MDWFlights to MKE