Chicago (MDW) to San Juan (SJU)
Flight time
≈ 4h 55m
Bearing
135° SE
Chicago (MDW) to San Juan (SJU) is 2,059 miles (3,314 km) as the crow flies — the great-circle baseline most distance-based mileage programs credit.
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What actually flies MDW–SJU
Filed traffic dataIn May 2026, Southwest Airlines was the only carrier flying nonstop MDW–SJU; the Boeing 737 MAX 8 was the most common aircraft at 80% of departures; flights ran 97% full.
Departures
10
May 2026
Seats
1,750
both directions
Passengers
1,696
both directions
Load factor
96.9%
RPM ÷ ASM
Who flies MDW–SJU?
Southwest Airlines was the only carrier to fly nonstop MDW–SJU in May 2026 (10 departures).
- WN
10 departures · 1,750 seats
Share of departures100.0%96.9%
Load
What plane flies MDW–SJU?
In May 2026, the Boeing 737 MAX 8 flew 80% of MDW–SJU departures — more than any other aircraft type.
- Boeing 737 MAX 8
8 departures · 96.8% load
80.0% - Boeing 737-800
2 departures · 97.4% load
20.0%
How has MDW–SJU traffic changed?
Nonstop MDW–SJU departures fell from 16 in June 2025 to 10 in May 2026.
Monthly nonstop MDW–SJU traffic, trailing 12 months through May 2026. Bars scale to the busiest month; months with no filed service show as zero.
June 2025
16 departures · 2,551 passengers
91.1%
Load
July 2025
16 departures · 2,600 passengers
92.9%
Load
August 2025
4 departures · 639 passengers
91.3%
Load
September 2025
0 departures · 0 passengers
—
Load
October 2025
0 departures · 0 passengers
—
Load
November 2025
8 departures · 1,133 passengers
80.9%
Load
December 2025
8 departures · 1,195 passengers
85.4%
Load
January 2026
8 departures · 1,141 passengers
91.4%
Load
February 2026
8 departures · 1,157 passengers
85.0%
Load
March 2026
16 departures · 2,373 passengers
95.1%
Load
April 2026
10 departures · 1,543 passengers
92.2%
Load
May 2026
10 departures · 1,696 passengers
96.9%
Load
By direction
Each direction is filed separately — they rarely match.
MDW → SJU
97.8% full
5 departures · 856 passengers
SJU → MDW
96.0% full
5 departures · 840 passengers
Nonstop MDW–SJU traffic has been filed since 2025.
Source: US DOT BTS Form 41 T-100 Segment (All Carriers). Data through May 2026; filings from 2025. Public domain (US Government work).
The airports
San Juan
PR
Luis Munoz Marin International Airport
Coordinates
18.44°N, 66.00°W
Hemisphere
N · W
Frequently asked
How far is Chicago (MDW) from San Juan (SJU)?
MDW to SJU is 2,059 miles (3,314 km / 1,789 nautical miles) measured great-circle — the shortest path over the surface of the Earth.
How long is the flight from MDW to SJU?
A nonstop covers the 2,059-mile great-circle distance in roughly 4h 55m of block time, before winds. Actual schedules vary a few percent by direction and aircraft.
What plane flies MDW–SJU?
In May 2026, the Boeing 737 MAX 8 flew the largest share of departures (80.0%), followed by the Boeing 737-800 (20.0%).
What mileage do I earn flying MDW–SJU?
Distance-based programs credit off the 2,059-mile great-circle figure, then apply your fare-class earning rate. Revenue-based programs credit off the fare instead.
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