San Juan to Chicago (SJU–MDW) — Airlines, Schedules & Connections

SJU Airport Page →
2,059 mi airlines charter/private
On-time Some delays Frequent delays
Connecting Flight Schedule 22 1-stop flights Verified 1mo ago
Nonstop Charter / private 1-Stop 2-Stop Hide separate tickets Hide overnight Hide codeshares
  Flight Airline AC Dep Arr Dur OTP Sched  
✈ Nonstop

No flights match your filters.

No scheduled airline flights on this route — it's flown by charter / private operators (). No nonstop flights on this route. connecting options below.

Last scheduled nonstop: Aug 2026.

✦ 1-Stop connections via 10 hubs
ATL Atlanta 6h 25m AFAMCV → AFAMDL Atlanta (ATL) to Chicago flights
TPA Tampa 6h 30m B6F9PXG → NJEWN Tampa (TPA) to Chicago flights
MCO Orlando 6h 40m ADB6EI → WN Orlando (MCO) to Chicago flights
MIA Miami 6h 42m 2IAAAS → EJALXJWN Miami (MIA) to Chicago flights
DTW Detroit 6h 44m DL → AFDLKE Detroit (DTW) to Chicago flights
FLL Fort Lauderdale 6h 46m ADB6F9 → WN Fort Lauderdale (FLL) to Chicago flights
PHL Philadelphia 6h 57m AAB6BA → UWDWN Philadelphia (PHL) to Chicago flights
BWI Baltimore 7h F9WN → WN Baltimore (BWI) to Chicago flights
JAX Jacksonville 7h 6m B6F9 → WN Jacksonville (JAX) to Chicago flights
RDU Raleigh/Durham 7h 9m B6F9 → WN Raleigh/Durham (RDU) to Chicago flights
✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
San Juan to Chicago
Connecting service available through multiple hubs.
1 Airlines 2,059 mi 4h 50m nonstop -1h behind

SJU–MDW had nonstop service from Southwest Airlines, last on the schedule in August 2026. There's no nonstop on it right now, so today you'd fly it with one stop. The connecting options below are sorted by layover. Nonstop, it's about 2,059 miles in 4h 50m.

Also explore Browse available seat maps SJU Routes MDW Routes SJU Live Flights MDW Live Flights SJU Delays MDW Delays
All flights from Chicago (MDW) Chicago to San Juan flights
Carriers on this route

Airline Landscape

Carriers that operated nonstop SJU–MDW service, compared side by side.
Airline Freq/wk Aircraft Duration Dep OTP Alliance Codeshares
WN Southwest Airlines 0 – – 63% – –
Alliance coverage
Unaffiliated: WN (0 flights/wk, 0%)
OTP based on airport-level delay snapshots. Duration ranges reflect seasonal/directional variation.
Connections

Connection Landscape

1-stop and 2-stop options for SJU to MDW.
1-STOP
One-Stop Connections
22
Hubs
~6h
Fastest
~20h
Longest
ATL ~6h 25m TPA ~6h 30m MCO ~6h 40m MIA ~6h 42m DTW ~6h 44m
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
1,444
Candidates
Two-stop connections loaded in the connections tab above.
Connections computed from published schedules with minimum connection time verification. Use the interactive explorer above the fold to filter by airline, tier, and layover time.
Reliability

On-Time Performance

What to expect at each end of your journey.
Outbound
SJU → MDW
63%
Moderate delays possible. Allow buffer time.
Departing
63%
Arriving
88%
Return
MDW → SJU
86%
Generally reliable. Most flights run on time.
Departing
86%
Arriving
95%
OTP = percentage of flights arriving within 15 min of schedule. Based on airport-level delay snapshots. SJU delays → MDW delays →
Alternatives

Other ways to reach Chicago from San Juan

Nearby airports with service to Chicago Midway International Airport.
Metric SJU→MDW STT→MDW EIS→MDW
Distance from SJU – 68 mi 96 mi
Nonstop airlines – 2 1
Weekly flights – – –
Flight time 4h 50m 4h 50m 4h 59m
Departure OTP 63% – –
Charlotte Amalie (STT) to Chicago flights · Beef Island (EIS) to Chicago flights
Airports within 200 miles of SJU with service to Chicago Midway International Airport.
Know before you go

Travel Essentials

Practical planning for this route.
Time Difference
-1h
Chicago is 1 hour behind San Juan.
SJU: AST · MDW: CDT

When it's 6:00 PM in San Juan, it's 5:00 PM in Chicago.
Distance & Flight Time
2,059 mi / 3,314 km
Nonstop flight time is approximately 4h 50m gate to gate.
Facts

SJU–MDW Quick Facts

Key statistics for the San Juan to Chicago route.
Route details
Distance2,059 mi / 3,314 km
Flight time4h 50m
Time difference-1 hour
Airlines (nonstop)1
1-stop connectionsAvailable
Origin: SJU
Full nameLuis Munoz Marin International Airport
IATA / ICAOSJU / TJSJ
TimezoneAmerica/Puerto_Rico
Passengers/yr13.0M
Elevation9 ft / 3 m
Destination: MDW
Full nameChicago Midway International Airport
IATA / ICAOMDW / KMDW
TimezoneAmerica/Chicago
Passengers/yr20.7M
Elevation620 ft / 189 m
FAQ

Frequently Asked Questions

Common questions about SJU to MDW flights.
Nonstop flights from Luis Munoz Marin International Airport to Chicago Midway International Airport take about 4h 50m gate to gate. The route covers 2,059 miles.
1 airline operated the nonstop from SJU to MDW: Southwest Airlines. The last scheduled nonstop was in August 2026. There's no nonstop right now, so today you'd fly it with one stop. See the connection options above, ranked by layover.
Not right now. The last scheduled nonstop was in August 2026. You can still fly it with one stop, and the connecting options above are sorted by layover. Nonstop, the hop took about 4h 50m.
Yes, 1-stop connections are available, ranked by layover time. Common connecting points include Hartsfield Jackson Atlanta, Tampa and Orlando.
On a single ticket, yes. Your bags are checked through to MDW and move between planes without you. On two separate tickets you collect your bags at the connecting airport and recheck them, so build in extra layover time.
Chicago is 1 hour behind San Juan.
Yes, return flights from MDW to SJU are available. Use the direction toggle at the top to view the return schedule.
Nearby alternatives include STT and EIS. See the Alternatives section for a full comparison.
Click the 'Search Flights' button to check availability and prices on Google Flights. You can also compare airlines and schedules on this page to find the best option.
See the On-Time Performance section for the latest delay data at both airports. This shows departure and arrival reliability to help you plan.
Route data is updated regularly from official airline schedules. On-time performance data comes from recent airport delay snapshots.

Flights from SJU to MDW

Luis Munoz Marin International Airport (SJU) and Chicago Midway International Airport (MDW) had nonstop service from Southwest Airlines, last on the schedule in August 2026. The nonstop is dormant right now, so the way to fly it today is one connection, and the options above are sorted by layover.

SJU to MDW Flight Duration and Schedule

Nonstop flight time from SJU to MDW is about 4 hours 50 minutes gate to gate. The route covers a distance of 2,059 miles (3,314 km).

Connecting Options and Alternatives

1-stop connecting options are also available, commonly via Hartsfield Jackson Atlanta, Tampa and Orlando. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Charlotte Amalie (STT) and Beef Island (EIS).