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

SJU Airport Page →
2,059 mi airlines 3/wk
On-time Some delays Frequent delays
Flight Schedule 5 flights Verified 2h ago
Nonstop 1-Stop 2-Stop Hide separate tickets Hide overnight
  Flight Airline AC Dep Arr Dur OTP Sched  
✓
→
WN1093
WN Southwest
7M8
1:10 PM
AST TB
5:20 PM
CDT
5h 10m
—
M T W T F S S
Prices
✓
→
WN2536
WN Southwest
737
2:20 PM
AST TB
6:40 PM
CDT
5h 20m
—
M T W T F S S
Prices
✓
→
WN512
WN Southwest
73H
2:35 PM
AST TB
6:55 PM
CDT
5h 20m
—
M T W T F S S
Prices
✓
←
WN1784
WN Southwest
7M8
7:45 AM
CDT
1:20 PM
AST
4h 35m
—
M T W T F S S
Prices
✓
←
WN2232
WN Southwest
7M8
8:50 AM
CDT
2:25 PM
AST
4h 35m
—
M T W T F S S
Prices

No flights match your filters.

No nonstop flights on this route. connecting options below.

✦ 1-STOP
✧ 2-STOP Loading...
San Juan to Chicago
1 carrier, 3 flights/week nonstop.
1 Airlines 3 Flights/wk 2,059 mi 5h 10m nonstop -1h behind 51 1-stop hubs

SJU–MDW is served by 1 airline with nonstop service. Southwest Airlines leads the route. The flight covers 2,059 miles in approximately 5h 10m. Beyond nonstop, 51 hubs offer 1-stop connections.

Also explore SJU Routes MDW Routes SJU Live Flights MDW Live Flights SJU Delays MDW Delays
Carriers on this route

Airline Landscape

All carriers operating nonstop SJU–MDW service, compared side by side.
Airline Freq/wk Aircraft Duration Dep OTP Alliance Codeshares
WN Southwest Airlines 3 737, 73H, 7M8 5h10-5h20 90% – –
Aircraft on this route
737 Boeing 737-700 – WN
73H Boeing 737-800 – WN
7M8 Boeing 737 MAX 8 – WN
Alliance coverage
Unaffiliated: WN (3 flights/wk, 100%)
OTP based on airport-level delay snapshots. Duration ranges reflect seasonal/directional variation.
Schedule

Weekly Schedule Pattern

Nonstop flight frequency by day of week, SJU to MDW direction.
Mon
0
flights
Tue
0
flights
Wed
0
flights
Thu
0
flights
Fri
0
flights
Sat
2
flights
Sun
1
flight
Departure time distribution
12 AM6 AM12 PM6 PM12 AM
Morning departures
Afternoon/evening departures
3
Nonstop flights
3
Outbound / wk
3
Return / wk
Connections

Connection Landscape

Beyond nonstop. 1-stop and 2-stop options for SJU to MDW.
1-STOP
One-Stop Connections
51
Hubs
~6h
Fastest
~25h
Longest
PBI ~6h 25m NAS ~6h 32m APF ~6h 36m OPF ~6h 36m PIE ~6h 38m
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
2,046
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
90%
Generally reliable. Most flights run on time.
Departing
90%
Arriving
70%
Return
MDW → SJU
76%
Generally reliable. Most flights run on time.
Departing
76%
Arriving
84%
OTP = percentage of flights arriving within 15 min of schedule. Based on airport-level delay snapshots. SJU delays → MDW delays →
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 5h 10m to 5h 20m.
Facts

SJU–MDW Quick Facts

Key statistics for the San Juan to Chicago route.
Route details
Distance2,059 mi / 3,314 km
Flight time5h 10m to 5h 20m
Time difference-1 hour
Airlines (nonstop)1
Weekly flights3 out / 3 return
1-stop connections51 hubs
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 approximately 5h 10m to 5h 20m. The route covers 2,059 miles.
1 airline operates nonstop service: Southwest Airlines.
There are approximately 3 nonstop flights per week from SJU to MDW. The return direction has about 3 weekly flights.
Yes, 1-stop connections are available through PBI, NAS, APF, OPF, PIE, FOK, LAL, PLS, FXE, CHS, RSW, IAD, SRQ, BCT, TEB, BED, IND, HPN, YYZ, PUJ, TEX, IAH, SCF, VNY, LAX, RDU, ALB, BDL, CLT, PHL, BWI, MCO, EWR, TPA, PVD, DCA, DFW, MIA, CVG, FLL, BOS, JAX, BNA, STL, ATL, ORD, DTW, MSP, AUS, HOU and DEN. These options provide additional schedule flexibility.
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.
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) are connected by nonstop service from Southwest Airlines. With 3 weekly departures, this is a regularly served route.

SJU to MDW Flight Duration and Schedule

Nonstop flight time from SJU to MDW ranges from 5 hours 10 minutes to 5 hours 20 minutes. The route covers a distance of 2,059 miles (3,314 km). There are approximately 3 weekly flights outbound and 3 return, totaling 6 flights per week in both directions.

Connecting Options and Alternatives

51 one-stop connections are available, with the fastest taking approximately 6 hours via PBI. Two-stop connections are also available via intermediate hubs.