Chicago to San José del Cabo (MDW–SJD) — Airlines, Schedules & Connections
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: May 2026.
Most recently operated nonstop flights — the month shown is when each was last scheduled. Most destinations remain reachable with a connection.
No discontinued nonstop flights on record for this route.
MDW–SJD had nonstop service from Southwest Airlines, last on the schedule in May 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 1,806 miles in 4h 21m.
Airline Landscape
| Airline | Freq/wk | Aircraft | Duration | Dep OTP | Alliance | Codeshares |
|---|---|---|---|---|---|---|
| WN Southwest Airlines | 0 | – | – | – | – |
Connection Landscape
On-Time Performance
Other ways to reach San José del Cabo from Chicago
| Metric | MDW→SJD | ORD→SJD |
|---|---|---|
| Distance from MDW | – | 15 mi |
| Nonstop airlines | – | 4 |
| Weekly flights | – | 15 |
| Flight time | 4h 21m | 4h 22m |
| Departure OTP | 100% | – |
Travel Essentials
MDW: CDT · SJD: MST
When it's 6:00 PM in Chicago, it's 4:00 PM in San José del Cabo.
US citizens enter Mexico visa-free for up to 180 days for tourism. Complete the immigration form (FMM) online or on arrival; the online version speeds up processing. Passport must be valid for the duration of stay.
Duty-free allowances: USD 500 in goods. Mexico prohibits importing certain foods and medications without documentation. Declare cash over USD 10,000.
MDW–SJD Quick Facts
Frequently Asked Questions
Flights from MDW to SJD
Chicago Midway International Airport (MDW) and Los Cabos International Airport (SJD) had nonstop service from Southwest Airlines, last on the schedule in May 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.
MDW to SJD Flight Duration and Schedule
Nonstop flight time from MDW to SJD is about 4 hours 21 minutes gate to gate. The route covers a distance of 1,806 miles (2,906 km).
Connecting Options and Alternatives
1-stop connecting options are also available, commonly via Nashville, Phoenix Sky Harbor and William P. Hobby. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Chicago (ORD).