Route guide

San Diego to Chicago (SAN-MDW): Nonstop Upgrade & Award Space

Southwest Airlines flies the SAN to MDW nonstop about 10 times a week. That's enough service to give you a real choice of departures, though premium seats don't sit unclaimed for long. 2LNR watches every SAN to MDW departure for confirmed upgrade and award space and can alert you when a date you're tracking opens up.

Data current as of July 21, 2026, refreshed on an ongoing basis as new schedules and seats are confirmed.

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10
Nonstop flights a week
1,725 mi
Nonstop distance
Free
To get started

Confirmed upgrade & award space on every SAN to MDW departure

2LNR tracks confirmed upgrade and award availability on American, Delta, and Alaska and across 30 airlines, segment by segment, date by date. Open the calendar for San Diego to Chicago to see which departures have real space, or watch the route and get alerted when space opens.

See real availability

Confirmed upgrade and award seats on each SAN to MDW departure, checked against live inventory so you know what is open before you book.

Set an alert

Premium inventory turns over fast. Watch this route and 2LNR notifies you when space appears on a date you are tracking.

Plan on the map

See SAN to MDW on the interactive route map, with schedules, connections, and route statistics.

Airlines flying San Diego to Chicago nonstop

Carriers operating SAN to MDW nonstop in the current schedule. 2LNR tracks confirmed upgrade and award space on each of them.

  • Southwest Airlines
See SAN to MDW on the interactive map →

Frequently asked questions about SAN to MDW

How far is Chicago from San Diego?
SAN to MDW covers about 1,725 miles nonstop. Flight times vary by aircraft and season; each scheduled departure on this page lists its own times.
Which airlines fly nonstop from SAN to MDW?
Southwest Airlines is currently the only airline flying SAN to MDW nonstop. 2LNR tracks confirmed upgrade and award space on every Southwest Airlines departure.
How many flights a week are there from SAN to MDW?
About 10 nonstop flights a week run between San Diego and Chicago in the current schedule, operated by Southwest Airlines. Frequency shifts by season; the calendar on this page reflects what's currently scheduled.
How do I check upgrade or award availability on SAN to MDW?
Open the SAN to MDW calendar on this page to see confirmed upgrade and award space by date. You can also set an alert on the San Diego to Chicago route, and 2LNR will notify you when space opens. It's free to start.

Never miss SAN to MDW upgrade or award space

Track confirmed availability, set alerts, and book with confidence. Free to start, no credit card required.

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