Route guide

Oakland to Chicago (OAK-MDW): Nonstop Upgrade & Award Space

Southwest Airlines flies the OAK to MDW nonstop about 11 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 OAK 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.

See OAK to MDW on the interactive map Get started free
11
Nonstop flights a week
1,840 mi
Nonstop distance
Free
To get started

Confirmed upgrade & award space on every OAK 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 Oakland 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 OAK 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 OAK to MDW on the interactive route map, with schedules, connections, and route statistics.

Airlines flying Oakland to Chicago nonstop

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

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

Frequently asked questions about OAK to MDW

How far is Chicago from Oakland?
OAK to MDW covers about 1,840 miles nonstop. Flight times vary by aircraft and season; each scheduled departure on this page lists its own times.
Which airlines fly nonstop from OAK to MDW?
Southwest Airlines is currently the only airline flying OAK to MDW nonstop. 2LNR tracks confirmed upgrade and award space on every Southwest Airlines departure.
How many flights a week are there from OAK to MDW?
About 11 nonstop flights a week run between Oakland 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 OAK to MDW?
Open the OAK to MDW calendar on this page to see confirmed upgrade and award space by date. You can also set an alert on the Oakland to Chicago route, and 2LNR will notify you when space opens. It's free to start.

Never miss OAK to MDW upgrade or award space

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

Get started free