Route guide

Philadelphia to Chicago (PHL-MDW): Nonstop Upgrade & Award Space

Southwest Airlines flies nonstop between Philadelphia (PHL) and Chicago (MDW), roughly 16 times a week. With Southwest Airlines operating this route so often, premium seats still turn over daily, and upgrade or award space can open and close within hours. 2LNR tracks confirmed availability on every PHL to MDW departure, so you know which flights have space before you book.

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

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16
Nonstop flights a week
667 mi
Nonstop distance
Free
To get started

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

Airlines flying Philadelphia to Chicago nonstop

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

  • Southwest Airlines
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Frequently asked questions about PHL to MDW

How far is Chicago from Philadelphia?
PHL to MDW covers about 667 miles nonstop. Flight times vary by aircraft and season; each scheduled departure on this page lists its own times.
Which airlines fly nonstop from PHL to MDW?
Southwest Airlines is currently the only airline flying PHL to MDW nonstop. 2LNR tracks confirmed upgrade and award space on every Southwest Airlines departure.
How many flights a week are there from PHL to MDW?
About 16 nonstop flights a week run between Philadelphia 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 PHL to MDW?
Open the PHL to MDW calendar on this page to see confirmed upgrade and award space by date. You can also set an alert on the Philadelphia to Chicago route, and 2LNR will notify you when space opens. It's free to start.

Never miss PHL to MDW upgrade or award space

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