Route guide

Chicago to Portland (MDW-PDX): Nonstop Upgrade & Award Space

Southwest Airlines flies the MDW to PDX nonstop about 6 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 MDW to PDX 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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6
Nonstop flights a week
1,747 mi
Nonstop distance
Free
To get started

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

Airlines flying Chicago to Portland nonstop

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

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

Frequently asked questions about MDW to PDX

How far is Portland from Chicago?
MDW to PDX covers about 1,747 miles nonstop. Flight times vary by aircraft and season; each scheduled departure on this page lists its own times.
Which airlines fly nonstop from MDW to PDX?
Southwest Airlines is currently the only airline flying MDW to PDX nonstop. 2LNR tracks confirmed upgrade and award space on every Southwest Airlines departure.
How many flights a week are there from MDW to PDX?
About 6 nonstop flights a week run between Chicago and Portland 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 MDW to PDX?
Open the MDW to PDX calendar on this page to see confirmed upgrade and award space by date. You can also set an alert on the Chicago to Portland route, and 2LNR will notify you when space opens. It's free to start.

Never miss MDW to PDX upgrade or award space

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

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