Chicago to Portland nonstop
Yes: Southwest flies direct from Chicago (MDW) to Portland (PDX) about 2 times a day, year-round.
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Chicago to Portland in numbers
Measured from US DOT filings, not estimated from distance.
- Distance and flight time
- 1,751 miles nonstop, about 4 hr 10 min gate to gate. Flight time is an estimate from the great-circle distance; the filings carry distance, not scheduled elapsed time.
- Seasonality
- Flew every month of the last year: busiest in September 2025 (19 flights a week), quietest in November 2025 (7 flights a week).
- Sep 2025: 19 flights a week
- Oct 2025: 12 flights a week
- Nov 2025: 7 flights a week
- Dec 2025: 7 flights a week
- Jan 2026: 7 flights a week
- Feb 2026: 7 flights a week
- Mar 2026: 13 flights a week
- Apr 2026: 14 flights a week
- May 2026: 14 flights a week
- Jun 2026: 18 flights a week
- Jul 2026: 19 flights a week
- Aug 2026: 17 flights a week
Flights a week by month, Sep 2025 to Aug 2026, from US DOT on-time filings. - Who operates the flights
- Southwest is the only carrier filing this pair.
- Fares
- Half of the 533 tickets in the US DOT fare survey for Q2 2025 sold between $150 and $300 one way, median $200. The survey runs a couple of quarters behind, so read it as the shape of the route's pricing rather than today's quote.
- Jul to Sep (Q3 2024): median $175 one way, middle half $125 to $250, 951 tickets
- Oct to Dec (Q4 2024): median $175 one way, middle half $125 to $275, 488 tickets
- Jan to Mar (Q1 2025): median $175 one way, middle half $125 to $300, 424 tickets
- Apr to Jun (Q2 2025): median $200 one way, middle half $150 to $300, 533 tickets
Jul to Sep, Oct to Dec and Jan to Mar trips were the cheapest (median $175 one way) and Apr to Jun trips cost the most (median $200), in the DOT ticket survey for Q3 2024 to Q2 2025. Bars show the middle half of one-way fares; the mark is the median.
Flying the other way? Portland to Chicago nonstop.
Other airports near Chicago with nonstops to Portland
Within about 100 miles of Chicago Midway International Airport
Also nonstop from Chicago (MDW)
Busiest other routes out of the same airport
- Atlanta (ATL) about 10 times a day
- Denver (DEN) about 7 times a day
- Dallas (DAL) about 7 times a day
- New York (LGA) about 6 times a day
- Kansas City (MCI) about 6 times a day
- Phoenix (PHX) about 6 times a day
- Washington (DCA) about 6 times a day
- Las Vegas (LAS) about 6 times a day
Staying in Portland?
Sort out where you'll sleep and what you'll do once you land.
Exploring Portland on foot? Take the free GPS audio walking tour
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