Departure at	Return at	Stops	Airline	Find tickets
29 October 2026	5 November 2026	Direct		RT from 273 USD

Departure at	Return at	Stops	Find tickets
20 September 2026	25 September 2026	1 Stop	RT from 566 USD
21 September 2026	26 September 2026	Direct	RT from 478 USD
22 September 2026	26 September 2026	Direct	RT from 472 USD
24 September 2026	28 September 2026	Direct	RT from 549 USD
28 September 2026	2 October 2026	Direct	RT from 500 USD
29 October 2026	5 November 2026	Direct	RT from 273 USD

Departure at	Return at	Stops	Airline	Find tickets
22 September 2026	26 September 2026	Direct		RT from 472 USD
29 October 2026	5 November 2026	Direct		RT from 273 USD

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Cheap Flights from MDW to PDX

The Cheapest Round-trip Tickets from to Portland

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The Cheapest Flights from to Portland for the Year Ahead

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Cheap Flights from MDW to PDX

The Cheapest Round-trip Tickets from to Portland

The Cheapest Flights for this Month from to Portland

The Cheapest Flights from to Portland for the Year Ahead

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