Departure at	Return at	Stops	Airline	Find tickets
9 October 2026	11 October 2026	Direct		RT from 258 USD

Departure at	Return at	Stops	Find tickets
9 September 2026	14 September 2026	Direct	RT from 417 USD
12 September 2026	13 September 2026	Direct	RT from 533 USD
13 September 2026	13 September 2026	1 Stop	RT from 304 USD
20 September 2026	25 September 2026	Direct	RT from 497 USD
21 September 2026	26 September 2026	Direct	RT from 411 USD
22 September 2026	26 September 2026	Direct	RT from 405 USD
28 September 2026	2 October 2026	Direct	RT from 361 USD
2 October 2026	5 October 2026	Direct	RT from 353 USD
9 October 2026	11 October 2026	1 Stop	RT from 258 USD
31 October 2026	5 November 2026	1 Stop	RT from 394 USD

Departure at	Return at	Stops	Airline	Find tickets
13 September 2026	13 September 2026	1 Stop		RT from 304 USD
9 October 2026	11 October 2026	1 Stop		RT from 258 USD

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Cheap Flights from MDW to PDX

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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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