We strongly encourage our readers to refrain from non-essential travel these next few weeks. Due to COVID-19 we will only feature fares that have availability for travel from September onward. We will continually assess if that needs to move to an even later date.
A good sale for nonstop service to/from Chicago
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Sample Travel Date:
- September 22nd – 29th
- Valid for travel from September – early October for Tuesday and Wednesday departures and returns. Availability is limited. Must purchase at least 1 day in advance of departure
How to Search for Availability:
- Use the Southwest Flexible Date Search Tool.
- PDX – MDW (Chicago – Midway) – PDX
- Miles Flown: 3,502 miles or 5.7 cents per mile
How to Buy:
- Book on Southwest.
Activities and Tours
- Viator – The world's largest marketplace for destination activities and tours
For more of the latest cheap Chicago Flight Deals:
- Go to the The Chicago Flight Deals page
For more of the latest cheap Portland Flight Deals:
- Go to the The Portland Flight Deals page
* The Flight Deal will receive a commission if you use the accommodation, car rental, activities, or travel insurance affiliate links to make a booking or apply and is approved for a credit card using our link above. Thank you for your continuing support.