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The September monthly Delta SkyMiles “flash sale” is out. First off you need to know how to search for open days since Delta tries to hide the multi-day feature on the home page. Then, since Delta also hides the SkyMiles award charts you need to look HERE on the blog to compare the user supported real Delta award charts. Then you can check the T&C to see what will work for you to save up to 20% off the normal LEVEL 1 award coach prices per Delta.com:
Destinations
Hawaii
Honolulu, HI (HNL)
Kahului, HI (OGG)
Kona, HI (KOA)
Lihue, HI (LIH)
Alaska
Anchorage, AK (ANC)
Fairbanks, AK (FAI)
Details Origins & Destinations – Select flights between the U.S. 48 to/from Alaska and Hawaii.
Main Cabin Award Fares starting at 20,000 miles round-trip plus taxes and fees* to/from Alaska.
Main Cabin Award Fares starting at 35,000 miles round-trip plus taxes and fees* to/from Hawaii.
Purchase By September 14, 2017
Travel Period January 8 – March 23, 2018

A quick simple multi-day search from Detroit to Hawaii shows many open dates. Keep in mind as a Medallion you can only get free upgrades from the west coast connecting cities including SLC & LAS. If you have a single flight number starting in DTW, ATL, NYC, MSP etc. that connects through the west coast you can NOT upgrade either unless you can get the rep to break the flight into two parts (with the same flight number).
(HT to THE GATE on BoardingArea.)
Advertiser Disclosure: Eye of the Flyer, a division of Chatterbox Entertainment, Inc., is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as CreditCards.com. Some or all of the card offers that appear on the website are from advertisers. Compensation may impact how and where card products appear on the site. This site does not include all card companies or all available card offers. Opinions, reviews, analyses & recommendations are the author’s alone, and have not been reviewed, endorsed, or approved by any of these entities. Some of the links on this page are affiliate or referral links. We may receive a commission or referral bonus for purchases or successful applications made during shopping sessions or signups initiated from clicking those links.
Responses are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser's responsibility to ensure all posts and/or questions are answered.