@Drwaz99 wrote:Here's my quick advice off the top of my head: First off, ditch Credit Karma except for keeping track of any changes to your TU and EQ profile. They use the VantageScore 3.0 scoring model which is rarely used. Same goes for their approval chances. They are simply marketing and not really based on anything solid.
Next, decide which cards you want the most as some lenders, mostly Barclays, so the Aviator Red and Jetblue cards, are incredibly inquiry sensitive. So if you go for one of those, you shouldn't apply for anything before them. Also keep in mind that Chase has the 5/24 rule, so no more than 5 accounts in the past 2 years.
Capital One, Chase and Citi all have prequalify tools you can use to get a better idea. Here as those links:
https://ficoforums.myfico.com/t5/Credit-Card-Applications/Credit-Card-Pre-Qualification-Links/td-p/4...
If you are able to bring down your revolving utility to below 8.9%, you'll get a score bump from that and it'll put you in a better place to be approved.
If you're curious, I was just approved for the Aviator Red and you can check out my thread to compare our profiles.
https://ficoforums.myfico.com/t5/Credit-Card-Approvals/Barclays-Aviator-Red-Approval/m-p/5474165#M57...
Think that's most of it, but haven't finished my coffee yet, so if you have any other questions, ask away!
+1 to everything said here.
If you can drop to below that magic 8.9 you will see a jump in scoring.
You need to pull your fico report and get accurate scores, sometimes its worth the $30 or $40 you pay myFICO to know exactly where you stand in the credit world.
CK is a useful tool for monitoring two of your reports, but, that's where it ends.
Welcome, @Anonymous. 
How old is your Discover card? This is important because your oldest card should be at least a year old if you're considering a Chase application.
If you're going the Chase route and a Sapphire product is your ultimate goal, I'd start with the Freedom Unlimited (FU). Points earned on your FU can eventually be transferred to a Sapphire product once you have one.
The Chase Sapphire Preferred (CSP) has a minimum credit limit of 5k, and Chase likes to see some "experience" with limits at that level before approving that card. That means that you should either have one 5k limit under your belt or a couple of limits that are close to that.
Capital One will likely approve a SavorOne card once Discover hits the one-year point. I'll let others comment on the other cards you're considering.
I'm a big fan of one card every six months, i.e. a card in month 1, month 7, month 13, month 19, and month 25. This will likely be enough to avoid denials based on too many recently opened accounts or too many recent inquiries. It also keeps you beneath 5/24. That's Chase's policy of automatically denying applications when one has opened five or more accounts in the past 24 months.
Because you've only applied for one card within the past year, I see no problem going for two once Discover hits the one-year point. That keeps you within the above "schedule." The main thing would be to stay at five or fewer cards in a 25 month period. There's some flexibility as to how you spread out your applications.
Dang, spent too much time typing! 
With the Discover card being 1.4 years old, I'd say go ahead and apply for a card or two as soon as you know what you want and once your utilization updates. For the record, I think your utilization was fine. But since you've lowered it, you might as well take advantage of it.
In addition to the sources mentioned above, Experian FICO 8 is available from Discover Credit Scorecard. This service is open to everyone as opposed to the TransUnion score that's available only to cardholders.