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This weekend marks the 10th annual Chicago Seminars!  I’ll be attending for the third time, having gone for the 2016 and 2017 Seminars as well.  I always enjoy my time there and make some great connections.  This year, I’ll be reconnecting with some friends from the last few Chicago Seminars and catching up with some of my colleagues in the gift card reselling world.

When I’m not chatting about points and miles with fellow addicts, I suppose I can squeeze some of the actual sessions in as well!  Here’s what i hope to learn at the sessions I’ll be attending:

Sweet Spots & Maximization with Hotel Points

I don’t use hotels as much as the average traveler, usually opting for AirBnBs or crashing with friends and family when I can.  Because of that, I find myself accumulating (and not using) lots of hotel points, primarily Hilton and Marriott.  (Not to mention the free nights from credit cards!)

I always prefer quantity over quality, so the cheaper the nights, the better!  I’ll be happy to come out of this session with more information on hotel points in general, and specifically with some Hilton or Marriott recommendations.

Maximize Las Vegas/Hotel Loyalty Crossover

The Vegas session is super timely!  My girlfriend and I have a weekend in Vegas planned for November, and I’m doing my best to save some money in the city.  This isn’t always easy, though I’ve been doing a lot of reading about loyalty benefits and comps in Vegas.

(SEE ALSO – Make Vegas Work For You: Fake Your Way to Free Things)

Points to Islands

Since this session is led by Stefan over at Rapid Travel Chai, I have no doubt it’ll be interesting!  I like to consider myself a mild chaser of every country.  I’m not about to hit 5 countries in 5 days, but I do want to see a few new nations every year.  With that goal in mind, sometimes island hopper flights (and similar hacks) are great opportunities to cross things off the list!  Some of these locations are really hard to get to, so I’ll be sure to take notes.

There are more islands than just Hawaii, you know..

Credit Cards Level 999

This session is sure to be packed.  A deep dive into credit card companies and banks is sure to draw some interest from our crowd of travel hackers at the Chicago Seminars.

New ways to bypass 5/24?  Hopefully!  But unlikely I think…

Think Out of The Box

Not really sure to what to expect here, but I’m looking forward to it!  We’ll be hearing about lesser known loyalty programs and how to use them to our advantage.

Maximizing Air France FlyingBlue

Flying Blue has snagged me some great value on flights in the past, and the SkyTeam network offers flights to all sorts of interesting places.  Primarily, I’m interested in finding all the award spaces that are hard to get to without Flying Blue.  Plus, since Flying Blue is a transfer partner of American Express Membership Rewards, Chase Ultimate Rewards, Citi ThankYou Points, and Capital One miles, these miles are super versatile!

Buying into Buyer’s Groups

2019 was a tougher year (for me) for reselling.  Not to say there aren’t deals out there, but I just haven’t taken advantage of as many deals as I used to.  I’m hoping I’ll learn about some high-quality groups that are worth the effort to learn the ins and outs.

If you’re interested in attending, check these out:

Are you going to the Seminars?  What are you most excited for??


Points With a Crew has partnered with CardRatings for our coverage of credit card products. Points With a Crew and CardRatings may receive a commission from card issuers. Other links on this page may also pay me a commission - as always, thanks for your support if you use them

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