Points and Miles and a Weekend in Chicago (Not Chicago)

Less than a week after returning from a 5-day family visit to Kansas, I was heading back to the Central Time Zone for the third time within a 30-day period. My life had been accelerated since Austin and just a week after that I learned about another conference that would add to the life-changing dynamic now known as the Epic Autumn of 2018 (“Epic Fall” just doesn’t work here). A guy from one of the Airbnbs we stayed at this summer in Peru saw me on a Facebook forum about airline miles and rewards points, and suggested I go to a meeting nondescriptly called the “Chicago Seminars.” It is an annual two-day frenzy of sessions about earning rewards points through credit cards, airline miles, preferred statuses, shopping portals and the like. Of course, I was familiar with frequent flier miles and am enrolled in most of the major airlines and a couple hotels, even though I rarely stay at chains. And I’d learned about the points and miles “world” at TravelCon. However, this crowd was beyond the relative simplicity of George Clooney’s million miles in Up In The Air. There is a lot more to “the game” than just going on a lot of business trips. In fact, some people accrue points without even getting on a plane. Between sign up bonuses and reselling money orders, it’s a whole world of point gathering that can allow travel to anywhere in the world and stay in luxury accommodations for next to nothing. But I’m getting ahead of myself.

Welcome Chicago Seminars

The Chicago Seminars started nine years ago and it has become the premier gathering for the biggest points and miles geeks in the country. They get together, trade knowledge, share secrets, and discuss the latest trends in the industry. The speakers all have blogs with affiliate links to the best credit card deals, endless tips on booking strategies, and the latest changes to various reward programs. I had initially debated whether the registration fee of $111 (plus airfare, lodging, etc.) would be worth it for me just to learn how to get more points, but after the first two sessions on Friday evening, I knew I would recoup those costs twofold if not more. It was also a time to meet new people and dip my toe into this interesting water. I was overwhelmed, but also knew that it could be what I make of it. I decided right away that I could learn some basics and easily be able to score some free tickets to my next international travel destination within less than a year and probably even less than six months. I had already signed up for the Chase Sapphire Reserve, which is one of the most highly coveted cards for die hard travelers.

Because I registered rather late and did not yet have the points to be able to secure a flight to Chicago, I had to piece together an itinerary that had me flying Spirit Airlines for the first time on the way, and United on the way back. I left Baltimore at 6AM Friday morning, October 19th, arriving just in time to log in and work remotely from the airport all day since the conference didn’t start until the early evening. Thankfully, the flight was uneventful and although the seats were not particularly comfy, I had no issues stowing my personal item under the seat in front of me and even snagged a roomy exit row seat. I had been nervous about flying Spirit after hearing so many bad reviews, but it was fine.

It was surely a blessing in disguise that the so-called “Chicago Seminars” took place in the nondescript suburb of Elk Grove Village near O’Hare instead of the lovely city that would have certainly been a distraction from the purpose of the trip. I stayed at a motel even cheaper than the Holiday Inn where the conference was taking place, and walked 20 minutes one way to get there (you know, for the step count). It was a straight shot, but very bleak. Despite this, the conference itself was thoroughly interesting and lively. Thankfully the Holiday Inn has an adjoining bar that must be thrilled to see this group each year, what with the bar tabs.

Chicago Seminars Panel

OK, so what did I actually get out of this? As I mentioned above, it was clear that it really is possible to accumulate enough points through sign-up bonuses, smart shopping, and regular spending to book an international trip and only pay taxes and fees ($5-20 is a fair guesstimate). This is doable within the first 3-4 months upon getting a new card, depending on the point values and all.

Top takeaways from the Chicago Seminars:

  • Select your destination and work backwards. In order to maximize the point value to get you to your preferred destination, you should research the airlines that go in and out of that location and work backwards to determine the best way of getting there rather than focusing on a particular airline or card initially…unless the points are like Chase’s Ultimate Rewards, which can be transferred to your airline or hotel of choice. Surprisingly, Wikipedia is a great resource to utilize by simply going to the destination airport and learning which airlines fly into that airport, then you can work your way towards your home airport.
  • Beware of 5/24. This is the “golden rule” to follow because it means that if you open five or more cards within a two-year period, you may be ineligible for a Chase card, which are arguably some of the best sign-up bonuses out there. There are some risk-takers out there that have gotten away without heeding this numeric, but given the coveted value of Chase cards, it’s not worth risking since the rewards are often much more valuable with them than other banks.
  • Use more apps. My smartphone is already a crowded field of multicolored icons, but there are several rewards-based and shopping apps that can help bolster your point values or earn you cash back. It can pay to have a sense of your preferred brands, shopping patterns, and what point values can get you. Drive a lot? Be sure to use apps like Gas Buddy or TruNow to maximize your points each time you fill up at the pump. Getting groceries? Try apps like Fetch or Shopkick, or your local grocery store chain’s app for savings and deals. There is Hopper for flight deals, Starbucks points for frequenters of the coffee chain, Kroger’s app for groceries, and United’s MileagePlus X, which goes well beyond air transportation. There are hundreds of different options to choose from in various areas of commerce, and in some cases you can combine efforts on multiple apps to get even more rewards.
  • Points are not all created equal. I used to think that you should get a card with the airline that you have or want miles on or one with the highest sign-up bonus, but it’s not quite so simple. Each airline and airline partner has a separate chart of miles, which I have come to think of like foreign currencies with various exchange rates. You have to know the best value of the points per airline and then determine how you want to spend them. If you are looking for a first class ticket on a particular airline, your strategy will be very different than if you just want the cheapest way to Hawaii.
  • Enroll in every frequent flyer program you may ever use. It can pay to have an established account on some airlines’ miles programs, so that when you actually end up flying with them, you could have an edge up on getting those points to accumulate and possibly using them, rather than having to wait for confirmation emails, points transfers, and other delays.
  • Phone agents are not always informed. Often times, airline phone agents are hastily trained, inexperienced, or just may not be as aware of the intricacies of their particular airline’s policies, procedures, or awards charts. Therefore, it pays to know exactly what you want or what you need help with when you call. For multiple-stop itineraries, you will need the assistance of an agent in order to book your award trip. If you research the routes and have the details in front of you and can give the agent those data step by step, you will save time, ensure you have the right trip, and make the agent able to do what you want them to do. If you have a complicated question, be sure to come prepared with an answer you think is correct after researching the website, and be persistent in confirming the answer. If it differs from what you had expected, you may need to call back several times and speak to different agents. It may be that rules have changed and the website had not been updated, and you may have to accept an undesirable answer. It doesn’t hurt to keep trying until you are satisfied that the answer is accurate and satisfactory.
  • Every situation is different. What works for you may not work for another person. Avoid the “groupthink” mentality and always be open to doing more research on your own rather than take anyone’s advice on a particular strategy. Use the resources to make your decision, keep it simple, and try to have fun. If it doesn’t work the way you think it will after applying these strategies, remember that you are still more knowledgeable about how points and miles work than you were before and chalk it up to a learning experience. Everyone has made mistakes from time to time. Deals come and then they go. Be flexible.
  • Don’t freak out about your credit score. This is a common worry when the thought of multiple credit card applications is brought up, and it isn’t to be dismissed. However, if you follow some simple tenets, pay your credit card bills in full and on time, and don’t close your cards, you shouldn’t be concerned about the long-term effect on your credit score. There could be a 2-5% dip in your score within six months of applying, but but that is not a hard and fast rule. As with just about everything in this hobby, results may vary.

FICO Calculation

Want to learn more or get in the game? Follow these blogs:

  • Award Wallet: includes a website and app for tracking miles and rewards points, assisting with booking tickets, and managing your airline, hotel and rental car accounts
  • Frequent Miler: tips for earning miles without flying, travel strategies, current deals, and lots of news from the industry
  • Million Mile Secrets: easy-to-navigate site with great resources for beginners and for comparing various cards and frequent flyer systems as well as inspirational stories of travel and how far your points can take you
  • One Mile at a Time: comprehensive, multi-author site with a plethora of detailed news articles and resources related to the industry

Start simple by finding your favorite site and use one of their links to sign up for your first card.  Focus on your dream destination and work backwards from there!




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