The 11 best travel tips from Chicago Seminars

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Last weekend I was at the Chicago Seminars, which is an annual event where travel pros share some of their best tips and tricks. The audience is a blend of readers and bloggers (like myself). It is a great time to meet new people and share ideas on how to “Travel More. Spend Less. Live Better.”

What are The Chicago Seminars?

The Chicago Seminars are held each October. It is a weekend event where approximately 400-500 people who love miles and points gather to discuss the latest trends, tips, and tricks.


Who can go to the Chicago Seminars?

The Chicago Seminars is open to anyone who has a passion for the miles and points game. All you need to do is sign up when registration opens. The registration fee starts at $105 (when you register early) and registration usually opens around April.


Where is the Chicago Seminars held?

The conference is held at the Holiday Inn Elk Grove Village, just outside of Chicago. It is near the O’Hare airport and the hotel offers a shuttle back and forth. The shuttle charges a small fee of $5 a person and runs every hour at the 30 minute mark (ie: 1:30pm, 2:30pm, 3:30pm), so it may be faster and more cost-effective if you share an Uber/Lyft or use a promo code (here are our referral links: $15 off first ride with Uber and $50 towards first ride with Lyft).


What is the schedule at Chicago Seminars?

On Friday, there is a welcome session for everyone, then a couple of timeslots for a few concurrent sessions to choose from. After that, everyone joins in the adjacent restaurant/bar for drinks, food, and networking.

Both Saturday and Sunday, breakfast and lunch is included, and you get a drink ticket for Saturday night’s evening reception.

On Saturday, you’ll experience a full day of sessions, with most time slots offering 2-3 choices of sessions… so that beginners and advanced guests can learn something new and share their tricks as well. The last session runs until about 6pm on Saturday, then it’s off to the reception.

On Sunday, each timeslot has only one option, but many of the speakers participate in each one. This year, the conference ended at 4pm, but I left at lunchtime to catch my plane home.


The Best Tips and Tricks from Chicago Sessions

Here are the best tips and tricks that I learned from the 2016 Chicago Seminars, in the order in which I attended them.  Out of respect for the presenters, I’m won’t share all of my notes, but I will share a few highlights and post links to any presentations that they shared.  I literally took about 30 pages of notes from the 2.5 days worth of sessions… if you want the full experience and knowledge, you need to sign up for next year’s Chicago Seminars.

Click the links in each section to go to the presenters’ post/presentation on the subject.


Award Travel for 5+ People

Dan is a fellow BoardingArea blogger from PointsWithACrew, and he has a big family, so he knows the difficulty of finding airline award space for many people.  The same goes with hotel rooms since each hotel chain has a certain capacity allowed in each room… and not every website will allow you to search space for larger groups.Expedia allows you to book hotels

Expedia allows you to book hotels with 4 or more people in the room.  So, search with Expedia, then the results will let you know which hotels in your destination city fit your party.  Then you can book directly with the hotel using your points.

When redeeming points, IHG Points Breaks are great deals at 5,000 points each room.  Book two rooms, then call the hotel to request adjoining rooms.


Mythbusters – Angelina

Angelina is a fellow BoardingArea blogger from Angelina Travels, and she talked about many of the myths people have about miles and points travel.  One of my favorite points she made is that it sometimes pays to buy points to redeem for a stay instead of paying cash for the room!

For example, I cannot recall the hotel name, but Angelina gave an example of a Hilton property’s beach villa which costs $2,462 per night.  Instead of paying cash, you can redeem 76,000 Hilton HHonors points a night.  You would pay $380 for those points (buying at 5 cents apiece)… AND you would get the added benefit of getting your 5th night free.


Credit Cards with Howie

On Saturday morning, we started out with a session by the Chicago Seminars organizer and writer at AwardWallet, Howie.

The goal for your cards should be to keep balances below 30% of your credit limit… and never let them exceed 50%!  Mortgage debt is considered “good debt” because you have to go through an extensive and highly scrutinized underwriting process.  Revolving credit card debt is considered “bad debt” because the process is so easy.  In most cases, you can apply and be approved within a couple of minutes.

Many people asked the question “when should you close a card?” and Howie’s answer was simple.  Credit cards are like any other financial product that you use.  Why would you refinance your mortgage or change your investment strategy?  When they no longer help you achieve your goals.  The same thing goes for credit cards.  When the benefits of a card no longer outweigh the costs (in cash or opportunity), then it is time to close, downgrade, or conver the card.


Advanced Credit Cards with Stefan

Stefan is a BoardingArea blogger at RapidTravelChai, and he is extremely knowledgeable on international travel, having visited 184 countries so far.

He did an extensive presentation on credit cards, but most important for you is the reminder to set a strategy.  Credit cards are good for more than just the initial sign-up bonus.  What are your goals?  You need to think long-term with your credit, incorporate anniversary benefits, and know which cards provide big spend bonuses.

Pay attention to the spend bonuses you receive at stores you frequent.  Many cards offer category bonuses for grocery, drug store, gas, restaurant, travel, etc.  And not all stores fall into the category that you think they would… for instance, some Targets and WalMarts are coded as grocery, while others are not.  If you are unsure which category a store is, look it up with the Visa Supplier Locator, MasterCard Supplier Locator, or the American Express Vicinity tool.


Perks That No One Talks About with Angelina

Angelina also did a presentation on the hidden perks that you can get with your credit cards and loyalty status.  She talked about the benefits of many programs, but what I liked best, is the ability to get lots of status with just one credit card.

If you have the American Express Platinum card (if you don’t, use our referral link to apply), you automatically receive Hilton HHonors Gold and SPG Gold loyalty status.  Now that Marriott has bought SPG, you can match your SPG Gold to receive Marriott Gold.  You can also use your Hilton HHonors Gold to become Best Western Diamond.  The Best Western status enables you to get Choice Hotels Platinum.  Some people say that you can use Best Western Diamond to match into Hilton Diamond.  Your Marriott, SPG, or Hilton status will get you Club Carlson Gold.  Hyatt Diamond used to be able to status match into, but with their upcoming changes, I’m not sure how that will work.  Hyatt status matches into MLife elite status as well.  I have the Chase Hyatt Visa, which gives me Hyatt Platinum and MLife Gold… which will also see changes in 2017.

Whew!!!  So much activity and awesome levels of status from one credit card.  If you have many of these other cards and continue to pay the annual fee just for the elite status they provide, you may be able to save some money and close the card if you use these status matches.


Earning Points without Traveling – Jen

Jen is another blogger from BoardingArea who blogs at DealsWeLike.  Jen talked about many of the awesome opportunities that have popped up in the past, such as the IHG Priceless Surprise promotion where you could earn 50K+ IHG points for mailing 3″x5″ cards.

The best current deal she talked about was expiring during the Chicago Seminars, but it was the opportunity to earn 12,000 Flying Blue points for a two-night stay booked through PointsHound.

Although there are no other deals to report at the moment, the best thing you can do is to follow your favorite bloggers via social media and their email newsletters to get advance notice whenever amazing deals become available.


Award Chart Sweet Spots – MileValue

Scott from MileValue always has great information about how to use your miles and points for awesome travel.  During this presentation, Scott talked about how to fly to many different travel destinations in Business and First Class.

One of my favorite redemptions that Scott talked about was transferring 40,000 SPG points to Asiana to redeem for a one-way First Class flight on Lufthansa.  And if you can route through Frankfurt, you’ll get to grab the elusive Lufthansa rubber duckie and experience their amazing First Class Lounge, including being driven in a Mercedes to the airplane!

To redeem, search United and book by calling Asiana.  Just be aware that Lufthansa only releases partner award space 15 days out… so be flexible to get in on this amazing experience!

Scott also did a live booking on American that you can check out here.


Maximizing Statement Offers and 5x Bonuses – Jen

Jen from DealsWeLike also gave a presentation about maximizing credit card statement offers and quarterly bonuses.  We also wrote about the 2016 Q4 5% bonuses in a post earlier this month.

Some of the best information I learned during this presentation is that the American Express Offers are loaded every day at 3am Eastern time and that you should pick one card to load up all of the offers you don’t want to see so that they don’t distract you when looking for new deals.

You should also consider creating one Twitter account for every Amex card you have so that you can sign up for the Twitter Amex Offers on each card.  Using a tool like TweetDeck will easily allow you to Tweet from all accounts at once, rather than Tweeting from each account manually.  I love tricks that save time!


101 Tips Tricks and Hacks – Stefan

Stefan from RapidTravelChai presented a massive amount of information in a short timeframe.  If travel doesn’t work out for him, he may have a career in being an auctioneer ahead of him!

The best tip of the 101, that I didn’t know of, is that you can have a second passport.  The 2nd passport is only good for 4 years vs. the 10 for your primary passport, but it is very useful when you need to send in your passport for visa applications or if you want to go to a country like Cuba and are a little wary of handing over your primary passport.

Other great tips are:

  • Don’t bring a guidebook, photocopy pages from the book instead, so you don’t look like a tourist.
  • Carry a certificate of vaccination.
  • Get a passport card as a backup ID card.
  • Always use VPN to protect your data.
  • Use the Google Translate app and download the language before you go.
  • Connect where you want to be stranded.  Life happens and flights get cancelled.  Would you rather be stranded in NYC or Topeka, Kansas?  Paris or some random country you have no interest in visiting?


Open Panel

The presenters joined an open panel to answer questions from the audience to start off Sunday morning.  The best tip was to consider reducing the limit on old cards that you never use.  This helps retain the longevity of the account to help your credit score, but also may provide an easier path to an automatic online approval, rather than needing to call the bank’s reconsideration line on a pending application.

If you’ve been denied for the Chase Sapphire Reserve card like me, consider speaking with a Chase Private Client banker and ask for a “trial” because you are considering moving your assets over from your other wealth manager.  Many people say that being a Chase Private Client is a way to bypass their new 5/24 Rule.


Hilton Breakout Session

Never use the Hilton HHonors app to check-in early, unless you know you won’t arrive at the hotel until later in the evening. Even when checking in on the app, you still have to go to the front desk anyway to receive your keys. When you check-in on the app, you secure a specific room, which (in most cases) eliminates the opportunity for an upgrade at check-in.

One of the recommended Hilton redemptions is for the all-suites Hilton Conrad in New York. The rooms often price out at $300-$500 a night, but can be booked most nights for 70,000 Hilton HHonors points or $125 + 28k Hilton HHonors points. This is a pretty fantastic deal for a high-end property in New York!


The Bald Thoughts

Even for an experienced traveler like me, it is great to attend conferences like The Chicago Seminars because you can meet some great new friends and learns tips and tricks from the presenters, as well as the guests.  It has been a few years since I attended The Chicago Seminars due to other travel and work conflicts, but I hope to be able to attend next year.



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