Cubs Convention Tips For the Newcomers

Cubs Convention tickets went on sale last week (November 1). It is an event that I have circled on my calendar each year since my first convention in 2015. I was hooked from the start.

Each year I meet Cubs fans either at the event or on social media that plan to attend (or are attending) for the first time. Let me preface this post by saying it is a must attend event, even if it’s just once. As a Cubs fan, you need to check out the Cubs Convention.

With that said, after five conventions I finally feel that I have earned veteran status and can offer some tips and tricks for the newcomers. Of course, I am no super veteran as the Cubs Convention has been around since 1986 and I know many fans that have been to many more conventions than myself. At any rate, after my first few conventions here are some tips if you are attending for the first time, or maybe you are a veteran and learn something new.

Biggest Piece of Advice

Soak it all in. Simple. When I attended my first convention in 2015 I went in with an open mind. I wasn’t seeking specific autographs, not wanting to meet anyone in particular, or find any special items. I did a lot of wandering that first year and tried to get a piece of everything. That way in subsequent years, I could develop a plan and have goals. Get there early on Friday. Walk around. Take in the sessions, play BINGO, jump in an autograph line. Be a Cubs Convention sponge.

Biggest Piece of Advice Part 2

This is almost as important, if not more important, than the above paragraph. Do not under any circumstances expect to meet Kris Bryant or Anthony Rizzo. Do not expect to get autographs of the latter, or Javier Baez and Willson Contreras, etc. Unless you wait in line and spend $300 for a meet and greet, you will likely not see any of the Cubs stars except from a hundred feet away while they are on stage for the Opening Ceremonies.

Before You Go – The Essentials

Comfortable shoes. If you take no other advice in this article, make sure you heed this one piece of advice. Buy a pair of walking shoes or special Dr. Scholl’s inserts. Or both. You will be walking. And standing. And walking. And standing. And standing. And standing some more.

Bring Cash

There are vendors that are cash only, and well cash is king. You can get by without cash on hand, but it’s always important to have some handy.

Food and Drinks

You can save a LOT of cash by bringing your own food and drinks. There are a couple restaurants in the hotel. The lines are long and the food is expensive. There is a concession stand outside the ballrooms, and the food is really expensive. Restaurants are nearby…but you guessed it. This is Chicago and it’s expensive. If you don’t want to bring a cooler with, a Walgreen’s is about two blocks away, so that’s a good option. It took me a couple years to finally break down and not pay the exorbitant food prices inside the convention. Also, if you’re a beer drinker….go to Walgreen’s and save about $6 per beer.

Portable Battery Charger

If your phone must be charged every day (or it lives on a charger), invest in a battery pack. Remember the part about standing in lines and walking…you won’t be near any outlets. Inside the hotel is also notorious for having poor cell service in turn sucking your battery quicker than usual.

Extra Bag

If you’re planning on buying memorabilia, bring an extra bag. Even the freebies can fill up your luggage quick, as I learned early on.


I am an autograph collector so I utilize a backpack to carry around all of my baseballs and 8×10 photos to get signed. I can also throw in any memorabilia I buy from vendor row.

Checking In

The convention begins on Friday with check in around noon. Get there early. The line for check in will be really, really long. It actually went by pretty quick (once the “gates” opened) last year. Typically, my friend Dave has done the checking in since he gets there a bit earlier than I arrive.

Friday Afternoon

After checking in work the hotel floors. Usually as Dave is waiting to check in, I will jump in line for the Cubs Garage Sale. Since I love the memorabilia aspect, this is great. You can buy a grab bag for $35 which includes a bag filled with stadium giveaways. It’s a heck of a deal for $35, and in past years I have been able to sell whatever I didn’t want inside for more than $35. The sale also includes random memorabilia and jerseys at discounted prices. One year a “game used” Gatorade cooler that was signed by a bunch of Cubs players was for sale. Another year had the complete set of bobblehead giveaways for sale for just $50. Unfortunately, those bobblehead sales are long gone.

Once I have gone through the garage sale I make my way down to the vendors floor. My first stop is Cubs Authentics. This place is awesome for game used stuff. Jerseys, hats, bats, baseballs, cleats, pants, bases all for sale. In the past I have bought a pair of James Russell game used pants, game used 2nd base from the 2017 National League Championship Series, random Cubs game used jerseys, and even an Edwin Jackson game used hat.

Also on Friday afternoon is a Cubs Authentics auction. This is high roller territory. You won’t find any game used stuff from Kris Bryant, Anthony Rizzo, Javier Baez, or any other stars in the Cubs Authentics booth because those high end items are being auctioned off. Not cheap! It’s fun to watch for a few minutes, then I’m off to check out the vendors.

The vendor area has expanded in the past few years. The first couple years I attended it was very small (maybe a few booths), and was told by long-time attendees that it was never like that. I’m happy they have expanded, as I’ve been able to find some pretty cool stuff in recent years.

After walking through the vendor area, we take a late lunch. Our tradition is going down to the world famous Billy Goat Tavern. No Coke. Pepsi.

Opening Ceremonies is a must-attend event for the weekend. If you are claustrophobic, either skip my advice of walking around and wait in line to guarantee a seat, or hang out by the back near the doors. I’m not a big crowds person, nor do I like waiting in line. My go-to for Opening Ceremonies is to hang out by the ballroom doors in the back of the room. It’s not quite as crowded (it’s crowded…but there’s room to breathe).

Friday Night

There will be two pieces of advice I offer that can be debated. Friday night’s activity is the first. Do you choose to stay at the convention and attend Ryan Dempster’s late night show, or splurge and go to Kerry Wood’s fundraiser at Harry Caray’s?

I choose the latter. It is a little pricey at $250 a ticket, but that includes all you can eat and drink. It will run you additional money because it’s for charity so you need to tip for drinks. Also, if you are lucky enough to get a spot at the bar to talk with the players and celebrity bartenders, it’ll take a generous tip to get a selfie ($10 or $20 should do it).

This event is so much fun, and I have attended each year I have gone to the Convention (since 2015). Since I have never attended Ryan Dempster’s show at the convention, I can’t offer my opinion, but from friends that do attend it’s a great part of the convention. And you’ll save a lot of money.


Are you going to get autographs? You’re in luck because you can go home with dozens of autographs. In the five years I’ve been attending Cubs Convention I take home between 20 and 25 autographs each year.

When you check in, you’ll receive a pull tab. Most likely you’ll open it up to reveal $5 off your purchase at the Cubs store. But if you get lucky, you’ll get a voucher for an autograph of a star player. Last year, I received an autograph from my pull tab for the first time: Cole Hamels.

The players sign in one hour increments, so you must be in line at that time to get the autograph. Same goes for the free autographs. Former players, and a handful of rookies or recent signees are available through the weekend. Regulars in the past have included: Bill Madlock, Steve Trout, Bob Dernier, Lee Smith, Jay Johnstone, Les Lancaster, Gary Matthews, etc.

Saturday Night

I have an unpopular opinion about Saturday night which I will get to in a moment. My advice for Saturday night for newcomers to Cubs Convention: play BINGO.

BINGO is the most popular event at Cubs Convention and is hosted by Wayne Messmer. The prizes always include a flag that has flown over beautiful Wrigley Field. It seems 95% of convention goers play BINGO.

With that said, get in line early. So many people try to play BINGO that they have to shut down the elevators to abide by the fire code. Don’t worry, they’ll fire up the elevators once the ballroom doors open and a mad dash for tables commence.

I hate waiting in lines, and the BINGO part actually isn’t that appealing to me. In fact, after three years I dreaded BINGO. I don’t play BINGO anymore. What do I do? I hang out in the hotel lobby and at the bar. It began in 2018 when I met a couple newcomers who also had a disdain for waiting in line. I encouraged them to play BINGO because it is something to experience, but they opted not to. We hung out in the hotel bar area, and several former Cubs showed up.

My favorite part of that night was sitting with Bob Dernier and his wife, and Bobby even let me wear both his Phillies and Cubs World Series rings (see above). We had a conversation for about an hour that largely revolved around anything but baseball (though Bobby does like to talk baseball). My wife and I were preparing for our honeymoon in Italy, and Bob’s wife was giving suggestions about various cities in Italy. Other Cubs in the bar that night included Tim Stoddard, Ray Burris, and Pete LaCock.

Final Thoughts

I’ll reiterate it. Go in with an open mind and have fun. Leave your expectations at home, because something seems to change every year. I try to remember that. Just because I make notes from last year’s convention doesn’t mean they’ll be valid for the next one. Have fun. Enjoy Cubs Convention!

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