December in Chicago: From The Eyes Of Bryan Croft, CEO Of Simply Stamps

One cold day this past December, two Floridians, my wife Amy the law school professor, and myself, the self-proclaimed rubber stamp and sign guy, packed all of our cold weather clothes and headed off to Chicago for a little winter rest, relaxation, and of course a healthy amount of work!

After a few hours surrounded by planes and airports, we made it safely to the famous Acme Hotel located just a few blocks off of Michigan Avenue. When we arrived, we were greeted by a cheerful Christmas Story inspired display in the front window. The warm twinkling lights were in stark contrast to the frigid Chicago temperatures and we couldn’t wait to get inside and switch our clothes to some of the warmer duds we’d brought along! The staff was excellent and didn’t hesitate to suggest some cool local places to check out during our stay.

Being the owner and CEO of Simply Stamps, I love small businesses, creative people, and having a good time so naturally, I couldn’t wait to get out and explore the city!

So where all did we wander?

harry caray steakhouse bar chicago1. Harry Caray’s Legendary Steakhouse

As a kid, I had a blast with baseball. Naturally, I grew up hearing the name Harry Caray pretty often! I couldn’t help myself when we wandered past his steakhouse. So I gathered the group and stopping in for a quick lunch and drink. I have few doubts that my inner child was smiling ear to ear.

2. Chicago Sports Museum

In keeping with the afternoon sports theme, while my wife went to check out some of the stores and do some shopping, I just walked next door to check out the Chicago Sports Museum. What started out as a quick stroll through a museum, ended two hours later with my head swimming from all the sports names, facts, and memorabilia that has become synonymous with American culture.

3. Pops

Back home in Florida with our three kids, it can be a real chore finding hip new bars to hang out at, not to mention finding the time, energy, and a sitter. But with no kids on this trip, Amy and I were able to kick back and relax – that’s where Pops came in! With its creative drink concoctions and cool atmosphere – we couldn’t have been more satisfied!

bottlefork restaurant chicago4. BottleFork

As much as we loved Pops, my wallet didn’t. So we meandered over to BottleFork, where we were lucky enough to have an awesome and energetic waiter with some killer drink suggestions – which is great for when you don’t have a clue what you want!

5. Sullivan’s Steakhouse

Being from Florida, it’s not every day we get the opportunity to go to one of Sullivan’s Steakhouse’s awesome locations – but when we do, it’s always a meal to remember! After a round of drinks at the bar, we were ushered to our table and our masterfully cooked steaks weren’t far behind.

6. Bongo Room

The next morning, we headed over to Wicker Park and added our names to a 45 minute wait – but boy were we glad that we did! Everything on the menu sounded so amazing, that we had a hard time deciding just what to order! In the end, the Bloody Mary with bacon was a must – yum!

ragstock clothing store chicago7. Ragstock

Remember that 45 minute wait we mentioned? Being an always-on-the-go business owner, I’m not really one to stand around and twiddle my thumbs. So we took a walk, and what did we find? This awesome little place called Ragstock! Given that our trip was a few weeks before the Holidays, we had an ugly sweater party to go to when we got home – but unfortunately had none to wear. Ragstock to the rescue! The employees were so nice, one sold me his ugly sweater right off of his back! #Score!

8. Saint Alfred

With all the walking we were doing, we decided to give it a rest and spend some time with family. When we finally caught our breath and were ready to keep walking around the city, we thought it may be a cool idea to check out a local small shoe and clothing business called Saint Alfred. No matter what your budget is, Saint Alfred’s has got a shoe for you! I myself walked away with an awesome pair of Adidas for $60!

9. The T-Shirt Deli

Up next on our travels was the famed T-Shirt Deli. A great concept, the T-Shirt Deli has the atmosphere and look of a deli but is instead all about made to order T-Shirts by using Sublimation and Screen Printing techniques. Now what would a stamp company know about printing? Probably not much, but the parent company to Simply Stamps is Holmes Stamp & Sign which has been busy making signs, stamps, and name tags since 1954. And while we don’t manufacture T-Shirts in our factory down south, we do know a thing or two about using these same printing techniques on more than our fair share of signs and name tags!

10. Emporium

If you’ve ever met me, (or know someone who has), you’d know that I am a huge proponent of fun! So imagine my level of excitement when I found Emporium! Doubling as a bar and an arcade, it’s hard to image a better idea for a fun, cool place!

emporium arcade bar chicago

11. Harolds Fried Chicken

While paying the tab at Emporium, I couldn’t help but notice a massive line over at Harold Fried Chicken and just couldn’t resist finding out why. #SpoilerAlert Best decision ever – it was awesome!

12. Violet Hour

Now being a stamp and sign guy, I naturally cringe at the thought of a local business NOT having at least one or two signs hanging up, but this place was one of a kind. Given that we were being showed around by local friends and family, we were able to find this place. Violet Hour had absolutely no signage whatsoever and was behind a door hidden among a black swatch of flowered wallpaper. I won’t ruin the special surprise inside but if you happen to be in the Wicker Park area of Chicago – you should definitely check it out!

trenchermans chicago bath house bar13. Trencherman’s

If you really want to witness something that you don’t get to see every day and happen to be in the Chicago area, you should check out Trencherman’s! Converted from an authentic old bath house, Trencherman’s is now a pool with a full service bar in the deep end – which may sound a little dangerous, but far be it from us to question a good thing!

14. Francesca’s Forno

What better way to kick back and relax after a refreshing dip in the pool, than with some seriously awesome pizza! Francesca’s Forno is where it was at! We swapped plates and had a great time sampling some of Chicago’s best pizza!

15. Glazed and Infused Donuts

Do we really need to elaborate on such an amazing sounding place? After Francesca’s a sugary sweet assortment of donuts was a must! No wonder this place has won Chicago’s Best Donut Award for YEARS!

the eataly chicago16. The Eataly

After we slept off the prior day’s caloric intake (ha, just kidding – calories don’t work that way, unfortunately), we were told we had to visit The Eataly! We promise it is every bit as great as it sounds and was worth the trip alone! Being a multi-level eatery, if you could name it, it was there! What did I finally settle on? A Prime Rib sandwich and a beer!

Finally after all the eating, drinking, and fun, it was time to get down to business. But despite all the cool things to look at on the tradeshow floors, I couldn’t get all of those cool places we visited out of my head! So when we got back to our sunny (and warm!) factories down in Florida, I had our guys put together some awesome custom logo stamps to send back to some of those places that stuck out the most in my mind!

After all the fun in Chicago, I can’t wait to see where my business travels take me next!

Bryan Croft
CEO & President
Holmes Stamp & Sign
Simply Stamps

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