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How to have a first-rate time in the Second City during Shoptalk Fall

For the first time, the folks behind the lollapalooza of retail industry conferences are holding a gathering in the Second City. Yes! Shoptalk Fall will occur at McCormick Place in Chicago, October 16-18.

Their reason for this inaugural autumnal event is the accelerating pace of change the world of retail is experiencing, particularly as it regards leveraging technology and data to find, connect, and nurture relationships with consumers.

They believed a single event couldn’t cover everything in this dynamic business sector, so Shoptalk Fall will now be held in addition to Shoptalk Spring in Las Vegas.

Reflective of that is the range and caliber of speakers set to share their experiences and insights, including execs from Crunchyroll, J. Crew, L’Oreal, Old Navy, and Rothy’s.

PebblePost will be there at Booth #H53. We hope you stop by to learn how our powerful brand of shared first-party data can help you acquire and retain customers–whether you’re strictly brick-and-mortar, e-commerce only, or a hybrid.

We help brands like yours improve the performance of their omnichannel strategy by boosting conversion rates by as much as 134% and delivering ROAS of as much as 50X throughout the consumer lifecycle.

While attending Shoptalk Fall, your focus will undoubtedly be on improving your marketing performance. But let’s be honest. You’re in Chicago, so why not enjoy the marvels of this city? 

This post gives you suggestions on how to have a first-rate time in the Second City during Shoptalk Fall.

Why Chicago is called the Second City

Most think Chicago’s nickname, Second City, reflects its rank as the second-most populous city in the United States after New York. That’s no longer the case. It’s now the third-largest after New York and Los Angeles.

The basis for this moniker is attributed to the Chicago Fire of 1871. The fire lasted for days and leveled all that was Chicago then. The city leaders opted to rebuild, suggesting the city was built twice. Hence, the Second City.

What to do in Chicago

Here are five activities to consider while in Chicago for Shoptalk Fall.

  • Culture
  • Laugh
  • Retail
  • Eat
  • Hockey

Culture Chicago

After walking miles of aisles and speaking with countless other attendees at Shoptalk Fall, a welcome change of pace is to stroll through any of Chicago’s fabulous art museums. 

The art institute

A prime example is The Art Institute of Chicago, a legitimate world-class museum that even the most discerning art lovers will appreciate. The Field Museum presents fascinating exhibits that show how it is “on a mission to explore, protect, and celebrate nature and culture.”

To soak up the city’s pop culture, consider The Chicago Gangsters and Ghosts Tours. It’s a chance to walk back to the Roaring Twenties when speakeasies around The Loop attracted bootleggers and gangsters like Al Capone. See where they frequented–places like the Congress Hotel, the Palmer House, and Death Alley–and plotted their next big caper.

Laugh Chicago

During Shoptalk show hours, be as serious as you need to be. Afterward, why not find a place to laugh out loud? That’s easy to do in Chicago.

Many consider Chicago one of the best places to experience stand-up comedy in the U.S. 

second city improve

Let’s start with the world-famous Second City Improv, the springboard of too many top-flight comics to count. No matter your sense of humor, this place has something to offer that’ll have you chuckling uncontrollably.

Another well-known venue is the Laugh Factory, a Chicago comedy institution prompting belly laughs since 1979.

Zanies Comedy Club, the third of Chicago’s long-standing homes of humor, showcases national headliners every night of the week.

Retail Chicago

The term “busman’s holiday” dates back to the end of 19th-century England, when bus drivers would go on excursions in, you guessed it, tour buses. While in Chicago, you can go on a retailer’s holiday and see some retail landmarks.

Start on State Street in the Chicago Loop to see the landmark Marshall Fields & Company store. It is rebranded now as Macy’s, but it is something to see. The iconic Magnificent Mile is close by, between Michigan Avenue Bridge and Oak Street. You’ll find 450 retailers–from famous department stores to cutting-edge boutiques.

Eat Chicago

If you want to find the newest, swankiest dining establishment in Chicago, go right ahead. It’s not that hard. Truth be told, Chicago is a serious foodie town. Still, when in Chicago, why not eat like a Chicagoan? If that’s your jam, here are some places highly praised by the locals.

Smoque BBQ 

This destination in the Northwest Side neighborhood of Irving Park delivers barbecue with nods to Kansas City and Memphis.

Pat’s Pizza and Ristorante

This spot in Lincoln Park has a storied history of popularizing tavern-style pies and sports, as well as some of the crispiest, thinnest pizzas around. 

Lula Cafe

For 25 years, this place has endeared itself to many in the Logan Square neighborhood for new American cuisine. Enjoy a breakfast burrito by day or roast chicken, beet bruschetta, and summer squash in the evening.

Redhot Ranch

It’s hard for Chicago hot dog stands to differentiate themselves, as most use the same product: dependable Vienna Beef. But Redhot Ranch has managed to stand out.

Alinea

This fine-dining institution is one of two Chicago restaurants with a full three-star Michelin rating. The ambiance of the Lincoln Park dining room is as amazing as the food.

Hockey Chicago

Chi-town, yet another nickname for this city, loves its pro sports teams. If you go to one of their games, you’ll feel there’s a special place in Chicago sports fans’ hearts for the Blackhawks. Even though the team finished second to last in the NHL last year, the cheers are loud, even boisterous, every time the puck drops.

PebblePost thought it would be fun to host a group of Shoptalk Fall attendees at the 2024-2025 season opener at the United Center. Interested? Act now, as seats are limited. Save your place behind the glass.   

Talk with PebblePost

This conference is called Shoptalk–whether it’s springtime or the cool days of fall–for a reason. It’s a terrific opportunity for us to talk–and trust me, there’s plenty to cover in terms of new and better ways from PebblePost for you to acquire and retain customers and reconnect with those who may have become dormant.

Let me suggest you schedule a meeting with us now to make your schedule at Shoptalk Fall easier for you to manage.

Set your preferred time and day here. The sooner you act, the better, as appointment slots fill quickly.

Our PebblePost solution specialists will be on hand, ready to help you solve your customer acquisition or retention challenges with amazing effectiveness, whether it’s 

  • Prospecting for new customers
  • Converting leads to customers
  • Reactivating lapsed customers
  • Making the most of holiday or tentpole sales events

Looking forward to seeing you in the Second City, the Windy City, Paris on the Prairie, or Chi-town–whatever you call Chicago–at Shoptalk Fall. PebblePost will be at booth # H53.

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