Upswell Chicago is now less than a month away! We hope you’ve had a chance to save your spot to experience some of the immersive community events happening during the main event this November! The lineup features 18 thoughtfully designed experiences in all – including seven community dinners and eleven Chicago Inside & Out tours guided by dynamic leaders from across the city. Vibrant local experiences are a cornerstone of the Upswell experience, which is all about going deep locally to uncover enriching and surprising insights that apply to changework and shared experiences across the board. With just a few tours left to highlight in the weeks before we head out to Chicago, we’re previewing our Loop tour this week.

If you’ve ever visited Chicago for any reason, chances are you’ve spent some time in this part of town. So you likely know that the Loop contains several of the city’s main attractions, and is essentially Chicago’s equivalent of Midtown Manhattan. We’ll say this right-off: don’t expect to make the traditional landmark rounds if you join us for this tour of the Loop. Now, if you want to make some of those rounds on your own time while you’re in town for Upswell, we won’t stop you. In fact, you’d be hard-pressed to be posted up in a more convenient part of town for spontaneous exploration of the Loop, because Upswell Chicago’s home base of Hilton Chicago is in the heart of it. We even put together a list of landmarks within a mile of Hilton Chicago earlier this year. So, yes, in a sense, we’re condoning independent exploration to some of the Loop’s more traditional standbys. But our Inside & Out tour will afford you a chance to experience the Loop a bit differently. We’ll get to exactly how, but first – as you may know from our other tour previews – we like to share a brief historical overview of the places we’ll visit this November. So, here’s the scoop on the Loop…

The Loop area is bounded on its north and west sides by the Chicago River, on its south side by Roosevelt Road, and its east side by Lake Michigan’s southern shore. The name Chicago actually comes from a word the Algonquian people of the Mascoutens and Miamis tribes (the earliest residents of south shore) assigned to wild leeks that grew along the river on the other side of their settlement (more on that in this set of Chicago trivia). Those early residents were forced to cede that land and were almost entirely gone from the area by 1833. U.S.-sponsored settlement of Lake Michigan’s south shore, and the area that would ultimately become the Loop, began early in the 19^th century. By the tail-end of that century, it became known as the Loop for an elevated railway that encircled the area. Early in the 20^th century, Chicago addresses became uniform with the Loop becoming the point of origin for Chicago’s modern street grid. In spite of damage done by the Great Fire of 1871, the Loop is to this day associated with many buildings that earned Chicago its reputation as a forerunner in modern American architecture. Its attractions number many. And it is home to the seats of both Chicago’s and Cook County’s governments.

Now, as for why this tour of the Loop will be unlike the usual visit to the area, hear us out because this ties into a bit of an emerging theme for Upswell. Earlier this month, we launched a new article supplement in print and digital editions of the Chronicle of Philanthropy featuring guest voices discussing the relationship between New Power and Old Power, and ultimately explaining why and how we’ll continue to explore the topic at Upswell Chicago. That New and Old Power dynamic is at the very heart of what you’ll see on this tour of the Loop. Though it’s the oldest part of town and the point of origin for the street grid of Chicago as we know it today, the Loop is home to a remarkable collection of tech activations and thoughtful modern urban design. It’s the best of new and old in Chicago intermingling, all within a stone’s throw of Upswell Chicago’s home base.

If you sign up for this tour, you’ll take a short walk from Hilton Chicago down to two new Chicago River activations – the Apple Store and the River Walk.

From there, you’ll make your way over to the Merchandise Mart, an impressive 140,000 square foot facility occupied by a number of leading digital startups, thriving technology and entrepreneurial accelerators, and industry-specific incubators. At the space of one such accelerator, 1871, you’ll be greeted by representatives from P33, a cross-disciplinary initiative to drive inclusive, global technology leadership for Chicago. They’ll guide you on a tour of Merchandise Mart, followed by a light lunch.

This tour exploring modern innovation happening in the oldest part of town is a prime opportunity to learn how technology, engineering, and adaptive re-use of the natural and built environment can unlock new economic prospects. The Loop is known best for its overt identity as one of the busiest commercial business districts in the country and a thoroughfare for visitors from all over as they explore some of the most quintessential Chicago landmarks. You’ll have a chance to look beyond the statuary and learn how a modern crop of Chicagoans are reimagining solutions for communities in Chicago and beyond.

This tour of the Loop is just one of eleven happening at Upswell this November. Choosing among them will be tough, but we guarantee they will all put you in an inspired headspace to kick off the first day of Upswell. We have just a few tours left to highlight, so stay close for those and much more news about the Upswell Chicago experience, but keep in mind that many Inside & Out tours can accommodate about 30 participants and will fill up. So, if you see one that you’re over the moon about already, don’t sit on saving your spot!