We write cool city guides.

We're a collective of photographers and writers creating bite-sized itineraries to help you explore Chicago.

We're a collective of writers and photographers experimenting with content and technology to help people build a deeper connection to Chicago. We started by producing bite-sized itineraries to help people explore Chicago, and then we introduced a text message service for personalized recommendations. Most recently, we built a mobile app to make finding the content you want even easier.

Over time, our experiment has evolved into a $5/month membership that gives people access to everything we've created.

We're constantly tinkering with new ideas, and here's what we've cooked up so far.

City Guides

Each week, we publish a Chicago city guide that lays out a carefully planned itinerary that gets you exploring all corners of the city. You won't find listicles or generic clickbait. We go out each week with our cameras and curate an experience that we think you'll love.

Text Message Concierge

After becoming a member, we provide you with a number you can text with questions about doing stuff in Chicago. Want us to plan a date? Family or friends in town? Text us.

We're active from 9 am to 9 pm every day. While we can't promise an immediate turnaround on all requests, we'll do our best to respond quickly. For now, we ask that you give us at least 24 hours to respond. In most cases, we'll get back to you a lot sooner.


Every so often, we'll work with the venues we feature and negotiate special experiences and deals. Find things like free shots of malort, a private after-show event with a magician, and discounts that more than cover the cost of an annual membership.

The redemption process is easy too. This isn't Groupon, there's nothing to purchase in advance, and we don't take any cut from businesses or charge them anything. Just find the deal in our app and click to redeem.

Everybody these days has some newsletter or some expensive subscription that they want to sell you. It's exhausting, but we really do think we're worth it.

The alternative is to cram ads into our website, and in our experience, that ultimately leads to pushing out the same low-effort content everybody else produces. At the end of the day, you don't need to read another article about the top 50 hamburgers in Chicago, and we certainly don't want to devolve into doing anything like that to keep the lights on.

Instead, we want to ensure that our core focus is on high-quality original content and providing an excellent service that makes it easy to make the most of your free time.

Yes! In fact, we have an entire space dedicated to helping parents find creative ways to explore Chicago with kids in tow. Just like our other city guides, we're creating bite-sized itineraries taking families on cool trips around the city and beyond.

In creating these itineraries, we didn't just want them to be about parks and indoor playgrounds, but we wanted to be thoughtful about making sure adults have fun too. Think things like kid-friendly breweries, family improv shows, camping with the little ones, and practical planning tips along the way.