Telluride Off-Season: Fabulous Chicago

01 May Telluride Off-Season: Fabulous Chicago

Describing Chicago as a second city is like describing Telluride as a second Aspen. It’s inaccurate and ruffles feathers on both sides. I love New York, and I love Chicago. But there can be no ranking. They are entirely different places just as Telluride and Aspen are entirely different places.

Here’s what I love about Chicago: it’s a city that feels like an out-grown town. When I go to see family there two or three times a year, and I run along the lake front, people almost always smile or nod when we cross paths. Like Telluride, Chicago is not a place where you can be anonymous. The city draws the introvert out of you.

This became all the more apparent to me when I returned to my favorite coffee shop, Intelligentsia, on my most recent trip to Chicago, and they recognized me. “Latte for the Colorado girl?” the man asked.

My first thought was that he made a good guess; I was wearing a Patagonia jacket and trail running shoes, pretty granola even for this laid-back city. I hadn’t been to Intelligentsia in over 3 months. Surely, he wouldn’t remember me from then.

But then he said, “Telluride, right?” and handed me a latte with a fern etched into the milk that was so beautiful, I wished I could carry my coffee home and display it as art. Walking home and sipping this unbelievably good latte, I marveled at the friendliness of a city this big. I wondered, too, why the rest of the world couldn’t make coffee this good.

Intelligentsia, and places like it, are another reason I love Chicago: the restaurants, coffee shops, hot dog shacks, taqueria stands, and bakeries are amazing. Here is my very short list of must do when I go to Chicago: Bittersweet Bakery—line for the sticky buns is out the door by 8AM; Spacca Pizza—only a guy who lived in Naples could make wood-fired pizza this good; Frontera Grill—Rick Bayless, the owner/chef, is famous but that doesn’t make his tortilla soup any less amazing; and Molly’s Cupcakes—cupcake shop with swings (and they serve Intelligentsia Coffee)—is there any better way to make everyone in a family happy?

These days, when we travel to Chicago, we go with our kids, and our activities are tailored towards them. But in this city, that’s ok because there are so many fun things to do. When it’s nice out, we head to the lake—to the Lincoln Park Zoo, or in the summer, to the beach and the farmer’s market. All are free and fabulous.

On the not-so-nice days, of which Chicago has a lot, we go to one of the many spectacular museums—the Field Museum, the Children’s Museum, the Shedd Aquarium, the Planetarium, and the Art Institute, to name a few. We also love to stroll along Michigan Avenue, Chicago’s most famous shopping street, and take our two girls to the American Girl Store.

Often, though, Chicago is best at the end of day. That’s when I usually run along the lake. I look at the city’s skyline and out over the water and think about the places I get to call home. One’s a remote mountain town with enough activities and restaurants to rival a great city; the other a gigantic city with a small-town attitude. How lucky am I that I get to spend time in both?