I actually had the pleasure of visiting family friends in Chicago when I was 14 years old. I was much too young to really grasp everything the city had to offer, but I do distinctly remember feeling like it held its own kind of magic. I’ve been meaning to go back to experience it properly ever since, and with Alexis Buryk‘s tips & tricks I know I’ll be well equipped when I do. Plus? There’s a whole gallery filled with lots more if you’re looking for it!
From Alexis.. Chicago is a city of ambles and sprawls, nestled and tall against the southwestern shore of Lake Michigan. Ignore what you’ve heard about it being a version of anywhere else. Meeting this Midwest city on its own terms is the only way to experience its real charms: the orange glow of its lights at night, the sips and tastes of its ever-bustling food and drink scene, the form and function of its remarkable and historic architecture, and the pleasure of being surrounded by genuine and friendly people.
While the Loop remains Chicago’s iconic physical center, the city’s true heart lies in its neighborhoods. Pick a spot and take a walk, or hop on an L train and go from downtown skyscrapers to cozy close-knit streets in a few minutes. I’ve lived here for four years, and never tire of the way in which Chicago unfolds without pretension. It’s simply a city that knows itself, and one that you should get to know, too.
EAT + DRINK
Coffee + Sweets:
Chicago has some serious bean culture, so while you’re here check out homegrown roasters Intelligentsia. They have various locations throughout the city, including their original and recently updated spot in Lakeview. You can also find them served at Floriole, a Lincoln Park bakery that has the most incredible selection of flakey and sweet goods, in a beautiful and airy space.
Brunch + Lunch:
Wicker Park’s Division Street corridor has lots of great nosh options, my favorite of which is Milk + Honey. Go for a late morning coffee and pastry, or something more substantial like their huevos rancheros made casserole style, and take home some of their granola. Publican Quality Meats in the West Loop is the place to go for top notch sandwiches and picnic possibilities.
Pizza, Burgers + Hot Dogs:
Check out local Lincoln Park favorite Pequod’s for deep dish delights, away from where most of the tourists dine. If burgers and true Chicago hot dogs (no ketchup, ever!) are more your thing, Lakeview’s DMK Burger Bar with its delightful options (lamburgers with tzatziki sauce? yum!) and Hot Doug’s dogs and duck fat French fries in Avondale are definitely the way to go.
Sips + Supper:
This category is bursting with delicious potential, because Chicagoans love their sips and suppers, especially when the weather is fine and you can sit outside. Tiny Lounge in North Center has great small plates to share and a solid cocktail and wine menu, while Scofflaw in Logan Square offers a charming atmosphere and plenty of spirits. Hopleaf in Andersonville has a staggering amount of beer on tap, including some great imports, while Revolution Brewing Company continues to astound with its original brews rotating constantly, and food that puts other pub grub to shame. If you’re looking for something just a little more fancy, make a reservation or cozy up to the bar at The Girl and the Goat, the incredible restaurant headed by Stephanie Izzard of Top Chef fame, which defies description, other than to say it is completely delectable and worth every penny!
Before heading out to wander the neighborhoods of Chicago, begin downtown where ornate 19th and 20th century architectural gems and the silvery structures of Millennium Park and Cloudgate (aka the Bean) are main attractions. Take a walk through the gardens and stop by the Art Institute of Chicago if an art-filled afternoon is on your mind. Architectural boat tours on the river are also a favorite of tourists and locals alike, for the education and sheer beauty of cruising along the Chicago river in a canyon of skyscrapers.
Up further north in the Gold Coast, you can meander among the mansions of Chicago’s elite, and make your way along the Lakefront Trail into Lincoln Park, where the city’s Greenmarket is held in warm weather every Wednesday and Saturday. And if you’re not completely exhausted yet, continue up towards Wrigleyville, and take in the amazing structure of the ballpark while ignoring the teeming crowds of boisterous revelers. Take in an improv show at the iO Theater, and finish your day with a nightcap after riding the Brown line L train back south towards a glittering cityscape.
There are so many walkable shopping corridors within the city, retail therapy is all too easy! For home items and antiques, check out Swedish neighborhood Andersonville between Foster and Bryn Mawr, where shops like Scout and Roost offer great curated finds while The Brown Elephant resale shop is like a treasure hunt, with the bonus of all your purchases benefiting the Howard Brown Health Center. The Halsted and Armitage corridors of tony Lincoln Park have upscale clothing and body care shops in their quaint brick buildings, while nearby Old Town features shops like the lush A New Leaf for exquisite flowers.
Lovers of bookshops and record stores should meander down Broadway in Lakeview or Milwaukee and North Avenues in Wicker Park. And for a more eclectic afternoon, Lincoln Square on the far north side has shops ranging from kitchen goods (The Chopping Block) to mind-stretching games (Marbles: The Brain Store) to an old-fashioned Apothecary (Merz).
Photographer: Alexis Buryk