It’s hard to say where Wicker Park starts and Bucktown ends, but if skyrocketing property values are any indication, the entire neighborhood is a hot commodity. Despite recent hipster migrations to Logan Square, Humboldt Park, and Pilsen, Wicker Park and Bucktown are still Chicago’s go-to areas for a bespectacled spectacle of beards, bikes, and baristas.
The intersection of North, Damen, and Milwaukee Avenues (a.k.a. Six Corners) is a good jumping off point for covering the neighborhood, especially since the Blue Line shudders to a stop right there. Descend the train platform stairs and you’ll be thrown into a cross-street Donut War between Stan’s and Glazed & Infused where everyone winds up a winner. To the south, you’ve got Wicker Park itself, a cozy little four acre expanse of grass, kids, and the occasional homeless dude. Stroll around its borders on your way to Dove’s Luncheonette, a modern Mexican diner with a tequila- and mezcal-focused drink menu. Across the street, you’ll find more cocktails hidden behind a sprawling mural that conceals the entrance to the speakeasy, The Violet Hour. Discover vintage gold of all kinds at Reckless Records, Myopic Books, Odd Obsession video and countless estate shops on Milwaukee Ave, before heading up Damen to hit the dancefloor at Danny’s, a true neighborhood staple, complete with themed nights and stiff drinks.
Changing. Rapidly. This neighborhood may be the fastest changing area of Chicago, so keep up with its growing roster of things to do for a culturally rich good time. Side bar: High Fidelity was filmed here. Team Cusack forever.
The 606 is Chicago’s answer to New York City’s High Line—the 2.7-mile trail set out along an old railway line allows for bikers, runners, and pedestrians to scoff at the peasants below.
On weekends, there’s a line for everything, so bundle up even if you plan to get sweaty at a Double Door soul music dance party.
In the past few years, Logan Square has transformed into ground zero for the midwestern bohemian aesthetic. You’ll find shops, bars, restaurants, and cafés, all frequented by some of the trendiest folks around.
Lula Café arguably put Logan Square on the map, and the nearby Longman & Eagle offers surprisingly affordable Michelin-starred meals. It would be remiss of foodies to not visit at least one of these classics. If it’s not freezing, catch a cab to Parson’s Chicken & Fish--the patio scene there is Instagram-worthy. At night, grab an expertly prepared drink at The Whistler, and hit the dance floor at Slippery Slope.
Trendy locals, frequent openings, and many of the best cocktail bars in Chicago.
Stop by the Illinois Centennial Monument to snap a photo of the iconic eagle-topped pillar. On summer weekends, events are often thrown in the surrounding park.
Many of the local highlights can be easily accessed by the California and Logan Square Blue Line stops, but the neighborhood is bigger than Sean Penn’s ego and may require cab rides—especially at night.
Lincoln Park is one of city’s ritziest neighborhoods, as evidenced by the many upscale boutiques, restaurants, and homes that line its streets. The neighborhood sits just north of downtown along the sprawling lakefront public park that shares its name. The park itself is home to running and biking trails, the Lincoln Park Zoo, and the largest farmers’ market in the city.
Lincoln Park is packed with attractions like the Chicago Historical Museum and the Lincoln Park Conservatory, so there’s plenty to see and do. Sweat off last night’s party stink with an intense Shred415 class; after all, hanging in this ‘hood means you’ve got to look the part. Post-workout (and hopefully post-shower), it’s time to eat. When it comes to food, you’ve got your pick of the litter, from the Michelin-rated Alinea (reservations required and tough to get) to the more reasonable offerings of Summer House Santa Monica. For live music, head to indie-favorite Lincoln Hall or blues-focused Kingston Mines; for live theater, book it to Biograph or improv ground-zero, iO.
Really, really nice houses interspersed with college students from DePaul University, which rests in its center.
The Lincoln Park Zoo. Why? It’s free and there are animals. No brainer.
It’s easy to spend a pretty penny in this ‘hood on food and drinks, but there are cheap eats if you know where to look. For a quick bite that won’t break the bank, visit burger joint, Butcher & The Burger.
Chicago’s culinary capital, the West Loop prides itself in all things trendy and delicious. If you’re looking for speakeasy sake bars, industrial beams, or all-night-long dinners to brag about for the rest of the year, this food lovers collective is where you want to be.
To be crystal clear… Au Cheval. It’s the best burger in the country and, trust us, Chicago is still parading that flag around. But don’t stop at double-decker cheeseburgers slathered with thick-cut bacon, dijonnaise, and a runny egg—West Loop is for the brave of heart. Pontificate over master-crafted cappuccinos at La Colombe, or lift your spirits at The Aviary, where the cocktails double as science experiments. Dinner in this gastronomic wonderland is anyone’s game, but you’ll get to pick between Top Chef winner Stephanie Izard’s Girl and the Goat, the inventive menu of Blackbird, or a dozen other restaurants that would be any other city’s culinary crown jewel.
Transforming Chicago’s food scene from a one-trick hotdog to haute cuisine.
Randolph Street Market, Chicago’s antique market and craft fair, runs year-round. If you’re the just-got-out-of-bed-and-still-look-put-together type, you were made for this– vintage clothing and mid-century furniture abound, but vendors sell out in a matter of hours.
West Loop has finally hit the too-trendy-to-find-parking marker. Avoid driving and get there via public transit on the Green Line or hitch a ride.
As the name implies, Wrigleyville revolves around one of Chicago’s most beloved (and most derided) sports franchises, the Cubs. Wrigley Field itself is a powerhouse of sports history surrounded by countless bro-y bars, which can be very fun if you’re in the right mood (read: drunk).
Follow the locals’ lead and start the day classy at Julius Meinl, a low-key coffee shop and eatery known for its authentic Austrian coffee and breakfast. If you’re entertaining friends, head over to Clark Street and take your pick of the endless sea of patio-centric sports bars. Hungry? If you’re looking for a more intimate bite, head over to Southport Avenue, which is usually less busy, even when hometown crowds are on the loose. Plus, it’s home to Chicago’s best old-school movie theater, The Music Box. End the night at a rock show at the Metro, or some beer and boardgames at Guthrie’s Tavern, two popular reminders that Wrigleyville isn’t just about sports bars and baseball.
Cubs logos and public urination as far as the eye can see
A quiet afternoon at Graceland Cemetery. Take the self-guided tour, pay respect to prominent Chicagoans, and marvel at how quiet (and sober) it is.
When the Cubs are playing at home, don’t even think about trying to park your car in the area unless you’ve got a crush on the tow truck guy.