West Loop

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.

Ideal Itinerary

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.

KEEP IN MIND

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.

Lincoln Park

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.

Ideal Itinerary

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.

KEEP IN MIND

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.

Logan Square

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.

Ideal Itinerary

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.

KEEP IN MIND

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.

Bucktown/Wicker Park

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.

Ideal Itinerary

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.

KEEP IN MIND

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.

Photo courtesy of Dove's Luncheonette.

River North

River North is where all the nine-to-fivers (or more accurately, seven thirty-to-eighters) come to eat, play, and party. You’ll still find most of Chicago’s classic must-eats (RIP Ed Debevic’s) side by side with bottle service dance clubs, high concept eateries, and secret speakeasies.

Ideal Itinerary

First off, skip breakfast. You’ll want to save room for the world-famous Italian Beef Sandwiches at Portillo’s, arguably the most Chicagoan of all Chicago restaurants. Next, head south for some skyline-ogling on the Chicago River Walk. Dinner is a culinary grab bag, but you can always trust hometown hero Rick Bayless to whip up some Mexican magic at Topolobampo or The Frontera Grill. If you’re in the mood for a cocktail, good things come to those who sneak. Hop in that line snaking out of an alley for a one-way ticket to a tropical paradise at Three Dots and a Dash tiki bar, or discover the hidden door in the basement of the Green Door Tavern, where you’ll be rewarded with the hourly cabaret acts of The Drifter.

KEEP IN MIND

In River North, you’ll get a lot of bang for a lot of bucks. Prepare for your wallet to lose some weight by the end of the night.

Pilsen

A neighborhood once inhabited by Czechs and other European immigrants, Pilsen today is a thriving Latino community that remains one of the buzziest destinations on the South Side.

Ideal Itinerary

Start off by checking out some art galleries on Halsted Street, which is also the place to be every second Friday of the month during the Pilsen Arts Walk. Next, grab some tacos at Don Pedro Carnitas, which probably uses sorcery to make its carnitas so delicious. Grab some boozy punch inside a cool basement at Punch House, or opt for coffee at Cafe Jumping Bean--it’s a keystone of the neighborhood.

KEEP IN MIND

While there is a Pink Line train that reaches the western edge of the neighborhood, you may be better off arriving in a Halsted Street bus or a cab.