Why not visit Chicago in winter? One of the largest cities in the U.S., the Windy City is known for its gorgeous architecture, world-class museums, comedy clubs, and live music venues.
It’s also home to some amazing restaurants. Chicagoans take food seriously, with neighborhood eateries that specialize in pizza, Greek, Chinese, German, Polish, and Southern cuisines.
Though it’s nearly impossible to narrow down your Chicago choices, if you’re spending a weekend in Chicago there’s a good chance you’re staying in the Loop — the part of Chicagoland that’s surrounded by a literal loop of train service.
And, while venturing will afford you some great food, there’s plenty to absorb just steps from your hotel. Here are the can’t miss places in the Loop.
There is simply no better breakfast than a burger topped with a fried egg from Au Cheval (800 W Randolph St.). Much cooler than the “diner” moniker it allows itself, Au Cheval is a cramped, simply lit spot in Chicago’s West Loop where Chicagoans and visitors alike put their name on the list to wait upward of an hour for a cheeseburger ($14.95) and fries loaded with Mornay sauce and a fried egg ($9.95). There are other things on the menu. But this burger lives up to all the hype, so order it. Pro tip: put your name on the reservation list and head over to the Lone Wolf Tavern next door to wait with a draft beer or a single barrel Old-Fashioned.
Gibson’s Bar & Steakhouse
If you’re seeking an Old Chicago vibe, Gibson’s (1028 N. Rush St.) is the place for you. Though there are older eating and drinking establishments, Gibson’s has the feel of a place where people with wads of cash go to eat steak with their backs firmly to the wall. From the leather bar stools to the guy playing Sinatra on the piano at a random Tuesday afternoon, everything about Gibson’s just feels like Old Chicago. Here’s the order: a classic wedge ($12.50), followed by a Prime bone-in strip ($59), and a carrot cake the size of the Sears Tower for dessert ($18.75).
Chicagoans also have a real love affair with doughnuts. There are many fine doughnut shops around Chicagoland, with Stan’s being the popular local chain. Hands down, however, Firecakes has the most delicious doughnuts in the city. There are five locations including River North in the Loop (68 W. Hubbard St). Made from a secret family recipe dating back to the 1930s, they don’t need an insane amount of bells and whistles. The daily selection includes apple fritters, jelly doughnuts, and birthday cake doughnuts — but the buttermilk old-fashioned remains a classic all by itself.
Three Dots and a Dash
It’s Chicago in the winter and the wind off Lake Michigan makes it feel like -20 degrees. What better time to tiki? Yes, it’s counterintuitive, but Chicago is home to some world-class tiki bars, including the award-winning Three Dots and a Dash (435 N. Clark St.). This speakeasy-style tiki bar is located in a back alley; you’ll then walk down a flight of stairs decorated in skulls to find this Polynesian wonderland that offers classic tiki and flaming rum drinks like Painkillers, Mai Tais, and Zombies ($15 - $18). The place is always filled with Chicagoans wistful for a trip to sunnier climes — if even for a few hours.
Billy Goat Tavern
One of the most iconic skits on Saturday Night Live was the Greek hamburger place where Dan Akroyd would cook “cheezeborger” and serve “no Coke, Pepsi.” That fictional diner was modeled after the original Billy Goat Tavern (430 N. Michigan Ave.) Though there are a number of locations now, the original is the only place to go. Located under Michigan Avenue (you literally have to walk down a frightening, dimly-lit flight of concrete stairs to get to the tavern), Billy Goat has been around since 1934, when a Greek immigrant named Billy Sianis opened the place. Not much has changed in nearly nine decades — including the prices. A flat-griddled “cheezeborger” costs $4.69, grilled cheese is four bucks, and a ham sandwich costs $4.49. Over at the vintage linoleum-topped bar, a pint of the tavern’s own ale costs under $5. The tavern also serves as part tribute, part time capsule of Chicago history as written by the reporters who worked at the Chicago Tribune just across the street.
Lure Fishbar Chicago
This New York-based seafood restaurant opened a Chicago branch (616 N. Rush Street) in River North, next to the 21c Museum Hotel. With the charm of a mid-century yacht club, Lure (the restaurant is owned by Broken Palate’s John McDonald) offers a fantastic array of sushi, seafood, and steakhouse items. Oysters are a must to start any meal, and Lure offers both East Coast and West Coast. Warm up from those cold winds blowing off Lake Michigan with a fragrant lobster bisque before tucking into a soul-satisfying plate of sea urchin bucatini. Don’t miss Lure’s “Bash” burger, named after its several wins at the South Beach Food & Wine Festival’s Burger Bash competition.
Cindy’s Rooftop at the Chicago Athletic Association
If you want to sip a cocktail while looking down on one of Chicago’s most beloved pieces of art — the Bean — head to Cindy’s (12 S. Michigan Ave.). Located inside the architectural wonder that is the Chicago Athletic Club, Cindy’s offers standard American fare — but you’re here for the cocktails and the view. Grab an Old Fashioned or an Apple of her Eye (made with vodka and spiced apple syrup) ($16 each) and take it to the heated outdoor patio overlooking Chicago’s Millennium Park and the city’s skyline. The best viewing time is twilight when the sun sets and the buildings light up one by one.
The Purple Pig
Michigan Avenue is Chicago’s main shopping street and, as such, you might rightly think any restaurant located on “Magnificant Mile” would be a tourist trap. The Purple Pig is a fine exception to this rule. Located inside an office building (444 N. Michigan Ave.), the Purple Pig’s Jimmy Bannos, Jr. won a 2014 James Beard “Rising Star Chef” award for his shared plate restaurant that serves what can best be described as Mediterranean-Americana.
As the name suggests, you’ll find plenty of charcuterie, crispy pig’s ears ($19), and pork ribs ($24). There’s also a fine selection of cheese from Illinois’ neighbor, Wisconsin, and an entire vegetable section that includes a roasted cauliflower dish made spectacular with the addition of tiny slices of cornichons ($15). The “Pig” also has a fantastic selection of wines by the glass, and a knowledgeable staff that will help you choose the perfect accompaniment to each dish.