You’re in Chicago for the first time ever. You’ve got 72 hours and an appetite for everything. Where do you start?
That’s a question we get asked a lot, and it’s a hard one to answer. There’s no doubt you’ll spend time wandering up and down the Magnificent Mile and checking out shops in the Gold Coast. But don’t confine yourself to eating all of your meals in these areas – that’s basically what we call self-inflicted dining entrapment. Many Chicagoans avoid Michigan Avenue like the plague, so make a point to eat in some of the surrounding neighborhoods to see what life as a local is all about. Also prepare for it to be unbearably cold or unbearably hot. That’s definitely what life as a local is all about.
This isn’t meant to be a definitive list of the city’s best restaurants – but seeing as these are spots we like to frequent, we think it’s a good start.
Pop in early to Rick Bayless’ casual sandwich joint for some excellent Mexican coffee and breakfast bites. The Wicker Park location has a full weekend brunch menu too.
Only go if you want to eat the best breakfast and brunch around. Southport Grocery also happens to be in a cool part of west Lakeview, close to Wrigley Field.
Hot dogs are on the grill. Who wants spicy mustard? There are endless places to get good dogs, but Portillo’s is centrally located and you can get an Italian beef too. Don’t miss out on the Chocolate Cake Shake. You’re on vacation.
What should you do either before or after checking out The Bean? Head to nearby Cafecito for some Cuban sandwiches, that’s what.
PQM is a butcher shop, cafe, bakery, and mini market. But its best role is as a little cafe for breakfast and lunch. From quality coffee to freshly baked breads, sandwiches, charcuterie, and more, PQM is the kind of place where seemingly simple dishes taste more complex than they sound.
You went to the zoo, you're wandering around Lincoln Park and Lakeview, you're hungry, and you need a quick bite. Act like you've been here before and head directly to Crisp on North Broadway. Order the Seoul Sassy chicken wings, which look like they came from real chickens and are marinated in a sweet sauce. You're going to want a lot of them.
Seafood tacos, po’ boys, and fries with foie gras. This cash only, funky and unassuming place won’t disappoint.
If you’re a first timer in Chicago, you’re probably on vacation, and if you’re on vacation then of course you need pie at lunch. Bang Bang serves excellent biscuit sandwiches to sooth your savory hunger, and then they’ll put you over the edge with some tasty pies. Enjoy it all on their patio out back which feels like a friend’s backyard more than a restaurant.
Green Street has really grown on us over the years, and they've hit their stride in the BBQ department. It's a Texas style spot, and we can't get enough of the brisket or sides. But Green Street is ideal for a first trip because it's casual, fun, and the kind of place you can hang over drinks. Hopefully you're drinking if this is a vacation.
Chicago may be known for its hot dogs, but this burger will win you over. It’s Chicago’s best burger, and we’re not alone in thinking it’s also one of the best in the entire country. Au Cheval doesn’t take reservations, so plan to kill some time checking out the rest of the West Loop while you wait, or just go next door to Lone Wolf for a drink.
Parachute is one of the best restaurants in Chicago. The Korean American food is innovative and excellent, and we’ve walked out of every meal here thinking it was more enjoyable than most of the meals we’ve had at other restaurants recently, and we eat at a lot of restaurants. Make a reservation beforehand and commit to a unique dinner in Avondale, a quiet neighborhood just outside of the center of town.
Monteverde is an Italian restaurant that's the best combination of nice but not fancy, reasonably priced, and most importantly, delicious. It's a cool spot you can go to with friends, family, or a date, and you're going to be blown away by the pastas. Also consider trying the ragu alla napoletana - a giant plate full of fusili pasta, sausage, meatballs, and a large braised pork shank in case the rest of it's not enough. It's a real Midwest kind of a dish.
Head back towards O’Hare, just don’t leave. Stop at Longman & Eagle in Logan Square, Chicago’s signature “hipster” neighborhood, for some upscale American cuisine and a killer whisky list.
Want to know how we like to spend any casual weekday or a Sunday nights? Hit up Athenian for a cheap and easy Kalamata Chicken dinner.
Get your meat indulgence on at this West Loop homage to German style beer halls. Make friends at a communal table or take a trip to the penalty box seating with a group of four.
Trying to make a reservation in advance is damn near impossible, but lucky for you, calling the day of is your best shot. If you can snag a coveted seat to experience this one of a kind BYOB tasting menu, consider it a great success.
Warning: This is not a regular night out. If you’re going to Alinea then you’ve obviously planned it in advance. But it’s worth planning, and it’s worth spending the money at least once in your life. The culinary spectacle performed by the team at Alinea is so unique, so mesmerizing, and so delicious that it will leave you with a childlike wonder you haven’t felt in a while.
Weiner Circle has pretty good hot dogs and cheese fries when you’re sober, it’s just way more fun late at night when you’re not. Order a chocolate shake if it’s past midnight on a raucous weekend. It’ll cost you $20 and you won’t get a shake, but do it anyway.
Yes, it’s just a McDonalds. But it’s the most ridiculous two story McDonalds you’ll ever see once the post-bar crowd rolls through. If that's you after a long night on Hubbard Street, this is the move. Talk about a sh*t show.
Imagine it’s cold, windy, snowing, and looks more like the apocalypse outside than just another Tuesday. Deep. Dish. Pizza. Escape to a dark place and drown your warm weather fantasies in some Chicago comfort food. Everybody has a favorite, but the caramelized crust at Pequod's is tough to beat. Get pepperoni.
Not quite deep dish pizza, but where else can you get pizza pot pies? It’s also in the basement of an old Lincoln Park walk up home rumored to be a former hot bed of Al Capone and his crew.
You can't come to Chicago without considering a steakhouse, and Gibsons is the iconic member of the bunch. It's good, it's fun, and it's in a happening part of town. Ultimately, Gibsons is a classic and that's why you should check it out. Don't skip dessert.