The J. Parker
What's better than sampling chef Paul Virant's pickled and preserved food at Perennial Virant, complete with a gorgeous view of Lincoln Park? How about getting to do so 13 floors up on the top floor of the Hotel Lincoln, where you now have a birds' eye view of the park, Lake Michigan, the John Hancock? Okay, so the stripped down bar menu isn't quite as generous as the main downstairs restaurant, but its still better than it has any right to be.
Tony Mantuano has popped up on this list quite a bit, don't you think? But how could I possibly turn down the sight of Millennium Park, and in particular the weaving metal strands of Frank Gehry's Jay Pritzker Pavilion bandshell, from Terzo Piano? Perched atop the Modern Wing of the Art Institute, this light-filled restaurant serves up modern Italian fare that won't weigh you down, but I'm not against grabbing a cocktail or two and just taking the view in.
Chicago Cut Steakhouse
When I think of steakhouses, I immediately picture some windowless hideout, where tuxedoed waiters shuffle around a room almost completely paneled in dark wood. For the most part, Chicago Cut Steakhouse has it all, except for the windowless part. Instead, two glass walls bathe the restaurant in light, which both allows you to better appreciate the massive dry-aged steaks and leaves you with a stunning view of the skyscrapers lined up along the Chicago River.
The Signature Lounge at the 96th
It's hard to think of a better view of Chicago than from the 96h floor of the John Hancock building, where you can stare the city's tallest towers in the eye. Most tourists wait in line for the observation deck on the 94th floor, and while it's worth the money, you have other options. One floor up is the Signature Room, which serves solid food that you'll have to pay dearly for. But make your way up one more floor to the Signature Lounge, where you can take in that epic view with a cocktail in hand.
I'll let our brunch expert, Matt Kirouac, discuss the beauty of dining at Caffè Oliva:
I haven't taken a vacation in years, but I manage to relax myself by setting my Gmail theme to "beach" and having brunch at Caffè Oliva. Eating brunch on a beach is my favorite form of staycation therapy, even if the sun does make it too hot to drink coffee, and I wind up sunburned.
I'll admit that it's hard to look away from what's on the plate at Tony Mantuano's Spiaggia, which is often mentioned as the best Italian restaurant in town. That's especially true when there's a pasta tasting menu to deal with. But in between courses, or even between bites, make sure to take in the view of Lake Michigan from the edge of the Magnificent Mile.
Of course, if you're not in for a splurge, Cafe Spiaggia offers almost the same view as its big brother. Plus, you can devour pizza while doing so.
Seven on State at Macy's
Unless you're used to executive room dining, you're probably not accustomed to a lunch time view in the Loop. That's especially true on the more affordable end of the spectrum. The great exception is the seventh floor food court at Macy's, where you can watch the crowds rush on State Street under the glow of the iconic Chicago sign. But as we've explored numerous times, this isn't any old food court. Here you can slurp one of our favorite bowls of ramen at Noodles by Takashi, devour a burger at Marc Burger, or try a tamale or two by at Rick Bayless's Frontera Fresco.
The Gage is mostly known as the surprisingly solid restaurant across from Millennium Park, but that kind of feels like damning it with faint praise. As our writers have discovered, there are a number of excellent options here. The only tip I have is to try and get a seat at the bar, so you can dine while gazing out at the park.
In some respects, North Pond is Chicago's Tavern on the Green—a picturesque getaway located just inside a beloved public park. But there the similarities stop. To start, North Pond is still open. And, for at least as long as chef Bruce Sherman has been there, North Pond is one of those rare special occasion restaurants actually worth paying for. That includes all the desserts from pastry chef Greg Mosko, so make sure to save room.
Kim & Carlo's Hot Dog Stand near Shedd Aquarium
When our staff picked out their favorite hot dog last month, Roger went with this surprising pick by the Shedd Aquarium. I didn't realize it at the time, but the combination of a great hot dog and the insane view adds up to one of the most quintessential Chicago activities one could do. I'll let him tell you all about it:
I don't have any facts to back this up, but hot dogs eaten alfresco just taste better. And I can't imagine a more delightful outdoor setting for crushing a Chicago dog (or two) than the majestic stone-and-flora cradle of the Museum Campus. But to ensure you're starting with a delicious dog to begin with, do this: walk straight away from the Shedd Aquarium's main entrance. Down a few steps, you'll run into Kim & Carlos Hot Dog Stand, a small but ambitious, family-run operation where the buns are steamed, the ingredients are impeccably fresh, and where you can't go wrong with your choice of wiener, even if you choose the vegan dog. Order up, take a seat, and enjoy the views.