For a place so focused on land animals, The Frontier's oyster program punches above its weight class. There's always a long list of enticing offerings. The shuckers do a fairly good job cracking and cleaning the shells. And, in a terribly gracious move, the restaurant discounts its bivalves not one but two nights a week ($2 oysters on Tuesdays; 10 for $12 on Thursdays).
Sometimes you just want oysters without the fuss. Fish Bar doesn't serve its oysters on silver trays, and I don't believe there is champagne on the menu, but it still cares about the bivalves. Each time we stop by, we're impressed by the fresh and varied selection. Plus, there's always someone capable of shucking them without leaving shell shrapnel all over the place.
GT Fish & Oyster
Take away the tasty housemade bottled hot sauces and the bright mignonette, and GT would still be one of our favorite spots for freshly shucked oysters in the city. That's because you can scarcely find fresher, more expertly shucked oysters anywhere else in town (outstanding brine preservation!). The ice-laden raw bar and oyster shucker are stationed front and center for everyone to see (which doesn't necessarily ensure freshness, but it certainly doesn't hurt). GT constantly updates its offerings with different, well-curated varieties (on a recent visit: Beau Soleils from New Brunswick and Imperial Eagles from B.C., to name just a couple). Slurp after 10 p.m. and your oyster bill is half price.
Maude's Liquor Bar
Maude's earns our vote for most handsome oyster presentation, and ranks high in terms of quality, freshness, and variety (a couple of delicious recent offerings: West Coasters Pacific Gold and Kusshi—the latter a personal favorite—and Salutes, from back east). Plus, there's something about knocking back oysters in the warmly lit and chicly Gallic surroundings of Maude's that makes the little guys taste that much better.
Here's where we acknowledge that Chicago hasn't always been a city flooded with fresh oysters. And why should it be? We're hundreds of miles from either North American coast. A few years back, reliable spots to snag a few slurpers seemed few and far between. But, from our perspective at least, that seemed to change when the Publican came along. We'd argue that it paved the way for some of the other places on this list to source high-quality oysters, shuck them deftly, and serve them freshly—by first demonstrating that an ambitious oyster program in the Midwest was indeed feasible. Take this recent selection as evidence: Coromandels from New Zealand, Kumamotos from California, and Malpeques from Prince Edward Island. Oh, and the salty, housemade oyster crackers and fantastic.
Shaw's Crab House
Shaw's Crab House is really two restaurants in one: a subdued and plush dining room where you want to order fresh fish fillets and sip ice-cold martinis, and a raucous, free-wheeling oyster bar, where beer is the beverage of choice. There is a time and place for both, and luckily you can get oysters no matter which side you choose. Thanks to the fact that this place goes through a lot of oysters, you're also basically guaranteed a fresh selection. They arrive with the standard cocktail sauce along with a particularly good frozen champagne mignonette.
Last year, it seemed like every single restaurant had to have fresh oysters on the menu, even if the place didn't give much thought or care to how they were served. But not The Savoy. The oysters here come expertly shucked on a bed of ice with a smoked tomato cocktail sauce and a wasabi mignonette. They go especially well with the Penitence Rye Stout, which is made specially for the restaurant by Greenbush Brewing Company.
Union Sushi + BBQ Bar
Union may well be the best deal in town for freshly shucked oysters. Every weekday from 5 p.m. to 6:30 p.m., oysters are just a buck apiece. And at Union they dress up the oysters for you; on a recent visit, Alpine oysters hailing from the East Coast were topped with tobiko, micro-curls of jalapeno, and a slightly spicy Asian sauce, providing a piquant counterpoint to the briny oysters. It's safe to say we could down a lot> of these.