Table Stakes: The Best of Chicago Food and Drink

Because every Chicagoan loves to eat, even if he must travel out of his neighborhood, we bring you Table Stakes: a series that answers man’s eternally recurring question (“Uh, what’s new?”), and recurs once every lunar cycle or so. 

For this month’s special edition, we’ve partnered with the hungry people at the Infatuation to find the best seats in the city — an ode to the best bar dining in Chicago. 

And to help you get out there before summer ends, we’re giving a $100 tab to five lucky winners to spend at any of the restuarants featured below. 

For more eats, we recommend checking out the Infatuation’s 2015 Summer Guide, filled to the brim with choice grub to take you all the way through summer’s end.

Bon appétit.

Bar Siena
The West Loop

The latest from superstar toque Fabio Vivani, think of Bar Siena as the younger, more energetic brother of Siena Tavern. Two floors. A large wraparound bar with a lot of action and a good-looking crowd. You know the drill. Italian. Really delicious Italian (menus right here). Wood-fired pizzas. Our choice: the Spicy Coppa, a red pie with smoked mozz, pecorino and oregano. Don’t expect anything less from the pastas, either. Wine list runs deep, natch. 

The Infatuation Recommends: Prosciutto Fig pizza with taleggio and honey. Salty and sweet is always a good idea.

832 W. Randolph St.
barsiena.com

Cherry Circle Room
The Mag Mile

Look, the Mag Mile is not for everyone. But there’s at least one spot on the avenue that is: the Gothic art deco Xanadu that is the Chicago Athletic Association Hotel. Past the Game Room you’ll find the Cherry Circle Room, a sexy corner space that’s perhaps more storied than any other dining room in the city.

It’s the same members-only restaurant that existed in the building since 1893. The bar: all original. Belly up and throw in an order for the pâté board — and then maybe split the roasted leg of lamb for two. Mind the historic cocktail menu: they’re all delicious.

The Infatuation Recommends: The OG bone-in ribeye. You’re not here to cut corners. 

12 S. Michigan Ave.
chicagoathletichotel.com

Charlatan
West Town

A charming corner bar nestled in West Town. The menu is next-level Italian grub (yeah, that’s a pig head up there, and you want that), with an unquestionably cozy bar to hit up. Dimly lit and always a local crowd. Here at the Charlatan, pastas come out simple, fresh and housemade. The black kale spaghetti should not be missed.

The Infatuation Reccommends: Pastas — they are all delicious. Take advantage of the half-orders and make sure to sample a few.  

1329 W. Chicago Ave.
charlatanchicago.com

Tack Room
Pilsen

There’s a lot to love about the Tack Room. For one, you need to get out this way more often. Second: live pianists from Thursday through the weekend. The Thalia Hall crew nailed it with this concept: small bites and solid cocktails. A perfect vibe for such an intimate space, which spills out on to the outdoor patio. Whether you saddle up out there or at the bar, the keys will ring heavy. Most certainly worth a trip to Pilsen. Bring a date.

The Infatuation Recommends: A burger and anything with bourbon to drink. 

1227 W. 18th St.
duseks.com/tackroom

La Sirena Clandestina
West Loop

Three years after opening, chef John Manion continues to make his mark on the city’s dining scene. A tough racket, given the explosion of stellar eats in the West Loop in recent years. But La Sirena is still one of our favorites in the area. What he’s doing with Latin flavors … you won’t find anywhere else. Dishes like the smoked ribs with piri piri jelly and coconut purée. Or the octopus and pork belly with watermelon and patty pan squash. Both offerings you’ll only find on the summer menu. Get there before its gone.

The Infatuation Recommends: Empanadas and a whole fried fish. Sounds simple, but the flavors say otherwise. 

954 W. Fulton Market
lasirenachicago.com