Bars in Crestwood

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For more than 20 years, comedians of all levels of notoriety have peddled their laugh-inducing verbal wares on Riddles Comedy Clubs’ stages. An airbrushed city skyline sits behind the corner stage, where such comedians as Jeff Dunham, Louie Anderson, and Drew Carey slung jokes to side-split audiences. A full bar with overhanging LCD TVs dispenses alcoholic and nonalcoholic whistle-wetters in between sets. Additionally, Riddles' lots house free parking for those driving from far-off locales or patrons who can't find a limo service that takes knock-knock jokes as payment.

5055 West 111th Street
Alsip,
IL
US

There's something different about Trio Bar. The dimly lit atmosphere might seem familiar, the crowds of friends may feel like family, the vodka-lemonade mix might taste like a distant summer afternoon—but there's a scent in the air that isn't common in bars. That's because Trio's kitchen sends out a steady stream of classic Chicago-style sandwiches stacked with roast beef and spicy giardiniera, Angus beef burgers on fragrant pretzel rolls, and homestyle Italian favorites. Housemade meatballs crown platefuls of spaghetti, and crispy thin-crust pizzas emerge with any combination of 23 toppings, including shrimp, basil, and zucchini. It's this mix of garlic, barbecue sauce, grilled rib-eye steaks, and freshly baked dough that fills the air and transforms something familiar into something entirely different.

Trio Bar's tables let guests enjoy this bounty peacefully while leaving plenty of room for crowds to stand, mingle, and cheer on Thursday-evening karaoke performers. Live DJ sets get the weekends rolling, and flat-screen televisions fill the rest of the nights with sports broadcasts and slow-motion replays of Garry Kasparov's most famous chess moves.

11845 Southwest Hwy
Palos Heights,
IL
US

Don’t let the shepherd's pie, fish 'n' chips, and draft beers fool you. Though Tilted Kilt snatches up the best cultural fragments of Scotland, England, and the Emerald Isle, the eatery started in Las Vegas. Restaurateur Mark DiMartino sought to combine the communal, rousing feel of pubs in the British Isles with the campy fun of American sports bars, pairing hearty food and traditional trappings with televisions and waitresses clad in mini kilts and alluring plaid halter-tops modeled after William Wallace’s eveningwear. Since its founding, Tilted Kilt locations have popped up in 25 states and two Canadian provinces, serving all manner of hybrid dishes such as the Scottish cheese steak, the Sloppy Jane made with sliced turkey or shaved rib eye, and the Tilted Guilt, an ice-cream sundae perched atop a cookie.

6401 95th St
Chicago Ridge,
IL
US

Sharing is encouraged at SIP Appetizer Bar. Mediterranean-inspired small plates arrive ready to be sampled and savored, packing big flavors such as cheese-stuffed lamb meatballs and beef with bourbon sauce into adorably miniature dishes. Equal variety is found in the drink menu, which boasts signature martinis alongside wine and beer. Even events at SIP are designed to encourage mingling?Wednesday Girls Nights, for example, feature tarot card readings, while Thursday evenings host open mics.

4911 W 95th St
Oak Lawn,
IL
US

True to its meat-loving Chicagoland roots, TCs Pub grills up deep-fried, bacon-wrapped hot dogs and stuffed burgers that are so big you can barely hold them together, let alone bite them. The sports pub is fresh off a recent remodeling, but the chefs still sling handcut french fries, ribeye sandwiches, and gooey pizza puffs that have kept locals and visitors coming back. Fresh salads and fried zucchini offer a vegetarian-friendly alternative. Diners can wash down their meal with one of the 28 beers that are on tap, or sip from an extensive selection of ciders, with flavors that include black cherry, peach, and pear. Game night and beer pong are some of the weekly events. On the weekends, people pack the dance floor to shimmy to live DJ and band music, or the syncopated clinking of spoons and forks.

9700 South Cicero Avenue
Oak Lawn,
IL
US

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