Clubs in Crestwood

Marcus Combs – Up to 45% Off Standup

Marcus Combs

The Apartment

$37.92 $21

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Veteran Chicago comic seen on HBO's Def Comedy Jam and Puff Daddy's Bad Boys of Comedy fills the stage with laughs

Take in 33rd-Floor City Views During an Intimate Jazz Soiree

Intimate Jazz Mixer

Chicago

$70 $70

Jazz vocalist Erin McDougald and her ensemble serenade guests as they mingle, sip cocktails, and watch the sun set over the Chicago skyline

Up to 53% Off Standup Comedy

The Comedy Bar

Near North Side

$30 $15

Upscale club partnered by Jim Belushi features local and nationally renowned comics

Stand-Up Throw Down – Up to 37% Off

Stand-Up Throw Down

Township

$14.25 $9

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Weekly showcase produced by Chicago comics features established and up-and-coming standups

Jazz at The Met – Up to 26% Off Fundraiser

Jazz at The Met

Metropolitan Family Services - Calumet Center

$50 $37

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Annual fundraiser for social programming features live jazz and blues along with dinner and a silent auction

Kingston Mines – Up to 42% Off Blues

Kingston Mines

Lincoln Park

$24 $14

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Legendary blues club stages performances by equally legendary blues musicians seven nights a week

UP Comedy Club – Up to 45% Off Standup

UP Comedy Club Presents: Kurt Braunohler, Donnell Rawlings, and The Sklar Brothers

Near North Side

$27.50 $15

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Chappelle's Show favorite Donnell Rawlings; frequent @midnight guests Kurt Braunohler and The Sklar Brothers

Up to 48% Off Comedic Burlesque Show

"Off Off Broadzway: Weight Loss Wishes and Dry Hump Dreams"

Stage 773

$28.75 $15

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Bawdy comedic burlesque troupe showcases new revue with audience interaction and plenty of double entendres

Select Local Merchants

Dance music pulsates through Red Velvet Lounge as party-goers indulge in late-night eats and specialty bar drinks amid a spacious nightclub. Bartenders pours out beverages from a fully stocked bar as guest saunter to the hardwood dance floor illuminated by the sporadic flickers of a colorful lights. Themed parties for Halloween and New Year’s Eve add variety to weekends, and Friday and Saturday nights introduce crowds to special-guest DJs and their finger-puppet entourages. Bites from the Lounge’s Italian-inspired menu fuel evening adventurers, with options including gorgonzola chips, Sicilian tilapia, and lemon-mascarpone torte.

11011 Southwest Hwy
Palos Hills,
IL
US

Intimo's menu whisks diners to the Italian countryside with a variety of authentic house-made entrees. More than 300 bottles of distinct wines hibernate in the 58-degree walk-in wine cellar. Director Frank Pecora fosters a relaxed, sophisticated atmosphere with dim lighting and sleek, dark wooden accents. Candles flicker atop tables draped in white linens, casting shadow-puppet adaptations of Godzilla vs. Fork and Knife on the exposed-brick walls.

7068 183rd St
Tinley Park,
IL
US

Casa De Montecristo stocks its ample humidors and regal environs with row after row of tasty smoking tobacco. A La Sirena Trident summons piquancy from the depths of the broadleaf ($9.95), while an E.P. Carrillo Elite hits only the most select flavor notes ($11.95). Casa De Montecristo also boasts a free VIP membership lounge, which can be accessed by calling ahead. The spacious smoking cavern teems with plush amenities such as leather chairs and private humidified lockers. Kick back in the bar and tune in to a flat-screen television, or recline in the theater room for a movie, game, or cigar-smoking tutorial led by Groucho Marx.

1332 W 55th St
Countryside,
IL
US

At Orange 13, swaths of burnt-orange organza and crystal chandeliers transform tables into secluded enclaves. At two granite-topped bars, bartenders pour 50 handpicked wines and mix martinis with top-shelf liquors. The chefs strive to match the sleek, sultry environs with a menu of creative fusion fare: they adorn a trio of buffalo, elk, and Kobe burgers with brie and bleu cheese and add zest to tender lamb chops with lemon-thyme glaze. To encourage an experience as fun as the cuisine is exquisite, live entertainment and DJs spin beats until 3 a.m., and high ceilings make it plausible that dancing giraffes appear, too. Live bands hit the stage at 8 p.m. on Fridays and DJs begin to spin sets at 11 p.m. on Saturdays.

14196 McCarthy Rd
Lemont,
IL
US

Olive or Twist pairs its 36 unique martinis, 20 bottled microbrews, and international wines with contemporary American fare concocted by chef Robert Nava. Shaken or stirred libations range from the Thin Mint martini, which comes in a Girl Scout box, to the Florida Key Lime Pie martini, a dram of Bacardi rum, Midori liqueur, and chocolate liqueur garnished with lime ($9–$11). Diners can also choose from brews including 3 Floyd's Alpha King pale ale ($5) to accompany small plates such as the potato-wrapped prawns with spinach, artichokes, and mustard-seed butter ($10). Tenderloin sliders topped with blue cheese and red-onion confit ($9) annex tummies before calling for reinforcements of classic American sandwiches ($6–$12) or large-plate entrees such as the jerk ribs with an auxiliary unit of saffron shoestring potatoes ($18). For dessert, sweet teeth delight in the banana split ($8) and apple-and-cheese strudel ($5), named after Frank Zappa's overlooked fifth child. Dinner patrons should call ahead for reservations amid Olive or Twist's low-lit tables and brick walls.

6906 W Windsor Ave
Berwyn,
IL
US

The rooftop garden and solar panels may be what cemented Simone’s status as a green certified restaurant, but the recycled pinball machines-turned light fixtures, bar top made of an old bowling alley, and bike-chain-chandeliers certainty didn’t hurt. Microbrews and craft cocktails complement the quality pub food at this eclectic spot.

960 West 18th Street
Chicago,
IL
US

Crestwood Scene