Clubs in Crestwood

David Spade at The Venue at Horseshoe Casino on Friday, September 26, at 8 p.m. (Up to 35% Off)

David Spade

The Venue at Horseshoe Casino

$46 $29.90


Boyish comedian of Tommy Boy, Grown-Ups, and Saturday Night Live fame entertains audiences with his acidic wit

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

Intimate Jazz Mixer


$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

Navy Pier Four Star Comedy Presents Morning Show Comedians at Pepsi Skyline Stage at Navy Pier (Up to 62% Off)

Navy Pier Four Star Comedy presents Morning Show Comedians

Pepsi Skyline Stage At Navy Pier

$33.30 $12.50


WGN Morning News' Mike Toomey, Ana Belaval, and Pat Tomasulo moonlight as standup comedians, showing off their skills at Navy Pier

Comedy Night with Benji Brown or The African King of Comedy Michael Blackson Live at Castle (Up to 54% Off)

Comedy Night with Benji Brown


$53.74 $25


Star of Wild ‘N Out and The Rickey Smiley Show and Ghana-born comedian get crowds rolling

The Second City's Deep Cuts or Improv All-Stars at UP Comedy Club on September 1–November 10 (Up to 43% Off)

The Second City's Deep Cuts or Improv All-Stars

UP Comedy Club

$24.50 $17


Annoyance Theatre founder Mick Napier directs a cast of top improv talent; revue about living in the Internet age collects past sketches

Yakov Smirnoff at Rialto Square Theatre on Saturday, September 27, at 8 p.m. (Up to 41% Off)

Yakov Smirnoff

Rialto Square Theatre

$47.25 $28


Soviet-born comedy icon who found fame comparing the US with the USSR is still yukking it up with society-deconstructing wordplay

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,

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,

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

It’s a difficult task to pull off—taking a hodgepodge of recycled odds and ends and creating something entirely new. Simone’s Bar, however, has proven up to the challenge. An architectural potpourri of artifacts salvaged from around the city, the Pilsen bar is best known for the retired pinball machines that line its walls. These ancient tables lend a retro vibe to the bar area, where microbrews and cocktails take the place of pins on a recycled bowling lane. Other idiosyncratic elements include chemistry tables from nearby Westinghouse High School, conveyer belts from Chicago’s Fanny May Candies factory, and a chandelier molded from bicycle chains and rocking chairs. Combined with the solar panels on the rooftop, these repurposed knickknacks have earned Simone’s status as a three-star certified green restaurant. Simone’s décor may come from all corners of the city, but its food is influenced more by the bar’s immediate surroundings. Empanadas and a grilled cheese sandwich with Chihuahua cheese nod to Pilsen’s proud Mexican heritage, as do burgers topped with jalapenos and guacamole. The drink menu also has a local slant, highlighting Chicago brews and craft cocktails that would feel right at home in one of the galleries on nearby Halsted Street.

960 West 18th Street

Sawtooth Restaurant

Though he relies primarily on local ingredients when crafting his Vietnamese cuisine, executive chef Kay Bui structures his menu around a principle that may seem foreign to American diners. He serves small plates in the context of a communal meal, as is common practice in Vietnam. Together, guests can explore the exotic tastes of charbroiled pork wrapped in rice paper, sautéed asparagus doused in a spicy brown sauce, or shrimp and crabmeat stir-fried with vermicelli noodles and mixed vegetables. Bartenders complement the kitchen’s output with house-infused spirits and an extensive wine list that highlights organic and biodynamic reds and whites. At Sawtooth Restaurant, meals unfold in one of three places: a spacious dining room notable for its earthy tones and clean lines, a lounge with custom booths and modular box tables, or a garden patio surrounded by exposed brick and patrolled by Indochinese tigers.

1350 W Randolph St

Only a true icon can name their venue Legends and get away with it. Luckily, famed blues artist Buddy Guy fits the bill. Known as ?the crowned king of Chicago?s electric blues scene,? Buddy has more than 50 years in music notched into his guitar strap, as well as six Grammy Awards and a coveted spot in the Rock & Roll Hall of Fame. Inside his beloved blues club, Guy can be seen on stage every January during sold out shows, easing into the playful stomp of Muddy Waters? ?Hoochie Coochie Man? and his soulful, woozy solo in ?Stone Crazy.? The performance space holds fans? intrigue with other performances throughout the year and has hosted such renowned musicians as John Mayer, ZZ Top, David Bowie, and Eric Clapton. Seven nights per week, live blues music drifts through the air while guests dine on southern Cajun soul food, from blackened bourbon shrimp to cat fish po? boys and chicken and sausage jambalaya. Music fans can sneak away from their meals to fawn over blues memorabilia such as original artwork, Grammys awards, and guitars signed by B.B. King, Carols Santana, and the late Stevie Ray Vaughan.

700 South Wabash Avenue

Crestwood Scene