The Time Out Chicago blog team

You don’t get named number five on North America’s 50 Best Bars list without taking some risks. Sip & Guzzle, a two-level cocktail haven in New York City’s West Village expertly stirs buzzy NYC nightlife with Japanese cocktail culture. And, now, for one night, and one night only, that acclaimed drinks team have partnered up with Hawksmoor Chicago, a Windy City favorite well-known for its midwestern hospitality and steak-and-seafood spread. RECOMMENDED: The first-ever Chicago Cocktail Classic will let you drink your way around the world What began in east London in 2006 has evolved into a culinary juggernaut with restaurants in New York and Chicago, earning Hawksmoor placement on the World’s Best Steak Restaurant list as well as James Beard Foundation mentions and Tales ofthe Cocktail accolades. So you can expect to be in very good hands with this pop-up match-up, which takes over the Chicago venue tonight, June 13 from 6 p.m. to 10 p.m. (final entry is at 9:30 p.m. Attendees can expect two different bar vibes, all in one epic night: Guzzle will bring crushable cocktails and highballs, while Sip will deliver refined, Japanese-style creations. Plus, the Hawksmoor bar team will also be serving up select cocktails from their own menu. Those boozy tipples will be available for purchase a la carte, on Hawksmoor's second-floor bar while supplies last. While walk-in imbibers are welcome, reservations are recommended—RSVP via Evite is encouraged but does not guarantee a...

What’s more thrilling than a high-speed NASCAR race? How about carb-loading right where the cars take off? This summer, Chicago Gourmet is rolling out one of its most daring (and delicious) experiences yet: a five-course Italian tasting menu served smack on the NASCAR Chicago Street Race track. On Wednesday, July 2, from 6 p.m. to 9 p.m., the race's start/finish line will transform into the city’s most unexpected fine-dining venue, blending Michelin-caliber cuisine with pit-lane vibes. As part of the Chicago Gourmet Festival’s new “Culinary World Series,” the event marks a high-octane kickoff to the city’s biggest food celebration and a once-in-a-lifetime chance to toast with wine where tires usually burn rubber. RECOMMENDED: The 25 best restaurants in Chicago you have to try in 2025 The chef lineup is stacked with Chicago stars, including Fabio Viviani (Siena Tavern, Bar Siena), Tony Priolo (Piccolo Sogno), Joe Frillman and Leigh Omilinsky (Daisies) and Steve Maak (Levy Restaurants). The night’s theme: bold Italian flavors, dished out trackside with flair. Diners can expect signature race-day cocktails from Jose Cuervo (the official tequila of the NASCAR Chicago Street Race, naturally) and a "Cup Series" of wine pairings from legendary Italian winery Marchesi Antinori. There’s even an emcee—culinary personality, Catherine De Orio—to steer the evening along. Tickets cost $250 per person, and proceeds benefit the Illinois Restaurant Association Educational Foundation, a...

One of Chicago’s most storied nightlife landmarks, the Green Mill Cocktail Lounge, is in the headlines again. But don’t panic just yet, jazz lovers: While the historic Uptown building that houses the century-old club is officially for sale, the Green Mill itself isn’t going anywhere. The two-story structure at the corner of Broadway and Lawrence, where Al Capone once drank and Billie Holiday once performed, hit the market earlier this week. The building spans more than 21,000-square feet and includes eight commercial units, including buzzy neighbors like Birrieria Zaragoza and Le Nocturne. Current owner Dave Jemilo, who bought the Green Mill in 1986 and the building in 2021 for $5 million, hasn’t publicly commented on the listing. However, sources familiar with the sale told Crain’s that the club’s operations are expected to continue uninterrupted, according to Block Club Chicago. That’s welcome news for locals and tourists who flock to the velvet-draped venue for nightly jazz, slam poetry and a dose of Prohibition-era Chicago lore. The Green Mill has long been a living time capsule: Its curved bar, vintage booths and dim amber lighting conjure the days when mobsters sipped whiskey in the infamous “Capone booth,” strategically placed with sightlines to both exits. If that weren’t enough intrigue, there’s also the tunnel system under the club, a relic of its gangster past. Once used for bootlegging and backroom escapes, the underground lair is accessible by a trapdoor...