The Time Out Chicago blog team

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...

Chicago's Pride Month celebrations are legendary, spreading LGBTQ+ culture, history and community at the best gay bars, the top drag brunches and, of course, the annual Pride Parade. (This year's parade festivities kick off on Sunday, June 29 at 11:00 a.m. with "United in Pride" as the 2025 theme.) But a far more everyday way of honoring the historic legacy and continuing vibrancy of Chicago's queer and trans communities is by simply hopping on a CTA train—yes, the annual eight-car, rainbow-hued Pride Train is back on the city's Red Line tracks during the whole month of June, this time sporting a snazzy new design. RECOMMENDED: The 21 most epic Metra day trips from Chicago Expect to see multi-hued vertical waving bars on the train’s cars, with the words “Ride with pride!” emblazoned on the sides. Bookending each train, black and brown stripes represent LGBTQ+ people of color, with transgender and classic Pride flag colors filling in the middle. But it doesn’t stop there: On the inside of each car, passengers can read not only inclusive and supportive affirmations, but also facts about local LGBTQ+ history, which is a new addition for this year. Photograph: Courtesy Chicago Transit AuthorityCTA Pride Train The first major transit agency to publicly support the queer community with a Pride Train, this beauty has been chugging along since 2017. “The CTA is excited to continue the tradition of celebrating the LGBTQ community with the unveiling of the 2025 Pride Train and...