The Time Out Chicago blog team

Chicago’s biggest country-music-meets-barbecue blowout just added another megawatt reason to block off your entire July. Windy City Smokeout announced that Blake Shelton will close out the 2026 festival on July 12, 2026, joining an already stacked lineup that includes nostalgic '90s acts and modern Nashville heavy hitters alike.  The five-day festival returns July 8–12, 2026, to its home outside the United Center, where the parking lots become a smoky, rowdy, star-packed sprawl that reliably sells out and has twice been named the Academy of Country Music’s Festival of the Year. This year kicks off with a Wednesday night concert headlined by Treaty Oak Revival, supported by Braxton Keith and Sterling Elza, while over 20 pitmasters from around the country prepare the slow-smoked lineup for the days ahead. From there, the headliners read like a crash course in country music across generations. Hootie & the Blowfish take over Thursday with a full-throttle '90s singalong. Friday brings reigning CMA and ACM Entertainer of the Year Lainey Wilson, while Jordan Davis joins the fun on Saturday night. And then Shelton closes the whole thing out on Sunday, bringing nine Grammy nominations’ worth of hits to what’s already billed as the festival’s biggest night. As always, the daytime hours are packed with rising stars and acts programmed to keep the music going from open to close. And Smokeout doesn’t stop at music: the festival leans into its food identity with special events like the...

“Have your main-character moment when you step through these doors,” Amanda Anderson tells me from the love seat at the front of The Last Chapter, the romance-only bookstore she opened in Roscoe Village two years ago. The sentiment fits; the shop practically invites an entrance. Velvet furniture, soft lighting and thoughtfully arranged shelves make the space feel equal parts bookstore and fanciful refuge. Even the photo booths—three of them, each its own tiny world—feel like winks at the genre: one lined with heart-shaped Post-its, another mossy with a glowing neon sign.  After years on Wattpad—home to fan-fiction epics and plot twists dramatic enough to make a high-school English teacher blush—and later at a marketing firm supporting indie romance authors, Anderson realized she wanted to build something offline and decidedly analog. She found it on a cheerful stretch of Roscoe Village, just blocks from where she grew up. After touring 36 potential spaces, she landed on 2013 West Roscoe Street. The place simply felt right, she says—like it had been waiting for her. RECOMMENDED: This Chicago thoroughfare is one of Time Out’s coolest streets in the world “This genre saves lives. This genre makes people feel so seen, and that should be celebrated,” she tells me with conviction. For Anderson, romance became meaningful in ways she never anticipated. After her godmother passed away from cancer, she found herself unmoored, moving through the world without the emotional vocabulary...

The holliest, jolliest time of year is right around the corner, bringing with it a beloved Chicago commuter tradition: hopping aboard a train or bus festooned with twinkling lights, commandeered by Santa and his elves and blaring holiday tunes at top volume. That’s right: the Chicago Transit Authority (CTA) has finally announced the schedules for its Holiday Train and Holiday Bus, revealing when you can expect to see Santa making pre-Christmas Eve journeys through the city. The CTA Holiday Train will begin running on Saturday, November 29, with trips scheduled on every CTA line throughout November and December as part of regular service. As usual, the six-car train will be headlined by an open-air platform hosting Santa and his crew of reindeer, as well as LED signs, colorful interior decorations and more lights than ever before. Photos with Santa have also returned, with designated photo op dates for both the Holiday Train and Bus. Photos will be taken by a CTA employee using your device, so free up some extra storage space for the occasion.  RECOMMENDED: These are the best spots to see dazzling holiday Christmas lights in Chicago right now Photograph: Courtesy Chicago Transit Authority If you prefer to experience holiday cheer at street level, you’ll be happy to learn that the CTA Holiday Bus will make an appearance on a whopping 19 routes throughout the city this year. This year’s bus will be adorned by a jovial wrap featuring Chicago landmarks, nods to...