The five coolest things visitors to Chicago should do right now

Head to Avondale and catch a concert at Sleeping Village, a relatively recent addition to Chicago's community of independent music venues. Local musicians are a constant presence on the stage here, including jubilant singer-songwriter Tasha (Nov 13, 20), experimental rockers Spirits Having Fun (Nov 23) and noisy post-punk outfit Melkbelly (Dec 3). Sleeping Village is also one of a network of local venues hosting the Tomorrow Never Knows festival in January, featuring sets from local multi-instrumental Sen Morimoto (Jan 20) and country-tinged act Jodi (Jan 23). Don’t forget to swing by the venue's bar, which boasts a robust selection of local beer and some solid cocktails.

We'll be honest: You might have trouble securing a reservation at this hot-ticket West Loop Italian spot, which debuted in September with killer chicken parmigiana (chef Lee Wolen, who also heads the kitchen at Boka, has long been known as a master of chicken) and one of the city's most stunning restaurant designs in recent memory. Boasting a menu packed with pasta, pizza and proteins, it's easy to order a slate of dishes (and a few glasses of wine) for you and your travel party to enjoy. To snag a table, you may want to skip the online booking system and show up in person around 5:30pm on a Monday or Tuesday, a server told us on a recent visit—odds are, you'll find an open table. 

Moreno's Liquors has stocked Little Village with shelves upon shelves of tough-to-find tequila and mezcal for more than 40 years. Head to the back of the store and you'll find a neon Chihuahua sign guiding you to Osito's Tap, a tucked-away speakeasy that once housed a Bohemian bar (a remnant of the neighborhood's Czech heritage) and an underground bookie joint. Since 2019, the bar has served a drink and food menu inspired by Little Village's Latinx community, with an especially strong showing of agave cocktails and michelada options alongside a robust draft beer list. As temperatures plummet, opt for the autumn-inspired Automnal cocktail (Paranubes Oaxaca rum, mazanilla sherry, ginger honey, lime, apple bitters) or other seasonal delights.

Chicago winters are often frigid, so consider planning a brief (and free!) respite this season in the form of an afternoon at the Garfield Park Conservatory, which boasts eight display gardens growing in tropical temperatures. From November 24 through January 9, visitors can roam through the annual winter flower show titled "Serenity," a calming exhibit which will fill the Conservatory's greenhouses with aromatherapy as well as blooming zinnias, cosmos, salvias and other cheery flowers. (Note that you'll need to make an online reservation before visiting, though a limited number of walk-up spaces are available daily.)