With an abundance of world-class cultural attractions and amazing architecture, you’ll never be bored in Chicago, regardless of the weather. But the Midwest’s largest city really comes to life in summer when days are longer, temps are warmer, and the calendar is jam-packed with al-fresco festivals and events. From an extended Lolla to “the Taste,” to the newest rooftop bars and the Heartland’s version of the High Line, there’s so much to see and do this summer in Chicago. It’ll be Labor Day before you know it, so we whittled the list down to 25 essential warm-weather activities.—Kristine Hansen

Windy City Smokeout


Want your ‘cue and country music all at once? Windy City Smokeout merges the two—plus lots of craft beer sourced from around the nation—in a weekend fest July 15–17 in River North. Hosted by Bub City and Joe’s Bar, two Chi-Town institutions, expect to see pitmasters (from farther-afield spots in Arkansas, Texas, Georgia, Mississippi, North Carolina, and Tennessee, plus a few Chicago eateries) and country-music stars (including Old Dominion, Chase Rice, and Phil Vassar) light up the night.

Plan Your Trip: Visit Fodor’s Chicago Guide