Winter: Go Skiing. No, Really.
When: December to April Where: Half a dozen ski areas Chicago is known for its winters. This is a city of extremes; wind blasts off the lake, chilling the Read More …
Fall: Catch a Film at the Chicago International Film Fest
When: Mid-October Where: North Side, but Especially The Loop Whether you’re a film fanatic or just trying to escape the first gusts of cold weather, the Chicago International Film Read More …
Fall: Expo Chicago
When: The last weekend of September Where: Navy Pier Art lovers of all ages and tastes will find something to love about Chicago—with its hundreds of galleries and world-renowned Read More …
Summer: Visit a Neighborhood Street Festival
When: All Summer Where: Everywhere but especially inside The Loop Chicago may be harsh, but the city shines in the summertime. Ample greenspaces, parks, and waterside activities make for Read More …
Year-Round Chicago Weekend Tips: Pop-Up Bars
When: Year-Round Where: All Neighborhoods, but Especially Lakeview, Wicker Park, and the West Loop Chicago houses one of the country’s best nightlife scenes. With dozens of breweries, taprooms, Read More …
Spring: Don’t Visit the Chicago River on St. Patrick’s Day
When: March Where: Anywhere but the Loop Each year, families and frat brothers alike descend on the Magnificent Mile to witness the annual St. Patrick’s Day Parade. Hosted on Read More …
Winter: The Empty Bottle Winter Block Party
When: February Where: Ukrainian Village Chicago is known for its summer block parties—they draw big-name musicians, thousands of attendees, and offer some of the best street food in the state. Read More …