After a wreath is laid at the eternal flame in Daley Plaza at 11am in remembrance of those who died serving in the U.S. armed services, Chicago's annual Memorial Day Parade marches down State Street (from Lake to Van Buren streets) beginning at noon. Crowds line the street waving flags and paying their respects as part of this Chicago tradition, which dates all the way back to 1870.
We’re probably not alone in saying that the weekend is always on our minds here at Time Out Chicago HQ. Like you (probably), we spend the workweek daydreaming about the next restaurant to obsess over and obsessively updating our concert calendars. Whether you’re museum-hopping, plotting a day trip to escape the city, or ready to ghost your original plans for something spontaneous, you’ll find plenty of ways to make the most of your weekend in Chicago.
Last updated May 18, 2026: Hunting for the best weekend plans in Chicago? From dedicated planners to last-minute adventurers, we’ve got you covered. This week’s highlights include Chicago's annual Memorial Day Parade, the return of Navy Pier's fireworks show and a whole slew of music festivals, with programming ranging from reggaeton to indie. We’ve also rounded up some of the best free events in Chicago, too, for good measure. Scroll down to discover the best events across the city!
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