THIS WEEKEND IN CHICAGO – Memorial Day Weekend Kicks Off Summer Season!

The official arrival of Summer 2025 arrives on June 20th; however, here in Chicago seeing that our summer season is short-lived, we will be celebrating the “unofficial” start of our summer season this Memorial Day Weekend! Here are just a few of the top things to do this holiday weekend.
The city will honor all men and women who have made the ultimate sacrifice in defense of our country for our freedom with their annual Memorial Day Wreath Laying Ceremony & Parade this Saturday. The Wreath Laying Ceremony begins at 11 a.m. at the Daley Plaza (50 W. Washington St.) where Gold Star families and representatives of the U.S. Marine Corps, Army, Navy, Air Force and Coast Guard participate in the ceremony. In addition, taps will be performed by the 484th Army Band. Afterwards, the Parade will kick off at Noon from State and Lake Streets proceeding south on State Street to Van Buren Street. Once again, veterans’ groups, active-duty service members, JROTC cadets, community organizations, and marching bands will be featured. Come join us as we honor all fallen service members as well as celebrating the strength and diversity of the Chicago community!
Celebrate the true essence of Memorial Day at Soldier Field 10 this Saturday (7 a.m.-2 p.m.) at 1410 Special Olympics Drive in the South Loop. Opening the event will be a playing of taps with a military salute. Then it’s time to tackle either the 10K or 10-Mile course through Chicago’s most iconic sights and finishing on the 50 Yard Line at Soldier Field. Afterwards, its time to unwind at the Post-Race Tailgate in Stadium Green featuring complimentary beer for those 21+, live music, and plenty of fun activities for the whole family. It’s time to Run, Celebrate, and Unwind!
Kick off summer at the 40th annual Belmont-Sheffield Music Fest this Saturday and Sunday (11 a.m.-10 p.m.) at 3200 N. Sheffield Avenue in the Lakeview neighborhood. This year’s Fest features tribute bands on the main stage; a community entertainment stage offering an exciting mix of neighborhood music acts; DJ sets; local artisans and vendors selling unique goods; delicious eats and drinks that include beer and wine vendors; and other surprises. This iconic street festival is a must attend event if you want to kick off the summer season in style!
Begyle Brewing and Dovetail Brewery will once again be hosting their annual spring party Mayfestiversary to welcome back Chicago’s best season this Saturday (11 a.m.-10 p.m.) and Sunday (11 a.m.-9 p.m.) between the breweries at the corner of Ravenswood and Belle Plaine Avenues in the Ravenswood Corridor. This event includes culinary delights from some of Chicago’s top food trucks, special beer tappings of 60 different beers, over 13 local bands, entertainment from DJs, kids’ activities, and much more!
Find the best vintage, antique & repurposed furniture, art, décor, vintage fashion, and global goods at the Randolph Street Market Festival presenting their Summer 2025 Garden Party this Saturday and Sunday (10 a.m-5 p.m.) at 1341 W. Randolph Street in the West Loop. This European style flea market features thousands of top-quality goods presented by 200 indoor/outdoor dealers from around the country. It also features market bars to quench your thirst, fun food, live bands, and DJ’s. It’s one of the country’s best loved treasure hunt fests filled with fun and excitement!
Summer Fireworks is back for the Summer of 2025 this Saturday (10 p.m.) through August 30th at Navy Pier (600 E. Grand Ave.) in the Streeterville neighborhood. Enjoy unforgettable nights on the Pier with breathtaking views and a fireworks experience not to be missed!
Sue Moss and Dean’s Team Chicago