THIS WEEKEND IN CHICAGO – May Brings Mexican Pride, Floppy Hats & Mint Juleps!
Look who has arrived this weekend – May! And to start this month off with a bang, May has brought with her some Mexican pride as well as floppy hats and mint juleps so we can join in on the exciting weekend she has planned for us!
Chicago is the place to eat and drink your way through Cinco de Mayo, which is this Monday; however, some festivities are taking place this weekend.
Come experience an authentic cultural celebration at Global Connections: Mexico Fest this Saturday and Sunday at Navy Pier (600 E. Grand Ave.) in the Streeterville neighborhood. This fest features amazing music, dance, performances, art, and more. Plus, don’t miss the captivating Public Art Photo Exhibition by Jorge Sanchez who shares a visual journey to celebrate the vibrant spirit of Mexican culture. Best of all, it’s a free celebration for everyone!
Get ready for the ultimate Cinco De Mayo Bar Crawl Fiesta this Saturday (4 p.m.-11 p.m.) at PB&J: Pizza, Beer & Jukebox (205 N. Peoria St.) in the West Loop. Enjoy a day packed with festive fun as you and your friends celebrate the vibrant culture of Cinco de Mayo in style. It’s going to be a wild night of partying and a bar crawl you’ll experience like never before!
Time to prepare for an unforgettable day of drinks, music, and good times at yet another Cinco De Mayo Bar Crawl this Saturday (4 p.m.-1 a.m.) beginning at Bourbon on Division (2050 W. Division St.) in the Wicker Park neighborhood. Dress in your best festive attire, along with a sombrero, as you embark on this bar crawl journey to visit the city’s most popular bars as well as enjoying delicious Mexican-inspired cocktails and traditional drinks. It’s an exciting event you don’t want to miss!
Voted Chicago’s finest Cinco de Mayo weekend bar crawl for 3 years in a row, get ready to fiesta like never before at Joy District’s Cinco De Mayo Bar Crawl Party 2025 this Saturday (8 p.m.-2 a.m.) located at 112 West Hubbard Street in the River North neighborhood. Celebrate Cinco de Mayo like you mean it with a night full of tequila, tunes provided by live DJs, and non-stop party vibes at 4+ River North hot spots. Shots, music, and Chicago madness, what more could you want!
Prepare for a day of floppy hats and mint juleps as Chicago establishments bring you their version of being in Kentucky for the Kentucky Derby with the following watch parties.
Enjoy derby day at the Happy Camper Rooftop (3458 N. Clark St.) in the Wrigleyville neighborhood this Saturday (3 p.m.-6 p.m.) for their Kentucky Derby Watch Party. Partake in the high energy with a white claw or a mint julep in hand as you tune into the races!
Here’s a link to other Kentucky Derby Watch Parties in Chicago!
Lastly, the Chicago Spring Market returns to the Artifact Events Center (4325 N. Ravenswood Ave.) in the Lakeview neighborhood this Saturday and Sunday (11 a.m.-5 p.m.). Once again, this event brings together 95+ independent makers specializing in art, design, fashion, home décor, and more. In addition, attendees can participate in DIY activities, take photos at the artists’ photo walls, enjoy delicious food and drinks, and fill their free tote bag with goods from small businesses. Bring your whole family along, as children under 12 are free and friendly pets are welcomed as well to this amazing event!
Sue Moss and Dean’s Team Chicago
