Your Ultimate MDW Guide to Chicago Fun

May 20, 2025

Get ready, Chicago, because Memorial Day is the official start to summer! Since the weather looks a little iffy, we have indoor and outdoor ideas for fun this weekend. I’ll be at Navy Pier on Saturday and might head over to Mayfestiversary in Malt Row, too! Let me know what you’re up to!

🎶 Stop by the Belmont-Sheffield Music Fest. They’ll have epic live music, great food & cold drinks, local makers and vendors, and lots of people watching! Friday, May 23 – Sunday, May 25.

👾 Visit the Elston Electric arcade and the Summersalt Market at The Salt Shed. This is easily one of my new favorite venues! Summersalt Market has so many goodies! I recommend checking it out if you are looking for unique finds. Many of the vendors only do pop-ups and do not have a brick-and-mortar shop. And Elston Electric is for all ages! It’s free to enter, lots of families, and we found free parking on Elston. Saturday, May 24 – Sunday, May 25.

🍻 Grab a pint at Mayfestiversary. Begyle and Dovetail breweries in Ravenswood will host a two-day street fest celebrating beer, bands, and community from May 24 to 25.

🍹 Have drinks at The Dock on Montrose. Relax on the sand with a full view of Lake Michigan and the skyline. Think: beachside cocktails, laid-back vibes, and it’s both kid- and dog-friendly!

🎡 Head to Navy Pier for Jewel-Osco’s Free A-MAY-ZING Family Event. I’ll be there! They’ll have giveaways, games, live entertainment, and tons of family fun. Saturday, May 24 from 12–4 PM.

💙 Take advantage of a free museum day at The Chicago History Museum. Check out interactive exhibits about the Great Chicago Fire, the city’s impact on the civil rights movement, and how Chicago has influenced American culture. We love it there!

Enjoy Electric Shuffle’s Memorial Day Weekend Specials. Only $5 shuffleboard games, $10 margaritas, and $4 beers. A fun indoor option if the weather turns!

🎸 Join the Crawfish Boil + Live Music at Ina Mae Tavern. Ina Mae’s is one of our favorites! Sunday, May 26.

🦁 Celebrate Summer Kickoff at Lincoln Park Zoo. Perfect for little ones—check out seasonal activities and animal encounters at this free zoo in the heart of the city.

🥕 Hit up a farmer’s market. Stock up on fresh produce, picnic snacks, and flowers to brighten your home. Green City Market, Logan Square, and more will be in full swing!

Have a great weekend!!

Christine

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