If you've lived in Chicago long enough, you know Memorial Day weekend isn't just a holiday - it's the moment we can start to shed our endless winter. The city collectively exhales, the lakefront opens up, the patios fill, and for the next four months, Chicago becomes the best city in the world. No debate.
Here's how Ivona and I are spending the weekend - and our top pics for you too.
The Memorial Day Parade: If you’ve never been - Don't Skip It
Friday, May 23rd. Downtown Chicago. The official kickoff begins.
Before the weekend gets fully underway, take a moment to be present for the parade and wreath-laying ceremony. It's easy to get swept up in the weekend's fun and forget what we're actually marking. Go. Stand on the street. Clap for the people who earned it. It sets the right tone for everything that follows.
Bike the Drive — And Why This One is Personal
If you're not already doing Bike the Drive, this is the year.
Every Memorial Day, Lake Shore Drive closes to cars and opens entirely to cyclists. It is one of those only-in-Chicago experiences - miles of open road hugging the lakefront, with the skyline on one side and Lake Michigan on the other. There is nothing like it.
But here's why this one hits differently for us personally.
Ivona and I are deeply involved with the Jackson Chance Foundation, and if you're a client of ours, you've likely heard us talk about it. Jackson Chance supports families in the NICU at Lurie Children's Hospital, Rush, and the University of Chicago, helping them stay close to their babies by paying for their parking during the most frightening time of their lives. It is an organization that does quiet, extraordinary work.
One of the Foundation's two signature fundraisers is an 111-mile bike ride from the Chicago lakefront all the way to Valparaiso, Indiana. That number, 111 miles, is not a coincidence. It honors Jackson Megie, the son of our dear friend Carrie Megie, who was lost on November 11, 2011 - 11.11.11. Carrie channeled the most unimaginable grief into something that has touched countless families since.
If you want to learn more or get involved with Jackson Chance, reach out to us - we'd love to talk about it.
Navy Pier Fireworks - Saturday Night, 10 p.m.
Go. It's not just a regular display.
Saturday night, May 23rd, Navy Pier lights up with its first fireworks show of the summer season. Get there early, grab a drink at Offshore (yes, it really is the largest rooftop bar in the world, and yes, the view justifies the wait), and find your spot on the waterfront. When those fireworks go off over the lake, you'll remember why you love this city.
If you want to go to the next level, book a fireworks cruise. Watching the show from the water with the skyline behind you is one of those Chicago nights you never forget.
The Riverwalk - All Weekend Long
The Chicago Riverwalk is my happy place from Memorial Day straight through Labor Day, and this weekend it will be absolutely buzzing.
Walk it end to end. Stop at Café Baci for a Campari spritz and watch the kayakers. Grab a seat at River Roast if you want a proper sit-down with water views. Pick up something quick from one of the vendors and just sit by the water for a while. The Riverwalk has this magical way of making you feel like you're on vacation in your own city, and this weekend, with perfect weather and the whole summer ahead, it doesn't get much better than that.
If you haven't explored the newer sections toward the east end, do it. The landscaping, the public art, the dog-watching alone is worth the walk.
The 606 - A Different Side of the City
If the lakefront gets too crowded for you (and it will), head to The 606.
This elevated trail runs 2.7 miles through Wicker Park, Bucktown, Humboldt Park, and Logan Square and on a holiday weekend, it has this incredible neighborhood-block-party energy. Families, dogs, cyclists, people grilling on their back decks below you, local murals at every turn. Grab a coffee just off the trail at Ipsento or have lunch along the trail at Wolf and Co - It is Chicago at its most authentic.
After your walk or ride, drop down into Logan Square or Wicker Park for brunch. Fat Rice, Café Robey, Lula Cafe - you can't make a bad decision in either neighborhood on a sunny May morning.
A Few More Honorable Mentions
The beaches officially open this weekend — North Avenue Beach will be packed and perfect, with volleyball, the lakefront bars, and that skyline view that still gets me every single time. Montrose is a little more relaxed if you want space to spread out.
Cubs at Wrigley — Friday through Sunday against the Astros. A day game at Wrigley Field in May is one of life's great pleasures. Get the Old Style, sit in the bleachers, talk to strangers. That's it. That's the whole plan.
Sueños Music Festival is taking over Grant Park on May 23–24, and the lineup is stacked. If you haven't been, it's become one of the best festival weekends of the whole summer.
The Real Bottom Line
Memorial Day weekend in Chicago is the city reminding you why you chose to live here — or if you're visiting, why you should consider never leaving. The lake is back, the patios are open, the people are out, and the energy is unlike anything else.
From all of us at the IK Group, have a safe and wonderful long weekend. See you out there.
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