Planning where to go on Memorial Day weekend in 2025? Whether you’re staying close to home or hitting the road, the Chicago area offers plenty of great options. This year, Memorial Day lands on Monday, May 26 — giving you three full days to relax and explore.
From waterfront fireworks to nearby wine country, the Midwest is packed with destinations worth checking out. And with Chicago event transportation available, it’s easy to get around while making the most of your time. Here's a look at some of the best places to be this Memorial Day weekend.
Stay Local: Memorial Day Weekend in Chicago
There’s no need to travel far to enjoy a full weekend of activities. The city is full of energy and offers tons to do for Memorial Day weekend in Chicago, from parades and fireworks to outdoor events and seasonal openings.
Watch Fireworks at Navy Pier
Start the long weekend with a fireworks display at Navy Pier. After the show, enjoy rides, live music, and food by the lake. Make time for the Centennial Wheel or grab a drink at Offshore, the rooftop bar with amazing skyline views.
Relax on the Beach
The beaches officially open on Memorial Day in Chicago. Head to North Avenue, Oak Street, or 31st Street Beach for sunbathing, volleyball, and jet ski rentals. Or just enjoy a peaceful lakefront stroll.
Hit the Festivals
Kick off summer at a few of Chicago’s most-loved street festivals:
- Suenos Music Festival: Latin music lovers, this one's for you.
- Mayfestiversary: A unique street fest featuring food trucks and craft beer in North Center.
- Belmont-Sheffield Fest: A fun neighborhood party with music, art, and drinks.
- Mole de Mayo: Celebrate Mexican cuisine and culture in Pilsen.
Dine Alfresco
Memorial Day is patio season in Chicago. Grab brunch with lake views, sip cocktails on a rooftop, or enjoy dinner by the river. Check out restaurants along the Chicago Riverwalk, or pop into a neighborhood garden patio for something more intimate.
Bike and Explore
Hop on a Divvy or join a tour to explore on two wheels. Ride along the Lakefront Trail, cruise through The 606, or check out vibrant neighborhoods like Logan Square, Lincoln Park, and Wicker Park.
Weekend Getaways Near Chicago
Ready to get out of town for a few days? You’ve got tons of solid options just 1-3 hours from the city. Whether you're chasing fresh air, quiet streets, or a cold drink by the lake, these spots are perfect for a quick Memorial Day weekend getaway.
Lake Geneva, Wisconsin (1.5 hours)
This lakeside town stays a favorite for a reason. At Lake Geneva, you’ve got boats on the water, local shops to wander, and breezy patios for lunch or drinks. Walk the full Geneva Lake Shore Path if you’re up for it — or just stroll a bit and take in the views. Book a lakeside hotel or find a cozy bed-and-breakfast that feels like summer vacation.
Michigan Wine Country (2 hours)
Head into Southwest Michigan, and you’ll find rolling hills, tucked-away wineries, and easygoing beach towns. New Buffalo, St. Joseph, and Sawyer all serve up a mix of lake views and tasting rooms. Drive the Lake Michigan Shore Wine Trail if you want to hit a few spots without rushing.
Starved Rock State Park (2 hours)
If hiking and waterfalls sound better than crowds, this is your place. Starved Rock is packed with trails, rocky canyons, and views along the Illinois River. Bring your hiking shoes, or make it an overnight trip and stay at the old-school lodge inside the park.
Galena, Illinois (3 hours)
This place feels like stepping into a postcard. Galena’s known for its old buildings, antique shops, and quiet countryside. It's a great pick if you want to slow down, unplug, and take a break from city noise for a few days.
Indiana Dunes National Park (1 hour)
Only an hour from downtown, you’ve got wide beaches, hiking trails, and miles of dunes to explore. Indiana Dunes is perfect if you want nature without driving all day. Spend a few hours or make it a full-day trip.
Final Tips for a Perfect Weekend
- Book early: Hotels, charter bus rentals, and restaurants fill up fast for the holiday.
- Plan around traffic: If you’re leaving the city, hit the road early or late to avoid peak congestion.
- Pack for variety: Chicago weather can be unpredictable. Bring layers and sunscreen.
- Honor the day: Attend a Memorial Day service or Chicago Memorial Day parade to reflect and pay respects.
Whether you’re staying in the heart of Chicago or exploring scenic surroundings, the Midwest offers something for every kind of traveler this Memorial Day weekend. From rooftop parties to quiet hikes, beach days to wine tours, there’s a perfect getaway waiting for you.
Drive Your Memorial Day Plans Forward!
Memorial Day weekend is your chance to welcome summer in Chicago or take a quick break outside the city. Whether you're heading to one of the many Chicago events Memorial Day weekend, relaxing in nature, or spending time in a quiet town, a little planning goes a long way. Lock in your ride, pack smart, and set aside time to honor those who gave their lives in service.
Ready to make it happen? Reach out to Ideal Charter Bus and book your coach or minibus today. Plan your trip, load up your bags, and get set for a weekend that feels like the start of something good.
