Updated Jun 10, 2025 - Things to Do
Chicago Memorial Day staycations
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ARRIBA Rooftop. Photo: Courtesy of Farm Bar.
A three-day weekend is often just enough time for a nearby getaway or about being a tourist in your own city, experiencing Chicago in a new, more relaxed way.
Driving the news: For Memorial Day weekend, here are some ways to enjoy the break in the city and suburbs.
Zoom out: OK, yes, the Kennedy is terrible, but it's not like you're getting on a flight!
Here are a few suburban options for the long weekend:
- Lake Forest: Deer Path Inn in the North Shore 'burb has themed getaways, like "A Good Book and a Spot of Tea" for book lovers and "Zero Proof Experience" for mocktail drinkers.
- Frankfort: As we've written before, this southwest suburban village is a gem that offers a cute, historic downtown with free concerts on Sundays.
- Dolton: If you're heading north back to the city, swing through Dolton to see Pope Leo XIV's childhood home.
Zoom in: Let's be real. There's plenty to do within city limits.
- Eat your way through town using one of our many "Food Fights" as a guide: hot dogs, burgers (veggie ones, too) and pies are a good place to start.
- Soak up some sun (wear sunscreen!) as beaches open Friday, including beachside eateries like Castaways.
It's patio season!
- Chicago Burger Company on the Riverwalk has free mini sliders and a pup menu Saturday.
- La Terrace at Sofitel in Gold Coast is a little respite from Mag Mile traffic
- BLVD Steakhouse in West Loop goes upscale with its outdoor dining room.
- ARRIBA Rooftop in Ravenswood has Tex-Mex food and great views of the North Side.