9:30am – Enjoy pastries outdoors at Plein Air Café
Enjoy breakfast in the sunshine on the tree-lined patio at Plein Air Café, a French workshop-inspired restaurant next to Frank Lloyd Wright’s Hyde Park home. In addition to biscuit sandwiches and mascarpone-stuffed French toast, you’ll find delicious spinach pancakes, mince pies and more.
11am – Take a self-guided kayak tour of the Chicago River
Kayak Chicago offers kayak and paddleboard rentals (along with guided tours) from three different locations, including Goose Island where paddlers can suit up and set off on the river. Paddling south, guests can head south into the architectural canyon of downtown, under bridges and near iconic buildings like the Marina Towers, the Willis Tower and the new St. Regis Chicago.
2pm – Picnic in the elevated park
Explore Chicago’s highest park: the 606 Elevated Trail, which runs 2.7 miles above Bucktown, Logan Square, and Humboldt Park, along a former railroad track. “I think of it as a mini version of New York’s High Line,” explains Bucktown artist and resident Laura Collins. “The foliage is beautiful in the summer and fall, so it’s a great time to walk and see the trees, and there are some fun off-trail spots like The Stop Along and Small Cheval. Both have outdoor seating, great food, and are great for allergy sufferers.”
4pm – Gangster and Ghost Tour
Once home to notorious gangsters like Al Capone, John Dillinger and Baby Face Nelson, Chicago is also known for its gangsters and Saturday Night Live alumni, and the best way to stroll down sordid memory lane is on a Gangster & Ghost Tour. Guided walking tours of the Loop, known as the “vice district” in the 1920s and ’30s, explore secret — and even haunted — hideouts, former speakeasies and underground tunnels.
