Under-the-Radar Excursion: For a low-key break from the bustling city center, take a stroll around The Lincoln Park Zoo, one of the last free zoos in the world.
Top Urban Hike: Got a weakness for granite facades? Wander the Loop—aka the financial district—for an architectural feast.
Best Treat: If you’re in thrall to a sweet tooth, head to Sweet Mandy B’s and get a cupcake. Seriously. This is one indulgence you won’t regret.
Coolest View: Sears Tower, eat your heart out. Visit the John Hancock Observatory instead—you can see across the lake to Michigan on a clear day! Plus, you can score a better view (and a pass on admission fees) if you visit the lounge for a drink.
Not sure where to spend your precious summer vacation days? Take our travel quiz to find a destination that matches your style.