Best Art Fair

Art fairs are a dime a dozen in Chicago, but Expo presents the highest-quality work from the most far-flung places. This year you’ll see pieces from 140 top-notch galleries in 16 countries, among them New York’s David Zwirner (Jeff Koons, Richard Serra) and Paris’s Galerie Daniel Templon (Jean-Michel Basquiat, David LaChapelle). It runs September 17 … Read more

Best Street Festival

No sad has-been bands here. This West Loop party has in recent years brought the Black Keys, My Morning Jacket, and Delta Spirit to its stages. If you have to wait in line for food, it may as well be from the likes of Publican Quality Meats, Tête Charcuterie, and BellyQ. Not a fan of … Read more

Best Tennis Lessons

Venus Williams, Andy Roddick, and John McEnroe have all hit the courts at the world-class Logan Square outpost of this mini-chain. But you don’t have to be a pro to enjoy the seven levels of instruction, from intermediate beginner to advanced ($72 for a private one-hour session). You may run into some familiar faces, too—Sasha … Read more

Best New-Book Store

It’s got all the hallmarks of a thriving indie bookstore: handwritten recommendations from discerning staff, book signings by celebs such as actor Nick Offerman, and tomes just idiosyncratic enough to thrill bibliophiles without alienating casual readers wanting James Patterson’s latest. Check out the extensive travel section in the basement.