Best High-End Florist

Those towering, flowering breathtaking spectacles in so many Gold Coast homes and hotels (Drake, Four Seasons) likely came from this century-old, family-owned florist. Mangel’s specialty: roses that would make Gertrude Stein gawk. If you’re looking to wow, this is the place. Prices start at $50 for a basic arrangement.

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 Shoe and Leather Repair

Calling Luis Coronel a cobbler is like calling Patrick Kane a skater. A certified cordwainer (meaning he has mastered the skill of building new shoes from fine leathers), Coronel and his team expertly repair and revive footwear, handbags, and leather apparel. Got a damaged $35,000 Hermès alligator bag? The Gus crew will track down a … 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 Men's Clothing Store for the Money

If you want to look sharp without being mistaken for a Eurodude, zip to sisters Sarah and Amy Blessing’s Bucktown boutique. The expertly curated mix of smart-casual clothes—slim John Elliott sweatshirts, Thom Browne tapered trousers, chunky Maison Margiela crewnecks—will nudge you just far enough outside your comfort zone.

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 Children's Bookstore

This whimsy-heavy spot does the typical kids’ bookstore one better: It hosts weekly storytelling sessions (Wednesdays at 10:30 a.m.), runs immersive day camps (this summer’s theme: superheroes; $40 for four sessions), and offers a monthly writing workshop ($40) for pintsize J.K. Rowlings.

Best High-End Hair Color

For natural-seeming highlights, the pros at Maxine are worth shelling out for. They’re masters of balayage (from $200), a technique in which color is hand-painted on individual strands, leaving you looking sun kissed, not streaky. The sleek white space feels as luxe as the Kérastase products they’ll massage in during your postdye blowout.

Best Kitchen and Bath Store

Sears it’s not: You’ll start off your trip to this eye-popping kitchen and bath showroom with a free iced tea or latte. Try out a Wolf rangetop (from $3,120) during free weekly cooking classes (a recent session: making the most of your farmers’ market haul). Flip the faucet to see how the water flows into … Read more