Grant Park Bistro

Grant Park Bistro offers that perfect blend of people-watching and privacy on its charming patio facing Michigan Avenue. The cocktail program punches above its weight—try their seasonal gin concoctions that somehow make even tourists bearable. While the bistro's French-inspired menu delivers solid bites (the steak frites is legitimately worth the splurge), it's the relaxed yet attentive service that keeps locals coming back.

The extensive beer list features enough local brews to impress your craft-obsessed friend without intimidating casual drinkers. Families are welcome, but the vibe shifts decidedly adult as happy hour kicks in. The patio fills quickly on sunny weekend afternoons, so snag a reservation or risk joining the wistful sidewalk gazers.

Your four-legged friend can tag along too—the staff keeps water bowls full and have been known to sneak treats to well-behaved pups. Just don't count on finding parking easily—the lot fills faster than your glass empties.