Chicago may be the Second City, but it’s second-to-none when it comes to Michelin-starred restaurants, world-class entertainment, and outdoor adventure for any type of traveler. While the major metropolis is typically known for brutal winters and deep-dish pizza, we’ve created an itinerary that explores another side of the city (don’t worry–pizza is still included) with a variety of cuisines, secret speakeasies, spots to show your kids, and outdoor oases that can be enjoyed all year round. Whether you’re headed to Chi-town later this month for the demconvention or looking for a family-friendly weekend getaway, these self-guided kayak tours, late-night live music lounges, and bucket list-worthy dining experiences are sure to give you the best taste of the Windy City. Tap the link in our bio for a three-day itinerary and send this to someone that’s planning to visit Chicago soon. ✍️: mattkirouacyork 📸: 1. Green Mill Cocktail Lounge by cosmic_ghost 2. littlegoatdiner by bokarestauran...