The Ultimate Chicago Experience: What to See and Do

Planning your first visit to Chicago? Don’t just snap a selfie at The Bean and call it a day—let Stacking Adventures hosts Crystal Hammond and Joe Saul-Sehy be your insider guides to one of America's most vibrant, layered, and delicious cities.

In this jam-packed episode, Crystal and Joe serve up their personal Top 5 experiences every first-time visitor to the Windy City has to try—plus a few lesser-known gems that even longtime locals might have missed. Think towering views from the not-Sears-anymore Tower, eye-opening museum visits, and—of course—deep-dish pizza debates that could make or break a friendship.

What You’ll Discover on This Chicago Adventure:

• 🎷 How to jazz up your nights: Chicago’s music scene is more than history—it’s still swinging.

• 🏛️ Museums worth the trip (and the ticket price): From science to surrealism, Crystal and Joe spotlight their go-to cultural stops.

• 🚢 Architecture on the water: Why skipping the Chicago River architectural tour is basically a rookie mistake.

• 🍕 The great pizza throwdown: Who serves the best deep-dish in town? Expect strong opinions.

• 🛍️ Mag Mile magic: Exploring iconic shopping, dining, and photo ops without blowing your budget.

• ✍️ Gear of the Day: The one travel item that helps you remember the trip (and not just through receipts in your coat pocket).

Plus, they share some of Chicago’s lesser-hyped treasures—from relaxing beaches to hidden eats and moments of Midwestern charm you won’t find in a guidebook.

Whether you're planning a weekend getaway or mapping out a longer adventure, this episode will leave you with a full Chicago to-do list, a hunger for hot dogs (with everything on it), and maybe even a new jazz playlist.

Looking for our cool, tested travel gear (including our NEW gear of the day pick)? Head to StackingAdventures.com/GoTD