Your Keys to the City: Chicago

Hundreds of Hours of Food, Culture & Lakefront Magic

Welcome to the very first installment of Your Keys to the City — a new monthly series that gives you an insider’s guide to exploring cities through a local lens. We’re kicking things off in one of the greatest summertime cities in the world: Chicago.

Whether you’re visiting for the weekend or looking to rediscover your own neighborhood, this is your go-to guide to living like a local. From iconic eats to hidden gems, lakefront strolls to cultural deep-dives — here’s how to spend the perfect 48 hours in Chicago.

48 Hours in Chicago: Your Dream Weekend Itinerary

We mapped it all out for you in our latest reel, including local-favorite restaurants, morning-to-night plans, and unexpected stops that capture the magic of the city.

🎥 Watch the Reel Here

Where to Eat + Drink in Chicago

Chicago is a food city through and through. These are some of our favorite spots to fuel up — whether you're craving comfort, cocktails, or something iconic:

• Pequod’s Pizza – Famous for its caramelized crust and neighborhood pizza shop feel in Lincoln Park.

• Chef’s Special Cocktail Bar – Where Chinese-American comfort food meets a creative cocktail list in Bucktown.

• 3 Arts Club Café – A stunning brunch spot nestled inside the Restoration Hardware gallery in the Gold Coast.

• Allez Café – An intimate Bucktown café perfect for slow mornings and strong espresso.

• The Wiener’s Circle – A Chicago classic. Come for the hot dog, stay for the sass.
  
  

Lakefront Local: How to Experience Lake Michigan Like a Chicagoan

The lakefront is where the city breathes — especially in the summer. Here's how to make the most of it:

• Sunrise Walks + Skyline Views: Start your morning on the Lakefront at 57th Street Beach + Promontory Park for unbeatable and uncrowded views.

• Hop on that Boat: Head to 59th Street Beach for your boat day + hop off at Burnham Harbor for a lakeside bar & grill.

• Hidden Beaches: Skip the crowds and check out spots like Foster Beach for a more chill vibe.
  
  

Culture Check: Where to Tap Into the Real Chicago

Want to go beyond the Bean? Chicago’s soul shows up in its culture. Here's where to experience it:

• Green Mill Cocktail Lounge – A legendary jazz bar once frequented by Al Capone. Timeless, moody, and unforgettable.

• Pilsen Murals & Galleries – Wander 18th Street and discover bold street art, community-rooted galleries, and authentic bites.

• Museum of Contemporary Art – A rotating lineup of edgy, thought-provoking exhibits just steps from the Magnificent Mile.

• DuSable Black History Museum – Deeply moving and historically vital. Tells a story too often left out.
  
  

Ready to explore? Your dream summer in Chicago is just a click away.

🔑 Access the Full Chicago Guide Here