The Windy City Chicago

If you’ve never been to Chicago, it can feel like stepping into the heart of the Midwest — friendly, a little breezy, and bursting with deep-dish dreams. But beneath the laid-back vibe, there’s an energy that welcomes you in. 

Chicago is alive. It hums with blues, art, innovation, and stories — and whether you’re here for the architecture, the museums, or a taste of jazz, it gives you something to cherish.

Just be ready: you’ll leave full, a little windblown, and completely charmed.

Where to Stay in Chicago

Choosing where to stay in Chicago depends on your style. Here are a few popular spots:


The Loop (Best for Architecture Lovers)

  • Stay at: The Palmer House Hilton or the Virgin Hotels Chicago
  • Central to Millennium Park, the Art Institute, and iconic buildings
  • Easy access to public transportation

 

River North (Trendy & Lively)

  • Stay at: The Godfrey Hotel, known for its rooftop lounge with city views
  • Walkable to the Magnificent Mile, galleries, and nightlife


Wicker Park (Hip & Artsy)

  • Stay at: The Robey — cool, industrial-chic hotel with a rooftop bar
  • Great for vintage shops, independent boutiques, and street art


Pro Tip: Hotel prices can vary widely. Look for deals in the shoulder seasons (spring or fall) for better rates.

Where to Eat (Yes, It’s That Good)

Chicago is a food paradise. From deep-dish to fine dining, here’s where to indulge:


Breakfast & Brunch

  • Wildberry Pancakes & Cafe (Downtown): Over-the-top pancake creations
  • Little Goat Diner (West Loop): Inventive diner fare by Stephanie Izard


Lunch

  • Lou Malnati's (Various Locations): The quintessential Chicago deep-dish experience
  • Portillo's Hot Dogs (Various Locations): A Chicago institution for hot dogs and Italian beef

 

Dinner

  • Girl & the Goat (West Loop): Globally-inspired dishes with bold flavors
  • Alinea (Lincoln Park): Multi-sensory, Michelin-starred dining experience (reservations essential!)


Dessert & Snacks

  • Ghirardelli Ice Cream & Chocolate Shop (Wrigleyville): Indulgent sundaes and chocolates
  • Garrett Popcorn Shops (Various Locations): The famous Chicago mix of cheese and caramel popcorn



Drinks

  • Cindy's Rooftop (The Loop): Stunning views of Millennium Park and Lake Michigan
  • The Violet Hour (Wicker Park): Hidden, speakeasy-style cocktail lounge

 

Top Travel Tips

  • 'L' Train over Taxi: It’s efficient, scenic, and connects you to all the neighborhoods
  • Dress in layers: Chicago weather can change in an instant (hence the nickname, Windy City!)
  • Explore beyond downtown: Each neighborhood has its own unique vibe and hidden gems