What To Do In Chicago For A Weekend

People are currently reading this guide.

Chicago: The Windy City, Not Your Average Weekend Getaway

Chicago, the city that birthed deep-dish pizza and gave us the blues, is a place where skyscrapers kiss the clouds and the spirit never sleeps. If you're planning a weekend escape and considering this Midwestern metropolis, let me tell you, you're in for a treat. But before you pack your bags, let’s dive into what this city has to offer.

Day One: A Taste of the City

Morning: Start your day with a hearty breakfast at Lou Malnati’s Pizzeria. Yes, you read that right. Breakfast pizza. Don’t knock it till you try it. After fueling up, head to Millennium Park. Take a selfie with The Bean (officially called Cloud Gate), and pretend you’re a character in a rom-com.

Afternoon: Cruise down the Chicago River on an architecture tour. You’ll feel like a real estate mogul as you gawk at the city’s skyline. Trust me, you’ll never look at buildings the same way again. Afterward, treat yourself to a Chicago-style hot dog. No ketchup, remember. It’s a rule.

Evening: Catch a live show at Second City, the comedy mecca that launched the careers of countless funny people. If laughter isn’t your thing, explore the vibrant nightlife in Wicker Park or Bucktown. Just beware of the craft beer scene – it’s a slippery slope.

Day Two: Culture Vulture and Foodie Extravaganza

Morning: Immerse yourself in art at the Art Institute of Chicago. They have everything from Van Gogh to Warhol. If art’s not your jam, the Field Museum is home to Sue, the largest T-Rex ever discovered. Who doesn’t love a good dinosaur?

Afternoon: Take a leisurely stroll through Lincoln Park, one of Chicago's green lungs. Rent a Divvy bike and explore the lakefront. Or, if you prefer to stay indoors, indulge in some retail therapy on Michigan Avenue, the Magnificent Mile.

Evening: Savour the ultimate Chicago experience: deep-dish pizza. Giordano’s is a classic, but there are plenty of other contenders. Pair your pizza with a cold beer and enjoy the city lights.

Day Three: Savor the Last Bites

Morning: Start your day with brunch at a trendy spot like Brunch. Trust me, the name checks out. Afterward, catch a game at Wrigley Field if there’s a Cubs game. Even if you’re not a baseball fan, the atmosphere is electric.

Afternoon: Visit the Navy Pier, a classic Chicago attraction. Enjoy the Ferris wheel, arcade games, and stunning lake views. Or, if you’re feeling adventurous, take a boat tour to see the city from a different perspective.

Evening: Bid farewell to Chicago with a rooftop bar experience. Enjoy stunning city views as you sip on a cocktail. It’s the perfect way to end your weekend adventure.

How to...

  • How to survive the Chicago winter? Layer up, invest in a good coat, and embrace the cozy indoor activities.
  • How to order a Chicago-style hot dog? No ketchup, relish, onions, tomatoes, peppers, celery salt, mustard, and a poppy seed bun.
  • How to navigate the L train? Get a Ventra card, learn the lines, and be prepared for crowds during rush hour.
  • How to find the best deep-dish pizza? Try Giordano’s, Lou Malnati’s, or Pequod’s, but don’t be afraid to explore other options.
  • How to experience Chicago like a local? Embrace the city’s unique culture, try new foods, and explore different neighborhoods.

Remember, this is just a starting point. Chicago is a city that rewards exploration. So, go out there, get lost, and create your own unforgettable memories.

5524240731083424429

hows.tech

You have our undying gratitude for your visit!