Chicago

The Windy City Beckons: A Guide to Exploring Chicago

Chicago, the “Windy City,” is known for its vibrant culture, stunning architecture, and delicious food scene. From deep-dish pizza to world-class museums, this city has something to offer everyone. If you’re planning a trip, let me help you navigate its many treasures!

Where to Visit:

• Millennium Park: This iconic park is home to the Cloud Gate sculpture (aka “The Bean”), the Crown Fountain with its interactive video displays, and the stunning Jay Pritzker Pavilion.

• Navy Pier: A bustling destination for all ages, Navy Pier offers breathtaking views of the city and lake, amusement rides, restaurants, shops, and free concerts during the summer months.

• Art Institute of Chicago: Marvel at masterpieces by renowned artists like Monet, Picasso, and Van Gogh in this world-class museum.

• Museum of Science and Industry: Explore fascinating exhibits on science and technology, from a working coal mine to a U-505 submarine.

• Field Museum: Discover the wonders of natural history at the Field Museum, home to Sue the T. Rex and other amazing artifacts.

What to Eat:

Chicago is a foodie paradise! Don’t miss these local favorites:

• Deep-Dish Pizza: A true Chicago icon, try Lou Malnati’s or Giordano’s for this delicious, cheesy treat. Be sure to order a slice (or a whole pie!) and experience the unique “crust-first” style.
• Chicago Hot Dogs: A classic Chicago hot dog is all about the toppings - mustard, relish, onions, sweet pickles, tomato wedges or slices, pickled sport peppers, green sweet pickle, chopped white onions, a dill pickle spear, mustard and bright green relish are all essential elements of this iconic local dish.
• Italian Beef: Another must-try Chicago delicacy! This juicy, slow-roasted beef sandwich is served on a crusty roll with a flavorful gravy and your choice of toppings like giardiniera (a spicy pickled vegetable relish) or sweet peppers.

Things to Do in Chicago:

• Enjoy the Architecture: Take a boat tour down the Chicago River (Chicago Architecture Foundation River Cruise) for breathtaking views of the city’s skyline and learn about its architectural history.

• Visit the Skydeck: Experience the thrill of standing on the glass ledge 103 floors above ground at the Willis Tower (formerly Sears Tower) Skydeck, offering stunning panoramic views.

• Explore Museums: Immerse yourself in art, culture, and science at world-renowned institutions like the Art Institute of Chicago, the Field Museum, or the Museum of Science and Industry.

• Catch a Game: Cheer on the Cubs at Wrigley Field or experience the roar of the crowd at a White Sox game at Guaranteed Rate Field.

• Enjoy Live Music: From blues to jazz to rock, Chicago’s music scene is vibrant. Catch a show at Kingston Mines for an authentic blues vibe or explore the city’s many other music venues like the Green Mill Cocktail Lounge.

• Walk the Lakefront: Enjoy a leisurely stroll along the beautiful Chicago lakefront, taking in the stunning views of Lake Michigan and exploring the city’s numerous parks, beaches, and attractions.

• Shop Till You Drop: Discover unique treasures in Chicago’s diverse shopping districts. For vintage finds, head to Wicker Park or the Magnificent Mile.

Where to Stay:

• Luxury Hotels:
  • The Peninsula Chicago: Known for its elegance and luxurious amenities.
  • The Langham, Chicago: Offers stunning views and a sophisticated atmosphere.
• Boutique Hotels:
  • The Robey: A trendy hotel with a rooftop bar overlooking the city.
  • The Thompson Hotel: Chic accommodations with a focus on culinary experiences.
• Unique Stays:

Where to Eat:

• Luxury:

  • Ever: This Michelin-starred restaurant offers a tasting menu that showcases modern, innovative takes on classic dishes.
  • Alinea: Renowned for its avant-garde cuisine and unique dining experience.

• Fine Dining:

  • Next Restaurant: Experience the acclaimed “next generation” of fine dining with a new, immersive menu every few months.

• Casual:

  • Portillo’s Hot Dogs: Enjoy a taste of Chicago history with their classic hot dogs and Italian beef sandwiches.
  • Lou Malnati’s Pizzeria: A local institution where you can savor the iconic “Chicago-style” pizza.

• Budget-Friendly:

• The Kimpton Allegro Hotel: Located in the heart of the city, this hotel offers a chic and affordable stay in the Loop.

Unique Stays:

• The Peninsula Chicago: Enjoy a luxurious experience with stunning views of Lake Michigan.

• The Thompson Hotel: Experience a chic and sophisticated stay in the Gold Coast neighborhood.

• The Getaway House: Escape to a secluded cabin near the city for a tranquil getaway.

• Stay in a Historic Landmark: Consider staying at the historic Drake Hotel, known for its elegant rooms and afternoon tea service.

• Enjoy the City’s History:

  • Explore the Past: Immerse yourself in history at the Field Museum or the Art Institute of Chicago.

• Experience Modern Luxury: For a more contemporary stay with an emphasis on comfort and amenities, there are many hotels along the Magnificent Mile.

• Deep-Dish Pizza Heaven: Enjoy a classic Chicago experience by indulging in deep-dish pizza.

• Taste the Classics:

  • Portillo’s Hot Dogs: This Chicago staple is a must-try for any visitor.
  • Garrett Popcorn Shops: Indulge in your choice of Chicago Mix (a blend of caramel and cheese popcorn) or a classic bag of buttered popcorn.

• Chicago Cuisine Adventures: Explore the city’s diverse culinary offerings, like the unique “Chicago-style” hot dogs at local shops like Portillo’s in Chicago.

• Enjoy a Slice (or Two!):

  • Deep Dish Pizza: A classic Chicago experience, and a perfect way to refuel after a long day of exploring the city. Beyond:

• The Art Institute of Chicago: Immerse yourself in art history with a visit.

• Chicago Cultural Center: Explore free exhibitions and performances in this architectural gem.

Explore:

• Deep-Dish Pizza: Enjoy a delicious meal, or enjoy a variety of deep-dish pizza options!
• Music Venues: Enjoy the vibrant music scene at legendary clubs like Kingston Mines and experience the bluesy heart of Chicago.

Next Level:

• Fine Dining: Enjoy a culinary adventure by indulging in Chicago’s culinary scene, from deep-dish pizza to fine dining with a unique “Chicago” twist.

• Music Venues:

• For the best Chicago-style pizza:

  • Pizzeria Bebu: Known for its creative toppings and thin-crust pizzas.
  • Pequod’s Pizza: This Chicago classic is known for its deep-dish pizza, but it’s a bit different: the crust gets caramelized on the edges and the cheese is on top

Enjoy:

• Deep Dish Pizza: Indulge in a “deep dish” experience with a variety of toppings and styles.

• For the best Chicago-style hot dog: Try it with everything!

  • The works: mustard, chopped white onions, sweet pickle relish, a dill pickle spear, tomato wedges or fries, a sprinkle of bright green fluorescent sweet pickle relish (Chicago-style)