Chicago

Ultimate Guide to Exploring Chicago: A Comprehensive Tourist’s Companion

Overview

Welcome to the Windy City! Chicago, a vibrant metropolis nestled along the shores of Lake Michigan, offers an eclectic mix of culture, architecture, food, and entertainment. This guide will help you make the most out of your visit by providing insights into places to go, activities, where to eat, where to stay, transportation, tips, and other points of interest.

Places to Go

  1. The Art Institute of Chicago: A world-renowned art museum housing an extensive collection spanning 5,000 years. Don’t miss the American art wing and works by Monet, Van Gogh, and Picasso.
  2. Millennium Park: Home to iconic landmarks such as Cloud Gate (The Bean) and the Crown Fountain.
  3. Navy Pier: Offers a variety of attractions, including the Ferris wheel, Chicago Children’s Museum, and boat tours.
  4. Skydeck at Willis Tower: Experience breathtaking views from the 103rd floor, including the famous Ledge glass balconies.
  5. The Magnificent Mile (Michigan Avenue): A premier shopping destination with stunning architecture, museums, and dining options.
  6. Lincoln Park Zoo: One of the oldest zoos in North America, free to enter, and home to over 1,100 animals.
  7. Shedd Aquarium: The world’s largest indoor aquarium, featuring marine life from around the globe.
  8. Field Museum: Dedicated to natural history, this museum is home to Sue, the largest Tyrannosaurus rex fossil ever discovered.
  9. Museum of Science and Industry (MSI): Explore interactive exhibits on science and technology, including a coal mine tour and a U-505 submarine.
  10. Grant Park & Buckingham Fountain: Relax in Grant Park, and enjoy the spectacle of the world’s largest rotating fountain during the summer months.

Activities

  1. Architecture River Cruise: Gain insight into Chicago’s architectural history on a boat tour along the Chicago River.
  2. Night Tour: Discover the city’s iconic skyline and landmarks illuminated after dark.
  3. Comedy Shows: Laugh it up at Second City, home to numerous comedy greats like Tina Fey, Steve Carell, and Dan Aykroyd.
  4. Baseball Game at Wrigley Field: Catch a Cubs game at the historic Wrigley Field.
  5. Blues & Jazz Clubs: Experience live music at venues like Kingston Mines, Green Mill, or Buddy Guy’s Legends.
  6. Rooftop Bars: Enjoy drinks with a view at rooftop bars like Cindy’s, Cerise, or the J. Parker.
  7. The Second City Training Center: Take an improv comedy class and tap into your inner comedian!

Where to Eat

  1. Girl & The Goat: Award-winning small plates restaurant specializing in innovative American cuisine.
  2. Alinea: A 3-Michelin-star restaurant offering a cutting-edge tasting menu experience.
  3. The Purple Pig: Delicious Mediterranean-inspired dishes and an extensive wine list.
  4. Lou Malnati’s Pizzeria: Famous for their deep-dish pizza, a Chicago must-try!
  5. Au Cheval: Highly acclaimed burger joint with a lengthy waitlist.
  6. Smoked: BBQ mastermind Chris Locher brings his Texas roots to the Windy City.
  7. The Signature Room at The 95th: Dine on fine dining with stunning views of Chicago from the John Hancock Center.
  8. Gibsons Italia: Classic Italian dishes in a lively atmosphere, featuring Chicago steakhouse favorite Gibsons Bar & Steakhouse’s signature dry-aged steaks.
  9. The Violet Hour: Artisanal cocktails and small plates served in a speakeasy-style setting.
  10. The Girl & The Goat Takeout + Grocer: Grab some of Stephanie Izard’s delicious dishes to go, or pick up groceries from her market!

Where to Stay

  1. Four Seasons Hotel Chicago: Luxury accommodations with stunning views and exceptional service.
  2. The Langham, Chicago: A five-star hotel offering spacious rooms and a tranquil rooftop pool.
  3. The Ritz-Carlton, Chicago: Upscale accommodation with an excellent location along the Magnificent Mile.
  4. The Robey: A stylish boutique hotel in Wicker Park, featuring a rooftop bar and restaurant.
  5. Eloise Hotel: A charming boutique hotel in Lincoln Park, offering unique rooms and exceptional customer service.
  6. The Hoxton, Chicago: Stylish accommodations with a vibrant lobby bar and an on-site restaurant.
  7. W Hotels Chicago – City Center: Modern luxury hotel with a rooftop pool and lounge, and a prime location in the Loop.
  8. Kimpton Hotel Allegro: A historic hotel in the heart of the Theater District offering comfortable accommodations and excellent customer service.

Things to Know

  1. Chicagoans are friendly and approachable, so don’t be shy about asking for directions or recommendations!
  2. The city is known as the “Windy City” not due to its weather but because of the city’s political leaders, who were known for their eloquence and persuasive speeches.
  3. Chicagoans often refer to their home as “Chi-town” or “The Chi.”
  4. Tipping in restaurants is expected, with a standard of 20% of the total bill.
  5. The city offers a comprehensive transit system, including trains (the ‘L’) and buses, making it easy to get around without a car.
  6. Summers can be hot and humid, while winters are cold with plenty of snow. Be sure to pack accordingly!
  7. The Chicago River flows south to north, contrary to most rivers. This unique feature is celebrated annually during the Chicago River Dyed Green event for St. Patrick’s Day.

Transportation

  1. Chicago Transit Authority (CTA): Operates an extensive network of buses and trains, including the iconic elevated trains (the ‘L’).
  2. Metra: Provides commuter rail service to nearby suburbs and cities.
  3. Divvy Bikes: A bike-sharing system with over 600 stations throughout the city, perfect for exploring Chicago’s neighborhoods.
  4. Taxis and Rideshare Services (Uber/Lyft): Widely available and affordable, especially during off-peak hours.
  5. Water Taxis: A fun way to get around downtown Chicago, with stops along the Riverwalk and at Navy Pier.

Tips

  1. Visit in the summer months for the best weather and outdoor events like Taste of Chicago or Chicago Pride Parade.
  2. Download a transit app (Chicago Transit Tracker, Transit App) to help plan your journey and avoid delays.
  3. Check out free activities like exploring Millennium Park, strolling along the Lakefront Trail, or visiting the Lincoln Park Conservatory.
  4. Don’t miss the Chicago Architecture Center for insightful exhibits about the city’s iconic buildings and skyline.
  5. Visit the neighborhoods of Wicker Park, Bucktown, and Logan Square for unique shops, restaurants, and street art.
  6. Take a day trip to nearby attractions like Frank Lloyd Wright’s Unity Temple or the Morton Arboretum.
  7. Chicagoans love their sports teams, so consider attending a game or tailgating at Soldier Field, Wrigley Field, or Guaranteed Rate Field.