Chicago

The Ultimate Guide to Travelling in Chicago

Welcome to the Windy City! Chicago is a world-class destination that offers something for everyone. From its stunning architecture and beautiful beaches to its vibrant music scene and world-class museums, there’s no shortage of things to see and do.

Places to Go

Landmarks and Architecture

  • Willis Tower (formerly Sears Tower): Take in panoramic views of the city from the Skydeck on the 103rd floor. Don’t forget to step out onto the Ledge for a thrilling experience.
  • Millennium Park: Explore iconic landmarks like the “Cloud Gate” sculpture (known as “The Bean”) and the Jay Pritzker Pavilion, which hosts free outdoor concerts and events during the summer.
  • ** Navy Pier**: This lakefront attraction offers boat cruises, an amusement park, and entertainment options for all ages.

Museums

  • Art Institute of Chicago: One of the top art museums in the country, featuring works by famous artists like Monet, Picasso, and Van Gogh.
  • Field Museum: Home to Sue, the largest and most complete T. rex skeleton ever found, as well as ancient Egyptian artifacts and a vast natural history collection.
  • Museum of Science and Industry: Explore interactive exhibits on science and technology, including a mirrored maze and a coal mine.

Neighborhoods

  • Wicker Park/Bucktown: Known for its trendy boutiques, art galleries, and restaurants serving international cuisine.
  • Logan Square: A hip neighborhood with a lively arts scene, vintage shops, and some of the city’s best Mexican food.
  • Pilsen: Chicago’s largest Hispanic neighborhood, featuring vibrant street art, authentic Mexican eateries, and a thriving cultural scene.

Parks and Gardens

  • Lincoln Park: One of the city’s largest parks, offering beautiful gardens, a zoo, and plenty of recreational activities like boating and biking.
  • Millennium Park: Home to the stunning Lurie Garden, which features over 200 species of plants and flowers.

Activities

Outdoor Activities

  • Kayaking or paddleboarding on Lake Michigan: Rent equipment and explore the city’s beautiful lakefront.
  • Walking or biking the 606 Trail: A elevated park built on a former rail line, offering stunning views of the city.
  • Sailing or taking a boat tour: Experience Chicago’s vibrant water culture and enjoy breathtaking views.

Indoor Activities

  • Shopping at Water Tower Place: An upscale mall featuring high-end retailers and dining options.
  • Spending an evening at a comedy club: Try out one of the city’s many comedy clubs, like Second City or Zanies.
  • Visiting a virtual reality experience: Explore immersive VR experiences at places like VR First Chicago.

Where to Eat

Classic Chicago Eats

  • Portillo’s: A Chicago institution serving up famous hot dogs and Italian beef sandwiches.
  • Pizzeria Uno: The birthplace of deep-dish pizza, offering a classic Chicago dining experience.
  • Al’s Beef: Another iconic spot for Italian beef sandwiches.

Trendy Restaurants

  • Au Cheval: A trendy diner known for its burgers and upscale atmosphere.
  • Girl & the Goat: A Mediterranean-inspired restaurant from Top Chef winner Stephanie Izard.
  • The Purple Pig: A small plates restaurant with a focus on Mediterranean cuisine.

Ethnic Dining

  • Xoco: Rick Bayless’s casual Mexican spot, serving up fresh tortas and soups.
  • Black Dog Gelato: A unique gelato shop featuring flavors like lavender honey and stracciatella.
  • Dusek’s: A Polish deli offering traditional dishes like pierogi and bigos.

Where to Stay

Luxury Hotels

  • The Langham, Chicago: An upscale hotel with elegant rooms and a stunning rooftop pool.
  • The Four Seasons Hotel Chicago: A world-class hotel featuring luxurious amenities and breathtaking views of Lake Michigan.
  • The Peninsula Chicago: A 5-star hotel offering high-end accommodations and exceptional service.

Boutique Hotels

  • The Robey: A stylish boutique hotel with unique rooms and a trendy rooftop bar.
  • The Hotel Julian: A chic boutique hotel featuring elegant rooms and a beautiful courtyard.
  • The Willa Lincoln Park: A historic mansion turned boutique hotel, offering luxurious suites and a relaxing atmosphere.

Budget-Friendly Options

  • The Holiday Inn Express Chicago: A budget-friendly option with clean rooms and free breakfast.
  • The Hampton Inn Chicago Downtown: A no-frills hotel with comfortable beds and a convenient location.
  • The Hostel B&B: A budget-friendly hostel with dorms and private rooms available.

Things to Know

Weather

  • Summer: Warm weather, hot days, and occasional thunderstorms. Average highs in the mid-80s (°F).
  • Winter: Cold temperatures, snowfall, and freezing rain. Average lows in the mid-teens.
  • Spring: Unpredictable weather with sudden temperature changes.

Safety

  • Be aware of your surroundings, especially at night or in crowded areas.
  • Avoid walking alone in dimly lit or deserted streets.
  • Follow local advice on safety and security.

Etiquette

  • Tip servers at restaurants and bars (15-20% is standard).
  • Use public transportation, walk, or bike whenever possible to reduce traffic congestion.
  • Respect local customs and traditions, especially in ethnic neighborhoods.

Transportation

Public Transportation

  • The ‘L’ Train: Chicago’s elevated train system with eight different lines and over 150 stations.
  • Buses: An extensive network of buses covering all areas of the city.
  • Water Taxi: A fun way to explore the city’s lakefront.

Taxis

  • Yellow Cab: The most widely recognized taxi company in Chicago.
  • Ride-hailing services: Uber and Lyft are also available in the city.

Bike Share

  • Divvy Bikes: A bike-sharing system with stations throughout the city.
  • Bike rentals: Several companies offer bike rentals for short-term use.

Tips

Insider Tips

  • Take advantage of free attractions, like Millennium Park and Navy Pier, to save money.
  • Try local restaurants instead of chain eateries for a more authentic dining experience.
  • Explore neighborhoods outside the downtown area for unique shops and cultural experiences.

Practical Tips

  • Pack layers for unpredictable Chicago weather.
  • Bring a water bottle to stay hydrated during outdoor activities.
  • Be prepared for crowds at popular attractions like Willis Tower or Millennium Park.

By following this guide, you’ll be well on your way to experiencing the best of Chicago. Whether you’re interested in architecture, art, food, or entertainment, there’s no shortage of things to see and do in this world-class city.