Chicago

The Ultimate Guide to Travelling in Chicago

Getting Started

Before You Go

  • Check the weather forecast: Chicago is known for its unpredictable weather, so pack accordingly.
  • Book your accommodations: Choose from a wide range of hotels, hostels, and Airbnb options.
  • Plan your itinerary: Decide on the places you want to visit and activities you want to do.

Places to Go

Downtown Chicago

  • Willis Tower (Sears Tower): Take in panoramic views of the city from the Skydeck on the 103rd floor.
  • Millennium Park: Explore iconic landmarks like the “Cloud Gate” sculpture, the Jay Pritzker Pavilion, and the Lurie Garden.
  • The Art Institute of Chicago: Discover world-renowned art collections, including works by Monet, Picasso, and Van Gogh.

North Side

  • Wrigley Field: Catch a Cubs game at this historic baseball stadium.
  • Lincoln Park Zoo: Visit the historic zoo, which offers free admission year-round.
  • The Lakefront Trail: Take a stroll or bike ride along the shores of Lake Michigan.

West Side

  • Garfield Park Conservatory: Explore the stunning botanical gardens and greenhouses.
  • The United Center: Catch a concert or sports game at this iconic venue.

South Side

  • Museum of Science and Industry: Discover interactive exhibits on science and technology.
  • Jackson Park: Visit the Osaka Garden, the Japanese Garden, and the Museum of Science and Industry.

Activities

Outdoor Activities

  • Take a stroll along the Lakefront Trail: Enjoy the scenic views of Lake Michigan and the city skyline.
  • Rent a bike: Explore the city on two wheels with Divvy Bike Share or other rental options.
  • Kayak or paddleboard: Rent equipment and explore the Chicago River or Lake Michigan.

Cultural Experiences

  • Take a food tour: Sample the city’s diverse culinary scene, from deep-dish pizza to Vietnamese cuisine.
  • Attend a festival: Chicago hosts numerous festivals throughout the year, including Lollapalooza and Pitchfork Music Festival.
  • Visit a museum or gallery: Explore world-class institutions like the Art Institute of Chicago, the Field Museum, and the Museum of Contemporary Art.

Where to Eat

Classic Chicago Eats

  • Deep-dish pizza: Try Lou Malnati’s, Pizzeria Uno, or Gino’s East.
  • Hot dogs: Visit Portillo’s, Alinea, or Gene & Georgetti.
  • Italian beef sandwiches: Head to Al’s Beef, Mr. Beef, or Johnnie’s Beef.

Trendy Spots

  • Girl & the Goat: Savor Mediterranean-inspired cuisine from Top Chef winner Stephanie Izard.
  • Au Cheval: Enjoy trendy diner fare and craft cocktails.
  • Blackbird: Discover modern American cuisine with a focus on local ingredients.

Where to Stay

Luxury Hotels

  • The Langham Chicago: Unwind in upscale accommodations with stunning city views.
  • The Four Seasons Hotel Chicago: Enjoy five-star amenities and service.
  • The Ritz-Carlton, Chicago: Relax in luxurious rooms and suites.

Budget-Friendly Options

  • Hostel One Chicago: Stay in dorm-style or private rooms at an affordable price.
  • Airbnb apartments: Rent a cozy apartment in a trendy neighborhood like Wicker Park or Logan Square.
  • Budget hotels: Consider options like the Freehand Chicago or the Field Hotel.

Things to Know

Safety

  • Be aware of your surroundings, especially at night.
  • Avoid walking alone in dimly lit areas.
  • Keep valuables secure and be cautious of pickpocketing.

Tipping Culture

  • Tip 15% to 20% at restaurants and bars.
  • Tip $1 to $2 per drink at cafes and coffee shops.

Weather

  • Pack layers for unpredictable weather.
  • Bring an umbrella or raincoat in case of rain.

Transportation

Public Transportation

  • ‘L’ train (elevated train): Use the Ventra app or buy a Visitor Pass for unlimited rides.
  • Bus: Pay with cash or use the Ventra app.

Ride-Sharing Services

  • Uber: Available throughout the city.
  • Lyft: Another popular ride-sharing option.

Taxi Services

  • Yellow Cab: Hail a traditional taxi on the street or book in advance.

Tips and Tricks

Insider Knowledge

  • Take advantage of free museum days, like the Art Institute’s Free Family Day.
  • Explore neighborhoods like Wicker Park, Logan Square, and Pilsen for unique shops and eats.
  • Visit during the off-season (October to May) for lower prices on accommodations and attractions.

Money-Saving Tips

  • Buy a Chicago CityPASS for discounted admission to top attractions.
  • Take advantage of happy hour deals at bars and restaurants.
  • Consider purchasing a Ventra card for public transportation instead of buying individual tickets.

Language and Currency

  • Language: English is the primary language spoken in Chicago, but you may encounter Spanish, Polish, and other languages.
  • Currency: The US dollar is the official currency.

Other Things to Know

Events and Festivals

  • Lollapalooza: A four-day music festival in Grant Park each August.
  • Pitchfork Music Festival: A three-day indie music festival in Union Park each July.
  • Taste of Chicago: A food festival featuring local cuisine in Grant Park each July.

Shopping

  • The Magnificent Mile: Upscale shopping along Michigan Avenue.
  • State Street: Budget-friendly options like H&M and Forever 21.
  • Wicker Park: Trendy boutiques and vintage shops.

This comprehensive guide should help you plan an unforgettable trip to Chicago!