A three-day itinerary for exploring Chicago

• Day 1: Magnificent Mile and Navy Pier
  Begin the day with a visit to the Magnificent Mile, a bustling shopping district in the heart of the city. The mile-long stretch has a variety of stores and boutiques to explore, and provides a great opportunity to experience the hustle and bustle of Chicago. Follow this up with a visit to Navy Pier, a historic landmark home to multiple attractions like the Ferris wheel, Chicago Children’s Museum and a variety of restaurants. End the day with a magical sunset aboard the Chicago Architecture River Cruise which offers breathtaking views of the city at night.
• Day 2: Millennium Park and Art Institute of Chicago
  Start the day at the famous Millennium Park, a sprawling 25-acre park featuring world-famous artworks such as the Cloud Gate sculpture, the Crown Fountain and other art installations. Marvel at the Art Institute of Chicago, which houses a vast collection of artworks from around the world, including the famous painting, A Sunday Afternoon on the Island of La Grande Jatte by Georges Seurat. Don't miss out on the panoramic views of the city from the Willis Tower's Skydeck, located in the financial district.
• Day 3: Chicago Riverwalk and Wrigley Field
  Start the day experiencing the Chicago Riverwalk, which runs through the city centre and provides a picturesque view of the skyline. Follow this with a visit to the Wrigley Field, a historic baseball stadium that's played host to many legends of the sport. After the game, take a stroll through the neighbourhood of Wicker Park, Bucktown and Ukrainian Village for a diverse range of dining options ranging from street food to high-end restaurants.

Time and Costs Estimates

• Magnificent Mile and Navy Pier (4-6 hours, $30-60 depending on activities chosen)
• Chicago Architecture River Cruise ($45-55 depending on the time of day)
• Millennium Park and Art Institute of Chicago (3-5 hours, $25-35 depending on activities chosen)
• Willis Tower's Skydeck ($25-35 depending on time of day and how many attractions you combine)
• Chicago Riverwalk and Wrigley Field (5-7 hours, $35-60 depending on activities chosen)
• Total Estimated Costs: $160-245

Transportation

If this is your first-time visiting Chicago or you are not familiar with the city, it is recommended that you use public transport or ride-sharing like Uber for safety reasons. You can get a Ventra card to ride CTA trains or buses which require tapping your card on terminals. A single ride costs $2.50 on trains and buses. With Uber, the costs vary depending on the time of day and location, and usually start at $10. Drive time may take longer depending on traffic and timing, so public transport or ride-sharing are highly recommended.

Useful Tips

Chicago has plenty of free events and neighbourhood festivals throughout the year. If you're interested in more museums or art galleries, consider purchasing the Chicago CityPASS which grants access to attractions listed in the itinerary as well as other tourist spots at a discounted rate.

Airports

Chicago O'Hare International Airport (ORD) is the primary airport in Chicago located 26 kilometres Northwest of the city centre while Midway International Airport (MDW) is 17 kilometres Southwest of the city centre. Both airports have served millions of travellers from all over the world and it's recommended that you plan ahead to arrive at the airport 2-3 hours before your flight since they tend to get crowded. Airports are accessible via CTA trains, buses and ride-sharing platforms like Uber and Lyft.