Adventurous 3-Day Trip to Chicago

• Day 1: Navy Pier & Millennium Park
  Start the day off with a visit to Navy Pier, a top Chicago tourist attraction with shops, restaurants, a Ferris wheel, and other attractions. Afterward, head to Millennium Park to see the famous "Bean" sculpture, explore gardens, and enjoy the scenery. End the day with a self-guided Segway tour through the city's landmarks.
  
• Day 2: Skydiving & Architecture Tour
  Start the day early with an adrenaline-pumping indoor skydiving experience. Then, take a Chicago architecture boat tour to learn about the city's famous buildings and skyline. End the day with a visit to the John Hancock Observatory for stunning views of the city.
  
• Day 3: Rock Climbing & Sports Game
  Start the day with indoor rock climbing at Maggie Daley Park. Next, head to Wrigley Field to watch a Cubs baseball game or to the United Center to watch a Chicago Bulls basketball game (depending on the season). End the day with a visit to one of the city's famous blues clubs, like Kingston Mines or Buddy Guy's Legends.
  

Time and Cost Estimates

• Navy Pier (3 hours, free entry)
• Millennium Park (2 hours, free entry)
• Segway tour (2 hours, $65 per person)
• Indoor Skydiving (1 hour, $60 per person)
• Architecture boat tour (1.5 hours, $35 per person)
• John Hancock Observatory (1 hour, $25 per person)
• Indoor rock climbing (2 hours, $20 per person)
• Sports game (3-4 hours, ticket price varies)
• Blues club (2-3 hours, cover charge varies)
• Total Estimated Costs: $200-$300 per person

Transportation

Chicago's public transportation system is one of the best in the country, with many options for getting around the city. The CTA offers train and bus services throughout the city and to suburbs. A 3-day pass costs $20 per person, and a 7-day pass costs $28 per person. Taxis and ride-sharing services like Uber and Lyft are also widely available.

Useful Tips

If you have more time, consider visiting the Art Institute of Chicago or taking a bike tour around the city. For those with less time, skip the rock climbing or blues club to make more time for other activities. Additionally, consider visiting during the off-season to save money and avoid crowds.

Airports

Chicago has two major airports: O'Hare International Airport (ORD) and Midway International Airport (MDW). O'Hare is the larger of the two and is located 17 miles northwest of downtown Chicago, while Midway is located 10 miles southwest of downtown Chicago. Both airports offer a range of transportation options, including taxis, public transportation, and ride-sharing services.