Chicago 2-Day "City Experiences" Itinerary

  1. Day 1: Art & History of Chicago
    Start your day at the Art Institute of Chicago (9:00 AM - 5:00 PM), located in Grant Park. Walk through the museum's impressive contemporary art galleries before making your way to the famous Thorne Miniature Rooms, which represent European interiors from the late 13th century to the 1930s. Take a quick lunch break at The Gage restaurant (11:30 AM - 10:00 PM) nearby, which offers classic American and British dishes. Afterward, visit the Chicago History Museum (9:30 AM - 4:30 PM) to learn more about the city's fascinating past. Finish the day with a stroll around Millennium Park, where you'll find the iconic Cloud Gate sculpture and the beautiful Lurie Garden.

    Total walking time: 28 minutes (1.4 miles) | Total tour time: Approx. 6 hours

  2. Day 2: Food & Fun in Chicago
    Start your day at Lou Malnati's Pizzeria (11:00 AM - 11:00 PM) and enjoy the famous deep-dish pizza that Chicago is known for. Afterward, head to the Lincoln Park Zoo (10:00 AM - 5:00 PM) and spend some time with the animals. Next, take a quick walk to the Chicago History Museum (world-class hot dog stand right behind it, Gene & Jude's) for a classic Chicago-style hot dog lunch. Later in the day, visit the Navy Pier (10:00 AM - 8:00 PM) and take a ride on the Centennial Wheel for a breathtaking view of the city skyline. Finish the night off by catching a comedy show at The Second City, Chicago's premier comedy club (check showtimes).

    Total walking time: 32 minutes (1.5 miles) | Total tour time: Approx. 7 hours

Time and Costs Estimates

  • Art Institute of Chicago (2-3 hours, $25 per adult)
  • The Gage (1 hour, $20-30 per person)
  • Chicago History Museum (2 hours, $19 per adult)
  • Lou Malnati's Pizzeria (1-2 hours, $20-25 per person)
  • Lincoln Park Zoo (2-3 hours, free admission)
  • Gene & Jude's (30 minutes, $5-10 per person)
  • Navy Pier (2-3 hours, free admission, $18 for Centennial Wheel ride)
  • The Second City (2-3 hours, $20-30 per person)
  • Total Estimated Costs: $132 - $167 per person

Useful Tips

If you have more time, consider visiting the Field Museum or taking an architecture boat tour on the Chicago River. If you have less time, skip the Lincoln Park Zoo and Second City comedy show. Public transportation is a convenient and affordable option for getting around the city. Don't forget to bring a jacket during the colder months and comfortable shoes since there is quite a bit of walking involved.

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