2 Days Exploring Chicago Itinerary

Start your day with a visit to the Skydeck Chicago at Willis Tower (Sears Tower), where you can enjoy breathtaking views of the city from the observation deck. Afterward, take a short walk to Millennium Park to see the iconic Cloud Gate sculpture, also known as 'The Bean.'

Head over to the Art Institute of Chicago, one of the oldest and largest art museums in the United States. Enjoy a leisurely lunch at The Purple Pig, known for its Mediterranean-inspired small plates.

Spend your evening at Navy Pier, which offers various entertainment options including rides, shops, and restaurants. For dinner, indulge in some classic deep-dish pizza at Lou Malnati's Pizzeria.