Chicago

United States (Illinois)

"Architecture, Lakefront Beaches & Deep-Dish Pride"

Chicago sits on the shore of Lake Michigan with one of the world's great skylines. The Chicago Architecture Center river cruise is the essential introduction, followed by Millennium Park's Cloud Gate, the Art Institute, and the Museum Campus with the Field Museum and Shedd Aquarium. Neighborhoods like Wicker Park, Pilsen, and Lincoln Park show the local side, while deep-dish pizza, hot dogs, and fine dining keep foodies busy. Summer brings beaches, festivals, and Cubs games at Wrigley Field.

Architecture river cruise, Millennium Park & Cloud Gate, Art Institute of Chicago, Navy Pier, Skydeck or 360 Chicago, Field Museum, Shedd Aquarium, Wrigley Field

May–October

Take the architecture boat tour first; use the 'L' trains; summer festivals fill hotels, so book early

A great long-weekend city for culture and food lovers. Sell summer for lakefront energy and festival season.

📍 Chicago skyline rising behind boats in Burnham Harbor