Chicago - Generated

18 Jun 2026 – 21 Jun 2026 · by alliearnold

Destinations

Chicago, United States

Begin your journey in the vibrant city of Chicago, capturing its distinctive skyline and indulging in a peaceful sunset walk along the shores of Lake Michigan.
Milwaukee, United States

Discover the charm of Milwaukee with its serene lakeside parks, impressive breweries, and a laid-back atmosphere perfect for unwinding.
Madison, United States

Enjoy the tranquil natural beauty of Madison, with leisurely strolls around its scenic lakes and visiting tranquil botanical gardens.
Chicago, United States

Return to Chicago for a final day of relaxation, ensuring a smooth end to your trip with a visit to one of its serene parks or museums.