#17: Chicago, Illinois
Chicago has a lot of big-city appeal, especially for travelers who love architecture, museums, food, sports, and lakefront views. Visitors come for deep-dish pizza, Millennium Park, Navy Pier, the Art Institute, river cruises, and skyline photos. In warmer months, it can feel like one of America’s most exciting urban getaways.

The trip can get expensive quickly in central areas, and the weather can be a real wildcard. Summer brings crowds around major attractions, while winter can be brutally cold and windy. Travelers who want a Midwest city break with fewer headaches might prefer Milwaukee or Madison.
