However, the real challenge starts with the planning. So, if you’re planning for a simple or grand vacation for your family, this city and its surrounding areas have something for you. It’s renowned for its gorgeous architecture, museums, and of course, the deep-dish pizza.īut beyond the city limits, you’ll find countless resorts that offer a peaceful escape from the city buzz.

Chicago, also known as the Windy City, is a lively metropolis at the heart of the Midwest.