I’ve always thought that Chicago has one of the most impressive skylines of any city. Combine that with world-class museums, the stunning Chicago River, and the Lake Michigan shoreline, and it’s clear that the Windy City is an incredible vacation spot. Plus, chowing down on a slice of piping hot, deep-dish pizza is one of my favorite Chicago pastimes.
My preferred way of exploring the city’s grid-like streets is on foot, always looking up to admire Chicago’s grand architecture. Although the midwestern hub is large, with many unique neighborhoods, most of the key attractions to check out during your first visit are fairly close to one another and accessible on foot.
Chicago has extremely cold winters and very hot summers, as well as distinct spring and fall seasons, so pack and dress appropriately for each season.
It can be tough to decide which of Chicago’s many museums to visit, from the history-heavy Field Museum—complete with a T-Rex skeleton—to the family-friendly Shedd Aquarium and Museum of Science and Industry to the Art Institute of Chicago, with works from impressionist masters. If you want to visit several, consider a Chicago CityPASS™, which offers free admissions and discounts.
Take a break at lakefront Millennium Park, a quick taxi ride from most of the museums. Snap photos of Lake Michigan, the skyline, and the famous Bean (Cloud Gate) statue, a mirrored monument that reflects the city and its visitors.
Chicago’s immense skyscrapers can be viewed from the ground, but seeing them from up above is a magical experience. Although you can visit the top of the Willis Tower, Chicago’s tallest building, it’s best to catch panoramic views of the city from the 360 Chicago Observation Deck in the John Hancock Building so you can spot Willis Tower.