For all of the many wonderful things about Chicago—it’s one of my favorite cities in the US, and a frequent ‘best big city’ winner in our Readers’ Choice Awards—eventually, even those who love the city as much as I do will crave a change of pace. Enter: the weekend getaway. During the four years I spent living in the area in my early 20s, I went on a fair share of weekend trips. From jaunts up north to Milwaukee to quick flights to Nashville, Chicago’s well-connected airport and nearby highways make it easy to arrive in a wonderful escape after a fairly short amount of travel.
Whether you’re looking for a sunny stay away from the city’s brutal winters or a nature-filled oasis just a short drive away, there are so many wonderful spots within a few hours of travel, many of which I’ve personally visited and can recommend. From girls trips and romantic escapes to solo vacations and family-friendly road trips, there is a destination for everyone on this list—and advice on where to stay once you get there. Read on for nine of the best weekend trips from Chicago—all within a three-hour drive or flight from the city.
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