Chicago is one of my favorite cities in the United States. They have nearly 100 museums, 23 Michelin Star restaurants (read What Are Michelin Star Restaurants?if you’re not sure what these are), a dozen 5-star hotels, tons of fantastic events, festivals, musical performances, and pop-ups around the city, world-class luxury shopping, and so much more. We’ve visited more than a dozen times in the last couple of years, and we always find something new to love in the Windy City, which is why I wanted to share my favorite things to do in this Chicago itinerary. I hope this helps you plan the perfect luxurious weekend getaway to Chicago, whether it’s for a mini-honeymoon, family vacation, an anniversary trip, or to simply explore somewhere new!