Key Takeaways Why a Full Week Most people give Chicago a weekend. Fly in Friday, see the Bean, eat deep-dish, fly out Sunday. And they leave thinking they know this city. They don’t. They saw a highlight reel. A week changes the math. A week lets you eat in the same neighborhood twice, which is when you find the place that isn’t in the guides. It lets you wake up on a Wednesday with nowhere to be until noon and discover that Chicago at 9 AM on a weekday, with the coffee shops full and
Key Takeaways Why a Full Week, Why Chicago Five days in Chicago is a great honeymoon. Seven days is a better one. The difference is pace. With a week, you don’t have to choose between the Art Institute and the architecture boat tour—you can do both, on different days, with a spa morning in between. You can eat at a West Loop restaurant on Monday and go back on Thursday because the pasta was that good and you’re married now and nobody’s keeping score. Chicago earns this kind of trip because it doesn’t perform romance
2026 Chicago Cubs Season Preview: Roster, Schedule & World Series Odds 📅 March 25, 2026 ⏱ 13 min read 🏟 Wrigley Field — 1060 W Addison St, Chicago This is the year. After a 92-win season and an NLDS run in 2025, the Cubs went all-in this offseason — landing Alex Bregman on a $175 million deal, trading for Edward Cabrera, locking up Pete Crow-Armstrong for $115 million, and rebuilding the bullpen from the ground up. The Friendly Confines haven’t buzzed like this since 2016. Here’s everything you need to know heading into Opening Day