More than 55 million people visited Chicago in 2024. I was one of them. Just 90 minutes away via my favorite mode of transportation, Amtrak, I may have made the trip once a month for the last few years. And in the last year, I visited many splurge-worthy favorites that brought me so much joy. Chicago has a magical feel — fantastic food, the river and lake to explore, and incredible people who call it home. It pulls you in.

And don’t let the weather scare you. Chicago is truly a city for all four seasons. I’ve spent spring afternoons, summer weekends, winter nights and fall days wandering around, dining at restaurants that blew me away, and, of course, people watching.

So if Chicago is on your travel bucket list, here are the accommodations, standout restaurants, and activities to add to

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