13. Chicago, IL

Must-eat/drink: A burger at Au Cheval

Don't leave without: An architecture boat tour, closing down a 4am bar, catching some comedy, getting out of Downtown

Weekend highlights: If you've never been to Chicago, it's understandable that there are certain obligatory boxes you're going to want to check, which is fine. Get that selfie in front of the Bean before hitting a museum or the aquarium if you must. Take an architecture boat tour (actually a fantastic intro to Downtown and the lakefront). Hit Second City or iO for some world-class comedy, and (obviously) consume the local holy trinity of deep dish, Chicago-style dogs, and Italian beef.

But you're doing yourself a serious disservice if you spend your whole weekend tethered to the Downtown area, because the neighborhoods are where you find the city's true pulse. Head north to Wrigleyville if sports are your thing, or to Lincoln Square for some Half Acre beer and incredible pie if they aren't. Head west and walk the 606, a repurposed discontinued train line linking four of the city's most vibrant (and delicious) neighborhoods. Head south to Bridgeport for the White Sox, yes, but also for Maria's, a hybrid beer bar/bottle shop some call a "slashie" that you won't want to leave. Just don't spend your whole weekend within a couple of blocks of Michigan Ave, because you're better than that. --Matt Lynch, executive editor