Claire Schlafly

2 weeks ago | theinfatuation.com | Adrian Kane |John Ringor |Josh Barnett |Claire Schlafly

The StopAlong’s bright, retro dining space in Wicker Park is full of old Star Wars memorabilia, arcade games, and cartoon paintings of superheroes stuffing their faces with pizza and burgers. And you should do the same because their Stop-In is one of the city’s best smashburgers. The two patties have a great char with just the right amount of saltiness, and they’re perfectly complemented by caramelized onions, pickles, and a tangy combo of special sauce and melty cheese.

3 weeks ago | theinfatuation.com | Nick Allen |John Ringor |Claire Schlafly |Sam Faye

Italian, overlooking the river, in the fancy St. Regis hotel, big-name chef—this Lakeshore East spot has “see and be seen” in its DNA. Couples with multiple summer homes linger over a casual $400 bottle of wine, while a rock band wearing cut-off jean vests and graphic tees eat rigatoni in a giant booth. And with the combined magic of dim lighting and remembering to pick up your dry cleaning, you will also feel like a pasta-twirling VIP.