Old Town

With 30-plus years of experience, and three locations in the city, A New Leaf has become a Chicago mainstay florist. Their arrangements, many of which include gorgeous exotic flowers, are available for delivery or pick-up. Next door to this shop is New Leaf's awesome event space, which has an outdoor courtyard and open, airy interior with exposed brick and cool industrial details. There's another location, also on North Wells, which is open seven days a week, and late, too. The third shop is in the Loop, and only open weekdays, but early (8am).

With 30-plus years of experience, and three locations in the city, A New Leaf has become a Chicago mainstay florist. Their arrangements, many of which include gorgeous exotic flowers, are available for delivery or pick-up. Conveniently, this location is open seven days a week, and until 8pm on weekdays. The other location on North Wells has an awesome event space next door with an outdoor courtyard and open, airy interior with exposed brick and cool industrial details. The third shop is in the Loop, and only open weekdays, but early (8am).

This legendary sketch and improv comedy troupe has churned out some of the country’s best comedians (Joan Rivers, John Belushi, Bill Murray, Tina Fey, and Stephen Colbert—and that’s barely skimming the surface). The group now has a permanent presence in Toronto and Hollywood, but its roots have been firmly planted in Chicago since 1959. You can catch one of their shows any night of the week, but you’ll want to pick up tickets well in advance as shows tend to sell out.

This Old Town juicery goes to great lengths to make their cold pressed juices (and smoothies, yogurts, salads, snacks…) live up to its name. A dedicated juice chef takes care of sourcing (all local, always organic), and the hilariously punny names make remembering your favorite blends easy (Juice Springsteen, Punky Juice-ster, Juice-tin Bieber—you get the idea). Plus, the space itself—all white save for the occasional bursts of neon—is nice for a mid-day breather.

With three locations and a newly minted event space—boasting two levels of exposed brick and a courtyard—A New Leaf is a pretty sizable operation with a boutique-y, refreshingly approachable sensibility, which is good since special occasion and wedding florals are their jam. In fact, we asked them to beautify a number of Chicago goop pop-related events. And while they happily take phone orders, we suggest stopping by the Old Town flagship in person to DIY a bouquet from a garden’s worth of cut flowers and color-coordinated ribbon wall. There's also an outpost in the Loop.

Chicago-based Intelligentsia ushered in a new wave of gourmet coffee shops, the kind where responsibly sourced and expertly roasted coffee is prepared using methods that, though time-consuming, result in a pretty perfect cup. As a rule, all outposts are aesthetically unique (five others are scattered in the Loop, Lakeview, Millennium Park, Logan Square, and Wicker Park), offer free Wifi, and loads of seating options. Plus, you kind of have to love the theme-dressed baristas.