Chicago

2119 S Halsted St, btw 21st and Cermak; Pilsen; 312.526.3385

From the Lula Cafe peeps, Nightwood's an intimate, rustic cafe adorned with mismatched antique gaslamps hung from a carved white oak ceiling. The wood-fire grill'd open kitchen slings a constantly rotating menu of heavily local, seasonal grub (applewood-rotisserie chicken, slow-roasted pork loin, Slagel Farm burgers, etc) along with after-eats like ganache-covered homemade pretzels and a panna cotta w/ Santa Monica tangerines, perky enough for a handful, just like Everclear lead singer Art Alexakis's.

2109 S Wabash Ave, at 21st; Near South Side; 312.753.5700

Just opened by the dude everyone sweats behind Funky Buddha Lounge, Shrine is a 8,000 square-foot temple to nightlife split up between an earth toned, leather banquette-encrusted Afro-music venue (hosting funk/soul acts, DJs, eclectic dancers, etc) with a gently curved 45-foot bar and African-inspired wood wall art, and a more intimate, upscale lounge dubbed Coup D'Etat, lined with antique leather couches which you can attempt to overthrow w/ the help of a small, elite segment of your friend apparatus.

The brainchild of a Chicago duo with an uncanny knack for living well sans job, BH is a repository for all things free/crazy cheap (pizza buffets, film screenings, cans of PBR), complete with advice, daily calendar updates, and a vigorous discussion forum guaranteed to keep you livin' the high life until you've got enough money to actually afford a can of the same.

4019 N Damen Ave, at Irving Park; North Center; 773.248.1935

Started by a trio of sisters in the renovated space formerly occupied by their parents' bakery, Espresso's an art-inspired coffeehouse decked out with for-sale local works (some by the owners) and a wrought-iron enclosed garden patio out back, serving up the usual caffeinated suspects along with smoothies (lychee, guava-strawberry), and housemade pastries, including sweet (strawberry/banana/Nutella) and savory (spinach/mushroom/feta) crepes, though French wrap totally fell off after MC Solaar.

500 West Florida St, Milwaukee, WI; 888.543.4766

The Milwaukee-based, century-old furniture warehouse turned luxe tough guy getaway is further upping their machismo with on-site motorcycle rentals for four or 24-hour time slots, with rates varying depending on the sweetness of your ride, which you'll unquestioningly pay rather than admit the only Fatboy you know lives in your bathroom mirror.