Cindy’s Rooftop
$$$ | The Loop
Hip, stylish rooftop bar and eatery at the Chicago Athletic Association Hotel with choice seasonal fare.
Pequod’s Pizza
$ | Lincoln Park
Casual, brick-walled pizza pub where deep-dish pies with caramelized crusts are served until late.
Lou Malnati’s Pizzeria
$ | Multiple Locations
Family-owned local chain for Italian classics + Chicago-style, deep-dish pizzas with butter crusts.
Happy Camper
$$ | Old Town
Classic and creative pies plus cocktails served in a warehouse setting with tire swings + Airstreams.
Beatnik on the River
$$$ | The Loop
Creative global eats + tropical cocktails, paired in a funky-ornate setting with riverfront seats.
Velvet Taco
$ | River North
Tacos with global flavors in a counter-service setting with beer + margaritas.
Signature Room at the 95th
$$$$ | Streeterville
Upscale spot high atop 875 North Michigan Avenue with wide views, American fare + a separate lounge.
Au Cheval
$$ | West Loop
The open kitchen at this upscale “diner” works with ingredients ranging from bologna to foie gras.
Small Cheval
$$ | The Loop, Gold Coast, Wicker Park
Au Cheval burgers, shakes, beer + cocktails served in rustic, take-out-friendly digs with a patio.
Aba
$$ | West Loop
Posh destination for elevated Mediterranean fare + cocktails, plus a lounge-style rooftop patio.
Cabra Rooftop
$$$ | West Loop
Chic hotel rooftop for chef-driven Peruvian sharing plates + ceviche with craft cocktails and views.
Big Star
$$ | Wicker Park + Wrigleyville
Mexican street food, plus margaritas + other drinks fuel a lively scene at this funky hangout.
3 Arts Club Cafe
$$ | Gold Coast
Posh haunt inside Restoration Hardware combining a coffeehouse, wine bar + American restaurant.
Bongo Room
$ | Wicker Park + Andersonville
Popular brunch place with inventive pancakes and other updated American breakfast + lunch items.
Cafe Ba-Ba-Reeba!
$$ | Lincoln Park
Spanish tapas, paella + pitchers of sangria fuel a lively scene at this classic Chicago restaurant.
Portillo’s
$ | River North + UIC/Near West Side
Chicago-born chain for hot dogs, Italian beef sandwiches and more, plus beer + wine, in retro digs.
RPM Steak
$$$$ | River North
Chophouse with a modern menu of prime cuts, raw-bar items + more in a sleek setting with banquettes.
Parlor Pizza Bar
$ | River North + West Loop + Wicker Park
Industrial-chic pizzeria offering wood-fired pies + a bar with craft beer, plus outdoor seating.
Pizza + Oven Grinder
$$ | Lincoln Park
Cash-only eatery in a historical brownstone serving its famous pizza-pot-pies plus grinders + more.
Gibson’s Italia
$$$ | West Loop
High-style Italian steak and pasta spot on 3 levels with a vast wine list, 2 fireplaces + a roof deck.
Paradise Park
$$ | Wicker Park
Warm, eclectic stop for classic and creative pies plus cocktails + beers served on a huge patio.