Outdoor drinking is nothing new at this Roscoe Village beer garden. Staff have enclosed the back patio and filled it with space heaters for imbibers.

Logan Square’s ambitious Asian-inspired brewpub from chef and owner Bo Fowler (Owen & Engine) has a spacious and partially-covered roof dec that faces out to Milwaukee Avenue. The restaurant’s juicy burgers and diverse noodle selection are a solid cure for rainy day blues.

Lettuce Entertain You Enterprises’ longtime Spanish wine bar and tapas spot has tented and heated outdoor tables.

Rooftop bar the Kennedy includes a swath of space under a retractable awning, along with usual rooftop accoutrements: fire pits, over-sized lounge chairs, TVs, plus food and drink. It’s on the seventh floor of Wicker Park’s newish Hyatt Place Hotel.

Tucked away in Old Town, this popular sports bar features a second-floor roof to keep fans dry.

Portuguese-inspired wine bar and seafood restaurant Porto houses an atrium with sliding windows and a retractable roof.

Rooftop bar the IO Godfrey comes equipped with a retractable roof that features gorgeous views of downtown Chicago, along with cocktails, brunch, and more.

The roof garden at trendy River North cocktail bar Celeste features open air drinking and dining amid lush greenery.

Riverfront destination Gibsons Italia has retractable glass roof and walls, as well as stadium-style seating to ensure beautiful skyline and river views. When it opened in 2018, it won Eater Chicago’s award for Most Beautiful Restaurant of the Year.

Cabra, the Peruvian-influenced restaurant from Top Chef champion and celebrity chef Stephanie Izard perched atop the Hoxton hotel, includes a trendy patio space with sweeping views of Fulton Market. It’s partially covered so diners can stay dry while devouring ceviche and goat empanadas.

Bold and bright, this bar inside the Wit hotel touts a massive retractable roof. There’s also an open-air space that was added in a well-timed 2019 revamp. ROOF previously functioned as a nightclub but recently switched to a more social distancing-friendly theme of Neapolitan-inspired pizzas and classic cocktails.

Athena’s spacious outdoor terrace is already a rarity in Greektown, but the restaurant tops itself with both a retractable roof and waterfall.

The fourth location from Quad Cities-style pizzeria Roots Handmade Pizza debuted last summer with glass retractable roof on Printers Row. It cost a cool $600,000 and takes about 20 seconds to retract.

Chef Kevin Hickey’s mega-hit in Bridgeport now sports an enormous heated tent that covers its charming backyard patio. Patrons can gobble up rotisserie duck, duck fat french fries, duck wings, and more in any kind of weather.

This top-notch brewery and taproom in Beverly features both a partially-covered rooftop space and retractable garage doors on the main floor. The open spaces allow for airflow but still keep patrons dry as they sip their beers and eat Neapolitan-style pizzas.