Keeping Warm in the Chicago Winter | PenCities Chicago

Keeping Warm in the Chicago Winter
January 14, 2018

Chi-Town sure can get chilly – but winter has its fun side. We’re talking ice-skating and hot chocolate, malt whiskies by roaring fires, art sessions and post-exhibition treats, comedy festivals and protein-heavy winter feasts. Stay warm and happy with help from this list of Chicago charmers.

What could be more magical than skating on The Pen’s rooftop Sky Rink, in the middle of a pine-tree winter wonderland, backdropped by Chicago’s skyscrapers and twinkling snowflake lighting? Skating is thirsty, hungry work: enjoy snacks and hot drinks in the heated lounge area, or indulge in Willy-Wonka-worthy treats at the Lobby’s cacao-tastic bar, Chocolate at the Pen. After-dinner desserts and delicacies, coffee, cappuccino and espresso will all be available; you could also sip champagne or a cocktail at The Bar. Get your skates on...

If ice, ice, baby isn’t really your thing, how about the Art Institute Chicago, instead? Spend a day with some of the art world’s greatest visionaries at the Renzo Piano-designed home and explore the Institute’s collection of 20th- and 21st-century contemporary Euro painting and sculpture, modern art, architecture, design, and photography. Refuel at Terzo Piano, Renzo’s indoor-outdoor dazzle-white masterpiece, which provides art-weary wanderers with primo produce and pizzas from Obama’s preferred pan-handler, Tony Mantuano. Come back in summer for the tempting terrace.

Another way to warm your cockles is at  Sketchfest, which celebrates its 17th edition this year. The comedy festival takes over the city from 11–21 January, with a series of LOL-prompting performances and events organised by Stage 773, an anchor of the Belmont Theatre District. Keep the chuckles coming with help from The Second City, whose witty alumni includes Tina Fey, Chris Farley, Bill Murray, and Keegan-Michael Key. This improv-based sketch-comedy company will be performing shows such as Dream Freaks Fall From Space and The Best of the Second City; you can also sign up for a comedy class to banish any residual January blues.

You’ll have laughed up an appetite after all that, so blow some serious Benjies at Maple & Ash: an opulent velvet- and leather-clad steak house in the upscale Gold Coast neighbourhood. Bold decor is matched by a bold menu, spotlighting burgers, sumptuous seafood and steaks as hefty as their price tags. Slink into the basement bar for potent cocktails and snacks. Chances are you’ll be so seduced by the food and feel, you’ll forget entirely what temperature it is outside…


Sky Rink / The Peninsula Chicago / 108 E Superior St / River North / +1 312 337 2888 / Winter 2017-2018 /

Chocolate at the Pen / 5/F / The Peninsula Chicago / 108 E Superior St / River North / +1 312 573 6695 / 7pm-10.30pm Fri-Sat /

Art Institute Chicago / 111 S Michigan / The Loop / +1 312 443 3600 / 10.30am-5pm daily, till 8pm  Thu /

Terzo Piano / 3/F / Modern Wing / Art Institute / 159 E Monroe St / The Loop / +1 312 443 8650 / lunch Mon-Sat, brunch Sun, dinner Thu /

Sketchfest / 1225 W Belmont Ave / Lake View / +1 773 327 5252 / 11-21 Jan 2018 /

The Second City / 1616 N Wells St / Old Town / +1 312 337 3992 /

Maple & Ash / 8 W Maple St / Gold Coast / +1 312 944 8888 / dinner Mon-Sat, brunch and dinner Sun /