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The Best Things to Do in Chicago Right Now

By Elaine Glusac

Dec 1, 2021

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The blend of Italian and Croatian food at Rose Mary brings in the crowds.

Photo by Jeff Marini

The blend of Italian and Croatian food at Rose Mary brings in the crowds.

Never mind the weather, Chicago has a host of possibilities indoors and outside.

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Emerging from the pandemic last summer, Chicagoans took to the streets to dine, exercise, and even listen to music. Fear not the coming winter. There are still plenty of new and exciting things to do in Chicago–curling, anyone?–whether you want the latest and greatest restaurant, Broadway-caliber theater, or a hotel room with the best possible view.

Snag a reservation at newly opened Rose Mary

Undaunted by the pandemic, Rose Mary opened last spring to packed houses and much acclaim. Chef Joe Flamm worked at the Italian groundbreaker Spiaggia when he appeared on season 15 of Top Chef and won. His first solo project, Rose Mary, which blends Croatian and Italian food, is an homage to his family (his wife is Croatian) and allows him to stretch his Italian prowess across the Adriatic, mixing both culture on a menu with homemade pasta, grilled clams, and cevapi with ajvar (your new favorite red pepper sauce) and kajmak (creamy cheese). Reservations are available 60 days in advance and are snapped up each release date.

The key to dining at Andros Taverna? Small plates, which let you sample lots of the menu.

Dine on innovative Greek food at Andros Taverna

Chef Doug Psaltis proved he could cook just about anything—barbecue, Italian, ramen and tiki-bar-friendly pupu platters among his repetoire—during his tenure with the restaurant giant Lettuce Entertain You. With the convivial new Andros Taverna in Logan Square he breaks away and reinvents Greek food for the foodie set in a lofty, wood-trimmed room. The open charcoal hearth is the center of the kitchen, blistering everything from whole lemony octopus to lamb chops. You could make a meal of the mezze small plates, served with wood-fired pita bread, but leave room for the whole fish or worth-its-$22-price-tag gyros.

Book a front row seat for producer Garth Drabinsky’s new show

Chicago’s theater scene is still lacking most of the tiny and mighty storefront stages that make this an unparalleled theater town. But some of the larger companies are back, including a new musical from Garth Drabinsky (the powerhouse producer behind Ragtime and others) called Paradise Square. Against a backdrop of Civil War draft riots, the musical makes the case for the comingling of Irish immigrant and freed Black cultures over dance. 

Take the kids to a puppet show presentation of The Snow Queen

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If you’re looking for a satisfying seasonal show, you can’t go wrong with the annual A Christmas Carol at the Goodman Theatre downtown. But for something different, head to Wicker Park, just a few miles west, to catch The Snow Queen at the always-inventive House Theatre, which has just reopened. This is Hans Christian Andersen’s classic fable told with puppetry and music in a way all ages can enjoy.

Grab nibbles and wine at the Windy City Playhouse

In one of the weirder mash-ups, chef Rick Bayless, of Frontera Grill fame, created A Recipe for Disaster at the Windy City Playhouse at Petterino’s in the Loop. The show is part a grazing opportunity—Bayless and daughter Lanie create six nibbles, one cocktail, and two wine pairings that guests enjoy during the show—while the audience is a fly on the wall in the high-stress kitchen at a restaurant where the pressure in on, as it’s “influencer night.”

Live music again? Indoors? Sign us up!

Catch a band at the intimate Winter’s Jazz Club

Music clubs are back and working hard to stay open with careful COVID policies. The wee jazz club Winter’s Jazz Club downtown manages to keep the beats going with a respectful audience screened for vaccination. This is the place to see a lot of Chicago talents, including vocalists Spider Saloff and Typhanie Monique, vibraharpist Thaddeus Tukes, and the trio Soul Message Band.

Return to the Hideout for new late night entertainment

Locals were overjoyed with the Hideout reopened this summer. The eclectic club is in a sort of industrial no-man’s land near the Chicago River on the North Side that seems always to be under threat of development. But it made it through the pandemic and now requires proof of vaccination to get in and masks while you’re not actively drinking. Expect a rotating performance schedule of comedy, jug bands, singer-songwriters, hip-hop, and more.

The Cleve Carney Museum of Art is worth the trek.

See exhibits at galleries old and new

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It’s a nearly 30-mile haul to get to suburban Glen Ellyn from downtown, but the new Cleve Carney Museum of Art makes it worth the trek with a stellar exhibition schedule. Though January 31, it has Tony Fitzpatrick: Jesus of Western Avenue, a retrospective of the popular Chicago artist whose collagist style can be seen on album covers, books, and at major museum collections such as New York’s Museum of Modern Art

The venerable Art Institute of Chicago has the pandemic-delayed blockbuster Thinking of You. I Mean Me. I Mean You. from contemporary artist Barbara Kruger, who focuses on provocative text, which seems fully in line with what’s happening today in the world of street art and memes but whose social commentary goes back to the 1970s.

Lagniappe: Hit a holiday pop-up

If you’re coming in December, don’t miss the Christkindlmarket, a European-style Christmas market in the Loop featuring traditional food and gifts (now through December 24), or the sibling spin-off outside of Wrigley Field on the North Side, which also has ice skating (now through December 31).

Spend the night at a great Chicago hotel

The rooms at Sable at Navy Pier are halfway along the pier, giving them great views of both lake and skyline.

Sable at Navy Pier

Book now: from $224/night, expedia.com

Other than Chicago Shakespeare Theater, Navy Pier hasn’t given locals, and anyone who wants to get off the beaten tourism track, much reason to visit. But the Sable at Navy Pier changes that by virtue of its clever nautical design and views for miles of the lake and the city skyline from rooms at the midsection of the 3,300-foot pier. You’d have to stay at a luxury hotel to get this kind of romantic ambience—well, at least in the quieter winter months; summer can be family madness on the pier. You’ll be walking, bike-sharing, or Ubering a lot from this lakefront location to get around, but you’ll always come back to those views.

Graduate Evanston

Book now: from $139/night, expedia.com

The year-old Graduate Evanston reps all thing Northwestern University in suburban Evanston. Part of the Chicago-based hotel group, the clever Graduate has fun with the university known for its business and journalism programs as well as the celebrities who have made it through the school’s performing arts program, including Julia Louis-Dreyfus and Zooey Deschanel (check out the caricature gallery). There’s a tweedy, lived-in, professorial aura to the common spaces, and its affordability makes it appealing both to Chicago visitors—it’s about a half hour L ride to downtown—and to those who want to explore Evanston, which has great beaches and independent shops and restaurants.

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