The Windy City Awaits

CHICAGO — Tired of being cooped up at home most of the past year and unable to partake in preferred pastimes and adult amusements? The 2021 NACS Show may be your opportunity to unwind and let loose in Chicago, where many hotels, shows and amenities have fully reopened and visitors are indulging in some long-overdue enjoyment.

Just be forewarned: You may need to wear a mask in public spaces. Social distancing will be in effect at McCormick Place and in other buildings across town. And some facilities and live events may have limited capacity. But the good news is that most favorite Chi-Town destinations and attractions are open and accessible, including several new features for 2021.

With this handy guide, we’ve made it easier to narrow down worthy attractions, which—at the time this story went to press—are scheduled to be open during your stay (although some paid events may have sold out).

No Chicago stopover would be complete without catching a live performance or experiencing an exclusive exhibit or fest. Here are several to choose from.

• BOZ SCAGGS. Few musicians have enjoyed a career as diverse and long-lasting as Boz Scaggs, an artist known for blending the blues with jazz and rock and creating lasting hits like “Lido Shuffle” and “Lowdown.” He’s back to play crowd favorites as well as his new album, “Out of the Blues.” Catch this legendary act in an intimate venue: North Shore Center. (Oct. 5; from $75; (847) 673-6300; northshorecenter.org/event/boz-scaggs)
• SIX. What do the many wives of Henry VIII have in common? A half-dozen of these queens were all beheaded, but now they’re back to wreak revenge in a stunning new pop concert that celebrates female empowerment, staged exclusively at the Broadway Playhouse at Water Tower Place. (Oct. 5–10; from $56.50; (800) 775-2000; sixthemusical.com/chicago)
• THE SECOND CITY 109TH REVUE. No stopover in Chicago is complete without visiting The Second City comedy club, where laugh legends like Belushi, Aykroyd, Farley, Candy, Carell and Colbert got their starts. The troupe’s 109th Revue offers an opportunity to witness fresh sketches, colorful characters, and edgy new material designed to provoke serious yuks. And because many of these skits involve improv, each show is guaranteed to be unique. (Oct. 2, 3, 6–10; from $49; (800) 896-8120; secondcity.com)
• LINCOLN PARK WINE FESTIVAL 2021. Love sipping vino from around the world? Make plans to partake in this sixth annual wine happening in Jonquil Park, which transforms into an open-air market showcasing wine and food pavilions. (Oct. 9–10; $50; (773) 868-3010; chicagoevents.com/events/lincoln-park-wine-fest)
• MARC ANTHONY. Bet you didn’t know that this singer/songwriter/actor—J. Lo’s former beau—is the best-selling tropical salsa musician in history. In fact, Anthony also boasts the Guinness World Record for the most No. 1 albums on the Billboard Tropical Albums year-end charts. Discover why Marc earns robust applause wherever he performs by claiming a seat at this Allstate Arena concert. (Oct. 8; prices vary; (847) 635-6601; marcanthonyonline.com)

While in Chicago, get outside and explore, or put your game face on for one-of-a-kind thrills.

• WILLIS TOWER SKYDECK. Like living life on the edge? Then come to the Ledge, a transparent glass box extending out 4.3 feet from the side of Chicago’s tallest building, Willis Tower (formerly known as Sears Tower). From that vexing but viewtastic vantage point, you can overlook much of the city and feel as if you’re levitating 1,353 feet and 103 floors above the ground. (Daily; from $30; (312) 875-9447; theskydeck.com)
• SHORELINE SIGHTSEEING ARCHITECTURE RIVER TOUR. Chicago history comes alive as you trek up and down the Chicago River by boat for a 75-minute ride custom narrated by a knowledgeable tour guide. Get the behind-the-scenes details on all the great skyscrapers and edifices, ways in which their designs were influenced, and how the city rebuilt itself after the Great Chicago Fire of 1871. (Daily; from $45; (312) 222-9328; shorelinesightseeing.com)
• CHICAGO BEARS VS. DETROIT LIONS. The Bears made a splash in the 2021 draft by choosing young phenom Justin Fields, who may have earned the job at starting quarterback by kickoff of this game. Bears fans certainly hope so, as Detroit will be revved up by its new QB, the battle-tested Jared Goff, formerly of the Rams. Come see two of the NFL’s most exciting teams duke it out for NFC North bragging rights on the gridiron at historic Soldier Field. (Oct. 3; prices vary; (312) 235-7000; chicagobears.com)
• CHICAGO WHITE SOX VS. DETROIT TIGERS. The Sox, one of baseball’s best squads featuring a solid pitching staff plus a laudable lineup of power hitters, should be angling for playoff dominance by the time you read this. Arrive in Chicago early during your NACS Show trip and you can see for yourself what all the fuss was about this year as the Pale Hose close out the regular season against their division rivals to the east, the Tigers. (Oct. 2, 3; prices vary; (312) 674-1000; mlb.com/whitesox)
• MIDNIGHT TERROR HAUNTED HOUSE. Voted a top 10 haunted attraction in the entire country (and No. 1 in Illinois) by readers of USA Today, Midnight Terror is known for its fresh frights added annually, ultra-detailed props, strategically positioned light and sound effects, terrifying live actors, and extreme attention to devilish details. Get a head start on Halloween by booking tickets now. (Oct. 2, 3, 8–10; from $25; (708) 571-0266; midnightterrorhauntedhouse.com)

Not everything in Chicago requires cash or credit. Give your wallet a break and partake in these no-charge area amenities.

• LINCOLN PARK ZOO. One of the best attractions in Chicago is also completely free and filled to the brim with exciting animals and fascinating creatures, including the zoo’s newest arrivals: a white-cheek gibbon, a red river hog and a male meerkat. During your visit, explore the penguin cove, macaque forest, primate house and more. (Daily; (312) 742-2000; lpzoo.org)
• GARFIELD PARK CONSERVATORY. Chicago is home to one of the biggest and most impressive botanical conservatories in the country. See thousands of plant species from around the globe found in eight indoor display gardens, among them the Palm House, Fern Room, Desert House, Aroid House, and Horticulture Hall. Then, walk through more than 10 acres of outdoor gardens, including a water lily pond and kid-friendly play spaces. (Oct. 2, 3, 6–10; (773) 638-1766; garfieldconservatory.org)
• CLOUD GATE AND CROWN FOUNTAIN. Millennium Park’s two most talked-about works of art often draw more crowds than any other attractions in town. Also known as “the Bean,” Cloud Gate is a 110-ton elliptical sculpture wrought of polished stainless steel plates that mirror everything around it. Crown Fountain, meanwhile, is comprised of a pair of 50-feet-tall glass block towers—each displaying various videos of Chicago faces—that bookend a shallow reflecting pool. (Daily; tinyurl.com/cloudgate21)
• NAVY PIER. The city’s second-most-visited tourist attraction, Navy Pier spans 50-plus acres and features shops, restaurants, a botanical garden, a funhouse maze, parks, an IMAX movie theater, Chicago’s Shakespeare Theater, various indoor exhibits, and, of course, its world-famous Ferris wheel. (Daily; (800) 595-7437; navypier.org)

Visitors to Chicago can always count on the city to debut fresh delights every year. Check out these all-new events designed to wow.

• IMMERSIVE VAN GOGH. Want to attend the hottest show in town, and possibly the country? Book tickets for this interactive and technologically groundbreaking art exhibit hosted at Lighthouse ArtSpace Chicago in the Germania Club building, boasting 500,000 cubic feet of visually stunning projections that animate the amazing works of painter Vincent van Gogh, including Starry Night, Sunflowers, The Bedroom, The Potato Eaters and more. (Oct. 2–4, 6–10; from $40; (844) 307-4644; vangoghchicago.com)
• MARVEL: UNIVERSE OF SUPER-HEROES. Our spidey sense is tingling, and it’s telling us to head to the Museum of Science and Industry to celebrate the superheroes of the Marvel universe. This popular exhibit presents more than 300 artifacts, from original comic book pages and movie costumes to interactive displays and sculptures. All your favorites are represented, including Captain America, Iron Man, the X-Men, Hulk, Spider-Man, Thor, Black Panther, Captain Marvel and more. (Oct. 2, 3, 5–10; from $22; (773) 684-1414; msichicago.org)
• CITY ON FIRE: CHICAGO 1871. Did Mrs. O’Leary’s cow actually kick over a lantern that started one of the deadliest and largest infernos in history? Learn the facts about the infamous fire that consumed much of Chicago 150 years ago in this all-new exhibit at the Chicago History Museum, which displays over 100 artifacts from the museum’s collection as well as multimedia and interactive elements and personal recollections from survivors of the blaze. (Oct. 1–3, 5–10; from $19; (312) 642-4600; chicagohistory.org)
• BIOMECHANICS: THE MACHINE INSIDE. This immersive exhibit at the Field Museum, back by popular demand after a national tour, reveals how animals fly, leap and speed across the earth, among other wildlife wonders. Learn how giraffes’ hearts can pump blood throughout their long necks and how luna moths rely on their antenna to detect a mate from up to 7 miles away. While at the Field, you’ll also have a chance to see Sue, the world-famous T-rex. (Oct. 2–4, 7–10; from $26; (312) 922-9410; fieldmuseum.org)
• THE ART OF BANKSY. We still don’t know the real identity of Banksy, one of the planet’s most mysterious and political creative minds. But you can witness this enigmatic artist’s acclaimed works firsthand by attending this show, which has taken up residence in Chicago’s West Loop. Prints, sculptures, canvasses, one-of-a-kind pieces and limited-edition works are included in this collection. (Oct. 2, 3, 5–10; from $40; banksyexhibit.com)