Chicago | January 4, 2022 1:35 pm

25 Very Fun, Very Chicago Things to Look Forward to in 2022

Weather and pandemic permitting

The Bean in Millennium Park
The Bean in Millennium Park
Sawyer Bengston

The last 20 months have been a mess — for many people, a cataclysm of grief, anxiety and upheaval. 

When we first started talking about how we’d like to end the year, editorially speaking, we decided we wanted to look forward — to happier, easier days (and later, livelier nights). Most of all, to spending our days out and about in the city we love, seeing what the world has to offer, without worry. 

We will [try to] maintain that optimism, whatever is trending on Twitter. There’s no going back to February 2020 — but some day soon, things are going to break, for the better. Here’s what we’ll be doing. 

1. King Spa

If you were describing King Spa to someone who had never heard of it before, it wouldn’t sound real. ‘Yeah, it’s a 34,000-square-foot Korean spa, filled with crystal spas, hot tubs, a movie theater and a cafeteria. Also, everyone wears matching outfits.” But it is real, and it’s perfect. Make 2022 the year you become a regular. 

2. Paper Machete @ The Green Mill

Chicago’s favorite “live magazine” — where comics, journalists and a bird puppet named Chad — takes the stage of the legendary Green Mill every Saturday at 3 p.m. If you haven’t seen it, get ready to become a superfan. 

3. Chicago Restaurant Week

Chicago has a lot of traditions — St. Patrick’s Day, making excuses for the Bears’ defense, etc. — but one of the best is Chicago Restaurant Week. Chicago’s one of the greatest food cities in the world and, for 15 blissful days, you can try multi-course meals at the best places in town for under $55. Mark your calendar for March 25-April 10. 

the food offerings at Chicago's Scofflaw
Some of the food offerings at Chicago’s Scofflaw

4. Chicago Pride

Chicago’s Pride Celebration attracts visitors from across the world — and for good reason, it’s one of the best events of the year. This year features Chicago Pride Fest on June 17-19, with the parade set for June 26. (And honestly, with hundreds of thousands of attendees, if you want a good parade-watching spot you might want to set your chair up … now.) 

5. Kaiser Tiger Curling

While we can’t predict the future, we do know that at some point during the Winter 2022 Olympics, you’ll think, “I’d probably be good at curling.” At Kaiser Tiger, you can try your hand with a broom — and celebrate at the bar after — with the bar’s regulation-sized curling rinks. 

6. Ruffles at Berlin

New York has Fashion Week, Los Angeles has the Oscars — but Chicago’s most glamorous event is the monthly show Ruffles at Berlin. Hailed as the “Met Gala of Chicago,” the show celebrates the imaginative fashion of the city’s queer community. 

7. The Hideout’s Talk Shows

If your 2022 resolutions include “learn more and drink better booze,” then The Hideout — one of Chicago’s most beloved venues — has you covered. (And if that’s not your resolution, there’s still time to change it.) The theater offers several can’t-miss live monthly talk shows — like the scholarly “A Scientist Walks Into A Bar” and “The Secret History of Chicago Music.” 

8. Randolph Street Market

Described as “one of the greatest street markets ever” (by us, just now), the Randolph Street Market features antiques, crafts, food and live music. There are occasional pop-ups during the winter months and the market returns in the spring. 

9. Tomorrow Never Knows (TNK) Fest

There are few things that Chicagoans will brave the January cold for — and TNK Fest is one of them. The festival — featuring musicians and comedians — is hosted at six independent venues across the city. This year’s fest is set for Jan. 19-23. 

10. The Lazy Bird Bar

The Lazy Bird has been named one of the best bars in the country and it lives up to the hype. With a menu full of classic cocktails and a lowkey location in the basement of the Hoxton Hotel, it’s a sure way to impress visitors and locals alike. 

11. Chicago Sky Home Games

Chicago’s WNBA team, the Chicago Sky, took home their first championship title in 2021, and 2022 is looking pretty good for them, too. Treat yourself to a home game — or, better yet, season tickets. 

12. Boxville

Shop small at Boxville — like, really small. The Bronzeville marketplace is made up entirely of shipping containers, giving shoppers a unique experience and entrepreneurs the chance to rent affordable spaces for their growing businesses. 

13. The Pink Squirrel

An evening filled with milkshakes and retro bowling? It’s just what your 12-year-old self hoped adulthood would be like. The Pink Squirrel is a 1960s supper club-themed bar that specializes in deliciously sweet cocktails, with decor that will have you re-downloading Instagram.

14. Music Box of Horrors

Already nostalgic for Halloween? Head to the Music Box Theater during the month of January for the Cinematic Void and Music Box of Horrors Festival. The beloved theater is screening creepy, beloved giallo films throughout the month. (We looked it up: Giallo are Italian thrillers.) Not your thing? The Music Box shows other movies throughout the year, and has a can’t-miss movie-themed bar next door. 

15. Chicago Auto Show

Normally, we’d advise you to stay as far away from McCormick Place as possible — but the annual Chicago Auto Show is a notable exception. The largest auto show in North America, the show features 1 million square feet of impressive vehicles. 

The 2018 Genesis G80 on display at the 2018 Chicago Auto Show
The 2018 Genesis G80 on display at the 2018 Chicago Auto Show
Raymond Boyd/Getty

16. Old Town Art Fair

With 200+ professional artists and 10,000 visitors, the Old Town Art Fair is a must-attend for both art lovers and people watchers. (And hey, with all your pandemic tie-dye endeavors, you’re pretty much a professional artist now.)

17. Storefront Improv Theaters

It may be freezing outside, but Chicago’s improv scene is hotter than ever. Check out the city’s amazing storefront theaters — like Logan Square Improv and CIC Theater — to see future stars in action. 

18. Andersonville’s Midsommerfest

This year, Andersonville was named the 2nd Coolest Neighborhood in the World – so they have a lot to celebrate at this year’s Midsommerfest (set for June 10-12). 

19. Elton John at the United Center

If seeing Elton John live is on your bucket list, now’s your time, because the Rocket Man added two Chicago dates on his farewell tour. 

20. Do Division

There are two seasons in Chicago: Winter and Street Fest Season. Celebrate the latter with Do Division, one of the most beloved festivals in Chicago, featuring two live music stages, a fashion show, food, and much more. 

21. Chicago Magic Lounge

Prefer your cocktails with a side of close-up magic? Us, too. At Chicago Magic Lounge, you can attend an elaborate show in the theater, or check out close-up magic in the bar area. (Plus you enter the lounge through a laundromat, which feels like a magic trick in and of itself.)

The Chicago Magic Lounge sets the bar high when it comes to after-hours entertainment
The Chicago Magic Lounge sets the bar high when it comes to after-hours entertainment
Chicago Magic Lounge

22. Lunar New Year

2022 is the Year of the Tiger, and Chicago’s Chinatown is throwing its giant annual Lunar New Year Parade on Feb. 13 to celebrate. 

23. Chef Driven Food Tours

What’s more fun than going on a food tour when you’re in a new city … unless it’s going on a food tour of the greatest city in the world, Chicago? 

24. LondonHouse Rooftop

Who says Chicago’s rooftops are just for summer? (Well, besides the weather and common sense.) But at LondonHouse, you can enjoy the views without the bitter cold, in festive rooftop igloos that provide shelter during the winter months. 

25. Kingston Mines

As tempting as it is to spend yet another night watching Netflix on the couch, make it a night to remember at Kingston Mines, one of the oldest continuously operating blues bars in Chicago.