Illinois is a veritable winter wonderland — and it’s all yours for the taking.
While it seems like all things queer take place in summer — Pride Fest, Pride in the Park, Market Days — Chicago welcomes our community year-round with open arms and adventures galore. Named the “Best Big City in the U.S.” for the sixth straight year by Conde Nast Traveler, this Midwest metropolis truly is the “middle of everything.”
Let’s see what fun we can get into, shall we?
Outdoor winter fun in Chicago
What’s more fun than lacing up a pair of ice skates and channeling your inner Adam Rippon? Doing it with Chicago’s skyline as your backdrop. Go for a twirl (or fall on your bum) at McCormick Tribune Ice Rink at Millennium Park. You’ll skate adjacent to world-class sculptures like the gleaming Cloud Gate (aka The Bean) and the towering video screens of Plensa’s Crown Fountain, or at the Ribbon at Maggie Daley Park. Winding through this tree-lined snakelike rink below the silver Gehry-designed bridge connecting the two parks, know you’ll have plenty of laughs and leave with great memories.
You can also saunter over to Christkindlmarket in Daley Plaza. This German-style outdoor market brings a festive holiday atmosphere to the heart of Chicago’s Loop. Stroll the stalls beneath towering skyscrapers to find everything from hand-blown glass ornaments and decorative beer steins to warm pretzels, sauerkraut-topped sausages, and ceramic boots filled with warmed mulled wine. And then, when the sun dips from the sky, hop in a rideshare to Lincoln Park Zoo for the ultimate outdoor holiday experience: ZooLights. This annual festival sees the urban zoo decked out in thousands of colorfully twinkling lights and anthropomorphic figurines delighting families and chosen families.
After all that outdoor fun, keep the festivities going at any one of the many bars in the Northalsted neighborhood. Here, gaggles of gays in puffy coats hiding skin-tight Ts and stunning drag queens dressed to the nines donning platform boots queue up to party the night away. Whether that’s at bustling video bar Sidetrack, sophisticated cocktail bar Elixir, corner tavern Roscoe’s for fabulous drag shows, or dive bar The Closet to get sweaty while drinking cheap beers on the packed dancefloor, there’s something for everyone here.
How Chicago warms up all winter
Chicago boasts some of the best restaurants in America and many of which are queer-owned. Check out Wood on Northalsted, Big Jones in Andersonville, Tweet in Uptown, The Dearborn in the Loop, Sepia in West Loop, and Split Rail in West Town. And many of these places are close to numerous cultural happenings.
Start on the Lincoln Park where you can take in The First Homosexuals, a groundbreaking exhibit at Wrightwood 659. Here, more than 100 paintings, drawings, prints, photos, and even film clips created between 1869 and 1930 will be on display showing the “first” homosexuals (based on the year the term was first used in Europe).
If you desire more traditional art, Chicago is home to some of the world’s best collections inside The Modern Wing at the Chicago Art Institute. Marvel at queer artists from Warhol to Hockney to Félix González-Torres, whose interactive installation depicting the AIDS crisis ushered in a debate earlier this year.
To truly escape the cold, yet feel like you’re in the tropics, both the Garfield Park Conservatory and the Lincoln Park Conservatory offer lush escapes for strolling before bundling up and heading back outside.
Chicago Plays
Head to the Loop to take in Broadway in Chicago, especially during Theater Week in February, and choose between 120 shows all over the city. Indie theaters like Black Ensemble Theater, About Face Theatre, and Theater Wit often have queer-themed shows. Don’t miss the ultimate wintertime show, “The Nutcracker,” performed by the Joffrey Ballet at the iconic Lyric Opera.
Chicago is a drag
Long before Drag Race took the world by storm, Chicago has been delighted with some of America’s best drag shows. The Baton Club, now in its new home in Uptown, has dazzled for more than 50 years with veterans like Chilli Pepper still bringing down the house. Lips in South Loop feels like you stepped into the Moulin Rouge with eight-foot-tall gleaming gold chandeliers and glass baubles hanging from the ceiling and pink leopard walls.
Roscoe’s is Northalsted’s ground zero for Drag Race-featured shows and contests. At Kit Kat Lounge, the Divas get up close and personal performing right at your table. And these days, you can’t swing a pussy pop without hitting a drag brunch. Head to Lakeview’s The River for a rowdy show where your ticket includes family-style brunch and bottomless drinks.
Simone’s in Pilsen hosts Brunch of Drag on the first Sunday of each month that features a $28 liquid brunch with the show, or for $10 more you get a meal to soak up that booze. And if you act quickly enough, you can snag tickets to the special “ladies who lunch” drag brunch at the iconic Walnut Room at Macy’s on State Street.
Looking to sex up your night with go-go boys? You don’t have to go far. Just look up at Lucky Horseshoe or Hydrate Nightclub in Northalsted or up to Atmosphere in Andersonville. Just remember to tip well.
Book a romantic getaway at a Galena B&B
Once you’ve had your share of urban adventures, head out of town for some R&R. Just a stone’s throw from the Mighty Mississippi River in the northwest corner of Illinois is the borough of Galena. This quaint town, with much of it listed on the National Register of Historic Places, is the perfect setting for a romantic winter getaway. You can easily hit the slopes at Chestnut Mountain Resort in the morning and have a couples massage at the Galena Day Spa or the Stonedrift Spa at Eagle Ridge Resort in the afternoon.
Main Street offers plenty of dining options from great burgers at Durty Gurt’s to the more upscale Alsatian bistro Fritz & Frites to the can’t miss classic Log Cabin Steakhouse, Galena’s oldest restaurant for their signature Greek chicken and Prime steaks. Galena is no stranger to artisan beverages either, as Blaum Bros. Distilling Company crafts a range of spirits such as straight bourbon and rye, vodka, and gin, often from local grains.
And when it’s time to truly get romantic, book your stay at the gay-owned Aldrich Guest House. This five-bedroom B&B is a quick jaunt off Main Street and claims both Abraham Lincoln and Ulysses S. Grant as guests (presumably not together but wouldn’t that be cheeky?). This cozy inn offers its award-winning hot breakfast each morning and then brings everyone together for wine and cocktails in the early evening. What more can you ask for? Oh, maybe their cannabis-friendly “potting shed” where you can partake in a little extra legal fun of your own.
Skiing, skating, sculpting … oh my!
We already talked about downhill skiing in Galena, but cross-country skiing and snowshoeing are big here, too. Whether you visit one of the Chicago-area forest preserves or venture out around the state, there’s no shortage of serene trails to cruise around.
Need more adventure? Grab your helmet and ice hooks and head to Starved Rock State Park. When the waterfalls freeze, the ice climbing hits peak adventure.
Prefer to see things on horseback? White Pines Ranch, about two hours west of Chicago, is a great place to bring your family – especially when the 200 wooded acres and horse trails get blanketed in soft snow.
Speaking of snow, you’ve never truly lived until you’ve seen it artfully crafted into a sculpture. Come January, the National Snow Sculpting Competition lands in northern Rockford when 50,000 other spectators see which frozen marvel will snag the prize.
Eagle watching? Wine tasting? Why not both?
During winter, about 3,000 majestic bald eagles fly to Illinois to nest and hunt,making it the best place outside of Alaska to see these beautiful birds. And the eagles roost throughout the state, so your chances of seeing them soaring overhead increase in January and February. From Alton and Oglesby to Quincy and Rock Island, towns come together to celebrate these stately creatures, with plenty of activities to occupy your time while waiting to spot one.
Admittedly, Illinois might not be the first place you think of when it comes to wine tasting, but you can(and should). No, we don’t mean ordering a bottle of pinot at dinner in Chicago. Rather go on a true wine adventure. The Shawnee Hills Wine Trail is a designated AVA in Southern Illinois and showcases rare grapes like chambourcin, chardonel, traminette, and frontenac as well as more well-known varietals like cabernet franc and riesling. This wine region, set between the Mississippi and Ohio rivers, is home to about 20 wineries, inns, restaurants, and stunning landscapes to create a memorable wine excursion.
So whether you want to ski the slopes, take in a show, or cozy up in front of a romantic fire, Illinois has everything you need for your queer winter adventure.
More information on how to get into the winter wonderland of Illinois
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