Windy City wonderland

14 Chicago experiences, from custom-made leather to a soaking tub with skyline views

Anyone who’s been binge-watching The Bear gets a sense of Chicago’s alluring dichotomy. From Italian beef (sandwich, that is) to the home of the James Beard Awards (the nation’s top culinary honors), Chicago proves time and again that lowbrow and highbrow make cozy bedfellows.

The range of experiences extends far beyond the plate. High-end shopping can be found on Michigan Avenue, but thrift stores hold those one-of-a-kind vintage finds. And while Northalsted — formerly known as Boystown — still contains the majority of the city’s gay bars, neighborhoods in every direction are making their mark with queer and ally business owners.

The city’s 77 distinct communities may send you into overload, but we’ve done the homework, uncovering unique things to do in Chicago, from smart splurges to quintessential Windy City finds.

Take in the Chicago skyline from a soaking tub

The Langham, Chicago

Resort experience in the city 330 N Wabash Ave · Chicago, IL 60611
(312) 923-9988

Chicago is known for its architecture and The Langham, Chicago delivers on all fronts. The Mies van der Rohe-designed building opened in 1973, with the hotel taking up residency in 2013. The lobby’s floor-to-ceiling windows exude dramatic elegance worth its five-star price tag, with rooms and suites featuring a neutral palette and deep soaking tubs.

For those looking to splurge more, Executive Club accommodations include butler service and access to the Langham Club, which serves afternoon tea and cocktails in a serene setting overlooking the Chicago skyline.

Dine al fresco on the Chicago River

Beatnik on the River in Chicago
Dine along the Chicago River at Beatnik on the River. Photo courtesy of Beatnik on the River

Packed with Insta-ready moments both inside and out, Beatnik on the River’s visual aesthetic reflects an eclectic mix of Moroccan, Mediterranean, and Italian influences. Highlights include a 40-foot-wide carved teak façade, crystal chandeliers from the Plaza Hotel in Los Angeles,  custom wall coverings by local artist Erik DeBat, and hundreds of plants and antiques amid 6,000 square feet of dining space.

Head next door to its sister space, GoodFunk, a natural wine bar that showcases small-production producers and bar snacks by chef Dustin Musgrave.

A VIP tour at the Museum of Contemporary Art Chicago

Museum Of Contemporary Art Chicago (MCA Chicago)

Modern and innovative installations and exhibitions 220 E Chicago Ave · Chiacgo, IL 60611
(312) 280-2660

Yes, the Art Institute of Chicago is typically a Chicago visitor’s first go-to when it comes to visual art, but why play favorites? The Museum of Contemporary Art Chicago, founded in 1967, is one of the world’s largest cultural institutions dedicated to contemporary art, boasting a collection of over 2,500 works.

“Descending the Staircase” (December 16, 2023 – August 18, 2024) will draw from the museum’s permanent collection to explore artistic approaches to the human body. Get up close and personal with a VIP tour (either before- or after-hours) for a one-hour guided exploration of the exhibits for a more in-depth look at the artists and the context of their work.

Discover the world’s only Michelin-starred brewery

Dining room snacks at Chicago's Michelin-starred Moody Tongue
Dining room snacks at Chicago’s Michelin-starred Moody Tongue. Photo courtesy of Moody Tongue

Chicago — in addition to its deep-dish pizza and beef sandwiches — is known for its beer. So much so that the city just launched its own Brew Pass, a mobile passport that offers perks at more than 20 of the city’s breweries. But Chicago’s beer culture is more than a frosty pint.

Moody Tongue is the world’s first wholesale brewery and restaurant to achieve Michelin star status, earning two stars in 2021, and again in 2022 under the helm of chef Jared Wentworth. The 28-seat fine-dining restaurant, minimalist in design, offers a tasting menu paired with selections from brewmaster Jared Rouben, and features luxe ingredients like golden osetra caviar, spiny lobster, and Westholme wagyu beef — one of the world’s best cuts from northern Australia.

For those looking for a more expansive experience of the city’s beer scene, the newly launched Chicago Brew Pass is like Pokémon for grown-ups, with prizes and special features offered at participating breweries.

Indulge in a private tour of Chicago’s best bites

Deep dish pizzaq
Deep dish pizza is a must on a private food tour of Chicago’s best eats. Photo: Shutterstock

Walk off those deep-dish pizza calories on Virgin Experience Gifts private food tour. Leave it to Sir Richard Branson, whose recently launched Virgin Voyages has caught the eye of queer travelers looking for LGBTQ+-friendly cruise options, to expand his empire to include bespoke on-the-ground travel experiences.

Depending on your appetite and stamina, the private Chicago food tour can last between four and eight hours and include that famous Italian pie, Garrett popcorn, a small-production chocolate factory, and more.

Watch a movie in a historical theater

Music Box Theatre

Historic movie house 3733 N Southport Ave · Chicago, IL 60613
(773) 871-6604

The Music Box Theatre, built in 1929, remains one of Chicago’s architectural gems. Known for screening foreign, independent, and cult film classics, visitors get a thrill from the mash-up architecture, which includes Italian and Spanish elements and a dark blue, cove-lit ceiling with twinkling stars. A custom electric organ, played for monthly silent film screenings, holiday sing-a-longs, and special presentations, adds a unique flair to the movie-going experience.

Special series and festivals offer cinephiles the opportunity to take a deeper dive into specific genres and filmmakers, including Music Box of Horrors, hip hop, and the films of Billy Wilder.

Locate leather goods for any and every occasion

Shopping on Michigan Avenue
Shopping on Michigan Avenue. Photo: Shutterstock

Over 250 retailers can be found along Chicago’s Magnificent Mile, including brands like David Yurman, Zegna, Hugo Boss, and MCM.

There’s no shortage of options for a wardrobe reboot but for those looking to level up with the latest high-end collections, head to the Oak Street District. More serene than the hustle along Michigan Avenue, Oak Street merchants include Hermes, Prada, Marc Jabos, and Giorgio Armani, where in-the-know shoppers can be the first to snag limited-edition collaborations and early releases.

For a different kind of design, head north to Andersonville, where Leather 64Ten creates custom-made harnesses and accessories with dozens of designs and materials to choose from. At its current location since 2005, the store and its staff continue to be a vital part of cultivating Chicago’s leather community.

Those who want to dig even deeper can visit the Leather Archives and Museum. Founded in 1991 by Chuck Renslow and Tony DeBlase, the community archive, library, and cultural hub is packed with memorabilia to explore.

Walk through a laundromat to discover Chicago’s magical pastime

Magician Benjamin Barnes at Chicago Magic Lounge
Magician Benjamin Barnes at Chicago Magic Lounge. Photo by Anjali Pinto

Magic has long fascinated theatergoers, dating back to the Vaudeville circuits of the early 20th century. But Chicago — much like the deep-dish pizza — put its own spin on things, thanks to Matt Schulien, the son of a restaurateur who reimagined tableside magic in a new setting. Johnny Paul at the LaSalle Hotel added a similar flair behind the bar, and shortly after, “close-up” magic became a thing.

Co-owner Joseph Cranford opened the Chicago Magic Lounge in 2018, tucked behind a laundromat façade (which pays homage to the building’s original use) in Andersonville. The space includes a 1930s-style speakeasy performance bar, a 107-seat theater, and a close-up gallery.

Head below ground to reveal a women-led cocktail lounge


Friendly neighborhood lesbian bar 2500 W Chicago Ave · Chicago, IL 60622


Chicago’s Ukrainian Village showcases traditional eateries, churches, cultural hubs, and a new wave of small businesses, including LGBTQ+-owned craft cocktail lounge Dorothy. Opened on Valentine’s Day 2020 (we all know what happened next), the cozy venue resiliently bounced back, and now attracts a queer and ally crowd symbolic of Chicago’s gay scene. Monthly events include the open mic Fruit Salad and Lust for Life, a monthly “rock n’ roll burlyq revue.”  

Sister venues include Split-Rail upstairs, where chef-owner Zoe Schor features fresh takes on comfort food like Nashville hot lamb ribs and whipped feta at dinner and craveable fried chicken and waffles at brunch, and The Martin, an adjacent art gallery founded and curated by Whitney LaMora.

Thinking about when to visit? Check out GayCities’ Chicago event listings to coordinate your travel with one of the city’s major happenings.

Don't forget to share: