The Ultimate 48-hour Chicago Gaycation

Aug 21, 2022

Chicago is the second largest city in the United States. It also has one of the largest gay villages, a very activity LGBTQ+ community, and there are iconic only-in-Chicago things to see, do, and experience. Together, these things have helped propel Chicago as a top choice for queer travellers.

Storefront on Northalsted in the famous BoysTown neighborhood in Chicago, Illinois.

If you haven’t been to Chicago before, or haven’t been in a while, these are the must-do things to plan on experiencing – whether you plan on visiting for two days or a week. Here are our top picks to make the most of your gay stay in Chicago!

The Bean in Chicago's Millennium Park.

Explore Northalsted 

Northalsted is one of the oldest and largest gay neighborhoods in North America. Commonly called Boystown, Northalsted Street is a melting pot of bars, restaurants, nightclubs, lounges, boutique restaurants and shops, and other services. 

Pride Crosswalk - Chicago, Illinois

One of the highlights of Northalstead is the Kit Kat Lounge, a great location for drag brunch with bottomless mimosas, an amazing selection of martinis, live drag shows, food, and evening lounge hang-out.

A drag queen performing at KitKat Lounge in Chicago.

Learn about LGBTQ History on The Legacy Walk 

For a half mile of the Northalsted Street, in Boystown, there are iconic bronze pylons that line the street. They are a defining marker of Chicago’s gay village, between Belmont Avenue and Grace Street. In total, there are 20 of the 25 foot tall, decorative steel pylons, coated in bronze, with rainbow rings, and lights, that line the street in pairs. They are more than just street art. They are a historic landmark and a monument to LGBTQ history. 

A bronze pylon with rainbow rings, a historic landmark, part of the Legacy Walk and monument in Chicago's Northalsted district.

One each pylon there is a bronze biographical memorial marker. Each one commemorating the life and work of notable LGBTQ individuals whose achievements helped shape the world. 

A bronze pylon with rainbow rings, a historic landmark, part of the Legacy Walk and monument in Chicago's Northalsted district.

The Legacy Walk plaques honour and recognize icons and moments of the LGBTQ movement, like Matthew Sheppard, Martha P Johnson, Freddie Mercury, the Stonewall Riots, the Pink Triangle, and more. 

A bronze pylon with rainbow rings, a historic landmark, part of the Legacy Walk and monument in Chicago's Northalsted district.

The Legacy Walk is an inspiring, moving, and educational opportunity to learn about queer history and the moments and people in time who made a lasting and positive change in LGBTQ+ rights and freedoms. 

A bronze pylon with rainbow rings, a historic landmark, part of the Legacy Walk and monument in Chicago's Northalsted district.

Take Iconic Selfies and Millennium Park

Located on Chicago’s waterfront, at the forefront of Chicago’s downtown, is Millennium Park. It’s a magnificent public space for art, music, architecture, gatherings, physical activity, play, and gardens. 

The Chicago city skyline from Millennium Park in downtown Chicago.

Millennium Park is comprised of three distinct park areas: Millennium Park, Maggie Daley Park, and Grant Park. These parks are not only fantastic public spaces but are home to some of the most iconic and Instagram-worthy locations in all of Chicago!

The Bean in Millennium Park in downtown Chicago.

Cloud Gate, popularly known as The Bean, is a sculpture by British artist Sir Anish Kapoor. It is the proud centerpiece of Millennium Park. If there’s one photo you want to get in Chicago, this is it. 

The Crown Foundation by Jaume Plensa in Millennium Park in Chicago.

Right alongside The Bean is the popular water feature, Crown Foundation by Jaume Plensa. Originally intended to be an art installation and water feature, it quickly became a popular summer water fountain to play and cool off. Two giant pillars, one on each end, have 1,000 digital faces that play in five-minute rotations. At the end of each rotation, the face puckers up and then shoot water from the mouth, providing a refreshing splash for joyful participants who line-up for a chance to be sprayed. 

Maggie Daley Park is connected to Millennium Park with a serpentine stainless steel and wood-planked bridge.

Maggie Daley Park is connected to Millennium Park with a serpentine stainless steel and wood-planked bridge. Maggie Daley Park offers a quarter-mile long ribbon of concrete for roller and inline skating in the summer, and ice skating in the winter. There is also a 40-foot climbing wall. 

The climbing wall in Maggie Daley Park in Chicago.

Throughout all the parks there are art installations, gardens, and quiet areas, providing a peaceful and tranquil spot to relax and enjoy the outdoors, while being just steps away from the bustle of the downtown core. 

Public art in Millennium Park in Chicago.

Drag Brunch at Lips 

Drag brunch is the quintessential part of any gaycation, and Lips Drag Queen Show Palace, Restaurant & Bar in Chicago’s south end is absolutely a must-do during your visit to Chicago. 

Drag Brunch at Lips Chicago.

Lips Drag Queen Show Place is exactly that. A giant palace. It’s a purpose-built space designed specifically for drag brunch perfomances. It’s over-the-top with chandeliers and disco balls, whacky wall-paper, and loud colors. It invites excitement and the energy that every drag show deserves. 

Drag Brunch at Lips Chicago.

Lips is the perfect place to celebrate your birthday or engagement. When your drag server comes by, let them know what you are celebrating. You’ll be provided a crown and you’ll be invited up on stage for a piece of celebration cake and to get your photo taken with some of the drag queens. 

Drag Brunch at Lips Chicago.

The drag queens are the life of the party at Lips. There is an entire line-up of drag queens ready to put on an original show every time. Each show is a completely different line-up of talent and songs, so you’ll never see the exact same show twice. The costumes and choreography are fabulous – and there’s not a single bad seat in the house because the queens perform all over the venue for each song. Remember to tip your queens! 

Drag Brunch at Lips Chicago.

Finally, the food and drink. After all, that is half of what makes drag brunch so fun. There are bottomless drinks – bloody mary’s, mimosas, sparkling, screwdrivers, and more. Plus, there are shots, cocktails, and all the other breakfast delights. The menu offers all the classic brunch options, from eggs benny and fried chicken with waffles, to fluffy pancakes to hamburgers. 

Drag Brunch at Lips Chicago.

Seriously, Lips Drag Queen Show Place is exactly where you will want to be on your gaycation to Chicago. 

See The Massive 3-D Interactive Model of Chicago at the Chicago Architecture Center 

Chicago is known for its skyscrapers and iconic skyline. The city has evolved over the decades and continuously redefines itself. The Chicago Architecture Center,  founded in 1966, has over 600 volunteers telling the stories of Chicago architecture with its half-million guests each year. 

Chicago model architecture in the Chicago Architecture Center.

The Chicago Architecture Center is home to the largest model of the city of Chicago. It’s an interactive 3-D model of the city. The all-white model took thousands of hours to build, and it showcases the historic and landmark buildings and streets. 

Chicago model architecture in the Chicago Architecture Center.

When the informational video, explaining the history and development of the city, isn’t playing, guests can use the interactive display to learn more about specific neighbourhoods and buildings. 

Chicago model architecture in the Chicago Architecture Center.

Hop Aboard the Chicago Architecture Foundation Center River Cruise  

The Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady is an absolute must-do activity when visiting the Windy City – it’s ranked the #1 tour in Chicago on TripAdvisor reviews. 

The Chicago Architecture Foundation Center River Cruise aboard Chicago's First Lady

Hop aboard Chicago’s First Lady Cruises – a two-story riverboat that offers stunning views of Chicago, making its way up the Chicago River, up both the left and right arms, and then into Lake Michigan. 

The Chicago Architecture Foundation Center River Cruise aboard Chicago's First Lady

On board the volunteer narrator will brilliantly share stories and information about buildings along the riverfront and the role they played in the city’s development, and redevelopment. 

The Chicago Architecture Foundation Center River Cruise aboard Chicago's First Lady

You will also learn about the city’s efforts to develop ‘river walks’, pedestrian walks along the river, which one day will all be connected. Learn how the Chicago River was once a dumping ground but has been redeveloped into an important and thriving asset for Chicago. 

The Chicago Architecture Foundation Center River Cruise aboard Chicago's First Lady

Not only is this a fun learning opportunity, but it’s a great way to relax, get some sun on the rooftop deck, have a cocktail, and take photos of Chicago from unique perspectives. 

The Chicago Architecture Foundation Center River Cruise aboard Chicago's First Lady

Have Authentic Chicago Deep Dish Pizza at Giordano’s 

A trip to Chicago isn’t complete without having deep dish pizza. Giordano’s is one of the most popular deep-dish pizzerias. There are locations throughout the city, including locations by Millennium Park and a few blocks from Boystown.

A trip to Chicago isn’t complete without having deep dish pizza. Giordano’s is one of the most popular deep-dish pizzerias.

Each location offers a full dining room with a full bar and a line-up of pizzas. If you’re new to deep dish, try the meat eater pizza – it’s a great first-time deep-dish experience. Know in advance that good things come to those who wait – you’ll want to order your deep dish as soon as you arrive, because it takes up to 45 mins to prepare. But it’s worth the wait! 

A trip to Chicago isn’t complete without having deep dish pizza. Giordano’s is one of the most popular deep-dish pizzerias.

Relax at the Spa

Not every minute of your trip to Chicago needs to be out exploring and experiencing the city. You need to plan time to relax. At the Godfrey Hotel Chicago, you’ll find a cute spa ready to help find your inner-calm and peace. A massage treatment from one of the professional staff is exactly what you’ll need as you wrap up your gaycation, before heading home and back to work. 

Stay at the Godfrey Hotel Chicago 

The Godfrey Hotel Chicago is a stunning luxury boutique lifestyle hotel located in downtown River North on Huron Street at LaSalle. With its iconic Cubist-influenced façade, each detail of this striking hotel has been designed with the guest’s experience in mind—a concept that is echoed throughout its state-of-the-art accommodations.

A guest suite at the Godfrey Hotel in Chicago.

This hotel’s location is perfect for everyone who wants to feel like they’re in their own little world: the I|O Rooftop Lounge offers stunning views of Chicago’s skyline, and the hip River North neighbourhood location means that guests will find themselves immersed in an exciting atmosphere as soon as they stroll through the doors.

A guest suite at the Godfrey Hotel in Chicago.

Make your reservation today at www.godfreyhotelchicago.com

More LGBTQ Travel Ideas from Choose Chicago 

Choose Chicago is the official sales and marketing organization responsible for promoting Chicago as a global visitor and meetings destination, leveraging the city’s unmatched assets to ensure the economic vitality of the city and its member business community. 

For more information, visit www.choosechicago.com and follow @choosechicago on Facebook, Instagram and Twitter. #ChicaGOandKNOW

A gay guy standing near a Progressive Pride flag on the Chicago Architecture Foundation Center River Cruise.

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Brian Webb

Brian Webb

Author

Brian Webb is the founder and editor-in-chief of HomoCulture, a celebrated content creator, and winner of the prestigious Mr. Gay Canada – People’s Choice award. An avid traveler, Brian attends Pride events, festivals, street fairs, and LGBTQ friendly destinations through the HomoCulture Tour. He has developed a passion for discovering and sharing authentic lived experiences, educating about the LGBTQ community, and using both his photography and storytelling to produce inspiring content. Originally from the beautiful Okanagan Valley in the southern interior of British Columbia, Brian now lives in Vancouver, British Columbia. His personal interests include travel, photography, physical fitness, mixology, drag shows.

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