Posted 21 days ago in Trending, pride month, lgbtq, events
2 MIN READ – Go down rainbow road and celebrate the LGBTQ community in the Chicago Loop this summer. Food and drink specials, drag brunch, and more are in store.
Macy’s Drag Brunch
Macy’s is hosting their wildly popular drag brunch in the Walnut Room on Saturdays, June 7 and 21. Enjoy delicious cocktails like their The Best Old Fashioned, along with live performances making for a booze-tastic weekend. A talented cast of performers will pay tribute to pride icons like Lady Gaga, Cher, Whitney, Madonna , Beyoncé, Janet and more! Learn more.
Go on a lgbtq-centered Walking tour
For June's Pride Month, join Tours With Mike at their Downtown LGBTQ Stories walking tour. Discover Chicago's hidden LGBTQ stories from the 19th century to today as you stroll through the city's downtown Book your Downtown LGBTQ Stories tour here.
For the fourth year in a row, Chicago Loop Alliance has adorned the iconic State Street with flags to commemorate Pride Month. The flags will be on display all of June, so while you're walking down State, be sure to stop and admire the flags, and maybe even snap a pic or two!
Pride night at the symphony center
Kick off Pride Month at the Symphony Center, Saturday June 7! Enjoy a preconcert celebration with beverages provided by Revolution Brewing and Sidetrack Chicago and drag performances by some of Chicago's finest entertainers. Learn more here.
Foozies Bingo at the Millroom
Attend a Bingo night with friends or a hot date at Industry Ale's new speakeasy the Millroom. All proceeds support The Trevor Project and its mission to uplift and protect LGBTQ+ youth. Book your ticket and learn more here.
Sip for a cause at The Renaissance Chicago Downtown Hotel
Located in the heart of downtown, The Renaissance Chicago Downtown Hotel is more than just a stylish place to stay—it's a vibrant, welcoming hub for the LGBTQ+ community year-round. A proud past recipient of the GayTravel Award, the hotel walks the walk with inclusive hiring practices—50% of its sales team identifies as LGBTQ+—and annual Pride celebrations that center joy, visibility, and giving back.
Guests can sip for a cause with custom Pride Month cocktails at Staytion Market & Bar and Raised, An Urban Rooftop Bar, where proceeds benefit local drag nonprofit Kiki Queens. In fact, the hotel has partnered with the group for years, even hosting a charity drag show at its rooftop bar in 2022. As a sponsor of Market Days and a supporter of queer-owned local businesses, The Renaissance is deeply committed to uplifting Chicago’s LGBTQ+ community—not just in June, but all year long.
History and Culture Package
This Pride Month, the Kimpton Gray Hotel invites guests to celebrate LGBTQ+ history and culture with its exclusive Pride Package. The offer includes two tickets for a guided tour of the Legacy Walk—the world’s only outdoor LGBTQ museum and a nationally recognized historic landmark—located in Chicago’s vibrant Boystown neighborhood. Guests will also receive a $10 Uber voucher to help get them there. Available for stays between June 1–30, this experience must be booked at least 72 hours in advance. Booking link here.
Cocktail of the Week
In celebration of Pride Month, JW Marriott Chicago is partnering with Center on Halsted to give back through their weekly “Cocktail of the Week” program. Throughout June, guests can enjoy a rotating lineup of vibrant specialty cocktails, including the Planter’s Punch, Pimm’s Cup, Division Bell, and Maggie Smith—with a portion of proceeds supporting the vital work of Center on Halsted. For those looking to unwind, the hotel’s exclusive couple’s spa package invites guests to relax side by side with a Signature Massage in a private suite for two—20% off when booked and mentioning the offer. Whether sipping for a cause or indulging in a luxurious escape, JW Marriott Chicago is offering meaningful ways to celebrate Pride all month long. Learn more here.
