- Trickery Chicago – this is a fun Magic show with a queer twist. Held in BoysTown on Halsted by Belmont, this is a great gay date night idea. It’s affordable, fun and available several nights a week. Aaron the magician is a delight.
- Legacy Project Tour – the outdoor museum that highlights queer individuals from all walks of life is beautifully on display throughout Halsted in BoysTown. You can walk and read the biographies of many queer luminaries. Tours are also available upon request.
- Chicago Pride Parade – the annual Chicago Pride Parade is a can’t miss event. If you’re in the city or a visitor, make sure to stop by anywhere along the route of the parade to pay respect and to join in on the festivities. The parade itself is loads of fun. Lots of floats and vendors make the rounds showcasing inclusivity, pride and history.
- Pride Fest – this queer outdoor music festival takes place the weekend before Pride and hosts several music stages with various local and national musicians and bands. If you’re looking for a terribly good time, this fest is it. It has music, food and lots of queer peeps. Fun times.
- Backlot Bash – a little something for the ladies for Pride month, the Backlot Bash is an outdoor fest in Andersonville that has great bands, lots of lesbians and fruity drinks. A lesbian hot spot to make new friends, meet someone or just dance with your besties.
- Market Days – this is the grandaddy of queer outdoor fests in Chicago. It’s held in BoysTown every August. Here you will find awesome Chicago cover bands like Sixteen Candles, Too Much Molly and others. The fest has plenty of food and drinks throughout and there are photo ops also. A fun time for sure. Check their website for the full musical line up.
- Big Gay Sal’s Pizza – this new Chicago LGBTQ+ owned pizzeria just opened up about a year ago and is already a local fave. Yummy pizza, drinks and an outdoor patio for Summer good times, make it a must visit while in Chicago.
- Queer Stride – this group headed up by queer lady Yoly Redrum, is all about getting you to walk or run with other queer folk in the city. They host monthly walks/runs and have a nice turnout with their walks. Great way to get some exercise and meet other like minded ladies or gents. Follow them on IG, to get info on their upcoming walks/runs.
- Sapphic Saturdays at Sidetrack – held last Sunday of the month at Sidetrack, this is a sweet dance party for lesbians and queer folks. Sapphic Saturdays features dancing, drag performances, special guests and a dedicated bar. Visit their IG for specific dates.
- Gay Comedy Show – watch queer comics live at Lincoln Lodge.
- Queer Speed Dating – at Hot Potato Hearts, they host a monthly queer speed dating evening. It’s a typical speed dating adventure with a series of 5 minute dates, but with a queer twist. As of this writing, it’s held at Hi-Lo bar (in Humboldt Park) on the last Monday of the month. Get your queer date on with Hot Potato Hearts.
- Watch Women’s Sports at Whiskey Girl – this cool womens sports bar is what we didn’t know we needed. Located in the Edgewater neighborhood in Chicago, they host regular nights of different women’s sports, everything from women’s basketball to women’s soccer and more. The place is roomy, friendly and great bartenders will fill you a drink. Also of note, is their New Years Eve night, which is a big ol’e lesbian party – not to be missed. In years past, they had Casino themed nights for NYE with DJ’s and all night dancing. It’s a can’t miss NYE event.
- Hike with the Queer Outdoor Club – The Queer Outdoor Club hosts regular hikes (mostly in the suburbs) and other outdoor events for those in the LGBTQ+ community. Check their IG page for upcoming hikes and events.
- Go NA with Queer Sober Social – if you’re looking to meet and mingle with those who are sober or sober-curious and queer, this is the group for you. Queer Sober Social is a Meetup group that hosts monthly events at local Chicago NA spots. One such event is their monthly outing held at Eli Tea Bar in Andersonville. But they have other events as well. Check their website or IG for event info. They also have a monthly Zoom meeting, the first Sunday of the month. Carly the creator and host, makes the Zoom meeting fun with break out rooms and plenty of icebreakers to get to know others. Fun sober times.
- Day Dancing w/Lovers & Friends CHICAGO – this very sexy and cool dance group meets once a month at various hot spots for day dancing for women, queers and allies over 30. Check out their IG page for upcoming events and ticket info. Get your groove on during the day (hours are usually 4-9pm) with this awesome queer dancing group.
- Attend a Drag Show – get DRAGALICIOUS at Hydrate Nightclub every Saturday at 9. Their website mentions that every Saturday night (for their Drag Revue) the show opens with a variety of exquisite QUEENS. And $5 Bud Light specials. The drag show has good reviews, both from locals and Chicago travelers.
- Explore Chicago Queer Neighborhoods – BoysTown & Andersonville
- Support Chicago LGBTQ+ orgs – Center on Halsted and Gerber Hart Library
- Dance the night away – at various gay clubs
- Go shopping at Out of the Closet resale shop – at Out of the Closet, you will find more than thrifty good finds, you will also find FREE HIV testing with same day results and proceeds of what you buy, go to support AHF: the AIDS Healthcare Foundation. Get some gently used merch, while supporting a good cause.
- Go shopping at CRAM – for sexy and stylish menswear, head straight to queer owned Cram in Lakeview. They have a full lineup of men’s clothing including shirts, pants, sexy underwear, shorts, bags and accessories. A must visit for cool men’s fashion.
- Volunteer with ChiPride.org – several opportunities are available to volunteer with this great local queer org. Check their website for details on current or upcoming volunteer opps.
- Go Queer Country Dancing – at Charlie’s Chicago, you can enjoy country music till your boots fall off. And fall off they will. They open late, have drinks galore and a cozy local vibe. Get your boot scootin hiney to Charlie’s for a gay ole country time. Located in Lakeview on Broadway.
- Visit Hollywood Beach – a/k/a Osterman gay beach; located in Edgewater, this small and cozy beach is great for a date, a picnic with your buds, a game of volleybal or frisbee and of course, some laps. A must visit during the Summer.
- Have Sunday Brunch – at Drew’s on Halsted. Whether you’re a local or traveling to Chicago, this gay hot spot is a must visit for Sunday brunch. Drew’s on Halsted in Lakeview, has for brunch the following: $49 dollar bottomless Mimosas which includes one entree and free sexy tunes by a local fave.
- Get a drink at Nobody’s Darling Bar – if you’re looking for a cute and cozy queer bar to hang out in, this is your spot. Located in Andersonville, this quaint black owned and queer owned bar is great for a weekend afternoon date, an evening nightcap, or a happy hour visit. Always a nice time, at Nobody’s Darling.
- Bike on Halsted – grab a city Divvy bike and bike the dedicated lane on Halsted in BoysTown
- Listen to Poetry – at Dorothy’s Lesbian Lounge (located in West Town) Dorothy’s has a unique mix of events all month long, from poetry readings to storytelling and comedy nights to queer open mic and even a silent book club. One of Chicago’s popular lesbian bars.
- Attend Midsommarfest – every June in Andersonville, this awesome queer friendly and street music festival hits the neighborhood and it’s a great time. You can expect quirky food, refreshing drinks and live music from great cover bands. This is one of the first and biggest Summer festivals to hit Chicago every year.
- Go to Pride Night – at various sporting events in the city, including Chicago Fire
- Check out LGBTQ+ Groups on Meetup – like the queer travel group and Single Lesbians in the City among others. Check out the events page for each group and see what’s available for you to attend. Most of these groups are active with lots of queer members and various upcoming events.
- Try your hand at Butch Boxing – Monthly meetup group (Butch Social) hosts the butch boxing at Title Boxing Club in Wicker Park. What a clever and cute idea. You get a heck of a workout, get to check out some cute butch babes and all for the low low low price of $10. (includes gloves) Deets on their IG page.
- Attend a Sneaker Ball – from the Lesbian Social Club. Check their IG page for details on this unique dancing event.
- Party after the Pride Parade – there are lots of parties that take place after the Chicago Pride Parade. One such party is the one hosted by the Lesbian Social Club that day of the parade at Moe’s Cantina in Wrigleyville from 1 to 6pm. The LSC hosts a variety of events throughout the month and you can keep up with all of them – via their IG page.
- Watch the Second City Outlaws Perform – Chicago’s very own queer country dancing group performs all over the city at various venues. To see where they will be rootin tootin next, check out their website or IG page for all upcoming events. This is a fun group and definitely worth checking out if you live in the city or traveling.
- Have a Burger at Mary’s Drag Diner – this LGBTQ+ friendly diner will serve up your usual American fare with a queer twist. The diner is a drag diner. Initially located in Andersonville, the new diner will soon reopen in a new location – Edgewater. Exact location is not yet known as its official opening date. Per a news report, it is slated to open in late Summer. Can’t wait to check this one out.
- Attend a Polyamory Cocktail Event – The Chicago Polyamory Connection hosts monthly cocktail nights at various locs in the city. Check their Meetup page for upcoming events.
- Read a Book – with the Chicago LGBTQ+ Diversity Book Club that hosts monthly meetings in person. All matters of books are selected each month and afterwards dinner, drinks and gossip at Wilde. A great way to read, meet new people and be a part of queer community.
- Buy Some Toys – In Andersonville, there’s a queer sex toy shop called Early to Bed. If you’re in the market for some new stuff for your bedroom, this is a great place to visit and check what’s new and sexy. From vibrators to strap on harnesses and more, you’ll find it at Early to Bed.
- Have Dinner – with Scene Free LGBT Chicago. They host monthly dinner outings at various city spots and welcome anyone in the queer community and allies. It’s a popular and active Meetup group with over 3,000 members. They also have monthly Sunday coffee at 10am.
- Watch a Queer Movie Online – The Bisexual Queer Alliance group on Meetup hosts a monthly queer movie night online. All kinds of movies are picked, from comedies to thrillers and sci fi to action and more. Join fellow queer peeps for a night of popcorn, snacks and drinks. All from the comforts of home.
- Attend a Singles Mixer – Sapphic Before Sunset has these on the regular, about monthly or so at various queer spots in the city. They have an upcoming mixer at queer bar Nobody’s Darling in Andersonville, for those over 30. Check out their IG page for details of this mixer and other upcoming events. You might meet a fabulous new friend, a possible new sexy partner or even just a Summer hottie.
- Ride a Bike – with Dykes on Bikes. This group has outings for bike rides all over the city for queers and of course – dykes. How fun! Get your helmet (required) and go on an awesome bike ride with your fave Chicago lesbians. Deets on IG page.
- Laugh It Up at Lavender Laugh Lounge – held at Whiskey Girl, the queer bar located in Edgewater. See and experience queer comics every Wednesday at 7pm. The Lavender Laugh Lounge is a LGBTQ+ comedy show you don’t want to miss. Visit their IG page to keep up with them.
- Enjoy Game Night – at Big Chicks in Uptown. This quirky queer bar is where it’s at, in Uptown. They have several events, including dancing till late on Saturdays, they have a game night monthly on Wednesdays from 6 to 10-pm. Plus yummy food and refreshing drinks.
- Get Your R&B Fix at Club Escape – a queer friendly bar and lounge in Chicago’s South side. They have weekly drag shows, dancing till late with R&B, old school and house music on the weekends. Outdoor patio in the Summer, touted as the largest LGBTQ+ patio in Chicago. Check them out for some great drinks, great dancing and great music.
- Calling All Queer Seniors! – The Center on Halsted (in Lakeview) has weekly pickleball sessions for those 55 plus. It’s held on Thursdays from 9am to 12pm. How very awesome is this? Get your paddle, your wiffle ball and your sneakers ready for some action on the court. FREE
- Attend Gay Chorus – The Chicago Men’s Gay Chorus has regular performances all over the city and state of Illinois. From their website, “through colorful performances that blend traditional choral music with musical theater, jazz and pop and a gay aesthetic – they aim to delight audiences”. Whether you’re a local queer or traveling, this show is a can’t miss when in the city.
- See Navy Pier Pride – I love Navy Pier and take all my guests (and dates) to it. It’s a little world of its own. From the popular ferris wheel to cool restaurants like Margaritaville and Casa Margarita and live music; Navy Pier is great. Well in June every year, they have a day of Pride – with live performances, storytelling, family activities and more. If you’re in the area, give this Pride event a try.
- Reeling Film Festival – this annual Chicago tradition of queer film is quite popular every year. Movies on rotation include indie films, comedies, thrillers and more – all with a queer theme. I’ve seen some gems through this festival and some not so nice gems. But it’s always fun to go and see new material. Held every September at the Landmark Century theater in Lincoln Park.
