Neighborhood Dating Guide: Northalsted

Northalsted, commonly known as “Boystown”, was the first “officially recognized gay village in the United States.” Donned with rainbow accents and a variety of pride flags, Northalsted is a location where people of any race, gender, or sexual orientation are not only accepted but celebrated! This neighborhood stretches from the 3100 to 3800 block of North Halsted, aptly naming the area. Nestled between Lakeview and the actual lake, there are tons of things to do and tons of places that make excellent first (or hundredth) date night spots! 

Looking for awesome date night spots around the rest of the city? Check out Pilsen, Ravenswood, and Logan Square!


The Legacy Walk

3245-3704 North Halsted Street Outdoor Streetscape Museum Historic Landmark, Chicago, IL 60657


Since October 11th, 2012, the Legacy Walk has stretched from 3245 to 3707 North Halsted Street, honoring pioneers in the LGBTQ community. If you’ve never taken the time to stop and read the bronze plaques, plan some time soon with your partner to take a nice walk, explore the neighborhood, and learn more about these important figures. Through the walk, you’ll learn about James Baldwin, Margaret Chung, The Pink Triangle, and many more. These days, old plaques are often replaced with new ones, so there’s always a new story to learn as you honor the folks that are incredibly important to the LGBTQ community. 


3453 N Halsted St, Chicago, IL 60657

Looking for a bit of fun and magic? Check out Trickery! With shows on Thursday, Friday, Saturday and Sunday, a trip to the Trickery makes for the perfect addition to an already entertaining date night. Guests call the Trickery “witty and mind-blowing”, and who doesn’t love to be slightly deceived in the name of entertainment? The Trickery is BYOB, so feel free to bring along your favorite drinks to sip on during the show. 


Laugh Factory

3175 N Broadway, Chicago, IL 60657


It’s often said that the quickest way to someone’s heart is through their stomach, and at the Laugh Factory, you’re sure to have a good belly laugh. With tons of shows each week, there’s pretty much always an opportunity to head out and go see some of the freshest new comedians in Chicago. One thing to note is there is a two drink minimum, but that’s easy to take on once you see their delicious cocktail menu. From Dirty “Dom”tini’s to prosecco, you’re able to wet your palette while tickling your funny bone. 

Reckless Records

929 W Belmont Ave, Chicago, IL 60657

If you and your partner love music but haven’t spent enough time digging for records together, it’s time to go to Reckless Records. With three locations across the city (one in Northalsted, of course), there is so much music to be discovered. Reckless Records also hosts tons of events with artists and signings, so keep an eye on the happenings in the chance that one of your favorite artists heads to town! We can’t think of a better way to amplify your date night than by finding your next favorite album and making it the playlist for your relationship. 

Progress Bar Chicago

3359 N Halsted St, Chicago, IL 60657


Progress Bar is known as one of Chicago’s best LGBTQ bars. With a cloud-like structure made up of over 19,000 stunning lights, Progress Bar is sure to light up your night. Here, not only will you find your favorite craft brews and cocktails, but daily specials and events make each visit unique from the last. From Industry Nights to Drag Shows to a rotating list of DJs on the weekend, Progress Bar has an incredible atmosphere that will keep you coming back for more. 

Drew’s on Halsted

3201 N Halsted St, Chicago, IL 60657


When you and your partner are looking for wonderful entertainment, there isn’t a place better than Drew’s on Halsted. With live music and shows on weeknights paired with their famous drag brunches on the weekend, Drew’s offers each guest an exciting time that you won’t soon forget. Along with a brunch menu, Drew’s has a full lunch and dinner menu full of dishes to curb any appetite. Each event comes with a $25 food and drink minimum, and reservations are recommended, so make yours today! 

Roebuck – DryHop

3159 N Broadway, Chicago, IL 60657

Is there any better combination in Chicago than beer and pizza? We don’t think so – and it certainly makes for an excellent date night! At Roebuck, indulge in delicious thin-crust pies as well as the best brews to come out of DryHop Brewers. Pair a flight with the Standard Bearer or Little Green Men. There are always events going on, too, so plan your night of pizza and beer with collabs, industry nights, and much more!

Featured Image: Progress Bar Chicago