Boystown, Chicago, is a lively neighborhood known for its rich culture and welcoming atmosphere. With its colorful streets, unique shops, and fun restaurants, it attracts visitors from all over. Whether you’re looking for great food, exciting nightlife, or simply a place to relax, Boystown has something for everyone.
Today, we will highlight some of the best things to do in Boystown. From amazing coffee spots to vibrant art installations, you’ll find plenty of activities to fill your day. Get ready to enjoy everything this fantastic neighborhood has to offer, no matter what your interests are!
Things To Do In Boystown Chicago
1. Stroll along the vibrant streets of Halsted Avenue
Walking along Halsted Avenue is a delightful experience. The street buzzes with energy from shops, restaurants, and lively bars. You’ll find a variety of colorful storefronts showcasing the area’s eclectic vibe.
As you stroll, take in the vibrant murals and art installations that reflect the community’s creativity. Stop at local cafes to enjoy a coffee or pastry while people-watching. The atmosphere is friendly, making it perfect for both locals and visitors.
Don’t miss the chance to check out unique boutiques. They offer everything from trendy clothing to handmade crafts. Each store carries a piece of the neighborhood’s spirit and charm.
Halsted Avenue is also proud of its LGBTQ+ culture. You can see signs of inclusivity and pride as you pass. It’s an essential part of the LGBTQ+ community in Chicago.
This stroll is more than just a walk; it’s an immersion into a lively and colorful area filled with stories and camaraderie. Come and enjoy all that Halsted Avenue has to offer.
Address: Halsted Ave, Chicago, IL 60657.
2. Visit the iconic Kingston Mines for a night of live blues music
Kingston Mines is a legendary venue for blues music lovers. It showcases incredible live performances every night. The atmosphere is vibrant and intimate, ensuring you feel part of the action.
As you enter Kingston Mines, you’ll notice the rich history resonating within its walls. This venue has hosted countless greats, and today’s artists continue that tradition. Just grab a drink, and settle in for a fantastic night of music.
Marvel at the talent on display. Multiple bands perform in separate rooms, catering to every blues taste. You can move from one performance to another, experiencing diverse sounds and styles.
Don’t forget to bring your friends! The upbeat vibe makes it an ideal spot for an entertaining night out. Dance along with the rhythms or just relax and soak it all in. It’s genuinely a unique experience.
So, whether you are a die-hard blues fan or a newcomer, Kingston Mines is a must-visit. Expect a night of unforgettable performances in a welcoming environment.
Address: 2548 N Halsted St, Chicago, IL 60614.
3. Enjoy a cocktail at the famous Sidetracks, known for its great bar scene
Sidetracks is one of Chicago’s top spots for cocktails and nightlife. This vibrant bar is famous for its lively atmosphere and creative drinks. As you step inside, you’ll be greeted by friendly faces and a welcoming vibe.
Get ready to enjoy a fantastic selection of cocktails. The menu features innovative combinations that cater to every taste. From classic drinks to new concoctions, there’s always something to excite your palate.
The outdoor patio is a highlight. It’s a perfect spot to relax with friends on warm evenings. The bustling atmosphere adds to your experience, making it a great place to socialize.
Entertainment is plentiful here, too! Sidetracks hosts events, karaoke nights, and special themed parties. You’ll find both locals and visitors enjoying the lively scene.
No matter the occasion, Sidetracks guarantees a fun time. Enjoy great drinks and join in the excitement that fills the air.
Address: 3349 N Halsted St, Chicago, IL 60657.
4. Explore the unique shops and boutiques along North Halsted Street
North Halsted Street is a shopper’s paradise filled with eclectic boutiques. Each store offers unique items that you won’t find anywhere else. As you walk, you’ll discover everything from fashion to home decor.
Take your time browsing the shops. Many showcase local artists and designers, fostering a creative community. You can find distinctive clothing pieces, artisan jewelry, and funky decor items, all reflecting the vibrant spirit of the neighborhood.
Stopping at local bookstores is a must. They often host readings and events, making them a hub for literary fans. You can find books that resonate with both locals and the LGBTQ+ community.
Each boutique tells its own story. Chat with the owners and learn about their inspirations. Their passion makes your shopping experience all the more enjoyable.
North Halsted Street is not just about shopping; it’s about supporting local businesses and enjoying a unique community atmosphere. Make sure to explore all it has to offer!
Address: North Halsted St, Chicago, IL 60657.
5. Check out the LGBTQ+ history at the Gerber/Hart Library and Archives
The Gerber/Hart Library and Archives is a treasure trove for LGBTQ+ history lovers. This unique library houses a vast collection of books, documents, and artifacts. It showcases the rich history of the LGBTQ+ community in Chicago and beyond.
When you visit, you can browse through numerous resources. The library hosts rotating exhibits that highlight significant historical events and figures. It’s a wonderful opportunity to learn more about the community’s heritage.
In addition to physical materials, the library also offers various programs. Workshops, discussions, and community events are designed to engage people and promote understanding. It’s a welcoming space for everyone.
Volunteers and staff are incredibly knowledgeable. They are happy to guide you through the collections and answer any questions you may have. Their passion for LGBTQ+ history is contagious!
Visiting the Gerber/Hart Library is an enriching experience. It’s not just a library; it’s a hub for education and community connection.
Address: 6500 N Clark St, Chicago, IL 60626.
6. Attend a drag show at the popular Roscoe’s Tavern
Roscoe’s Tavern is a well-known venue for drag shows in Chicago. This lively bar guarantees an entertaining night filled with energy and talent. Each performance is a showcase of creativity, humor, and style.
As you enter, you’ll instantly feel the buzz in the air. The colors, the laughter, and the lively music create an exciting atmosphere. Make sure to arrive early to grab a good spot and enjoy a drink while you wait.
Each drag show features talented performers pushing the boundaries of art and entertainment. They often include lip-syncing, comedy, and dazzling costumes. Audience participation makes it even more fun, allowing you to become part of the action!
Roscoe’s is also famous for its themed nights and special events. From trivia nights to charity fundraisers, there’s always something happening. This makes it a great place to visit more than once.
Whether you’re a longtime fan of drag shows or a first-timer, Roscoe’s Tavern offers an unforgettable experience filled with laughter and joy.
Address: 3356 N Halsted St, Chicago, IL 60657.
7. Relax in the lush greenery of the Alfred Caldwell Lily Pool in nearby Lincoln Park
The Alfred Caldwell Lily Pool is a hidden gem in Lincoln Park. This tranquil oasis features beautiful landscapes and serene water features. It’s an excellent spot for relaxation and reflection away from the city’s hustle and bustle.
As you enter, the lush greenery surrounds you, creating a peaceful atmosphere. Walking along the pathways, you can admire lovely ponds filled with vibrant lilies. The natural beauty invites you to unwind and enjoy the tranquility.
This area is perfect for nature lovers. You can spot various birds and wildlife while taking a leisurely stroll. The setting is ideal for a quiet afternoon spent reading or meditating.
Don’t forget to bring your camera! The scenic views and charming bridges provide perfect photo opportunities. The location transforms with the seasons, offering unique sights year-round.
Visiting the Alfred Caldwell Lily Pool is a delightful escape into nature. It’s a refreshing break where you can recharge while surrounded by beauty.
Address: 1252 W Fullerton Pkwy, Chicago, IL 60614.
8. Discover local art at the Boystown Mural on North Halsted Street
The Boystown Mural is a vibrant celebration of LGBTQ+ pride and artistry. Located on North Halsted Street, this stunning piece of public art deserves a visit. The mural captures the spirit of the community through colorful imagery and powerful messages.
As you approach, you’ll immediately be drawn in by its magnificent colors. The mural reflects themes of love, acceptance, and diversity. It serves as a reminder of the progress made and the challenges still faced by the LGBTQ+ community.
Take time to admire the intricate details and artistry. Each section tells a story, inviting you to reflect on the history and identity of the community. It’s more than just art; it’s a statement of pride.
Snap some photos to commemorate your visit. The mural is an iconic backdrop for selfies and group shots. It highlights the area’s commitment to inclusivity and love.
Visiting the Boystown Mural is not just an artistic experience; it’s a meaningful one. It connects you to the heart of Boystown and its rich cultural heritage.
Address: 6 W Roscoe St, Chicago, IL 60657.
9. Participate in the annual Chicago Pride Parade, one of the largest in the country
The Chicago Pride Parade is a landmark event celebrated each June. It’s one of the largest and most vibrant pride events in the United States. Thousands come together to celebrate diversity, love, and equality in a joyful atmosphere.
As the parade kicks off, the streets come alive with colorful floats and enthusiastic crowds. Participants decorated in rainbow colors spread joy and positivity. You’ll feel the sense of community and acceptance all around you.
Expect a lively atmosphere filled with music, dancing, and inspiring speeches. The parade showcases various organizations, businesses, and activists standing up for LGBTQ+ rights. It’s a powerful reminder of the progress made over the years.
Joining in is easy! Whether you watch from the sidelines or participate, you’re part of something special. Bring your friends and family to experience the love and unity this event fosters.
The Chicago Pride Parade is a celebration of authenticity. It’s an unforgettable experience that leaves you feeling uplifted and inspired.
Address: Starting point at Montrose Avenue and Broadway St, Chicago, IL 60657.
10. Visit the historic Theatre on the Lake for live performances
Theatre on the Lake is a historic and cherished venue for performances in Chicago. Set right on the water’s edge, it offers stunning views and an intimate setting. This unique backdrop enhances every show, providing a memorable experience.
The theatre hosts a variety of performances. From plays to musicals, there’s something for everyone. You can catch local talent as well as established artists gracing the stage. The quality of performances is consistently impressive.
The atmosphere is warm and inviting. You’ll enjoy a close connection to the performers, making each show feel personal. The intimacy of the space allows for a unique shared experience among the audience.
Make sure to check the schedule for different events. The lineup often features themed nights, special guest artists, and more. Each event is a chance to discover new talent and enjoy captivating stories.
Visiting Theatre on the Lake is a wonderful way to enjoy a night out. Immerse yourself in the performing arts as you take in the beautiful surroundings.
Address: 2401 N Lakeshore Dr, Chicago, IL 60614.
11. Check out the entertainment at the LGBTQ-friendly venue, Smart Bar
Smart Bar is a staple in Chicago’s nightlife scene. Known for its welcoming vibe, this LGBTQ-friendly venue offers fantastic entertainment and dancing. As you enter, you can feel the energy pulling you into the experience.
The club features a superb lineup of local and international DJs. Each night promises a mix of high-energy beats that will get you moving. Enjoy the immersive sound system that enhances every track played.
Smart Bar also hosts special events and themed parties. These events attract an eclectic crowd, creating a rich and diverse atmosphere. It’s a great place to meet new people while enjoying the vibrant nightlife.
The bar serves innovative cocktails and drinks, perfect for keeping the party going. Relax with friends and soak in the lively ambiance as you toast to a fantastic night.
Whether you’re dancing or mingling, Smart Bar guarantees a memorable experience. It’s an essential part of Chicago’s nightlife, celebrating love and acceptance.
Address: 3730 N Clark St, Chicago, IL 60613.
12. Take a scenic bike ride along the Lakefront Trail, accessing Boystown easily
Biking along the Lakefront Trail is a treat for nature lovers and fitness enthusiasts alike. This scenic trail stretches for 18 miles alongside Lake Michigan. It offers breathtaking views of the water and the Chicago skyline.
As you ride, enjoy the fresh air and the soothing sounds of the waves. The trail is well-maintained, making it suitable for all skill levels. You’ll encounter fellow cyclists, joggers, and walkers along the way.
The route provides easy access to neighborhoods, including Boystown. You can explore the local shops, cafes, and parks once you reach your destination. The blend of outdoor activity and community exploration is enjoyable.
Make sure to pause and take in the stunning scenery. Several spots along the trail are perfect for taking photos or enjoying a picnic. It’s an ideal way to connect with both nature and friends.
Biking the Lakefront Trail is an adventure you don’t want to miss. It’s an experience that combines fitness, beautiful views, and unforgettable memories.
Address: Lakefront Trail, Chicago, IL 60613.
13. Enjoy brunch at the trendy brunch spot, Toast
Toast is a beloved brunch destination located in the heart of Boystown. Known for its delicious food and inviting atmosphere, it’s the perfect spot for a weekend meal. The menu features a variety of creative dishes, all made with fresh ingredients.
From classic breakfast staples to innovative brunch options, there’s something to satisfy every palate. Make sure to try their famous French toast or savory omelets. Each dish is beautifully presented and incredibly tasty.
Toast’s cozy interior creates a welcoming vibe. It’s an ideal place to gather with friends and enjoy leisurely conversations over coffee. The friendly staff adds to the overall positive experience.
Don’t forget to check out their drink specials! The brunch cocktails, including mimosas and bloody Marys, are well-crafted and refreshing. They perfectly complement your meal.
Enjoying brunch at Toast is a delightful experience. It’s a combination of great food, good company, and a comfortable atmosphere that keeps guests coming back.
Address: 3431 N Halsted St, Chicago, IL 60657.
14. Explore the nightlife at The Chalet, one of the oldest gay bars in the area
The Chalet is a historic gay bar that has stood the test of time. It’s known for its welcoming atmosphere and vibrant nightlife. This iconic venue offers a unique blend of fun, entertainment, and community spirit.
The Chalet features a spacious outdoor garden perfect for socializing during warmer months. Inside, the décor is charming, creating a cozy yet lively environment. Live DJ sets and themed nights attract a diverse crowd who come together to enjoy great music and dancing.
The bar also serves delicious drinks. Their creative cocktails and friendly bartenders keep the conversations flowing as you mingle. Enjoy the lively entertainment and feel the sense of belonging.
Make sure to check the event calendar! Regular drag shows, karaoke nights, and special parties create an exciting atmosphere. Each visit feels different as you participate in the ever-changing events.
Visiting The Chalet is a fun outing that connects you with the community. It’s a celebration of authenticity in a beautifully inclusive environment.
Address: 3724 N Broadway St, Chicago, IL 60613.
15. Attend film screenings and events at the Chicago Filmmakers
Chicago Filmmakers is a vibrant center for independent film and creativity. It promotes diverse voices and showcases unique filmmaking talent. With regular screenings, it’s a great spot for cinema lovers to explore fresh and innovative works.
The film programs often focus on LGBTQ+ themes and stories, making it an inclusive space for everyone. You can attend thought-provoking documentaries, narratives, and experimental films. Each screening invites discussion and reflection.
Beyond screenings, Chicago Filmmakers also hosts workshops and events. These opportunities allow you to connect with filmmakers and learn about various aspects of production. It’s a chance to dive deeper into the art of storytelling.
As you explore the facility, you’ll find a supportive community of film enthusiasts. Engaging discussions often follow screenings, encouraging connections among attendees.
Visiting Chicago Filmmakers is a rewarding experience. It celebrates creativity and the power of storytelling, inviting everyone to find their narrative.
Address: 5243 N Broadway St, Chicago, IL 60640.
16. Visit the Broadway Armory Park for diverse recreational activities
The Broadway Armory Park is a fantastic community space offering various recreational activities. Located in a historic armory building, it features modern amenities catering to all ages. You can find exciting programs ranging from sports to arts and fitness.
The park’s facilities include a gymnasium, fitness rooms, and multi-purpose spaces for events. Whether you’re interested in joining a sports league or attending a fitness class, there’s something for everyone. Families especially appreciate the playground and outdoor areas.
Also, local community events frequently take place here. Seasonal festivals and open houses invite residents to come together and celebrate. It’s a great opportunity to connect with neighbors and enjoy the vibrancy of community life.
Make sure to explore the nearby areas as well. The park is conveniently located close to a variety of shops and cafes, making it easy to enjoy a day out.
Visiting Broadway Armory Park is a fulfilling way to engage with the community. It encourages health, creativity, and connection among its visitors.
Address: 5917 N Broadway St, Chicago, IL 60660.
17. Indulge in a sweet treat at the beloved bakery, Sweet Bites
Sweet Bites is a delightful bakery known for its mouth-watering desserts. From cakes to cookies, each treat is made with love and care. The aroma of freshly baked goods fills the air, inviting you to indulge your sweet tooth.
Popular items include delectable cupcakes, brownies, and pastries, all beautifully decorated. Don’t miss their unique flavor combinations that surprise and delight every palate. Each bite is a little piece of heaven!
The cozy atmosphere is perfect for relaxing with friends or grabbing a quick snack. Take a seat, enjoy your treat, and pair it with a cup of coffee for a perfect afternoon.
Sweet Bites focuses on using high-quality ingredients. This dedication to quality shines through in every delicious creation. Plus, the friendly staff are always eager to help with recommendations!
Visiting Sweet Bites is an enjoyable experience that makes your day a little brighter. Treat yourself to something sweet—you won’t regret it!
Address: 2800 N Broadway St, Chicago, IL 60657.
18. Experience the Boystown Halloween Parade, a festive celebration every October
The Boystown Halloween Parade is a lively and colorful event held every October. This festive celebration is known for its fun costumes and community spirit. Locals and visitors alike come together to participate in this Halloween extravaganza.
The parade features creative floats, energetic performers, and plenty of excitement. Expect to see a wide variety of costumes, ranging from spooky to hilarious. It’s a chance for everyone to celebrate together while showcasing their creativity.
Live music, dancing, and entertainment fill the streets, adding to the vibrant atmosphere. Families and friends gather to enjoy the festivities and share in the cheerful ambiance. It’s a true celebration of community and inclusivity.
Joining the parade is easy! You can participate or simply find a spot along the route to cheer on the participants. The experience is lively and unforgettable.
Don’t miss the Boystown Halloween Parade, a unique opportunity to experience this vibrant community’s spirit. It’s a festive event that truly captures the essence of autumn fun.
Address: Halsted St & Addison St, Chicago, IL 60657.
19. Relax at the picturesque Montrose Beach, just a short ride away
Montrose Beach is a beautiful escape from city life. Located along Lake Michigan, it offers stunning views and ample space to unwind. This popular beach destination is perfect for sunbathers, swimmers, and anyone looking to relax by the water.
The sandy shores make it ideal for lounging and enjoying a sunny day. You can bring a picnic to savor while soaking up the sun, or just kick back and enjoy the calming sounds of the waves. The beach is a great spot to read or take in the scenic beauty.
Don’t forget your water gear! Swimming is refreshing, and the lifeguards ensure a safe and fun experience. You may also want to wander along the trails nearby, where you can enjoy more of the natural beauty.
Mornings and evenings are particularly lovely, as the sun rises or sets over the lake. It’s a breathtaking sight that shouldn’t be missed.
Montrose Beach is the perfect getaway to relax and recharge. Enjoy the lovely atmosphere and embrace the beach vibes!
Address: 4400 N Lake Shore Dr, Chicago, IL 60640.
20. Enjoy a drink at The Files Rooftop Bar, taking in stunning views of the skyline
The Files Rooftop Bar offers an amazing drinking experience with unparalleled views of the Chicago skyline. Located atop a stylish venue, it provides the perfect ambiance for a night out with friends. The atmosphere is lively yet relaxed, ideal for sipping cocktails and enjoying good company.
The drink menu features creatively crafted cocktails, beer, and wine. Each drink is expertly prepared, making it a great choice for any palate. You can indulge in their signature drinks while reveling in the beautiful scenery.
As the sun sets, the city lights begin to sparkle. It’s a breathtaking view that enhances your rooftop experience. Comfortable seating invites relaxation as you take in the stunning vistas surrounding you.
Also, check for special events and themed nights that add fun twists to your visit. The energetic vibe and friendly service ensure you’ll have a memorable experience.
Visiting The Files Rooftop Bar is more than just a drink; it’s a celebration of Chicago’s vibrant nightlife and stunning beauty.
Address: 4141 N Marine Dr, Chicago, IL 60613.
Final Thoughts
Exploring the vibrant Boystown area in Chicago promises a rich array of experiences. From lively nightlife to meaningful history, each itinerary offers something unique. You can immerse yourself in the local culture, whether attending a parade or savoring delightful treats. If you’re looking for more seasonal fun, check out the things to do in Chicago in winter to keep the adventures going. As you visit, you’ll connect with the community and celebrate the spirit of inclusivity. Each stop reveals the charm and vibrancy of this iconic neighborhood. The enticing activities create lasting memories and foster a sense of belonging.