25 Best & Fun Things to Do in Boystown Chicago

Address: 3040 N Halsted St, Chicago, IL 60657.

4. Savor rooftop drinks at Sidetrack

Sidetrack is a lively hotspot known for its stunning rooftop bar in Boystown. The rooftop offers fantastic views of the neighborhood while you sip on your favorite cocktails. It’s the perfect place to unwind after a long day.

At Sidetrack, you can enjoy a vibrant atmosphere filled with energy and laughter. The bar features a diverse drink menu, from craft cocktails to local beers. It’s an ideal spot to gather with friends or meet new people.

On weekends, the rooftop often fills up with patrons enjoying the sun and music. As the sun sets, the ambiance becomes even more inviting. You might catch a fun themed night or event happening during your visit.

Aside from the drinks, Sidetrack also offers a friendly staff that makes your experience memorable. You’ll feel welcomed the moment you step in. Whether you want to dance or just relax, Sidetrack caters to all moods.

Plan a visit to this popular destination for a great social experience. The rooftop at Sidetrack will surely become a favorite spot during your time in Boystown.

Address: 3349 N Halsted St, Chicago, IL 60657.

5. Dance the night away at Hydrate Nightclub

Hydrate Nightclub is one of the premier spots for nightlife in Boystown. Known for its vibrant atmosphere, you can expect an unforgettable night out dancing. The club regularly features top DJs spinning the latest hits and classic favorites.

The lighting and sound systems enhance the club’s energy, creating a fun and inviting environment. You’ll find a diverse crowd enjoying the music and letting loose on the dance floor. It’s a place to express yourself freely.

Many nights feature themed events, special performances, and drag shows that add to the excitement. Make sure to check out the schedule for any events happening during your visit. You might catch a memorable performance that you’ll talk about for years.

Hydrate also has a welcoming atmosphere, where everyone feels accepted and included. It’s a place where friendships can form under the disco lights. Consider arriving early to secure a good spot on the dance floor.

Whether you’re a local or a visitor, Hydrate Nightclub promises an exhilarating night out. The energy, music, and camaraderie make it a must-visit location in Boystown.

Address: 3458 N Halsted St, Chicago, IL 60657.

6. Catch a magic show at Trickery

Trickery is a unique boutique magic show experience in Boystown. Here, you can witness incredible illusions and mind-blowing tricks performed by talented magicians. The intimate setting allows for a magical experience you won’t soon forget.

Each performance showcases a blend of comedy and magic, making it fun for attendees of all ages. The interactive nature of the show invites audience participation, adding to the excitement. You might find yourself in the spotlight!

Trickery is a BYOB venue, so you can bring your favorite drinks to enjoy during the show. This adds a personal touch and makes the experience even more enjoyable. Grab a few friends and make it a fun night out.

Seating is often limited, so be sure to book your tickets in advance. The performances are usually scheduled throughout the weekend, providing multiple opportunities to catch a show.

If you’re looking for a night filled with laughter and amazement, Trickery is the place to be. Experience the art of magic in a delightful setting.

Address: 1520 W. Irving Park Rd, Chicago, IL 60613.

7. Visit Our Lady of Mount Carmel Church

Our Lady of Mount Carmel Church is a historic gem in Boystown. This beautiful church was built in 1922 and serves as a welcoming place for many. The architecture and interior design are stunning, making it worth a visit.

The church offers regular services, but you can also admire the artwork and stained glass windows. These details tell stories of faith and community. Walking through the church, you can feel a deep sense of peace and history.

Besides attending services, many appreciate its community outreach programs. The church is involved in various charitable activities, supporting those in need. It’s a wonderful example of how faith can nourish a community.

Visitors often comment on the welcoming atmosphere. The congregation is known for its friendliness, making people feel at home regardless of their background. It can be a valuable stop for reflection during your time in Boystown.

Plan a visit to Our Lady of Mount Carmel Church to enjoy its beauty and community spirit. It’s a heartfelt addition to your Boystown experience.

Address: 608 W. Belmont Ave, Chicago, IL 60657.

8. Take a stroll down North Halsted Street

North Halsted Street is the heart of Boystown, brimming with energy and activity. A stroll down this vibrant street offers a unique blend of shops, restaurants, and bars. It’s a lively neighborhood that showcases the spirit of the LGBTQ community.

As you walk, you’ll find colorful storefronts and businesses that cater to diverse interests. Local boutiques showcase unique fashion and accessories. You can also discover specialty shops that celebrate LGBTQ culture.

The street is dotted with popular restaurants, offering various cuisines to satisfy your palate. Whether you’re in the mood for a casual bite or a fine dining experience, you have plenty of options. Don’t forget to stop by a café for a refreshing drink.

In addition to shopping and dining, the people-watching along North Halsted Street is fantastic. The vibrant atmosphere draws locals and visitors, creating a welcoming community feel. You might even stumble upon an outdoor event or festival!

A walk down North Halsted Street captures Boystown’s essence. It’s a fun way to connect with the culture and community spirit of the neighborhood.

Address: North Halsted Street, Chicago, IL 60657.

9. Participate in Pride celebrations

Participating in Pride celebrations is an essential part of the Boystown experience, especially during summer. Each year, Chicago erupts in color and joy during its Pride Month festivities. Attendees come together to celebrate love, diversity, and equality.

The parade is a prominent highlight, featuring fantastic floats, vibrant costumes, and lively music. People from all walks of life join the festivities, showing their support for the LGBTQ community. It’s a beautiful sight of unity and acceptance.

Beyond the parade, various events take place throughout the month. These may include festivals, parties, and community gatherings. Each event offers a unique opportunity to enjoy live music, performances, and local food vendors.

Pride celebrations foster a sense of belonging. They provide a chance to learn about LGBTQ issues and history, making it a meaningful experience for everyone. Many local businesses also participate in the celebrations, further embracing the spirit of Pride.

Make sure to attend the next Pride events in Boystown. It’s an unforgettable opportunity to celebrate community and acceptance.

Address: Various Locations, Chicago, IL 60657.

10. Explore the Boystown Historical Society

The Boystown Historical Society offers a fascinating glimpse into the neighborhood’s rich LGBTQ history. This society plays a crucial role in preserving and sharing stories that shaped the community. Visitors can learn about the milestones and struggles of LGBTQ achievements in Chicago.

Through exhibitions and archives, the society showcases key events, figures, and moments that marked Boystown’s evolution. The passion behind this organization shines in every display. It’s a must-visit for anyone interested in understanding the community’s journey.

Engaging with the materials allows visitors to appreciate the strides made for LGBTQ rights. You’ll find photographs, documents, and personal stories that highlight both hardship and triumph. Each piece tells a vital part of the community’s narrative.

Additionally, the society often hosts workshops and guest speakers. These events encourage dialogue and support further learning. Visitors will leave feeling informed and connected to the history of Boystown.

Exploring the Boystown Historical Society is more than just an outing; it’s an enriching experience. It’s an essential stop for those wanting to delve deeper into LGBTQ culture and history.

Address: 444 W. Belmont Ave, Chicago, IL 60657.

11. Visit the nearby Belmont Harbor

Belmont Harbor is a picturesque getaway located along Lake Michigan. Just a short distance from Boystown, it’s an excellent spot for relaxation and outdoor activities. The harbor provides a beautiful view of the water and city skyline, making it perfect for photos.

You can enjoy a leisurely day by walking or biking along the paths that line the harbor. The scenic views invite visitors to soak in the natural beauty surrounding them. Bring a picnic to enjoy on the grass or by the water’s edge.

Belmont Harbor also offers boating options for those who love being on the water. Rent a kayak or sailboat to explore the lake, or simply watch the boats come and go. It’s a fun way to experience the vibrant atmosphere of the harbor.

During the summer, the area fills with activities, including festivals and outdoor concerts. Various events enrich the community vibe, attracting locals and visitors alike. It’s a wonderful opportunity to engage with the energy of the city.

A visit to Belmont Harbor adds a refreshing break to your Boystown experience. It’s a lovely way to connect with nature while still enjoying the urban setting.

Address: 2400 N Lake Shore Dr, Chicago, IL 60614.

12. Check out the Nature Boardwalk at Lincoln Park Zoo

The Nature Boardwalk at Lincoln Park Zoo is a hidden gem just a short ride from Boystown. This unique boardwalk weaves through wetlands and is perfect for nature lovers. You can observe local wildlife while enjoying a peaceful stroll.

As you wander along the boardwalk, you’ll encounter various plants and animals that call this area home. It’s an excellent opportunity for birdwatching or simply appreciating the tranquility of nature within the city. The scenic views of the zoo and the surrounding area add to the experience.

The boardwalk is also a fantastic spot for families. Kids can explore and learn about the different ecosystems and species present. Educational signs along the paths provide fun facts and insights.

If you’re looking for a break from the urban hustle and bustle, this is a great place to visit. The combination of nature and a leisurely stroll is refreshing and rejuvenating.

Spending time at the Nature Boardwalk enhances your Boystown trip by connecting you with the natural world nearby. It’s a peaceful escape you won’t want to miss.

Address: 2001 N Clark St, Chicago, IL 60614.

13. Dine at The Chicago Diner

The Chicago Diner is a beloved institution known for its delicious food and welcoming atmosphere. Located just a short distance from Boystown, this diner is famous for its vegetarian and vegan options. Both locals and visitors rave about the menu!

As you enter, you’ll feel the charming retro vibe. The diner serves up classic American comfort food with a twist. Signature dishes like the Vegan Corned Beet Reuben and milkshakes are crowd-pleasers.

The Chicago Diner prides itself on using fresh ingredients. Every dish is made with love, ensuring a satisfying meal for everyone. It’s an excellent choice for those looking for hearty and flavorful options.

The friendly staff adds to the experience. They are known for their hospitality and make everyone feel at home. Whether you’re dining solo or with a group, you’ll be well taken care of.

A visit to The Chicago Diner is a must during your time in Boystown. It’s not just a meal; it’s a delightful dining experience that leaves you wanting more!

Address: 3411 N Halsted St, Chicago, IL 60657.

14. Attend a performance at the Broadway Playhouse

The Broadway Playhouse at Water Tower Place is a fantastic venue for enjoying live theater. This theater showcases a variety of performances, from musicals to plays, making it a cultural highlight near Boystown. Check their schedule for upcoming shows when you visit.

With its intimate setting, the theater ensures that every seat provides a great view of the stage. You’ll feel the energy of the performers up close, making for a memorable experience. Grab a ticket to see a beloved classic or a new production; there’s always something exciting on stage.

The Broadway Playhouse also hosts special events and workshops. These engaging activities invite guests to dive deeper into the world of theater and performance art. It’s an opportunity to learn more while enjoying the magic of live performances.

Dressing up for a night at the theater adds to the fun! Many attendees enjoy a pre-show dinner at nearby restaurants to make it a special occasion. It’s a wonderful way to spend an evening in Chicago.

Make sure to check out the Broadway Playhouse during your time in Boystown. It’s a key part of the vibrant arts scene in the neighborhood.

Address: 175 E Chestnut St, Chicago, IL 60611.

15. Explore the Art Institute of Chicago

The Art Institute of Chicago is a must-visit for art lovers of all kinds. This world-renowned museum boasts an impressive collection of artworks, from classic to contemporary. Just a short trip from Boystown, it offers a rich cultural experience.

Inside, you’ll find masterpieces from artists like Van Gogh, Monet, and Grant Wood. The museum’s galleries are thoughtfully organized, allowing for an immersive exploration of art history. You can easily spend hours wandering through this artistic haven.

In addition to the permanent collection, the Art Institute frequently hosts special exhibitions. These showcase various themes and artists, providing fresh insights and perspectives. Be sure to check their calendar for current exhibits during your visit.

Don’t forget to explore the museum shop for unique gifts or mementos. The café serves delicious refreshments, making it easy to relax during your time there.

Visiting the Art Institute of Chicago enriches your experience in Boystown. It’s a cultural gem that showcases the depth and beauty of artistic expression.

Address: 111 S Michigan Ave, Chicago, IL 60603.

16. Relax at Lakeview’s lovely parks

Lakeview boasts several lovely parks perfect for outdoor relaxation and recreation. Whether you’re looking to unwind or enjoy some fresh air, these green spaces are ideal. From small pockets to larger parks, there’s something for everyone.

One highlight is Lincoln Park, featuring beautiful pathways, gardens, and recreational facilities. You can take a leisurely stroll, have a picnic, or attend community events. It’s a vibrant space that attracts both locals and visitors.

For a quieter alternative, check out parks like Wrigley Field Rooftop Park, offering stunning views and a peaceful atmosphere. Many people enjoy bringing a book or watching the world go by. It’s a great way to recharge after a busy day exploring.

Lakeview parks often host outdoor fitness classes and cultural events. This makes them active community hubs where neighbors come together. Participating in these activities fosters connections and fun experiences.

Spending time in Lakeview’s parks is a wonderful way to appreciate the outdoors. It adds balance to your busy itinerary in Boystown.

Address: Various parks in Lakeview, Chicago, IL 60657.

17. Go shopping at local boutiques on Halsted

Shopping at local boutiques on Halsted Street is a delightful experience. The area is home to various unique stores offering fabulous finds. From art to fashion, you can discover treasures that reflect the vibrant LGBTQ culture.

Many boutiques feature clothing and accessories designed by local artists and designers, making it a great place to find one-of-a-kind items. You might explore shops dedicated to LGBTQ-themed merchandise, showcasing pride and creativity.

Some boutiques focus on handmade goods, offering everything from jewelry to home decor. Browsing through their selections allows you to find thoughtful gifts or something special for yourself.

Walking the streets also lets you interact with friendly shopkeepers who are passionate about their work. They often share stories about the products and their inspiration, enriching your shopping journey.

Don’t miss out on this shopping experience in Boystown. Supporting local businesses creates a lasting impact while adding joy to your visit.

Address: Halsted Street, Chicago, IL 60657.

18. Experience live music at Progress Bar

Progress Bar is a lively venue in Boystown, known for its engaging atmosphere and live music. A hotspot for music lovers, you can enjoy a variety of performances, from local bands to tribute acts. It’s a great place to unwind and enjoy an exciting night out.

The bar often features themed nights, making every visit unique. Whether you’re into karaoke, drag shows, or open mic events, there’s something happening to cater to different tastes. The friendly staff ensures a warm and inviting experience.

While enjoying the tunes, sip on a drink from their diverse menu. You’ll find everything from craft cocktails to specialty shots. The bar promotes a fun social environment, making it easy to mingle with others.

Plus, the ambiance adds to the live music experience. With an intimate setting, you won’t miss a beat or a lyric. It’s a spot that truly captures the spirit of Boystown.

Check out Progress Bar for a memorable night filled with music, fun, and friendship. You won’t want to miss out on this vibrant aspect of local nightlife.

Address: 3359 N Halsted St, Chicago, IL 60657.

19. Visit the Chicago Botanic Garden

While a bit of a drive from Boystown, the Chicago Botanic Garden is worth the visit for plant enthusiasts and nature lovers. This beautiful garden features stunning landscapes, walking paths, and a variety of plant collections. It’s an oasis of serenity just outside of the city.

The garden consists of several themed areas, including the Rose Garden, Japanese Garden, and even a Fruit and Vegetable Garden. Each section offers unique beauty and inspiration for visitors. Whether you’re looking for a peaceful walk or a place to relax, you’ll find it here.

Seasonal events, such as flower shows or educational workshops, add to the experience. These events often attract families and friends, making it a perfect outing for everyone.

The garden also provides opportunities to learn about sustainable gardening practices. Knowledgeable staff and volunteers are available to answer questions and share tips.

Visiting the Chicago Botanic Garden adds a lovely natural escape during your stay in Boystown. It’s a perfect mix of beauty, education, and tranquility.

Address: 1000 Lake Cook Rd, Glencoe, IL 60022.

20. Take part in volunteering at local LGBTQ+ organizations

Volunteering at local LGBTQ+ organizations in Boystown is a rewarding experience. The community thrives thanks to the efforts of many dedicated activists and volunteers. It’s a fantastic way to give back while supporting causes you care about.

Many organizations focus on providing resources, advocacy, and education for the LGBTQ+ community. You can engage in various activities, from outreach programs to participating in events. No matter your skills or interests, there’s a role for you!

Volunteering allows you to meet like-minded individuals who share your passion for equality and inclusion. Building connections strengthens your ties to the community. You can learn from others while making a difference in people’s lives.

During events, volunteers often help with logistics, planning, and execution. You can play a vital role in creating memorable experiences for the community. It’s an excellent way to immerse yourself in the culture and values of Boystown.

Consider setting aside time during your visit to volunteer. It’s a meaningful way to contribute and feel the spirit of community!

Address: Various Organizations in Boystown, Chicago, IL 60657.

21. Try delicious culinary delights at a local food festival

Local food festivals in Boystown are a tasty way to experience the neighborhood’s diverse culinary scene. Throughout the year, various events celebrate food, culture, and community. These festivals attract food lovers ready to sample unique dishes.

You will find everything from gourmet food trucks to local restaurants showcasing their specialties. Each booth offers a chance to taste different flavors, reflecting the diverse community of Boystown. It’s a food lover’s paradise!

Live music and entertainment often accompany the festivals. You’ll enjoy not only delicious food but also a lively atmosphere. It’s a fantastic way to soak in the culture while indulging your taste buds.

Many festivals also feature cooking demonstrations and competitions. You can learn tips from local chefs and discover new dishes to try at home. Participating in these events creates a sense of connection to the community.

Don’t miss the chance to enjoy local food festivals during your visit. It’s a delightful experience that combines flavor, fun, and community spirit!

Address: Various Locations in Boystown, Chicago, IL 60657.

22. Join a workout class or event at the Center on Halsted

The Center on Halsted offers various workout classes and events that promote health and wellness. Whether you’re a fitness enthusiast or a beginner, there’s something for everyone. Joining a class is a fun way to stay active while meeting new friends.

You can choose from yoga, dance, and fitness classes that cater to different skill levels. The welcoming environment makes exercise enjoyable and accessible. Participating in group classes fosters motivation and camaraderie.

The Center also organizes social events and health workshops. These gatherings focus on building community connections and encouraging healthy lifestyles. It’s a supportive space where everyone can feel comfortable pursuing their wellness goals.

Engaging in fitness activities promotes both physical and mental well-being. Working out while surrounded by like-minded individuals can be uplifting. You might even discover a new passion or hobby!

Consider adding a workout class to your itinerary at the Center on Halsted. It’s a great way to blend physical health with community spirit during your visit to Boystown.

Address: 3656 N Halsted St, Chicago, IL 60613.

23. Enjoy a picnic at Alfred Caldwell Lily Pool

Alfred Caldwell Lily Pool is a beautiful, serene oasis just a short trip from Boystown. This hidden gem provides a peaceful setting ideal for a picnic. The lush gardens and tranquil waters create an inviting atmosphere for relaxation.

The landscape is carefully designed to showcase various plants and flowers, making it a picturesque place to unwind. As you stroll through the gardens, you might even spot butterflies and birds adding to the beauty of the site.

Bring along some of your favorite snacks or takeout from a local eatery to enjoy by the lily pool. The soothing sounds of nature provide a perfect backdrop while you savor your meal. It’s a wonderful way to recharge during your adventures in the area.

In addition to picnicking, the lily pool offers ample opportunities for photography. Capture the beauty of the flowers and the tranquil water, which make for stunning images to remember your visit by.

Don’t miss the chance to experience the natural beauty of Alfred Caldwell Lily Pool. It’s a lovely complement to your time in Boystown, providing a quiet escape amidst the lively urban atmosphere.

Address: 125 W Fullerton Pkwy, Chicago, IL 60614.

24. Explore historic landmarks in nearby Lincoln Park

Exploring historic landmarks in Lincoln Park is a delightful way to dive into Chicago’s rich history. Just a stone’s throw from Boystown, this vibrant neighborhood is home to several notable sites. From preserved homes to museums, there’s much to discover.

One prominent landmark is the Lincoln Park Conservatory, which showcases stunning botanical exhibits. The building itself is a historic treasure, providing a breathtaking backdrop for photos. You can wander through tropical plants and seasonal displays, immersing yourself in nature.

Additionally, visitors can explore the historic homes in the area that date back to the late 19th and early 20th centuries. Many of these now serve as museums, offering insight into life during that time. Historical tours are often available to enhance your experience.

The scenic parks in Lincoln Park also host events and festivals throughout the year. Immerse yourself in community activities while enjoying the beautiful surroundings.

Taking time to explore the historic landmarks in Lincoln Park enriches your understanding of the city. It’s a perfect complement to your visit to Boystown!

Address: Lincoln Park, Chicago, IL 60614.

25. Join a walking tour of LGBTQ+ history in Chicago

Joining a walking tour of LGBTQ+ history in Chicago is a fantastic way to learn about the city’s rich cultural heritage. Various tours are available that highlight significant events and figures in LGBTQ+ history. These tours provide insight into how Boystown became a pivotal area for the community.

Throughout the tour, knowledgeable guides share stories of activism, milestones, and struggles faced by the LGBTQ+ community. The guides often bring to life the experiences of those who fought for equality and representation in Chicago.

As you travel through the streets of Boystown, you’ll see important landmarks, memorials, and art installations that commemorate key moments. Each stop offers an opportunity for reflection and education, making it both enlightening and engaging.

Participating in these tours allows you to connect more deeply with the community’s history. You can walk alongside individuals passionate about preserving and sharing this vital narrative.

Consider including a walking tour in your plan while in Boystown. It’s an inspiring way to appreciate the strides made for LGBTQ rights and culture over the years.

Address: Various Locations in Chicago, IL 60657.

Final Thoughts

Boystown, Chicago, is a vibrant and welcoming neighborhood rich in history and cultural significance. From bustling nightlife to serene parks, there’s always something to explore. Engaging with local businesses, attending events, and learning about LGBTQ+ history offers a memorable experience for visitors. If you’re interested in exploring even more of Illinois, check our recommendations on places to visit in Illinois.

As you wander through the streets, the spirit of community and acceptance is palpable. The diverse activities available ensure that everyone can find something that speaks to them. Whether it’s enjoying a delicious meal, catching a live performance, or taking a leisurely stroll, Boystown has it all.

Embrace the opportunity to connect with this dynamic community and the stories that shaped it. Your visit will undoubtedly leave you richer in experience and understanding. Boystown invites you to celebrate love, pride, and individuality. And if you’re considering a weekend getaway, don’t forget to explore our suggestions for best weekend getaways in Chicago.