20 Best Things To Do In Wicker Park, Chicago
Nestled within the larger West Town community area of Chicago, Wicker Park stands as a vibrant and eclectic neighborhood known for its rich history, diverse culture, and artistic flair. It's a hub where the past and the present collide, creating a dynamic environment filled with vintage architecture, trendy boutiques, flavorful cuisine, and lively entertainment venues. The neighborhood’s diverse array of offerings attracts a colorful mosaic of residents and visitors, from artists and musicians to foodies and fashionistas, all seeking to experience the unique charm and energy that define Wicker Park.
1. Discover Urban Nature Along The 606
One of Wicker Park’s hidden gems is The 606, a 2.7-mile-long elevated trail that connects Wicker Park, Logan Square, and Bucktown. Originally a disused railway line, The 606 has been transformed into a lush, urban green space perfect for jogging, cycling, or leisurely walks. This trail is a must-visit for outdoor enthusiasts looking for a breath of fresh air in the heart of the city.
Visitors can enjoy stunning views of Chicago's skyline from the various observation points along The 606, making it ideal for photography or just taking in the scenery. Public art installations and seasonal landscaping add an artistic flair, and the trail connects several parks, providing a serene escape from the city's hustle and bustle. For those looking for things to do in Wicker Park, exploring The 606 is a great way to combine nature, art, and exercise.
Insider Tip: Start your walk on The 606 early in the morning or around sunset to avoid crowds and experience the trail’s most serene moments. These times also offer the best lighting for photos, especially with the skyline views.
2. Step Back in Time with Retro Threads at Kokorokoko
For fashion enthusiasts, Wicker Park’s Kokorokoko boutique is a haven for retro clothing and accessories. Specializing in 80s and 90s vintage fashion, this store offers unique finds like neon windbreakers, acid-washed jeans, and funky fanny packs. Kokorokoko’s curated selection brings back the bold colors and patterns of past decades, making it a go-to spot for anyone wanting to add a nostalgic flair to their wardrobe.
Shoppers can also browse a variety of vintage accessories, including oversized hoop earrings and chunky necklaces that complete any retro look. Whether you're a local or visiting Chicago, Kokorokoko is one of the top vintage stores in Wicker Park to explore.
Pro Tip: For the best finds, visit Kokorokoko on weekdays when the store is less busy. You’ll have more time to browse and a better chance of snagging rare, one-of-a-kind pieces before the weekend rush.
3. Unleash Your Inner Gamer at Emporium Wicker Park
For a night of nostalgia, head to Emporium Wicker Park, an arcade bar that blends the fun of old-school gaming with a laid-back bar atmosphere. Packed with classic arcade games like Pac-Man and pinball, Emporium offers a unique experience for those seeking entertainment in Wicker Park. Whether you're a gamer or just in it for the vibe, Emporium brings together the best of gaming and nightlife in Chicago.
The bar also features a wide selection of craft beers, unique cocktails, and non-alcoholic options, making it a great hangout spot for all tastes. Emporium frequently hosts themed parties, live DJ sets, and other special events, adding to its vibrant atmosphere.
Expert Advice: Check Emporium’s event calendar in advance—some of the best nights are during their themed parties or live DJ sets. Arrive early to grab a seat and maximize your gaming time before the venue fills up.
4. Step into the Time Machine at Dove's Luncheonette
For foodies visiting Wicker Park, Dove’s Luncheonette is a must-visit spot that combines retro vibes with delicious Southern-inspired dishes. This vintage-style diner features classic comfort food with a twist, offering everything from chicken-fried chicken to pozole rojo. The 1960s-inspired décor, complete with a long counter and vinyl stools, creates a nostalgic atmosphere perfect for a cozy meal.
Beyond its hearty menu, Dove’s also serves up an immersive experience with vinyl records playing in the background and vintage photographs adorning the walls. Whether you’re stopping in for breakfast, lunch, or brunch, this Wicker Park gem promises a flavorful and memorable dining experience.
Travel Tip: If you’re planning to visit Dove’s Luncheonette during the weekend, go early for brunch. It gets busy fast, and arriving before the rush ensures a cozy seat at the counter without a long wait.
5. Quench Your Thirst at Dive Bars Along Milwaukee Avenue
Milwaukee Avenue in Wicker Park is home to some of Chicago’s best dive bars, offering an authentic, laid-back atmosphere. Popular spots like The Flat Iron and The Violet Hour attract locals and visitors alike with their eclectic vibes and affordable drinks. Whether you're into craft cocktails, local beers, or simply looking to relax with friends, Milwaukee Avenue has something for every kind of night out.
Dive bars in Wicker Park are known for their character, featuring retro jukeboxes, worn-in pool tables, and walls decorated with local art and graffiti. These bars often stay open late, providing an easygoing atmosphere for a casual night out in one of Chicago's trendiest neighborhoods.
Pro Tip: Make The Violet Hour the last stop on your dive bar crawl. Its craft cocktails are the perfect way to end the night on a more refined note, and their quiet, dim-lit ambiance offers a relaxing contrast to the lively energy of Milwaukee Avenue’s other bars.
6. Experience Artistic Flourish at the Flat Iron Building
The Flat Iron Building is a key landmark in Wicker Park, known for its role in supporting Chicago’s vibrant art scene. Inside this triangular building, you'll find dozens of artist studios, making it a cultural hub for local creatives. The building hosts open studio events, where visitors can explore the artists' workspaces and see a wide range of artwork, from paintings to sculptures and installations.
Art lovers can wander through the building’s graffiti-adorned halls and take in the dynamic creativity that defines Wicker Park. For a deeper dive into the local art scene, plan your visit during the Flat Iron Arts Festival, when artists open their doors to the public, offering a behind-the-scenes look at their creative process.
Insider Tip: The best time to visit the Flat Iron Building is during one of their open studio nights, usually held on the first Friday of every month. You’ll get to meet the artists in person, see works-in-progress, and even purchase pieces directly from the creators.
7. Feel the Beat at The Hideout
One of Wicker Park’s most beloved live music venues, The Hideout, is a hidden gem located just a short walk from the main streets. This intimate venue, tucked away in a cozy, unassuming house, has been a staple of Chicago’s music scene since the 1930s. The Hideout offers a unique atmosphere where the lines between performer and audience blur, making every show feel personal and engaging.
With a lineup that ranges from up-and-coming indie bands to local favorites, The Hideout is the perfect place to experience live music in Wicker Park. But it’s not just about the tunes—this venue also hosts events like political talks, community gatherings, and even dance parties, contributing to the rich cultural fabric of Wicker Park.
Pro Tip: For an unforgettable experience, try to catch one of The Hideout’s special events like a “Soup and Bread” night, where you can enjoy homemade soups while listening to live music in a cozy, community-focused setting.
8. Enjoy Stand-Up at The Comedy Clubhouse
For those who prefer their entertainment with a side of laughter, The Comedy Clubhouse is a must-visit in Wicker Park. This intimate venue showcases local talent in a range of comedic formats, from improv to stand-up and sketch comedy. Whether you're a seasoned comedy fan or new to the scene, The Comedy Clubhouse promises an evening full of laughs in a cozy, laid-back environment.
What sets this venue apart is its focus on supporting up-and-coming comedians, offering a stage for new performers to hone their craft. The Comedy Clubhouse also doubles as a training center, providing workshops and classes for aspiring comedians. With affordable ticket prices and high-quality performances, this Wicker Park staple is an excellent spot for a night of laughter.
Insider Tip: For the best comedy shows, opt for the Friday night performances when local troupes bring their A-game. Shows often sell out, so it’s smart to book tickets online in advance.
9. Embrace Outdoor Family Fun at Wicker Park
At the heart of the neighborhood lies Wicker Park, a beautiful green space that offers a peaceful retreat from the bustling city streets. This park is perfect for families, couples, and solo visitors looking to enjoy a sunny day outdoors. Featuring well-maintained gardens, a historical fountain, and a large playground, Wicker Park is a favorite spot for both locals and tourists.
During the warmer months, the park comes alive with community events such as outdoor yoga classes, farmers' markets, and even movie nights. For families, the playground is a hit with its slides, swings, and sandbox, making it an ideal place for kids to burn off some energy. Whether you're having a picnic, people-watching, or exploring the park’s many walking paths, Wicker Park offers a perfect blend of nature and community.
Expert Advice: Pack a picnic and head to Wicker Park on Sundays in the summer for the farmers' market. You can grab fresh, local produce and artisan goods, then relax on the lawn while listening to live music.
10. Find Fashionable Gems in Wicker Park’s Unique Boutiques
Wicker Park’s boutique shopping scene is one of the most unique in Chicago, offering a wide variety of independent stores where you can find one-of-a-kind fashion pieces, accessories, and home goods. Unlike chain stores, these boutiques reflect the neighborhood’s creative spirit, making shopping here an experience in itself.
Some popular spots include Penelope’s, which features a mix of contemporary designer wear and indie brands, and Store B Vintage, where you can find meticulously curated retro clothing and accessories. Whether you’re on the hunt for a statement piece or just browsing, Wicker Park’s boutiques offer a shopping experience that caters to diverse styles and tastes.
Pro Tip: Want to score great deals? Visit Wicker Park’s boutiques during sales season, typically at the end of each season, when stores like Penelope's and Store B Vintage offer major discounts on high-quality items.
11. Revel in the Performing Arts at The Den Theatre
Wicker Park’s vibrant performing arts scene is perhaps best exemplified by The Den Theatre, a venue known for its eclectic lineup of performances. Whether you’re in the mood for a gritty drama, an uproarious comedy, or an experimental piece, The Den Theatre delivers something for everyone. Its intimate performance spaces, with exposed brick walls and a cozy atmosphere, provide the perfect setting for an immersive theatrical experience.
The Den Theatre frequently collaborates with local theater companies, ensuring a diverse mix of shows on its calendar. In addition to plays, the venue also hosts stand-up comedy, improv shows, and musical performances, making it a dynamic cultural hub in Wicker Park.
Insider Tip: To fully immerse yourself in Wicker Park’s performing arts scene, keep an eye out for special collaborative events between The Den Theatre and local theater companies. These unique performances often feature cutting-edge, experimental works you won’t see anywhere else.
12. Sip Coffee with a Twist at The Wormhole Coffee
For coffee lovers, The Wormhole Coffee in Wicker Park offers more than just your average cup of joe. This quirky café is filled with 80s and 90s memorabilia, including a life-sized replica of the DeLorean from Back to the Future. It’s the perfect spot for those who appreciate retro pop culture and high-quality coffee in equal measure.
The Wormhole’s menu is as inventive as its décor, featuring specialty drinks like the peanut butter mocha “Koopa-Troopa” that has developed a cult following. Whether you’re working on your laptop or catching up with friends, The Wormhole offers a unique atmosphere that blends great coffee with nostalgic charm.
Pro Tip: Try to visit The Wormhole Coffee during off-peak hours (late morning or early afternoon) to snag one of the comfy couches in the back. It’s the perfect spot to settle in with a laptop or book while sipping on their famous peanut butter mocha.
13. Dig for Musical Gems at Reckless Records
Music lovers and vinyl collectors flock to Reckless Records in Wicker Park, a local institution known for its extensive collection of records, CDs, and cassettes. Reckless Records has been serving Chicago’s music community for decades, offering a meticulously curated selection that spans genres like classic rock, jazz, indie, and electronic.
Beyond the records, the store also sells music-related memorabilia, turntables, and vintage posters. The staff are highly knowledgeable and can help you find hidden gems or offer recommendations based on your musical taste. Whether you're a seasoned vinyl collector or a casual music fan, Reckless Records is a must-visit spot in Wicker Park.
Expert Advice: If you’re looking to sell your old vinyl or CDs, Reckless Records buys collections. The best time to visit is during the week when staff have more time to evaluate your items and offer fair prices.
14. Marvel at Creativity in Wicker Park's Art Galleries
Wicker Park’s art scene is as diverse as the neighborhood itself, with a range of galleries showcasing contemporary art, pop culture pieces, and multimedia installations. Jackson Junge Gallery is a standout, featuring a collection of works by both emerging and established artists. Another popular spot is LVL3 Gallery, known for its minimalist space that often highlights up-and-coming international talent.
Art lovers can spend hours exploring these galleries, many of which offer free entry and host regular exhibitions, opening receptions, and artist talks. For those interested in Chicago’s creative community, Wicker Park’s galleries offer a window into the city’s artistic soul.
Pro Tip: Check out Jackson Junge Gallery during their opening receptions—many galleries offer complimentary drinks, giving you the chance to meet artists and discuss their work while enjoying a relaxed evening of art and conversation.
15. Savor Authentic Flavors at Big Star
Big Star is one of the most popular restaurants in Wicker Park, serving up authentic Mexican street food with a modern twist. The laid-back taqueria is known for its wide variety of tacos, from traditional options like al pastor and carne asada to creative vegetarian offerings. Its outdoor patio is a favorite spot for dining in the warmer months, and the vibrant atmosphere inside ensures a fun dining experience year-round.
In addition to its delicious tacos, Big Star offers an impressive selection of tequilas, mezcals, and craft cocktails. Whether you’re in the mood for a casual lunch or a lively dinner with friends, Big Star is a Wicker Park institution that delivers on both flavor and ambiance.
Insider Tip: If you want to avoid the long lines at Big Star during peak times, grab takeout and enjoy your tacos in nearby Wicker Park. The park is just a short walk away and provides a peaceful setting for a casual meal.
16. Unwind in Elegance at The Violet Hour
For those looking for a more refined nightlife experience, The Violet Hour in Wicker Park is the place to go. This award-winning cocktail lounge is known for its expertly crafted drinks and sophisticated ambiance. Hidden behind an unmarked mural, The Violet Hour offers an intimate and elegant setting where you can enjoy classic cocktails as well as creative, seasonal concoctions.
With its luxurious décor, dim lighting, and attentive service, The Violet Hour provides the perfect backdrop for a date night or a special celebration. The bartenders are true mixology experts, ensuring that each cocktail is a work of art in itself.
Pro Tip: Ask your server for the bartender’s choice when you can’t decide on a drink at The Violet Hour. Their expert mixologists love crafting custom cocktails based on your preferences, making for a personalized, one-of-a-kind experience.
17. Enjoy Farm-to-Table Goodness at Wicker Park Farmers Market
Held seasonally in the park, the Wicker Park Farmers Market is a Sunday tradition that draws locals and visitors alike. Here, you’ll find a wide variety of fresh, locally sourced produce, artisanal cheeses, baked goods, and more. The market places a strong emphasis on sustainability and supporting local farmers, making it a must-visit for anyone interested in farm-to-table living.
Beyond food, the market also hosts live music and offers educational activities, making it a fun stop for families or anyone looking to enjoy a leisurely Sunday in Wicker Park. Whether you’re picking up fresh ingredients for the week or just browsing, the Wicker Park Farmers Market is a vibrant and lively spot.
Expert Advice: For the best selection of produce at Wicker Park Farmers Market, arrive early. Vendors often sell out of popular items like organic fruits, homemade pastries, and artisanal cheeses by midday.
18. Relish a Culinary Experience at Antique Taco
For a fresh take on Mexican street food, head to Antique Taco, a beloved eatery in Wicker Park. This cozy restaurant offers a unique farm-to-table approach to traditional tacos, elevating classic recipes with high-quality, locally sourced ingredients. Favorites on the menu include the garlic shrimp tacos and the pork carnitas tacos, each bursting with bold flavors and served on house-made tortillas.
The rustic, vintage décor aligns perfectly with the restaurant’s name, creating a warm, inviting atmosphere. Whether you’re stopping in for a quick bite or a leisurely meal, Antique Taco promises a memorable culinary experience. Pair your tacos with one of their signature drinks, like the rosemary margarita, for the full experience. This is a must-visit for taco lovers looking for an upscale twist on a street food favorite.
Insider Tip: Don’t leave Antique Taco without trying their seasonal specials, which rotate throughout the year and often feature unique flavor combinations you won’t find on the regular menu.
19. Discover Literary Treasures at Myopic Books
Book lovers should not miss Myopic Books, one of the largest and most charming independent bookstores in Chicago. Nestled in the heart of Wicker Park, this multi-level store features a vast collection of used and rare books, making it a haven for bibliophiles. From classic literature to obscure titles, Myopic Books offers an eclectic mix of genres across its three floors, allowing visitors to lose themselves in the labyrinth of shelves.
The bookstore’s cozy, nostalgic atmosphere makes it easy to spend hours browsing through its selection. Myopic also hosts a variety of events, including poetry readings, live music, and discussions, further cementing its role as a cultural hub in Wicker Park. Whether you’re hunting for a literary gem or just want to soak in the atmosphere, Myopic Books offers a unique experience for visitors to Wicker Park.
Pro Tip: Set aside plenty of time to explore Myopic Books’ extensive collection. With its three floors of books, it’s easy to get lost in the stacks—so give yourself at least an hour or two to fully browse this literary treasure trove.
20. Explore Vintage Chic at Store B
For those with a passion for retro fashion and mid-century modern décor, Store B Vintage in Wicker Park is the ultimate destination. This boutique specializes in meticulously curated vintage clothing and accessories, as well as a wide selection of antique home furnishings. Each item at Store B tells a story, offering shoppers a chance to own a piece of history with items from past decades.
The store is known for its commitment to quality, ensuring that every piece is in excellent condition. From 1960s dresses to 1980s jackets, Store B is a treasure trove for vintage enthusiasts. Even if you’re not looking to buy, a visit to this boutique is like stepping back in time, with staff members more than happy to share the history behind their carefully selected items. It’s the perfect place to find one-of-a-kind pieces that reflect Wicker Park’s eclectic style.
Expert Advice: Store B Vintage receives new inventory frequently, so if you’re on the hunt for a specific item or just want to stay ahead of the trends, visit regularly or follow them on social media for updates on new arrivals.
Conclusion
Wicker Park, with its bohemian spirit and eclectic offerings, stands as a testament to Chicago’s cultural richness and diversity. This vibrant neighborhood, with its blend of historic charm and modern innovation, invites people from all walks of life to explore its treasures and experience its unique vibe. The colorful tapestry of arts, cuisine, fashion, and entertainment that Wicker Park weaves creates a dynamic and inclusive environment where every corner has a story to tell, and every experience is a brush stroke in the larger painting of Chicago life.
Whether you're a local rediscovering the myriad of experiences the neighborhood has to offer, or a visitor exploring its multifaceted charm for the first time, Wicker Park leaves you with a richer, more nuanced understanding of the cultural kaleidoscope that is Chicago. It’s a place where every visit is an adventure, and every adventure is a memory in the making.
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FAQ
1. What is the best way to get to Wicker Park from downtown Chicago?
The best way to get to Wicker Park from downtown Chicago is by taking the Blue Line CTA, which has a stop right in the neighborhood. It’s a quick, convenient option, with the ride taking about 15-20 minutes.
2. Where can I find the best tacos in Wicker Park?
Antique Taco is one of the best spots in Wicker Park for tacos, offering a farm-to-table take on classic Mexican dishes. Big Star is another popular option, known for its authentic street tacos and vibrant atmosphere.
3. Are there family-friendly activities in Wicker Park?
Yes! Wicker Park offers a variety of family-friendly activities, including its namesake park with playgrounds, gardens, and community events. The Wicker Park Farmers Market is another great option for families, offering fresh local produce and live entertainment during the warmer months.
4. What should I wear when visiting Wicker Park?
Wicker Park has a laid-back, trendy vibe, so you’ll see a range of fashion, from vintage chic to casual streetwear. If you’re planning to visit during the summer, comfortable shoes are a must for exploring the neighborhood’s boutiques, parks, and restaurants.