Best Things to Do in Wicker Park, Chicago

Wicker Park stands as a gem in Chicago, Illinois, seamlessly merging tradition with contemporary vibes. This vibrant enclave is a canvas where art, gastronomy, melodies, and fashion paint a vivid picture of human talent and innovation. Often dubbed one of the most eclectic, hipster spots in the nation, its charming dive bars, myriad art spaces, retro clothing boutiques, and forward-thinking ethos embody the essence of counterculture and progressiveness.

If you’re in search of a one-of-a-kind, sensory-rich experience, Wicker Park should top your list. Dive into this distinctive neighborhood for an unforgettable weekend escape!

1. Eat Tacos at Big Star

Big Star captures attention with its towering star signage, marking its transformation from a gas station to a dining hotspot. Grab a taco from the counter and settle in the semi-shaded area for some delightful people-watching—though the flavors might just steal all your attention. Here, tacos are elevated beyond the usual cilantro and onion, featuring unique toppings like pineapple, pumpkin seeds, and simmered mushrooms. During the sunny season, snagging a spot can be a challenge, so be ready to enjoy your feast on the move.

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2. Explore the Outdoors at The 606

Once an overlooked rail line, The 606 now thrives as a versatile 2.7-mile recreational trail weaving its way through Chicago, including the vibrant Wicker Park on Bloomingdale Avenue. More than just a pathway, The 606 celebrates urban artistry, featuring captivating murals, architectural wonders, and inviting community spaces. The trail is alive with events, from fun runs and bake-offs to concerts, art workshops, and yoga sessions, beckoning all to participate. Even if no events coincide with your visit, a simple stroll along this trail promises discovery. It meanders through distinct neighborhoods like Humboldt Park, West Town, and Logan Square, each showcasing its unique charm and attractions.

3. Hang Out in the Park

Don’t miss a visit to the namesake park when in Wicker Park. Spanning four acres, this verdant space offers a playground, lush community gardens, athletic fields, and a heritage-rich fountain. Beyond its greenery, the park pulses with activity, featuring an array of gardening programs, movie nights, live music performances, farmers markets, and much more. It’s truly a hub of community life and leisure.

4. Enjoy Some Quality Time in the Park

At the heart of the community lies Wicker Park’s eponymous green oasis. Stretching over 4.7 acres, this park is a magnet for locals and visitors alike. Boasting a grand fountain, baseball fields, basketball courts, dog-friendly zones, and a dedicated children’s play area, it’s a vibrant space that caters to varied interests. Whether you’re in the mood for basking under the sun, engaging in a spontaneous game, indulging in floral fragrances, or relishing an open-air movie, Wicker Park offers it all. Interested in delving deeper into its history and offerings? The Chicago Parks District page is a treasure trove of information about this cherished neighborhood haven. 

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5. Shop Vintage Apparel at Kokorokoko

Despite its quirky name, Kokorokoko stands out as a cherished vintage clothing haven, making it a top pick for thrift enthusiasts. While the area boasts numerous vintage boutiques, Kokorokoko frequently emerges as the crowd favorite. And it’s not hard to see why. The moment you step in, it feels like entering a stylish New York boutique—thanks to its sleek design, ample natural light, and meticulously organized layout that’s a visual treat. The store offers an impressive collection of 80s and 90s fashion: think denim jackets, parachute pants, patterned shirts, glittery hats, and vibrant neon dresses. Take your time perusing; you might just stumble upon a nostalgic piece that whisks you back to the iconic 90s era.

6. Find the Way In at The Violet Hour

For decades, Chicago has held a rich legacy as a mecca for cocktail aficionados, tracing its roots back to the spirited 1920s. The city’s illustrious history in the realm of handcrafted gourmet food and beverages is undeniable. Today, hidden gems like The Violet Hour continue to uphold this cocktail tradition. Nestled in the heart of Wicker Park, The Violet Hour stands out not only for its rotating menu of pre-Prohibition concoctions but also its unassuming entrance concealed behind a vast mural. To uncover this secret haven and delve into its eclectic drink offerings, check out The Violet Hour’s official site.

7. Shop on Milwaukee Avenue

Milwaukee Avenue defies Chicago’s traditional grid system, running diagonally and adding a unique flair to the cityscape. Particularly in Wicker Park, this stretch of Milwaukee is a treasure trove of distinctive boutiques, eateries, and coffeehouses. Vintage fashion enthusiasts will be delighted, as a single block boasts multiple stores, with notable mentions like Vintage Underground and Store B. For a delightful brunch experience, make a stop at the renowned Bongo Room, or satiate your sweet cravings at Jeni’s Splendid Ice Cream.

8. Emporium Wicker Park

Emporium Wicker Park is a nostalgic haven in the heart of the city, artfully blending the charm of yesteryears with today’s delights. Imagine stepping into an ambiance reminiscent of a classic tavern, awash in the glow of neon lights, enhanced by an industrial design and a lively crowd. You’re greeted by an array of games—pool tables, pinball machines, foosball tables, and more, each promising a trip down memory lane. As you revel in playful competition, sip on exquisite beers and ales brewed on-site, heightening the experience. With a lineup of live shows and musical events, your time at Emporium Wicker Park promises to be more than just fun—it’s the perfect prelude to the city’s myriad of attractions.

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9. Hop on the 606 Trail

If a day of strolling, cycling, or soaking in urban vibes is on your agenda, Wicker Park serves as an ideal starting point. Perfectly positioned for you to embark on the 606 trail, this neighborhood offers a unique city experience. The 606, a transformed relic of an old elevated train line, is now a public park adorned with pathways, verdant patches, rest spots, and creative art installations. This urban oasis stretches across Chicago’s west side, weaving from Humboldt Park through to Bucktown. To map out your journey and dive into the myriad offerings of this quintessential Chicago landmark, visit the official 606 website.

10. Walk or Bike the Bloomingdale Trail

In 2013, Mayor Rahm Emanuel introduced a visionary project to transform the disused Bloomingdale Line tracks into a captivating 2.7-mile-long public park known as “The 606,” paying homage to Chicago’s area codes. This remarkable park hosts a wide array of events throughout the year, complemented by a diverse collection of both permanent and temporary art installations along the trail. The segment of the 606 trail situated in Wicker Park is affectionately referred to as the “Bloomingdale Trail” and is recognized as the heart of the entire 606 projects. For those eager to explore this urban gem, Friends of the Bloomingdale Trail offers 75-minute guided tours of either the West End or the East End on select dates.

11. Time for a nightcap

As the sun sets, Wicker Park undergoes a captivating transformation. While the streets pulse with activity during the day, the neighborhood takes on an entirely different energy at night. A gathering of eager patrons quickly assembles outside the discreet entrance of The Violet Hour, and their anticipation is well-placed; this renowned cocktail bar is celebrated for its exceptional handcrafted drinks.

For a delightful conclusion to your exploration of Wicker Park, consider indulging in a classic old-fashioned (or perhaps two) at Neon Wilderness, located on Milwaukee Avenue. This relative newcomer strikes a perfect balance between the charm of traditional taverns and the allure of contemporary lounges, creating a cozy and inviting atmosphere in which to unwind after a bustling day of adventure.

12. Immerse in the Retro Vibe of Dove’s Luncheonette

Dove’s Luncheonette stands as a beloved dining destination, celebrated for its nostalgic décor that transports diners to Chicago’s bygone eras. As a proud member of the award-winning One Off Hospitality Group, which boasts a range of esteemed establishments in the city, Dove’s Luncheonette has established itself as a renowned eatery specializing in Tex-Mex cuisine. Their menu is a testament to freshness and quality, featuring a delectable array of tamales, relleños, salads, and burgers, all crafted from the finest ingredients.

The restaurant has also earned acclaim for its enticing selection of cocktails, beers, and other beverages inspired by the flavors of the South, adding to the overall appeal of this exceptional dining experience.

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13. Explore the Flatiron Arts Building

At the heart of the Wicker Park community lies the Flatiron Arts Building, a cherished destination for creative souls throughout Chicagoland and a gateway to experiencing the emerging talents of local artists firsthand. Predominantly housing studio spaces, this unique establishment warmly welcomes the public within its walls. Inside, you’ll discover a multitude of theaters and performance venues, as well as The Railcar, a popular escape room game that adds an exciting twist to the artistic landscape.

Moreover, the artists of the Flatiron routinely throw open their studio doors to host exhibitions, gatherings, and events throughout the year, creating a dynamic and ever-evolving cultural hub. For those eager to delve deeper into the essence of this renowned artistic complex, a visit to the official Flatiron website is a valuable resource to explore further.

14. See a Show at a Wicker Park Theater

Wicker Park has long served as a sanctuary for artists across a spectrum of disciplines, encompassing playwrights, directors, actors, and designers who contribute to the vibrancy of Chicago’s performing arts scene. Within this neighborhood, a rich tapestry of performance spaces thrives, showcasing productions from both established and cutting-edge theater companies.

Take, for example, The Den Theatre, an expansive arts complex boasting multiple stages. It plays host to a diverse array of live performances and proudly houses resident theater companies such as Firebrand Theater and Haven Theatre, adding to the neighborhood’s cultural richness. Further exploration of Wicker Park reveals innovative and thought-provoking productions in Collaboraction’s adaptable performance studios, as well as thrilling performances at the historic Chopin Theatre, further enhancing the neighborhood’s reputation as a creative hub for the performing arts.

15. Celebrate the Summertime at Wicker Park Fest

Summer in Chicago often revolves around the excitement of attending open-air street festivals, and among the city’s largest and most beloved outdoor gatherings is the annual Wicker Park Fest. For over 16 years, individuals from across Chicagoland have flocked to Wicker Park every summer to revel in three action-packed days filled with entertainment, delectable cuisine, fashion showcases, and captivating music performances. While Wicker Park Fest offers an array of delightful activities and attractions suitable for all ages, the true highlight lies in its music lineup. Previous editions of the festival have featured a diverse array of musical talents, ranging from local favorites and emerging artists to renowned international headliners. For further details about Wicker Park Fest or to plan your visit, please visit the official festival website.

16. Listen to Live Music at a Wicker Park Venue

Wicker Park has established itself as a prime destination within the Chicagoland area for live music enthusiasts. Although Double Door, a longtime fixture in the neighborhood’s music scene, initiated its departure from the area in 2017, Wicker Park continues to offer an array of venues where music aficionados can enjoy their preferred tunes. Local establishments such as Smoke Daddy and Nick’s Beer Garden consistently feature a dynamic lineup of emerging artists. Furthermore, Subterranean, a cornerstone of Wicker Park’s vibrant music culture, remains a hub for live performances spanning various genres, in addition to hosting DJ nights and dance parties.

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17. Flat Iron Building

The United States boasts several iconic “Flat Iron Buildings,” distinctive triangular structures typically situated at the convergence of three roads. Wicker Park, not unlike other locales, possesses its own Flat Iron Building, a historical gem dating back to the 1920s. Since the 1980s, this architectural marvel has undergone a transformation into a thriving artist’s colony, solidifying its status as a prominent hub for visual and performing arts within the neighborhood.

With over 40 artist studios, a tattoo parlor, a theater, and various other creative spaces, the Flat Iron Building welcomes all visitors to explore its premises and admire the diverse array of artworks on display. However, the real delight comes on the first Friday of each month when the Flat Iron Building graciously opens its doors to the Wicker Park community. This monthly event becomes a vibrant showcase of paintings, sculptures, and an array of captivating artistic creations. To elevate the experience, musical performances and other entertaining shows are often featured, making it a must-attend occasion for all art and culture enthusiasts.

18. The Comedy Clubhouse

For those seeking hearty laughter, The Comedy Clubhouse stands as the ultimate destination. This esteemed club holds the distinction of being the top-rated establishment of its kind in the entirety of Chicago, drawing enthusiastic crowds to every performance in search of quality entertainment.

Their roster of comedians boasts the talent to effortlessly coax laughter through a combination of improvisation, stand-up routines, and scripted performances. In fact, some of these comedians have ascended to stardom through appearances in popular television shows like Parks and Recreation, The Office, and The Mindy Project. As a result, patrons can anticipate uproarious skits and theatrical acts that will leave them in fits of laughter.

To enhance the experience, The Comedy Clubhouse offers a delightful assortment of drinks, including both non-alcoholic options and refreshing alcoholic beverages, ensuring that the merriment is perfectly complemented by satisfying refreshments.

19. Embrace Your Inner Geek

When was the last time you truly indulged your inner pop culture enthusiast? Whatever your geeky passions may encompass, Wicker Park offers a haven certain to ignite your interests. Along Milwaukee Avenue, there’s The Wormhole Coffee, an ’80s-themed coffee shop that brews up fresh roasts within a snug, nostalgia-filled setting. Here, you can immerse yourself in vintage video games and an array of retro sci-fi memorabilia, including a life-sized DeLorean.

A bit further along this vibrant street, you’ll encounter Emporium Arcade Bar, an expansive establishment housing a plethora of arcade and pinball games, as well as classics like skeeball and air hockey. Throughout the year, Emporium also plays host to various events, including immersive pop culture-themed “pop-up” experiences inspired by beloved TV shows and movies.

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20. Shop for Stylish Apparel in the Many Boutiques Around Town

Wicker Park stands as a beacon of fashion excellence in this part of the United States, and it’s an absolute must-visit for anyone with a penchant for style. Sprinkled throughout the neighborhood are a myriad of boutiques, each a treasure trove of carefully curated fashion items that cater to diverse tastes and preferences, rendering Wicker Park a true haven for fashion enthusiasts.

Penelope’s, for instance, is a charming haven that showcases the latest trends from both American and European fashion brands, boasting a collection that spans from casual attire to glamorous accessories, all elegantly displayed.

At Ragstock, fashion seekers will discover a fusion of hip, unique pieces that seamlessly blend the allure of new and vintage garments, making it an ideal destination for those in search of one-of-a-kind clothing.

For the sartorially inclined gentlemen, Mildblend Supply Co. offers a splendid array of top-notch leather goods, denim jeans, rugged footwear, and more, ensuring that style-conscious men can find their perfect wardrobe additions.

Buffalo Exchange offers a unique twist, allowing you to not only browse for hip and trendy apparel but also trade or sell your own vintage clothing. It’s a dynamic hub where fashion aficionados can explore and exchange their fashion treasures.

21. Build Your Music Collection at a Wicker Park Record Store

For all the music enthusiasts out there, Wicker Park is a treasure trove of record stores tailor-made for those on a quest to acquire elusive vinyl pressings or rare out-of-print tapes to enrich their collections. Whether you’re a dedicated music aficionado with a penchant for collecting or simply looking to leisurely peruse the stacks for hidden gems, Wicker Park’s array of record shops have you covered.

In the neighborhood, your options are abundant. There’s the expansive selection at Reckless Records, where shelves are brimming with musical treasures waiting to be discovered. Then, you have Shuga Records, boasting an extensive assortment of vinyl records and cassettes, a haven for audiophiles seeking both classics and rarities. Lastly, The Exchange offers a cornucopia of discount tapes, CDs, records, and DVDs, providing a diverse array of musical and cinematic delights for all tastes.

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22. The Wormhole Coffee

A distinct emblem of 1980s culture within Wicker Park is The Wormhole Coffee, a renowned fixture in the neighborhood. Stepping inside feels like entering a time capsule, complete with a DeLorean parked inside and adorned with posters celebrating classics like Ghostbusters and Indiana Jones—iconic hits from the ’80s.

However, what truly beckons patrons to this establishment are the aromatic coffees, meticulously roasted and brewed in-house. With these delectable beverages and the inviting, snug atmosphere, The Wormhole Coffee promises a delightful coffee-drinking experience that stands on its own merits. The ’80s theme serves as a delightful bonus, adding an extra layer of nostalgia to the mix.

23. Browse the Numerous Art Galleries

Wicker Park, closely associated with hipster culture, naturally serves as a hotbed for artistic expression, with a plethora of art galleries encapsulating this creative movement. Beyond those located within the Flat Iron Building, the neighborhood boasts numerous art hubs discreetly tucked along its streets, often hidden within unassuming structures.

One such gallery is Dreambox, a haven for contemporary art enthusiasts showcasing works by both emerging talents and established local artists. For those seeking the cutting-edge or avant-garde, Johalla Projects offers a spacious canvas for artists exploring a diverse array of themes and mediums.

The Vertical Gallery, on the other hand, channels its focus toward urban and street art, spotlighting graffiti masterpieces and captivating graphic designs that leave a lasting impression. Meanwhile, LVL3 operates as an artist-run exhibition space, specializing in providing a platform for up-and-coming local artists to exhibit their creations to a broader audience, bridging the gap between the underground and mainstream art scenes.

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24. Start the Day With a Wicker Park Brunch

Forget any parental advice to the contrary; when you find yourself in Wicker Park, it’s abundantly clear that brunch reigns supreme as the most essential meal of the day. This vibrant Chicago neighborhood teems with renowned eateries where you can savor the delightful fusion of breakfast and lunch. Indeed, several Wicker Park restaurants consistently earn their place on the city’s prestigious lists of top brunch destinations.

Among the illustrious Wicker Park brunch establishments, you’ll discover iconic names such as Dove’s Luncheonette, Bongo Room, Mott Street, and Hash, to name just a few. These culinary gems offer a tantalizing array of brunch delights that cater to a wide range of palates and preferences.

And for those yearning to dine al fresco, don’t miss the opportunity to add the exquisite patios at Big Star and Handlebar to your list of must-visit places. These outdoor spaces not only offer delicious brunch fare but also provide a picturesque backdrop for enjoying your meal in the fresh air.

25. Sip on Hot Cocoa

Chicago’s winters can undoubtedly send shivers down your spine, but fear not, for there’s no cozier remedy than a steaming mug of hot chocolate. Mindy’s Hot Chocolate presents a tempting array of seven distinct cocoa concoctions, each adorned with a delectable house-made marshmallow.

Should you crave an extra kick, you have the option to craft a customized spiked cocoa by infusing it with your choice of brandy, whisky, rum, or cognac. And if you’re in the mood for some delectable bites to accompany your drink, Mindy’s Hot Chocolate has you covered with a comprehensive menu that spans brunch, lunch, dinner, and a delightful array of desserts. It’s the perfect haven for indulgence on those frosty Chicago days.

26. The Bongo Room

Conceived by the creative minds of best friends Derrick Robles and John Latino, The Bongo Room made its debut back in 1993 along Damen Avenue. Although the restaurant has since found its home on Milwaukee Avenue, its unwavering commitment to delivering distinctive and seasonally inspired breakfast and brunch fare remains unchanged.

While the pancake and French toast selections undergo regular transformations to showcase seasonal delights, certain cherished classics remain staples on the menu. Among these enduring favorites are the hearty breakfast burrito and the delectable vegetarian croissant sandwich, ensuring that patrons can always savor a familiar, satisfying meal at The Bongo Room.

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27. Dinner and a show

Wicker Park is a magnetic neighborhood that attracts both locals and tourists, and a significant part of its allure lies in its diverse culinary scene. Whether you’re in the mood for trendy gastropubs, Michelin-starred dining, or groundbreaking fusion cuisine, you’ll find it all here. Among the newer dining establishments, Mott Street stands out with its imaginative array of Asian-style small plates and a cheeseburger that’s considered one of the city’s finest. From kimchi and Oaxaca empanadas to whole branzino fried in coconut fat, the menu seamlessly blends innovation with indulgence.
If you’re craving barbecue accompanied by live blues music, Smoke Daddy is a must-visit spot. Load your tray with pimento-style hush puppies, Kansas City-style burnt ends, pulled pork, ribs, and more, but be sure to stock up on napkins to tackle the delicious mess. Alternatively, you can opt for a time-tested Wicker Park gem: The Bristol, renowned for its handcrafted pasta, locally sourced produce, and charming rustic ambiance.
For post-dinner entertainment, consider catching a show at Broken Nose Theatre, a pay-what-you-can theater company known for its thought-provoking new works, including contemporary plays and musicals. Another excellent option is The Den Theatre, where you can enjoy the latest productions, such as “Girl in the Red Corner,” a compelling tale of self-discovery running until March 2. If you’re a music enthusiast, check out the lineup at the beloved Subterranean, a bi-level music venue that always promises an exciting night out.