Chicago: Wicker Park/Bucktown

The beloved “Windy City” has thrilled many a tourist near and far with its captivating skyline and electrifying nightlife—leaving no avid urban explorer without a multitude of bustling activities and attractions are that only unique to Chicago. From the lunchtime symphony rehearsals at Grant Park Music Festival during the summer months to the Art Institute of Chicago exhibition openings—the choices of entertainment are endless. But for those more adventurous spirits who want to explore Chicago’s more “hip “vibe—Wicker/Bucktown would be the place to do it. Beginning its foundation in 1837, when Chicago was assimilated as a city, the Irish made Wicker Park a community all their own—building homes and the establishing businesses for what would become the core of the Wicker Park District. Cigar manufacturers, clothing boutiques, antique furniture and musical instruments shops, to name a few, lined the main streets of North Avenue, Milwaukee, and Damen, bringing the industrial scene to life and creating the diverse ethnic appeal Wicker Park is known for today.


Top 10 Attractions

Infamous for its live music performances and intoxicating blend of people, personalities, and eccentricity—Wicker Park makes for an illuminating, if not interesting, day tour or night on the town at some the neighborhoods hottest spots.

1. Double Door has earned the reputation of being an eclectic spot for music lovers to get a taste of Chicago’s local talent. Catering to the 21-and-up crowd, native Chicagoans and out- of-towners alike can jam to the genres of rock, heavy metal, punk, hip-hop, funk, soul, and everything in between. This diverse music venue has been bringing the noise—the good noise that is—since 1994—highlighting on its stage some of the most unsurpassed up-and- coming local talent this city has ever seen. Head down to the hidden depths of the lower level where you’ll find The Dirtroom, a bar that hosts comedy nights and acoustic shows. With an airy space of red tinted lights, glowing tea light candles, and spacious bar spanning the length of the room—it’s sure to be an experience that appeals to all the senses.(1572 N. Milwaukee Ave, Chicago, IL 60622.

2. Empty Bottle is an urban jungle for alternative rock enthusiasts tucked right onto the corner of Western and Cortez. With humble beginnings in 1992—this hole-in-the-wall bar in Ukrainian Village (a neighborhood just south of Wicker Park) became the place where one could play pool for 50 cents, drink beers to their heart’s delight for a buck-fifty, and jam to the jukebox tunes with everything from Monster Magnet to Bill Monroe. An upgrade in 1993 to a somewhat larger hole-in-the-wall with a righteous sound system and slew of great shows was what truly put this basement juke joint on the map. Cover charges are fairly inexpensive, ranging from $3-$20. If that isn’t accommodating enough for your wallet—come once a week to check out artists like The Hoyle Brothers, Handsome Tyrants, and a variety of other line- ups give a show for free. 1035 N. Western Ave, Chicago, IL 60622

3. The Flat Iron Arts Building represents the true history of the Wicker Park community and is a haven where writers, painters, and every other form of creativity come to indulge in music, art, and a little inspiration. Opening its doors in the Wicker Park district of West Town in 1980, this century old building houses the art of a variety of local artists. An out-of-towner can expect a laid-back atmosphere with a showcase of some of the most exquisite, urban wall paintings their eyes have ever seen and a chance to get up close and personal with artists whom created it. Wonder through the maze of this triangular landmark (on the “First Friday” of every month) and take in the unequivocal talent that these artists display as they open up their living spaces/studios for public viewing. Play pool, groove to live musicians, and embrace the cool vibes that gives this neighborhood its charm. 1579 N Milwaukee Ave, Chicago, IL 60622.

4. Chicago Food Planet Tours started in 2006 with the goal of giving Chicago residents and food enthusiasts a culinary experience that was unique and off the beaten path. Creator, Shane Kost and Director of Tour Operations, Nicki Tader, began their journey down the path of food paradise by exploring some of Chicago’s most diverse and historic neighborhoods in search of the finest ethnic cuisine. They sampled everything—from fresh Vietnamese cinnamon and Rooibos red teas to the flawless potato pancake. Inspired by these unique experience, Chicago’s first culinary walking tour was born, beginning with Gold Coast and Old Town Food Tour (est. 2006), then followed by Bucktown/Wicker Park Food Tour (est. 2008), and the rest was history. Participants not only get to savor a wide range of food, but also get to immerse themselves in the in Chicago’s rich culture, architecture, and entertainment. (830 North Michigan Avenue, Chicago, IL 60611.

5. Wicker Park Fest is praised as Chicago’s best street festival of the summer—a reputation that is highly deserved. Stretching down Milwaukee Avenue from North to Paulina, city goers swarm the streets to enjoy an amazing lineup of food, performances, and artisan vendors. One can feed their artistic taste through the performing arts of dance and poetry or browse the various shops and boutiques the line the Milwaukee Avenue strip. The admission fee is $5 (which is donated to local non-profit organizations) and from Saturday to Sunday (12pm- 10pm), tourists and Chicago natives can jam to the tunes of live bands and DJs from a variety of genres. Wicker Park Fest has become one of Chicago’s most sought after summer events and is sure to be a memorable experience for any traveler venturing into this unique area.

6. Green Music Fest kicks off the Summer Solstice with a fun-filled weekend fused with live music and green vendors, retail, art and crafts. Appealing to its eco-conscious aesthetic, Green Fest was created to cater to Chicagoans whom were committed to humane environmental practices and to connect with companies that practiced sustainability through their products, ideas, and services. Visitors can get a taste of fresh organic foods and even bring the kids to along for live performances catered especially to them. Admissions are a suggested $5 donation and runs through weekend of June from Saturday to Sunday (noon- 10 pm.) Stop by this event and celebrate with a community that is both hip and socially responsible.

7. The Ukrainian Institute of Modern Art set out to be an institution that preserved and promoted contemporary Ukrainian art to its highest standards. Those standards are expressed by exhibiting pieces that profoundly represent Ukraine’s heritage of the brave immigrant that ventured from Poland and Russia to an unknown land to start a new life. UIMA’s brings life to its century old art through exhibitions, readings, concerts, films, and lectures—all of which display the artist’s creative process through color and form. Chicago visitors have a variety of membership options and can join for as little as $45. UIMA is a great way for tourists to explore Chicago’s Ukrainian Village and connect with Ukraine’s vibrant culture and artistic talent. 2320 W Chicago Ave, Chicago, IL 60622,

8. Chicago’s Children’s Theatre has been providing entertainment to the children and adults of this of great city since 2005 and hit the ground running with the success of its 2006 production, A Year with Frog and Toad. Since its founding, CCT has prided itself on creating an environment where the community can come to experience diversity and education through theatrical performance. With an extensive volunteer program and an array classes and activities for children, including summer camp—the Chicago Children’s Theatre exemplifies an organization that is as much about enriching as it is entertaining. Shows are performed weekly (with the exception of Monday) and general admission is $36 ($26 for children). Bring the kids, or just yourself—and let your inner child be inspired.

9. Chicago Polish Museum was founded in 1935 and is one of the oldest and largest ethnic museums in the United States of America. Hailing from the first Chicago’s first Polish neighborhood, this establishment promotes Polish culture and history through Polish American art, sculptures, paintings, drawings, and lithographs by well recognized artists. While touring this rustic space, visitors can indulge in an abundance of exhibits such as lectures, movie and slide presentations, concerts, theater performances, and meeting with scholars and artists from all over the world. Admission is $7 for adults, $6 for seniors and students. Don’t forget to stop by the gift shop on your way out and browse the intricate collection imported Polish dolls, jewelry, and hand-carved wooden items. Take a piece of Polish history and keep it for a lifetime. 984 N. Milwaukee Avenue, Chicago, IL 60622.

10. Funky Buddha Lounge represents Chicago’s energetic nightlife with an atmosphere of antique décor and mural covered walls, giving party-goers a pleasing visual display of its cultural decadence. Nighttime explorers have the option of relaxing with friends in an environment of refined privacy or merging into the crowd and dancing to a variety of genres created by Chicago’s leading DJ’s. Weekly events such as Funk Fridays and Classic Saturdays add to the diversity of this trendy city spot and allow attendees to experience the essence that makes Funky Buddha so appealing to the masses. Admission ranges from $20- $30, but you get in for free if you make it to the door before 11pm. If you’re looking for a low- key environment with great music—Funky Buddha Lounge is definitely worth the trip. (728 W Grand Ave, Chicago, IL 60610.


Top 5 Hotels

4.3 Star- Ruby Room Chicago: (Avg. from $186 per night) Located in Ukrainian Village, West of Wicker Park. Amenities include a full-service spa, a library, and a hair salon. Yoga classes are also available. Boutiques and restaurants are nearby.

3 Star- Wicker Park Inn: (Avg. from $97 per night) Located in the heart of Wicker Park. This is a charming Bed and Breakfast establishment that gives you an authentic feel for the Wicker Park neighborhood. Close access to restaurants, shopping, and galleries on Milwaukee Avenue.

4.1 Star- Hotel Felix: (Avg. from $152 per night) Located 2.5 miles from Wicker Park in the River North neighborhood. A completely eco-friendly hotel with Wi-Fi and spa services. Just steps away from the Magnificent Mile and the loop.

5 Star- Four Seasons Hotel Chicago: (Avg. from $598 per night) Thriving art scene and captivating view located along Lake Michigan. Fitness facilities, spa, and dining are available. Just steps away from shopping and the Art Institute of Chicago.



3 Star- House of Two Urns Bed and Breakfas: (Avg. from $99-249 per night) A Bed and Breakfast establishment that has been hosting guest for 22 years. Dining, art galleries, and live music and film festivals are within a short walk, bus, or cab ride. Free Wi-Fi.

Wicker Park gives it visitors an extensive list of cuisine to satisfy just about any craving while staying in a low-price range. $ Big Star, Mexican Cuisine, 1531 N. Damen Ave, (773) 235-4039, Sun-Fri: 11:30am- 2amSat: 11:30am-3am, Best tacos in the city and located right off the Damen Blue Line Train Stop. Can get a bit crowded, but has a very lively atmosphere. (Trendy/Bar scene); $$ Bongo Room, American Cuisine 470 N Milwaukee Ave, (773) 489-0690, Mon-Fri: 8am-2:30pmSat-Sun: 9am-2pm, Great breakfast spot for people watching and delicious banana pancakes; $$People Lounge, Spanish Cuisine, 1560 N Milwaukee Ave (773)227-9339, Su-F 5PM-2AM, Sa 5PM-3AM,Spanish tapas restaurant with friendly staff and DJs spinning world music;$$ Piece Brewery & Pizzeria, American Cuisine,1927 W North Ave,(773) 772-4422, M-Th 11:30AM-1:30AM, F 11:30AM-2AM, Sa 11AM-3AM, Su 11AM-1AM. Thin-crust pizza and micro-brews. Live music and Karaoke on Thursdays.



The variety of boutique and shops, selling everything from cigars to vintage Dooney and Bourke bags, are what gives Wicker Park its cool, hipster aesthetic. Walk down Milwaukee for a unique shopping experience of resale music, books, and vintage clothing stores. Myopic Books, Una Mae’s Freak Boutique, (Vintage and contemporary clothing), Kokorokoko (Men’s and women’s vintage clothing from the 80s-90s), Reckless Records, Buffalo Exchange, American Apparel, and The Boring Store, just to name a few. If you want to shop at a more contemporary retail shopl, you can head in the opposite direction down North Avenue where you’ll find Lululemon, Marc by Marc Jacobs, Akira, and Scoop NYC.



The city of Chicago has a very comprehensive and easy to navigate transportation system, so getting around is not a complex task. Wicker Park in conveniently located right off the Chicago Transit Authority’s (CTA) Damen Blue Line trains stop. It’s an elevated subway train that runs from O’Hare International Airport, passing through the core of Wicker Park, and runs 24 hours a day. Visitors can also take hop on one of the many bus routes and a take a taxi. You can find information about bus and train schedules by utilizing “Trip Planner” on the Chicago Transit Authority website.


Taylor Goldblatt

After years of research, travel, and dreams, I have created this website for people like you who want to experience the things that only America can offer. My passion is to explore and share America's greatest destinations and attractions. Follow me on Twitter @USCityTraveler for additional travel tips and ideas.

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