undefined Itinerary

Start your day with a delicious brunch at The Bongo Room. This local favorite is known for its creative and indulgent breakfast dishes, such as their famous chocolate tower French toast. Afterward, take a walk down Damen Avenue and explore the many art galleries and boutique shops.

Visit the historic Flat Iron Arts Building, which houses several art galleries and studios. Take your time browsing the diverse collection of artwork and maybe even purchase a unique piece to take home. Afterward, satisfy your sweet tooth at Stan's Donuts, a beloved local spot for gourmet donuts.

Enjoy dinner at Piece Brewery and Pizzeria, where you can savor delicious thin-crust pizzas and enjoy their handcrafted beers. Afterward, head to Emporium Arcade Bar, a retro-style bar filled with vintage arcade games and pinball machines. Grab a drink and challenge your friends to a friendly competition.

Start your day with a visit to the 606 Trail, a former elevated railway that has been transformed into a beautiful greenway. Take a leisurely walk or bike ride along the trail and enjoy the scenic views of the city. Afterward, grab a quick bite at Big Star Bakery, known for their mouthwatering pastries and baked goods.

Explore the neighborhood's vibrant street art scene by taking a guided tour with Chicago Street Art Tours. Learn about the artists and their inspirations as you discover hidden murals and graffiti throughout the neighborhood. Afterward, visit Myopic Books, a local independent bookstore with an extensive collection of new and used books.

For dinner, head to Antique Taco, a trendy restaurant serving up delicious and creative tacos with a twist. Pair your meal with one of their craft cocktails or a refreshing agua fresca. Afterward, head to Subterranean, a popular live music venue known for hosting both local and national bands across a wide range of genres.

Start your day with a visit to the iconic Robey Hotel, located in a historic Art Deco building. Enjoy a delicious breakfast at their rooftop restaurant, Up & Up, while taking in panoramic views of the city skyline. Afterward, explore the neighborhood's unique thrift stores and vintage shops.

Immerse yourself in the local art scene by visiting the National Museum of Mexican Art. This free museum showcases a vast collection of Mexican art, from traditional to contemporary. Afterward, grab a refreshing drink at Violet Hour, a speakeasy-style cocktail bar known for its expertly crafted drinks.

Indulge in a memorable dinner at The Publican, a renowned restaurant that specializes in rustic European cuisine and features an impressive selection of craft beers. Afterward, catch a show at The Den Theatre, a local theater known for its innovative and thought-provoking productions.

Start your day with a delicious breakfast at Dove's Luncheonette, a retro-style diner serving up classic American comfort food with a Mexican twist. Afterward, explore the neighborhood's many independent boutiques and specialty stores, where you'll find everything from handmade jewelry to unique home goods.

Visit the historic Wicker Park Bucktown Library, a beautiful building that dates back to 1894. Browse the extensive collection of books and admire the stunning architecture. Afterward, enjoy a leisurely bike ride along the nearby Bloomingdale Trail, a 2.7-mile elevated park that offers stunning views of the city.

For dinner, head to Giant, a trendy restaurant known for its innovative and flavorful dishes. Their menu features a mix of American and Asian-inspired cuisine, with an emphasis on seasonal ingredients. Afterward, grab a nightcap at The Violet Hour, a renowned cocktail lounge that offers an extensive menu of handcrafted drinks.