36 Hours in Wicker Park / Bucktown
There is so much to do in Chicago that sometimes it is hard to fit it all in one trip. So, we will be sharing our favorite activities in our favorite neighborhoods that you can do in just 36 hours. The Wicker Park / Bucktown area is known as vibrant, artistic, and culturally rich. It's a neighborhood that's both classic and contemporary, making it a perfect location for prospective homeowners, or a day of shopping & dining! (note: it’s also where Heyday founder Meg lives!)
From eclectic boutiques to unique coffee shops & restaurants, Wicker Park has something for everyone. Here are a few of our neighborhood spots if you plan to spend 36 hours in Wicker Park / Bucktown:
Pompette (Lunch + Wine)
Start your day exploring Wicker Park / Bucktown with lunch & wine at the charming café Pompette. Pompette's sophisticated and welcoming atmosphere perfectly complements the neighborhood's aesthetic. Their dishes are prepared with locally-sourced ingredients, and it’s one of our favorite spots to meet with friends, clients, or family when we’re in the neighborhood.
WilderHouse (Shopping)
Wilderhouse is a local gem where you can explore a unique selection of curated home goods, furniture, and decor. Their finds are sustainable and handcrafted, so it’s one of our favorite spots to share with local clients. Whether you're furnishing your new home or looking for unique décor items, Wilderhouse is the perfect place to explore and indulge your aesthetic senses.
Club Lucky (Dinner)
After you’re tired from a day of shopping and exploring, cozy up in a booth at Club Lucky. This iconic neighborhood restaurant combines the ambiance of a 1940s supper club with an expansive menu of pasta and Italian classics. With its vintage-inspired décor and welcoming staff, Club Lucky is one of our favorite “if you know, you know” spots in the neighborhood.
Wicker Park Inn (Only B&B in the City!)
When you’re ready to settle in for the night, immerse yourself further in the charm of Wicker Park at the Wicker Park Inn, Chicago’s ONLY bed & breakfast. This inn offers luxury service with cozy accommodations, plus we love that it’s female-owned and run!
Ipsento + the 606 (Morning Coffee & walk)
Kickstart your morning with the best brew in town (our humble opinion) at Ipsento. Their menu is full of expertly crafted coffee, tea, and signature drinks, and they are the perfect companion for a stroll along the 606 Trail, an elevated urban park that offers spectacular views of the city.
These local gems are just a few of our favorite spots in Wicker Park / Bucktown. Whether you're a prospective homeowner or just exploring the neighborhood, we encourage you to start here, and then explore on your own!