live like a local.
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“Our family of four loved our stay in Chicago, the location was fantastic–short walk to all kinds of restaurants and the train. If you want a comfortable place that is central to an awesome neighborhood, this is the one.”
Cindy, July 2024
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“This place was an absolute gem. The location couldn’t be better—walkable to everything you want in Wicker Park… We had a wonderful stay!”
Leslie, Dec. 2025
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Amazing place to stay. Location and amenities were everything could have asked for and more. The hosts were incredibly responsive and made the apartment feel like a home for the month I was there!
John, Feb 2025
Stay in the heart of Chicago’s most vibrant creative hub. Our home at stayinbucktown.com puts you steps away from the best “Six Corners” has to offer.
🚶 The Great Outdoors: The 606 & Local Parks
- The 606 (Bloomingdale Trail): Just a short stroll away, this 2.7-mile elevated park is Chicago’s version of the High Line. It’s perfect for a morning jog, a sunset bike ride, or a scenic walk through four distinct neighborhoods.
- Wicker Park: Head to the neighborhood’s namesake park for the Sunday Farmers Market, community gardens, and a great dog park.
- Holstein Park: A local staple in Bucktown featuring a public pool and wide-open green spaces for a relaxed afternoon picnic.
Your Guide to Bucktown & Wicker Park
☕ Coffee & Breakfast Rituals
- Wolf & Company: Our personal favorite for an all-day cafe experience right near The 606.
- Stan’s Donuts & Coffee: A Chicago legend located at the Damen Blue Line stop—don’t miss their Biscoff pocket.
- The Bongo Room: Famous for high-end, seasonal brunch. Be prepared for a wait on weekends—it’s worth it!
🍴 Award-Winning Dining & Nightlife
- Club Lucky: A Bucktown institution since 1990. Go for the old-school Italian vibe and the famous “Killer Martinis.”
- Big Star: The ultimate spot for tacos and bourbon on a massive sunny patio.
- Chef’s Special Cocktail Bar: Incredible American-Chinese food and some of the best craft cocktails in the city.
🛍️ Boutique Shopping & Culture
- Milwaukee Avenue: Spend an afternoon browsing vintage shops, indie bookstores like Myopic Books, and local boutiques that you won’t find anywhere else in the world.
- Flat Iron Arts Building: The historic heart of the local arts scene. Check out “First Fridays” to see local artists in their studios.
Where you’ll stay.