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How to spend a perfect fall day in West Bucktown, Chicago

Chicago may be considered the “Second City” but the nearly 300-year old town always seems to be providing visitors–and residents–with more reasons to fall in love with it. Those only vaguely familiar with Chicago might know it as the birthplace of the modern skyscraper, or the playground for Ferris and company in Ferris Bueller’s Day Off. But as the leaves begin to turn brown, there is a side of the city that visitors and natives alike would be surely remiss not to explore: West Bucktown.

Why we love it

West Bucktown is settled just west of one of Chicago’s more well-known neighborhoods, Wicker Park, but West Bucktown doesn’t rely on its neighbors for a good time! Home to some of Chicago’s best restaurants and a host of serene greenspaces (no Cloud Gate crowds here!), the neighborhood felt like a perfect fit for our Chicago home, Common Maplewood. In addition to being fully-furnished and offering all-inclusive amenities for only $1000/month, Common Maplewood’s location also puts residents in the heart of this truly one-of-a-kind neighborhood–while also offering easy access to some of Chicago’s more well-known destinations. If you ask us there’s no better time to get to know a city than during the changing of seasons, so here’s how to spend a perfect fall day in West Bucktown.

Sip and stroll

Whether coffee or tea, cold brew or a pumpkin spice latte (no judgment!) there’s no better place to enjoy your morning cup o’ joe than atop the 606: a converted-railway-turned-elevated-park that offers the best possible views of several Chicago neighborhoods, including West Bucktown. Grab a cup of coffee at Ipsento 606 to-go to take on your stroll, and enjoy the sights in between sips. Whether you walk the whole way or stop off to explore at one of the park’s 12 access points, the 606 is a great way to elevate a fall morning.

Let’s stop for a bite…

In addition to being ideal for some light people-watching, the 606 is also a perfect gateway to some of West Bucktown’s best eats–no matter your mood. Small Cheval, a stripped-down burger and fries joint, is situated just off of the 606 and exists to satisfy all your savory better-than-fast-food needs. If that’s not your jam, plant-based comfort food purveyors Handlebar are only a short walk from the 606 and offer a wide selection of fall comfort vittles.

Turning a page

After filling up on vegan chili at Handlebar, skip over to Myopic Books on Milwaukee Avenue to burn off brunch. The renowned used bookstore is home to three floors housing over 60,000 books between them. After you’ve pored over the pages, pay a visit to any (or all) of Milwaukee Avenue’s other shopping destinations: from upscale streetwear shop Saint Alfred to record/collectible shop The Exchange. If your sweet-tooth kicks in, Jeni’s Splendid Ice Cream is across the street. Any flavor is sure to satisfy, but our pick is the autumnal brambleberry crisp.

Bucktown brews

After a day of eating, shopping, and sightseeing your way through West Bucktown and its surrounding neighborhoods, settle in for a drink at Bucktown favorite Remedy. The decidedly un-pretentious cocktail bar’s name is a fitting one as Remedy offers an oasis-like reprieve from a busy day bouncing around West Bucktown. Should your late-night appetite rear its head when your cup runs empty, you can finish your perfect fall day with a slice at Blue Line Pizza across the street.

Though slightly more under the radar than neighboring Bucktown and Wicker Park, West Bucktown is chock full of exciting attractions with fun new experiences to be had around nearly every corner. Interested in coliving in West Bucktown? Explore Common Maplewood and discover a side of the Second City you’ve never seen.

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