WICKER PARK / BUCKTOWN

Division Street is chock full of bars and restaurants of every kind, including Smoke Daddy BBQ, Parlor Pizza Bar, The Perch Kitchen and Tap, Fatpour, and The Fifty/50, just to name a few! Once you’ve hit every spot on Division, head up Milwaukee Avenue for more fun! Small Cheval may be small in menu selection, but it is mighty in serving up one of the best burgers, fries, and shakes you’ll find! On a perfect Chicago summer evening, start with some tacos and margaritas at Big Star, head over to the Whiskey Business rooftop and enjoy one of their more than 100 whiskeys, and finish out the evening with late-night pizza and cocktails at Paradise Park’s patio. 

For one of the best Saturdays ever, start by meeting some friends for brunch at Etta (hello bread and pastries). Later that day, check out Tortello for some handcrafted pasta in a casual dining setting (or try out one of their at-home pasta kits!). Start out the evening with a rooftop cocktail and city skyline views at the Rooftop at The Up Room on the 13th floor of the Robey Hotel and finish it off with a nightcap at The Violet Hour, a pre-prohibition style bar serving up artisanal cocktails. 

The options are endless. 

Love the outdoors? Go for a walk, run, or bike ride along the Bloomingdale Trail at the 606 or visit one of the many stunning parks, including Walsh Park on Ashland and the neighborhood’s namesake, Wicker Park, just south of the North & Damen intersection. 

Is music more your jam? The neighborhood is full of entertainment venues from live music, to DJs, to burlesque dancers! Subterranean – a 2-story venue on North & Damen that features all of the above; The Hideout on Wabansia – a prohibition-era space with live music and dancing on Saturday nights; Davenport’s Piano Bar & Cabaret – the name says it all; and Bourbon on Division – a late-night watering hole that happens to have an amazing venue spaces upstairs, featuring musicians and DJs throughout the year. 

In need of a laugh? Check out The Comedy Clubhouse – one of the top-rated comedy clubs in the city. 

Love art? The many artists renting studio space at the Flat Iron Arts Building on Milwaukee & Damen open up their spaces to exhibit their work every Friday from 5-10PM, no admission charged. 

During the summer months, you can find one of the best Farmer’s Markets in Chicago in Wicker Park (the actual park)! The streets of Chicago come alive with Street Fests throughout the summer, and Wicker Park/Bucktown is no exception – check out the list of all festivals below!

Farmers Markets:

• Wicker Park Farmer’s Market- every Sunday 8AM-2PM (beginning May 15th)
• Wicker Park – 1425 N Damen Ave

Street Fests:

• DoDivision – early June
• Wicker Park Fest – late July
• Bucktown Art Fest – August