Experience Wicker Park like a local with this self-guided walking tour!
Learn the history and experience the cultural highlights through a 1.8 mile walk around Chicago’s trendiest neighborhood. With over 150 restaurants and a bustling shopping scene, Wicker Park is a welcoming place to shop and indulge with a rich history to pull it all together! There are many things to see in Wicker Park.
Be sure to also take a look at our full list of self-guided Chicago tours.
Self Guided Walking Tour
Located northwest of The Loop, directly off the Blue Line. Get off the Damen exit (map), hit all the stops, or skip around to the ones that interest you the most. You’ll find plenty of vintage shops and dive pubs along the way, so even if you stray, you’ll be sure to have a great time in Wicker Park! Be sure to read our post on mass transit options in Chicago.
Wicker Park is also a good place to find an inexpensive hotel. Check out Tripadvisor's top 30 cheap hotels.
Stop #1: Stan’s Donuts & Coffee (1560 N Damen Ave) $$
Start your tour with the best donut and coffee in Chicago; go see Stan. Turn left as you exit the Blue Line’s Damen stop, and the neon-pink sign welcomes you to indulge! Employees recommend the Glazed Old Fashioned, but the Nutella Pocket is sinfully delicious for chocolate lovers.
The staff are extremely friendly (be sure to read their name tags), and the entire store is adorably Pinterest worthy. Be sure to tag a picture of your favorite treat for Instagram (@stansdonutschicago). http://www.stansdonutschicago.com/
SUN-WED 6:30am-9pm | THURS 6:30pm-10:00pm | FRI-SAT 6:30am-10:30pm
Stop #2: Big Star (1531 North Damen Avenue) $
If you’re hungry, cross the street to the delicious bourbon and beer-centric taco joint, Big Star. Possibly the most popular restaurant in Wicker Park, with namesake from the 2003 painting ‘Red Star’ by local Chicago poet, actor & artist Tony Fitzpatrick.
Their inexpensive and mouth watering Tacos Al Pastor and their $3 Whiskey Shots make this a popular hotspot day and night. Cash only, and 21 and over after 8 P.M, http://bigstarchicago.com/.
DAILY 11:30am-2:00am | SAT 11am-3am
Stop #3: Wicker Park (1425 North Damen Avenue)
You’ll see Wicker Park just southeast. 4.03 acres of dedicated public park, with luscious gardens maintained by volunteers of the Wicker Park Garden Club.
Businessman/politician Charles Wicker can be found sweeping up the place, so be sure to take your picture with him! http://www.wpgarden.org/
DAILY 6am-11pm
History Lesson:
In 1870, Charles and Joel Wicker (brothers) began development of what they hoped would one day become an attractive neighborhood for the middle and upper class.
The Great Chicago Fire of 1871 resulted in folks of all cultural and financial backgrounds moving to the area, developing beautiful brick and stone homes (which we’ll see later).
Continue on to see the grandiose fountain dedicated to Mayor Richard M. Daley in 2002. You’ll come out on Milwaukee Avenue, then turn left.
Stop #4: Nick’s Beer Garden (1516 N Milwaukee Ave) $$
You’ll see many trendy eateries (over 150) on Milwaukee Avenue, so feel free to wander, but definitely check out the luau-infused bar with local, regional, and national craft beers.
With no cover charge, Nick offers live music on the weekends, and is a central location of the Wicker Park nightlife. Stop in and say hello, and maybe try a new beer! http://nicksbeergarden.com/.
DAILY 4pm-4am | SAT 1pm-5am | SUN 1pm-4am
Stop #5: Myopic Books (1564 N Milwaukee Ave)
Continue west on Milwaukee and you’ll find...a three story used book store; YES!
This gem is located near the corner of Milwaukee and North Avenue, and has that enticing old book smell (you know the one). Climb the stairs amidst seemingly endless stacks, or catch a poetry reading! Knowledgable staff are always ready to help you. http://www.myopicbookstore.com/
DAILY 9am-11pm
Stop #6: Flatiron Arts Building (1579 N. Milwaukee Avenue)
This all artist studio building boasts visual art in all its forms. It’s impossible to miss this triangular beauty, as it forms the intersection of Damen, Milwaukee, and North Avenue.
It might surprise you to know that this building has been around since 1913, built by Holabird and Roche (of the early skyscraper Tacoma Building fame). Shops, studios, and salons are all available at this location. http://www.flatironartsbuilding.com/
Stop #7: Piece Brewery and Pizzeria (1927 W North Ave) $$
Grab some lunch before you head to your next stop. Thin crust lovers will find a new favorite pizza joint just south on North Avenue. Start with the warm spinach and tomato dip, then grab a personal lunch pizza with some of the on tap beer. http://www.piecechicago.com/
M-W 11am-10:30pm |THU 11am-11pm |FRI/SAT 11am-12:30am |SUN 11am-10pm
Continue east on North Avenue, then make a left onto Hermitage Avenue. Take in the neighborhood architecture as you walk to our next stop.
History Lesson:
Imagine what it was like in 1870, when the Great Chicago Fire forced people to relocate to this area, changing the landscape of the community to a include a unique blend of German, Norwegian, Jewish, and Polish populations.
New homes were made of brick and stone (because we saw what happened to wooden ones!), with magnificent mansions belonging to the wealthy built next to working class homes.
Stop #8: St. Mary of the Angels Church (1810 N. Hermitage Ave)
To your left is the gorgeous St. Mary of the Angels, one of fourteen churches built by architects Worthmann and Steinbach. Breaking ground in 1914 and completed in 1920, this Roman Catholic church was administered by the Congregation of the Resurrection until 1990.
Since then, it has been run by the Opus Dei. Originally founded by the Polish, the church now holds mass in Polish, Spanish, and English in the 2,000 seat nave. Take in the architecture, with a dome that reaches 125 feet from floor to ceiling. http://sma-church.org/
DAILY: Dusk to Dawn. Services every Sunday.
Stop #9: The 606 Elevated Path (1801 N. Wood St)
Be among the first to visit this newly opened bike and running path on Bloomingdale Avenue! Enter the convenient ADA accessible ramp on Wood Street, and you’ll see Wicker Park from 20 feet up in the air!
Over a decade in the making, The 606 offers residents of five neighborhoods the opportunity to escape urban life for a 2.7 mile stretch of fully landscaped park system. Walk along the padded path until you reach the Damen exit.
DAILY 6am-11pm
