Destination Main Streets

Wicker Park (Chicago), Illinois

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Wicker Park is popular in Chicago for its shopping, nightlife and its hipster culture. Known as one of the hipster capitals in the U.S. (second only to Williamsburg in New York) it also made a top five list compiled by Forbes and Nextdoor of hipster neighborhoods. If you're wondering the hipster subculture is often identified with gentrifying neighborhoods, alternative music and art scenes, organic and artisanal foods, and alternative lifestyles. The word is also commonly used as a pejorative as hipsters don't normally refer to themselves as that. But that over simplified definition should give you some sense of what you would find in Wicker Park as the area has under gone considerable gentrification in recent years.

Wicker Park was originally found around a park with the same name. After the Great Chicago Fire of 1871, many displaced people moved out to the area. Northern European immigrants came to the area, including merchants many of whom were brewers, who built large homes in the Italianate and Victorian Gothic styles. In the mid twentieth century, the area fell on hard times. In the eighties and nineties, the area began to stabilize. Festivals were estabilished to promote the arts. People moved back in attracted by the affordable real estate close to downtown ("The Loop"). Today, the area still maintains a gritty feel. But real estate prices have sky rocketed. Many chains have begun to displace the independent merchants in the area. But Wicker Park continues to be a community in transition.

Wicker Park and nearby Bucktown are many times commonly associated together as one area. In fact, they share a Chamber of Commerce. But some consider the dividing line between the two communities to be the Bloomingdale Trail with Bucktown to the north and Wicker Park on the south. The three Main Streets for Wicker Park are Damen Avenue, which runs north and south, North Avenue, which runs east and west, and Milwaukee Avenue, which is a diagonal road and runs northwest to southeast. All three of these roads meet in the heart of Wicker Park and form a Six Corners intersection that some infamously refer to as "The Crotch" due to its rowdy nightlife. Wicker Park is about four miles from The Loop. You can get there by the CTA rapid transit elevated "L" Blue Line. The Damen Avenue station is in the heart of Wicker Park.

Photo Gallery

We start our tour of Wicker Park in Chicago, Illinois on Damen Avenue on the community's northern boundary, which is the Bloomingdale Trail.  The trail is a former elevated railroad line that was recently transformed into an urban trail with a parklike setting.  North of the trail is the community of Bucktown.
We start our tour of Wicker Park in Chicago, Illinois on Damen Avenue on the community's northern boundary, which is the Bloomingdale Trail. The trail is a former elevated railroad line that was recently transformed into an urban trail with a parklike setting. North of the trail is the community of Bucktown.
Crossing underneath the Bloomingdale Trail we are now in Wicker Park.  Although the trail divides Wicker Park from Bucktown, the two communities are actually quite often associated with one another.  There are many shops and restaurants along Damen Avenue both north and south of the trail.  We'll continue working our way south.
Crossing underneath the Bloomingdale Trail we are now in Wicker Park. Although the trail divides Wicker Park from Bucktown, the two communities are actually quite often associated with one another. There are many shops and restaurants along Damen Avenue both north and south of the trail. We'll continue working our way south.
Looking south along Damen Avenue, we see more shops and cafes.  Poking up in the distance on the right side of the photo, we see a high-rise building that's quite familiar in Wicker Park.  We'll see more of it in upcoming photos.
Looking south along Damen Avenue, we see more shops and cafes. Poking up in the distance on the right side of the photo, we see a high-rise building that's quite familiar in Wicker Park. We'll see more of it in upcoming photos.
Here are some familiar chains and boutiques along Damen Avenue.  Wicker Park has been known for its hipster scene, which includes independent retailers and alternative lifestyles.  However, in recent years, gentrification has caused more chains to move in.
Here are some familiar chains and boutiques along Damen Avenue. Wicker Park has been known for its hipster scene, which includes independent retailers and alternative lifestyles. However, in recent years, gentrification has caused more chains to move in.
Across the street, we can see some more familiar fashion boutique chains.  Wicker Park is also known for having a gritty atmosphere.  However, stretch of Damen Avenue is quite clean.
Across the street, we can see some more familiar fashion boutique chains. Wicker Park is also known for having a gritty atmosphere. However, stretch of Damen Avenue is quite clean.
Here we see a variety of retail in a variety of architecture.  On the left, you get a better view of Wicker Park's Northwest Tower.
Here we see a variety of retail in a variety of architecture. On the left, you get a better view of Wicker Park's Northwest Tower.
We continue heading south along Damen Avenue.  Boutiques, restaurants and bars line the street.
We continue heading south along Damen Avenue. Boutiques, restaurants and bars line the street.
Across the street, where Damen intersections with Concord Place are more shops, businesses, and plenty of traffic as we get closer to the heart of Wicker Park.
Across the street, where Damen intersections with Concord Place are more shops, businesses, and plenty of traffic as we get closer to the heart of Wicker Park.
These chains made interesting use of this renovated historic fire department.  Notice how the large windows in the front look like they were once the garage doors to the fire house?
These chains made interesting use of this renovated historic fire department. Notice how the large windows in the front look like they were once the garage doors to the fire house?
Across the street we see more shops and businesses.
Across the street we see more shops and businesses.
Walgreen's now occupies the historic Noel State Bank Building originally built in 1921.   Even if you don't need to pick up sundries, it's definitely worth to go inside and check out the architecture on the inside of the building.
Walgreen's now occupies the historic Noel State Bank Building originally built in 1921. Even if you don't need to pick up sundries, it's definitely worth to go inside and check out the architecture on the inside of the building.
We make it to the intersection of North Avenue, Milwaukee Avenue, and Damen Avenue.  This is the heart of Wicker Park's commercial district.  The intersection forms six corners instead of the standard four corners.  Some refer to the area as Six Corners, but this can be confused with another area in Chicago in Portage Park.  Others refer to this area by the less flatering name of The Crotch.
We make it to the intersection of North Avenue, Milwaukee Avenue, and Damen Avenue. This is the heart of Wicker Park's commercial district. The intersection forms six corners instead of the standard four corners. Some refer to the area as Six Corners, but this can be confused with another area in Chicago in Portage Park. Others refer to this area by the less flatering name of The Crotch.
Here's a view of the Northwest Tower.  Some call it the Coyote Building because of its shape.  The building is a twelve story art deco high-rise that was the tallest building in Chicago outside of the Loop at the time it was built.  Currently, it is being converted into a hotel.
Here's a view of the Northwest Tower. Some call it the Coyote Building because of its shape. The building is a twelve story art deco high-rise that was the tallest building in Chicago outside of the Loop at the time it was built. Currently, it is being converted into a hotel.
The blue line of the CTA "L" will take you to Wicker Park and the Damen Avenue station is located right in the heart of the neighborhood.  Stan's is a popular donut chain around Chicago.
The blue line of the CTA "L" will take you to Wicker Park and the Damen Avenue station is located right in the heart of the neighborhood. Stan's is a popular donut chain around Chicago.
Now we'll start working our way east along North Avenue, one of the three Main Streets of Wicker Park.  This one runs east and west.  Here you can see the Flatiron Arts Building, which for years has served as a home for artists with its many studios on the upper floors.
Now we'll start working our way east along North Avenue, one of the three Main Streets of Wicker Park. This one runs east and west. Here you can see the Flatiron Arts Building, which for years has served as a home for artists with its many studios on the upper floors.
Looking back westbound along North Avenue, we see the Northwest building in the distance, serving as a landmark for the center of Wicker Park.
Looking back westbound along North Avenue, we see the Northwest building in the distance, serving as a landmark for the center of Wicker Park.
More shops and some unique architecture along North Avenue, including the glass block windows and the painted billboard on the sidewall.
More shops and some unique architecture along North Avenue, including the glass block windows and the painted billboard on the sidewall.
Here's a more modern building on North Avenue.  At this intersection, you have Wolcott Avenue on the north turning into Elk Grove Avenue on the south.
Here's a more modern building on North Avenue. At this intersection, you have Wolcott Avenue on the north turning into Elk Grove Avenue on the south.
North Avenue is also a major highway running through Chicago.  It's Illinois State Route 64.  So you're bound to drive by some billboards along the way.
North Avenue is also a major highway running through Chicago. It's Illinois State Route 64. So you're bound to drive by some billboards along the way.
Speaking of interesting billboards, we turn around and at the same intersection we see this unique piece of advertising painted on the side of a building.
Speaking of interesting billboards, we turn around and at the same intersection we see this unique piece of advertising painted on the side of a building.
This restaurant has an interesting outdoor patio area with a lot of shade provided by the trees.
This restaurant has an interesting outdoor patio area with a lot of shade provided by the trees.
Across the street are more shops, restaurants, and a yoga studio.
Across the street are more shops, restaurants, and a yoga studio.
This is a view looking back westbound along North Avenue.  You can see another billboard for folks driving through the area.  This one is electronic.  In the background is the Northwest Tower.
This is a view looking back westbound along North Avenue. You can see another billboard for folks driving through the area. This one is electronic. In the background is the Northwest Tower.
We continue east along North Avenue.  This is a more modern residential block with boutiques on the ground floor.
We continue east along North Avenue. This is a more modern residential block with boutiques on the ground floor.
Something you don't see too much of along this stretch.  Some historic buildings.
Something you don't see too much of along this stretch. Some historic buildings.
Just next door is this building that's unfortunately built back away from the street to provide surface parking.  Doesn't help the pedestrians though.
Just next door is this building that's unfortunately built back away from the street to provide surface parking. Doesn't help the pedestrians though.
A little further east on North Avenue and Wood Street we see this locally-owned cafe across from some more modern apartment houses.
A little further east on North Avenue and Wood Street we see this locally-owned cafe across from some more modern apartment houses.
Here's a view of North Avenue, showing off a wide variety of architecture.  We are almost at our furthest point before we turn around and head back, and yet we can still see the Northwest Tower still off in the distance.
Here's a view of North Avenue, showing off a wide variety of architecture. We are almost at our furthest point before we turn around and head back, and yet we can still see the Northwest Tower still off in the distance.
We make it to North Avenue and Paulina Avenue.  This is the furthest east I went on North Avenue before I turned around and went back to the heart of Wicker Park.  But our tour is not over yet.
We make it to North Avenue and Paulina Avenue. This is the furthest east I went on North Avenue before I turned around and went back to the heart of Wicker Park. But our tour is not over yet.
We head back to the heart of Wicker Park ("The Crotch" if you want to call it that) and from there head down Milwaukee Avenue, the third Main Street area in Wicker Park.  This is a diagonal street that goes northwest to southeast.  We will be heading southeast.
We head back to the heart of Wicker Park ("The Crotch" if you want to call it that) and from there head down Milwaukee Avenue, the third Main Street area in Wicker Park. This is a diagonal street that goes northwest to southeast. We will be heading southeast.
This is another view of the Flatiron Arts Building that we saw in a previous photo.  You can see there are businesses on the ground floor.  The upper floors are occupied by artist studios.  The name comes from the shape of the building formed by the triangular block that it is on.
This is another view of the Flatiron Arts Building that we saw in a previous photo. You can see there are businesses on the ground floor. The upper floors are occupied by artist studios. The name comes from the shape of the building formed by the triangular block that it is on.
Going down a little further are some shops selling familiar brands and a bar, all housed in historic properties.
Going down a little further are some shops selling familiar brands and a bar, all housed in historic properties.
Looking back, we can see the Northwest Tower.  This stretch is a bit more historic than what we have seen before.
Looking back, we can see the Northwest Tower. This stretch is a bit more historic than what we have seen before.
You'll notice quite a few bars in some of these pictures.  Wicker Park sometimes gets a reputation for having a rowdy scene on the weekends.  The nickname for its main intersection "The Crotch" is said to come from what you can smell there on a Saturday night.
You'll notice quite a few bars in some of these pictures. Wicker Park sometimes gets a reputation for having a rowdy scene on the weekends. The nickname for its main intersection "The Crotch" is said to come from what you can smell there on a Saturday night.
Wicker Park is an up and coming area but with a gritty feel.  In this shot, you can see the newer clean building on one side, while that ATM gives you a feeling about the other part of Wicker Park's personality.
Wicker Park is an up and coming area but with a gritty feel. In this shot, you can see the newer clean building on one side, while that ATM gives you a feeling about the other part of Wicker Park's personality.
Here's a collection of shops and other businesses along a busy stretch of Milwaukee Avenue.  This area is part of the Milwaukee Avenue Historic District.
Here's a collection of shops and other businesses along a busy stretch of Milwaukee Avenue. This area is part of the Milwaukee Avenue Historic District.
The Peoples Gas Light & Coke Company Building is an example of Classic Revival architecture.  In its day, it was Chicago's first utility.  The Coke was for power, not the drink or the drug.  Today the store front is separated into two shops.
The Peoples Gas Light & Coke Company Building is an example of Classic Revival architecture. In its day, it was Chicago's first utility. The Coke was for power, not the drink or the drug. Today the store front is separated into two shops.
Across the street, we have a view looking southeast along Milwaukee Avenue.  Hey look, someone else is taking pictures.
Across the street, we have a view looking southeast along Milwaukee Avenue. Hey look, someone else is taking pictures.
Doctor's offices mix with cafes and other businesses along Milwaukee Avenue.  Here you see a modern structure next to historic buildings.
Doctor's offices mix with cafes and other businesses along Milwaukee Avenue. Here you see a modern structure next to historic buildings.
This is a view of the intersection of Milwaukee Avenue and Honore Street.
This is a view of the intersection of Milwaukee Avenue and Honore Street.
And across the street are a collection of more businesses housed in buildings featuring a variety of architectural styles.
And across the street are a collection of more businesses housed in buildings featuring a variety of architectural styles.
Continuing southeast we see more boutiques and cafes.
Continuing southeast we see more boutiques and cafes.
Here we see some more shops and restaurants housed in some historic buildings.  The water tower is a nice touch.
Here we see some more shops and restaurants housed in some historic buildings. The water tower is a nice touch.
The stretch takes on a bit of that gritty appeal even if its part of the decor.  Wicker Park is known for its hipster vibe so it would make sense that a business housed here would have Brooklyn in its name.
The stretch takes on a bit of that gritty appeal even if its part of the decor. Wicker Park is known for its hipster vibe so it would make sense that a business housed here would have Brooklyn in its name.
Just next door, like Brooklyn before it, Hollywood Cleaners also borrows its name from another famous urban area.  The large quirky billboard also adds a nice touch.
Just next door, like Brooklyn before it, Hollywood Cleaners also borrows its name from another famous urban area. The large quirky billboard also adds a nice touch.
Across the street, are some more businesses that seem to have that hipster vibe.
Across the street, are some more businesses that seem to have that hipster vibe.
Some more independent businesses along this stretch of Milwaukee Avenue.
Some more independent businesses along this stretch of Milwaukee Avenue.
We continue down Milwaukee Avenue for one last picture.  You can definitely get a sense as to how the area is transforming.  The jeans billboard is interesting.  This concludes our tour of Wicker Park.
We continue down Milwaukee Avenue for one last picture. You can definitely get a sense as to how the area is transforming. The jeans billboard is interesting. This concludes our tour of Wicker Park.

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