There are so many reasons to love Chicago and its incredible street art is one of them. All kinds of wonderful murals and other colorful artwork are scattered all over the city’s neighborhoods… on buildings, walls, underpasses, bridges, stairways. This art form has dramatically increased in the Windy City over the past decade, along with its quality, diversity and creativity.

If you want to see some of it, I have a few ideas for you. They include seriously artistically impressive works or simply fun artsy walls for a great Instagram shot (I went for an eclectic blend). For out-of-town visitors, tracking them down will take you to many cool Chicago neighborhoods, which are all worth exploring. For those living in Chicago, this list can be a guide to a fun field trip around the city.

Here are 12 awesome instagrammable walls in Chicago, along with their locations:

1. Greetings From Chicago!

I have to start with “that famous Chicago sign”. To get this shot, you will need to venture to Logan Square, which a very cool historic Chicago neighborhood. You can take an Uber, of course, but if you are an out-of-town visitor, I suggest taking the El (the elevated train) for a total Chicago experience. Hop on the Blue Line and get off at the Logan Square stop. This mural is in a parking lot, just south of the train station.

The artwork was created by Victor Ving, a former graffiti artist from New York City who has been traveling the country and creating similar works in other states. Apparently it only took him four days to paint this mural. Can you figure out which Chicago icons are portrayed in each of the letters? Bonus points if you get the meaning of the second “C”!

Location: Logan Square, 2236 North Milwaukee Avenue

Greetings from Chicago is one of awesome instagrammable walls in Chicago - Passports and Spice

2. Flamingo Rum Club

One flamingo, two flamingos, three flamingos, four… How fun is this wall with its pink birds and tropical plants? Located in River North, it is easy to get to for out-of-town visitors who don’t have time to venture to other Chicago neighborhoods beyond the downtown area. To get a picture of the full wall, you will have to time your shots with the traffic light nearby and hope for not many parked cars.

Inside those fun walls is the Flamingo Rum Club, a Caribbean Inspired Rum Club & Cabaret in case you want to… you know, flamingle after you “gram” your shots.

Location: River North, 601 North Wells Street

Flamingo Rum Club is one of awesome instagrammable walls in Chicago - Passports and Spice

3. Have Wings, Will Fly

I first saw “wings on a wall” a few years ago in a photo somebody posted on Facebook from Nashville. I vowed to go there just to take that cool picture. These days, pairs of wings, feathery, giant, colorful, black and white or other types, can be found everywhere. There might be more than one pair in Chicago waiting for you to put on, but I just discovered this one in the Fulton Market area. It is very close to the Restaurant Row on Randolph which includes many Chicago’s most famous eateries such as Girl and the Goat, Belly Q, Bar Siena and my personal favorite, Leña Brava, by legendary Chef Rick Bayless. Another one easy to reach from the city center.

Location: Fulton Market, corner of Lake Street and Morgan Street

Wings is one of awesome instagrammable walls in Chicago - Passports and Spice

4. A Fast Girl 

This is one bad ass larger than life mural which almost caused me to have an accident as I drove down Milwaukee Avenue and slammed on the brakes when I caught a glimpse of it. Ironically, when I got out of the car and got closer, I saw that it says “fast girls”…

Thanks to the signature, I learned that the author is Chicago’s Jas Petersen, “a young, intelligent and rebellious hybrid force in the contemporary art world”, according to her website. Jas seems to be celebrating women of all shapes, colors, dreams, moods and attitudes… the wonderful complex creatures that we are. I found another one of her girls that same afternoon at LACUNA (see #12), but there are many others scattered around Chicago.

Location: Goose Island, intersection of Milwaukee and Chicago Avenue

A Fast Girl is one of awesome instagrammable walls in Chicago - Passports and Spice

5. All You Need is LOVE…

I was actually in search of another love themed wall in Bucktown, which I never found (I’m guessing it must have been covered over by the time I made it to the neighborhood), but my trip was not in vane: I found not one, but four cool LOVE signs on Damen Avenue. That’s a whole lot of love, in black and white or color, your pick.

The author is Matthew Hoffman, a Chicago based artist and designer who has become famous with his You Are Beautiful project, intended to better the world in small ways. If you live in Chicago, you have likely seen those words somewhere in the city, be it on tiny stickers, large billboards, fences or murals. How awesome is that?!? On this particular building on Damen, Hoffman’s work had been commissioned by the real estate brokerage firm @properties for their office building. Thinking I need to get a sign like this for my own office…

Location: Bucktown, 1873 North Damen Avenue

Love in Black and White is one of awesome instagrammable walls in Chicago - Passports and Spice

Love in Color is one of awesome instagrammable walls in Chicago - Passports and Spice

6. The Running Chicken

Why did the chicken cross the road? To make it into this article, of course. A chicken on human legs running along North Avenue might not get the highest artistic scores in the street art category (I think it is supposed to call attention to a restaurant around the corner), but it certainly makes the list of awesome instagrammable walls in Chicago. Don’t forget to do the chicken dance when your take your picture (it will turn out even better, trust me)!

Location: Bucktown/Wicker Park, 1840 West North Avenue

Running Chicken is one of awesome instagrammable walls in Chicago - Passports and Spice

7. The Whoot Mural

Known simply as the Owl, this mural has been whooting on Belmont Avenue below the Kennedy Expressway since 2014. The author is Tony Passero, a modern Chicago artist and creator of several other beautiful murals in the city (see #9). You may start to recognize his artworks because of his style, which often explores themes through repetition and patterns. Just how cute is this owl?

Location: Avondale, 3360 West Belmont Avenue

The Owl is one of awesome instagrammable walls in Chicago - Passports and Spice

8. The Abstract Wall

If you enjoy abstract art, you will like this one. I’ve seen this wall included in several Chicago fashion blogs, as a background to some sassy young model in color coordinated clothes. I’m listing it here so you can pick your outfit ahead of time.

Just kidding! I’m listing it here because it is in Andersonville, a very cool Chicago neighborhood, worth venturing to. It is known for its diversitySwedish roots, small-town charm and quirky personality. You will also find many of the city’s newest and hippest stores and restaurants, almost all independent, locally-owned businesses.

Location: Andersonville, 5625 North Clark Street

Abstract is one of awesome instagrammable walls in Chicago - Passports and Spice

9. CoyWolf Mural

Remember those patterns and repetition I told you about in #7? Here is another mural by Tony Passero. I’m including it not only because it is very cute, but also because it is located just below the 606 Trail, a 2.7 mile biking and walking trail built on an abandoned CTA rail line, another cool thing to experience in the Windy City.

Location: Bucktown, North Damen Avenue at the entrance of 606 Trail

CoyWolf Mural isis one of awesome instagrammable walls in Chicago - Passports and Spice

10. Sea of Flags 

Nothing Like the Holidays, one of my favorite movies shot in Chicago, shows this wall in its opening credits. The movie takes place in Humboldt Park, the west side Chicago neighborhood, which proudly displays its Latino heritage through architecture, stores, restaurants and many murals.

About one quarter of Humbolt Park residents are of Puerto Rican descent and this mural is a proud celebration of their roots. It depicts Fiesta Boricua, an important cultural and music event, which takes place in the neighborhood every September. It is also an intentional statement by the recently deceased artist, Gamaliel Ramirez, who included figures from the Puerto Rican independence movement holding Puerto Rican flags, alluding to the period when it was a felony to display the Puerto Rican flag in public on the island.

Location: Humboldt Park, corner of Divison Street and Campbell Avenue

BONUS: I discovered this handy Humboldt Park Mural guide, if you would like to learn more about the area and see more of its fabulous murals.

Sea of Flags is one of awesome instagrammable walls in Chicago - Passports and Spice

11. La Calavera

Pilsen, the lively Mexican neighborhood of Chicago, is known for its incredible murals which blend art, heritage and activism. There is so much street art in the area, my camera was working overtime and it wasn’t easy to decide which mural to share here. In the end, I chose La Calavera (the Skull) on 16th Street because it conveys much of the Pilsen culture. It is part of a long row of other murals along the railway wall you can admire. For more examples of cool Pilsen murals, check out this article by wttw.

Location: Pilsen, 16th Street and Ashland Avenue

BONUS: Since you are in the area, you should make a stop at the 18th Street El Station (Pink Line) for another extraordinary and different example of street art. The entire train station is decorated with colorful murals painted by local artists from Pilsen. The project was led by art teacher, Francisco Mendoza, who invited his students and anybody else in the neighborhood “who could paint” to participate. The result is an incredible, one-of-a-kind art collage celebrating Mexican culture and heritage.

La Calavera is one of awesome instagrammable walls in Chicago - Passports and Spice

12. Typewriter Words of Wisdom

Have you heard about the LACUNA Lofts? Me neither, until very recently. It is a giant building, which used to be the world’s largest macaroni factory (not kidding!), but it has been recently converted into the coolest office and retail space. It is also a unique venue for private events (apparently lots of hip Chicago weddings have taken place here lately). LACUNA now houses many established and newer artists, as well as small businesses.

The reason I’m listing it here is that there is some awesome wall art to be found on all sides of the building (including another one of the Fast Girls); too much to share everything here, but trust me, worth checking out!

Location: South Side/Pilsen, LACUNA Lofts, 2150 South Canalport Avenue

Typewriter Words of Wisdom is one of awesome instagrammable walls in Chicago - Passports and Spice

Have fun exploring Chicago’s street art and our city! Drop me a line if you find another remarkable example worth sharing. It was hard to stop at twelve and I can see Part 2 of this blog post in the future…

PS: Special thank you to my teenage son who drove around the city with me in search of content for this article and made it extra fun. He also took all the pictures I shared on my Instagram account (@passportsandspice). I love him immensely. Even before he did all this.

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12 Awesome Instagrammable Walls in Chicago

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I love travel, especially to international destinations. I get fired up by unique adventures, memorable experiences, and discovering other cultures. I enjoy sharing it all on my blog, along with my photography and travel tips.

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