Chicago: Street Art & Graffiti Walking Tour on the 606

Summary

Chicago’s murals and graffiti come alive on foot with locals

You’ll walk Chicago’s 606 trail with a local guide who knows the city’s street art inside out—expect hidden murals, real stories from artists, and even a surprise coffee stop. The tour ends in Logan Square over food and drinks if you want them. You’ll leave seeing Chicago differently—and maybe noticing colors everywhere after.

What’s the experience like?

I was late because I got lost in the deli section—honestly, who puts stairs behind a counter stacked with pastrami? Our guide just grinned when I finally made it upstairs, like this happened all the time. There were only six of us, mostly locals except for me and some guy from Toronto who kept saying “sick” every time he saw a mural. The room smelled faintly of coffee and old wood. It felt like we were about to join a secret club instead of a street art tour in Chicago.

We headed out onto the 606 trail, which is way more than just an old rail line—there’s this low hum from bikes zipping past and the distant thump of music from someone’s open window. Our guide, Marcus, grew up nearby and seemed to know every tagger by name (or at least their Instagram handles). He pointed out one mural that looked almost alive in the morning light—layers of spray paint so thick you could see where someone had changed their mind mid-stroke. I tried to get a photo but my phone caught more glare than color. Oh well.

Halfway through, we ducked into Ipsento for coffee (and bathrooms—thank god). The barista handed me something called a “honey latte,” which sounded weird but tasted like summer if summer was made of caffeine. Marcus told us to keep our eyes open for “the surprise.” Turned out to be a quick chat with one of the artists whose work we’d just seen outside—she laughed when I asked how long it took her to finish that wall (“longer than you’d think, shorter than my landlord wanted”).

The last stretch up Milwaukee Ave was full of quick detours—one minute we’re weaving past bus stops, next we’re squeezing between dumpsters to see a piece hidden behind a bakery. My shoes got dusty; didn’t care. We ended at Logan 11 where everyone just sort of flopped down with beers and fries. No big speeches or anything, just people talking about what they saw or missed or might come back for. I still think about that blue-and-orange mural near the train tracks—it’s probably faded already, but it stuck with me anyway.

Step-by-step itinerary

Day 1 — Explore Chicago's street art and murals

• Meet in upstairs dining room
• Walk down the 606 urban corridor
• Stop at Ipsento for restroom and refreshment
• Walk up Milwaukee and side streets to view art
• End at Logan 11 for drinks and food

Top questions

How long is the Chicago street art walking tour?

The tour covers about 2 miles over roughly 2 hours.

Where does the Offbeat Street Art Tour start?

The meeting point is in the upstairs dining room above the deli counter at the store.

Is there a bathroom break during the tour?

Yes, there’s a stop at Ipsento where you can use restrooms or grab coffee.

Does this Chicago street art tour include food or drinks?

No meals are included, but you can buy refreshments at Ipsento or Logan 11 at your own expense.

Is this walking tour suitable for all fitness levels?

The route is suitable for most people able to walk 2 miles comfortably within 2 hours.

Are service animals allowed on this street art tour?

Yes, service animals are permitted on this tour.

Does the tour end at the same place it starts?

No, it finishes at Logan 11 (2230 N California Ave) in Logan Square.

What’s included

Your day includes guidance from a local expert who leads you along Chicago’s 606 trail and through side streets packed with urban art; there’s time for restroom breaks and coffee at Ipsento along the way before finishing up in Logan Square where you can relax with food or drinks if you’d like before heading off again.