Exploring Chicago by Bike

When arriving in Chicago, I met up with a great friend of mine, Sydney. She got us a place to stay in Wicker Park, a safe neighborhood with a lot of Puerto Rican influence. We slept in an old complex building with blue doors, corroded brick walls, and years of rust. It reminded me a lot of “Hey Arnold”, a Nickelodeon show I watched growing up. I pictured animals running out the door every day we opened it to explore the city.


It appeared to become a reoccurring ritual of ours to get coffee in the morning. A coffee shop called Dark Matter in particular. The place, besides having a clever name, is small but not to be underestimated.  Pretty sure I had the best cortado of my life several times there. I’m not sure how the coffee is made differently, but I guess that’s part of the magic.

We took the metro to Navy Pier, where we heard of a spot Sydney could rent a bicycle. The place is called Bobby’s Bike Hike. After she got a bike to use at an affordable cost, we went over to my friend’s brother’s house to pick up mine that I had shipped through Bike Flight. Kenny was super cool and kept my bike for a few days until I got there. Sydney and I assembled it in front of his apartment building in Northern Chicago near Wrigley Field. Then, we rode down the bike path from Foster Beach along Lake Michigan towards downtown. This is a must if you are cycling in Chicago. The bike path is safe, well built, and the view is gorgeous. Oh yeah, we also got a Chicago dog at Budacki’s before riding down the path and those were DELICIOUS.




Chicago streets can be a bit intimidating. We rode on Milwaukee Avenue to downtown on a Sunday and that was pure anxiety. It seems as though everyone in the city is bustling around that area whether its shopping, eating, socializing, or all of the above. Super hip area for sure, but for biking, I would avoid it. Especially on the weekend and especially especially because of the six way intersection at North and Milwaukee.

I’d also like to mention that the time of year we visited directly influenced our experience in Chicago. Spring is gorgeous in many states. Yet, Chicago has it’s very own. Tulips sprouted from the parks, the flower beds of apartment complexes, and even from the cracks in the pavement. The flowers are everywhere and in various colors that you wouldn’t know existed.



20180502_181357964_iOSYou can also tell that the tulips directly affect the locals. I haven’t experienced a winter in comparison to a winter in Chicago, but I can imagine that I would be in a better mood with sunshine and flowers springing about myself. People were friendly, humming, barbecuing and celebrating the Spring season. This house in our neighborhood even had a seasonal tree in their front yard.

I could also definitely tell what time of year it was when I visited the bike shop. Ciclo Urbano is right down the street of where our Airbnb was. There were tons of folks gathered getting their bicycles tuned up for cycling weather. It reminded me of Yellow Bike Project in Austin. Many cyclists that knew each other, lots of old bike parts, and character splattered all over the walls depicting the neighborhoods’ eclectic culture. They fixed my brakes before I began my bike tour and even gave me some tips on routes I should take heading up north to Milwaukee. Great service and super friendly bunch.


Of course, when visiting Chicago, you gotta visit the big ol’ bean in Millennium Park. You can’t cycle around the park unfortunately, but it’s not terrible to walk your bike through either. There is a great amphitheater, tulips bordering tulips, and the bean reflects the city back at you like a fun house mirror. It’s pretty neat.