Insider’s Look at the Friendly Neighborhoods Bike Tour

by tour guide Matt K.

When I learn that someone is new to Chicago and has a few days – or even just a few hours to kill – my first question is: what have you got planned? Often the reply comes back: We’re going to the Shedd Aquarium, Art Institute, Navy Pier, shopping on the Mag Mile, Cubs game, etc. All fine activities if you’ve never been to Chicago. Then I ask another question: Do you plan on getting out to the neighborhoods? And just as often I get a puzzled look – the NEIGHBORHOODS?

So many people visit Chicago but never stray far from Loop area. I find myself cluing people in to the fact that the neighborhoods offer just as much as downtown – it’s where we live, work and play! That’s why I’m always excited to show people my home town the best way I know how – on a bike.

Setting out from Navy Pier and riding north along the lakefront bike trail, we visit the Gold Coast.  As we leave the hustle and bustle of downtown behind us, high rises give way to tree-lined streets. Here can be seen some of the most expensive real estate in the city. The neighborhood boasts a number of mansions that date to the end of the 19th century as Potter Palmer developed the area after the Chicago Fire of 1871.

Continuing north we enter the Old Town Triangle. The area originally played host to German immigrants throughout the second half of the 19th century with many buildings looking as though they were plucked from small German villages. It is here that one can view one of the few surviving structures of the Chicago Fire – St. Michael’s Church.


Next stop is Italian ice at Annette’s in Lincoln Park.  Around the corner from De Paul University, this little gem has perhaps the best Italian ice in the city. Sporting flavors like blood orange and lychee, there’s something for everyone!

Perhaps my personal favorite portion of the tour occurs after our stop at Annette’s as we ride through Lincoln Park. Taking a meandering course, we make our way through the quiet, tree-lined streets enjoying a slower pace perfect for appreciating beautiful homes, old and new, and the many parks before circling back to Wells street.



As we head back downtown, riders are given unrivaled views of the city that’s made Chicago a Mecca for Architecture aficionados for the past century. As the city looms overhead, it’s hard to imagine that the city was founded in 1833 with only 200 residents.

Finally, we cruise along the River Walk almost at water-level passing some of the most iconic structures in Chicago like the Trump Tower and the Wrigley Building before returning to Navy Pier.

Whether you’re a life-long Chicagoan or a new arrival to the 2nd City, our neighborhood tour will give you a new appreciation of this amazing town and its neighborhoods. See you soon!