Biking through a Chicago summer evening

  • Biking through Chicago

One of the absolute highlights on any Trek that goes through Chicago in the summer is without a doubt, Bobby's Bike Hike! Some of our tours have it included but if yours doesn't, you should still totally book one yourself. There's nothing more epic than biking through the heart of a great city in the early evening hours on a warm summer night. You get to see the city come alive!

I always like to start the first night in Chicago off with a dinner of the famous deep-dish pizza. This stuff is more like a pie than a pizza. Seriously. It's around 3 inches thick and stuffed with layers upon layers of gooey cheese, red sauce and whatever toppings you want. It's great. Once you're stuffed with pizza, what better thing to do than go for a bike ride, right?

Biking through Chicago

Biking through Chicago

Bobby's offers tours all day but our favorite time to do them is in the evening. The ride takes in glorious sweeping views of the Chicago skyline from the beautiful lakefront trail. Now this is a biking city, which means you won't be the only ones out and about on the bikes. This is a good thing because it means the city is bike friendly and cars are more aware and considerate of bikers than they are in other big cities. The guide will still have several safety cues and signals that you'll use while in the streets, but you'll have a blast ringing the bells and "whoop-whoop"-ing across the city.

As the tour goes on, the sun disappears and the lights of Chicago come on. The ride ends several miles and hours later with more views of the area. If you don't end the tour sporting a huge smile, then something's wrong. This is the best bike tour I have ever been able to do!

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