Chicago’s Lakefront Trail is Better Than Their Pizza

The first stop of our big East Coast bike vacation was Chicago and the Lakefront Trail. Our main destinations were New York City and Washington DC, but we planned a quick 24-hour pitstop in Chicago. Biking along the shores of beautiful Lake Michigan was a big enough draw to make the short side trip.

The Lakefront Trail offers 18.5 miles of uninterrupted, paved bike path along Lake Michigan on one side and the towering Chicago skyline on the other. Unfortunately when we visited, it was a downpour, but we wouldn’t be deterred since it was our only day in the city. We donned our rain jackets (thank goodness we thought to pack them!) and headed out despite the dubious looks from the bike rental workers. 

We walked our bikes by Millennium Park, toward the water down E Monroe St. Luckily the bike rental shop was only a few blocks from an easy crossing of the four-lane Lake Shore Drive and access to the Lakefront Trail. We started basically right in the middle of the trail and decided to go left on the trail heading North first because our end destination was Wrigley Field. 

The trail mainly parallels Lake Shore Drive and offers water views the majority of the miles. I grew up on a lake, but Lake Michigan was nothing like any lake I’ve ever seen. I couldn’t grasp the sheer size of it as it looked more like an ocean than a lake. Since we were riding in a rainstorm, the ridiculous lake waves made the ride even more memorable. 

Just under two miles in, we arrived at Ohio Beach which was the start of my absolute favorite stretch of the ride. For nearly two miles the concrete of the Lakefront Trail is literally touching the water of Lake Michigan. Remember how I said the lake waves made the ride more memorable? The GIANT waves were big enough they were flowing all the way across the trail to the stairs bordering the path. It was insane and honestly a little scary. 

We had to stop and time parts of our ride as the waves were leaving so we didn’t get washed away or soaked. My husband did make the unfortunate mistake of putting his foot down as a wave crashed it absolutely soaking his shoe and ankle. I’m sure the lake views on the trail are gorgeous on a sunny day, but the added thrill of the waves made this ride unforgettable.

After we cleared the alternating concrete and sand beaches, the trail kept meandering along the shores of the lake and through some nice green parks. I would imagine the trail is pretty populated usually when it’s not being used during a rainstorm. 

After 6 quick miles we left the trail via an underpass on Roscoe St. Wrigley Field is only a 1-mile detour from the trail with some easy street biking. We circled the field until we found the main field sign at the corner of Clark and Addison before heading back to the trail. On the return ride the skyscrapers of downtown Chicago are more prominent. Granted, it was cloudy but we could still see parts of the buildings peeking through.

We followed the same way back and then went an additional 3 miles past our starting location for a total of 18 miles. The headwind made the ride back a bit slower, I definitely understood why Chicago is known as the “Windy City”. We had to cut the ride short to return our bikes within the two hour rental time window, plus we were soaked through at this point and it was getting dark.. 

What better way to warm up after a chilly, wet ride than with some authentic Chicago deep dish pizza? We’ve been dying to try the deep dish and may have been a contributing factor on our decision for the Chicago pitstop. This might be a hot take, but I did not enjoy the pizza. I was not a fan of the giant amount of toppings and having the sauce on top instead of as the base layer was not my favorite. It also takes at least 45 minutes to cook so be prepared for a long restaurant wait. 

We finished the night off by stopping at the famous Cloud Gate sculpture, better known as the “Bean”. It’s a well-known landmark of Chicago and a must see. The park is also home to quite a few other art pieces like the crown fountain. There was a music festival when we visited, but be sure to explore the park further if you have time.