Ride 21: Illinois
The Prairie State
State: Illinois (#21)
Area: Chicago
Route: North Branch Trail, Skokie, Evanston, North Shore Channel Trail, Lakefront, riverwalk/downtown loop, Wicker Park
Final Mileage: 51.27
Final Elevation: 1,184 ft.
Date: May 24, 2026
After our brief visit to the Quad Cities, our crew took off for Chicago, where the real party began. Whereas the first leg of the trip only included Alex, Bing, and Michael, we had a coterie of friends and family awaiting us in the Windy City.
Upon learning that we were bringing the project back to the upper Midwest, Michael’s longtime friends, Nathan and Raffie (whom some of you might remember from our Minnesota ride), decided to come down from the Twin Cities for the long weekend. Alex’s wife, Mary Kate, also came up from Springfield. And some in-town friends joined as well: Chris and Caroline (and baby Gustav). Over the course of our time here, different combinations of this group convened to explore some of Chicago’s best sights together.
We decided to dive right into things on the first night with a group dinner at a Polish restaurant near our Airbnb called Staropolska, which may well have been the best meal of the trip.
Saturday was a full day of exploration around Chicago, beginning with a tour of the iconic Wrigley Field, home to the Cubs.
After a tasty lunch at Tac Quick and an afternoon of errands, we headed into town to catch a show as the storied Second City, which has launched the careers of many an SNL cast member. Afterwards, another fantastic meal, this time at the highly regarded nearby establishment, Topo Gigio.
The following morning, we woke early to hit the road, only to be greeted by the sound of a thunderstorm. Thankfully, things had slowed to a drizzle by around 9:30, and we set out to the starting point for our ride: a nondescript, suburban Target parking lot. And this time, we added Nathan as the fourth member of our crew!
Our route began in the northern suburbs on the North Branch Trail, which took us through some beautiful green spaces.
We eventually hopped off the trail and headed east through Skokie (home of a historic, fascinating Supreme Court case) all the way to Evanston and Northwestern University. The beautiful campus grounds sat right next to Lake Michigan, giving us our first glimpse of the main attraction of the day. It was right around this time that the clouds disappeared, the sun emerged, and a nice breeze drifted off the lake to cool us.
This was also where we bid adieu to Bing, who had to leave for a wedding. Alex, Nathan, and Michael looped around Evanston and headed back west toward the North Shore Channel Trail, which would bring us much closer to the heart of the city. Before long, we were at the entrance to the Lakefront Trail, which runs 18 miles along Lake Michigan on both the north and south side of the city and offered some of the most spectacular views of the entire trip.
We also ran into a cheer squad a little ways down the trail!
We finally came upon the Chicago Riverwalk, where we stopped for a quick lunch and some good people-watching.
From there, we headed south to complete the segment of our route inside The Loop, which took us past more beautiful views all the way down to Soldier Field, home of the Chicago Bears (and which Nathan, a diehard Packers fan, made sure to remind us is also owned by Green Bay).1
Finally, we snaked our way out of downtown and headed back north, cutting through neighborhoods like Wicker Park and riding across the peaceful Bloomingdale Trail. Alex smartly altered the route so that we ended our ride at the Airbnb rather than our starting point, giving us time to get cleaned up before a few of us headed back out for one last activity: a boat ride on the city’s river.
To cap off the evening, the riverboat gang grabbed a bite at a the legendary Billy Goat Tavern, a divey burger joint on a dingy street under Michigan Avenue with cheap eats and a fascinating history.
Between the weather, friends, food, and activities, we agreed by the end of the trip that Chicago ranked highly on our list of rides to date—perhaps even in the top five.2 It was certainly an unforgettable one, and a great way to bank ride #21.
Side note: the Bears should stay at Soldier Field. It is a beautiful venue and a way better location than northwest Indiana.
With 21 rides now under our belt, we mean this as high praise!