If you’ve been following our journey since the beginning, you know how monumental each big city is that we cruise into. However, nothing compares to the sheer excitement we felt crossing Lake Michigan one final time on our Loop to pull into Chicago.

Growing up along the Mississippi River in eastern Iowa, Chicago was “our big city,” being only two and a half hours from home. I have many memories of day trips and weekends driving to Chicago for Broadway shows, shopping and Cubs games, so arriving by boat was an experience I’d never had. What’s unique about cruising into Chicago is that the skyline comes into view roughly 20 miles before you even get to land, so for us at our speed, we were able to admire the beautiful horizon for hours. 

We could not have asked for a better weather window on our last day in Lake Michigan. All I can say is that Mother Nature was extremely kind to us as we made our way through the lake, with nary a scratch on us or the boat after seven jumps in the world’s largest lake located entirely within a single country.

As we made our way to land, we could not have been more eager to pull into the brand-new Navy Pier Marina, Chicago’s only all-transient marina. Docking at the iconic Navy Pier, a place I grew up visiting, could not have been more nostalgic. Upon pulling up, you’re greeted with the classic Navy Pier Ferris wheel and smiling dockhands ready to assist. One thing we immediately noticed was the movable cleats, placed on a track so the dockhands could adjust to your boat’s specific needs. 

Being in the heart of the city allowed us access to anything and everything we wanted to explore while in town. With hundreds of restaurants and shopping options, groceries, public transportation, and green space for Ripley within walking distance, we could not be in a more perfect place for our time in Chicago. What’s even more spectacular is looking back at the skyline right outside our boat. A scene I’ll remember for the rest of my life. 

What makes Chicago most special is the distance to our family and friends. Each night has been packed with familiar faces we haven’t seen in months, filling our hearts with joy and the motivation to continue on this incredible journey. A couple of places we’ve already enjoyed include: 

• The Dearborn, an urban American tavern in the heart of Chicago’s Loop
• Sushi-San, a sushi joint with a menu from Master Sushi Chef Kaze Chan
• The Gatsby Speakeasy, a prohibition era-inspired speakeasy above Bourgeois Pig Cafe in Lincoln Park
• Old Town Ale House, self-proclaimed as “The Best Dive Bar in Chicago”
• Timothy O’Toole’s, Chicago’s favorite sports bar since 1992
• London House Rooftop, offering unbeatable views of Chicago’s skyline

Clearly, we’ve been around town and we still have a few days left. Still on the list is a visit to the farmers market, checking out a Cubs game at Wrigley Field, and finally, cruising down the Chicago River on our very own Northern Attitude. We can’t recommend Navy Pier Marina enough for its central location, five-star accommodations and commitment to Loopers. We’ve felt nothing but welcome, taken care of and safe.

Cheers to continuing on this grand adventure.