Slow Travel: Come Sail Away on Chicago’s Lake Michigan

[updated July 2019]

Let’s do some sailing on Lake Michigan, the largest freshwater lake in the United States. Read on for more about Chicago sailing plus a video about sailing in Chicago!

 

Chicago is a one of the largest cities in North America.  In this city of almost four million people, there is something for everyone whether you live here or are just here on a visit to tour Chicago: world-class theater, professional sports, cutting edge restaurants, fortune 500 companies, and arts of all kinds.  And then in addition to all that…we are lucky to have this huge body of water right outside our door, virtually creating one big park and beach as the front yard of the city.

Sailing on Lake Michigan

Lake Michigan’s surface area of 22,400 square miles, makes it the world’s largest lake within one country and the fifth largest overall.  When you stand on the beach in Chicago, it is impossible to see across the lake to Indiana or Michigan. Sorry, coastal folks, but we have our own virtual ‘ocean’ without the seaweed or the salty burning-eyes and it’s pretty damn cool. Sailing on Lake Michigan is a very popular thing to do all summer long. Grab some friends (especially ones who own sailboats!) and get out there!

Boating in Chicago

The Chicago Park District’s nine lakefront harbors stretch from Lincoln Park in the northern part of the city to Jackson Park in the south. When you think boating, you probably think Miami or Southern California or even Seattle. But with accommodations for more than 5,000 boats, the Chicago Harbors surprisingly make up the nation’s largest municipal harbor system.  That’s right…Chicago.

Chicago Sailing

I’ve been out on the lake before in various tour boats and even a bit above it in a 4-seater plane, but this summer I got to enjoy the lake from a friend’s sailboat.  My friends Christine and Bill invited us out on the lake for a day of Chicago sailing. I couldn’t say ‘yes’ fast enough.

 

    

“I’m on a boat!”

Video of Chicago Sailing on Lake Michigan

Take a look at this short video of our day:
If you can’t see the embedded video or would like to see it in sparkling HD, please go here – it’s worth it!

 

Chicago Sailing Culture

Riding my bike out to Montrose harbor made me more aware of this whole lake/boating culture here in Chicago that I am SO not a part of.  It’s a whole other world out there.  Just walking onto the dock felt like we were in Margaritaville.  People with Hawaiian shirts milled about.  Reggae music was playing out of at least two stereos.  Folks were wheeling their big plastic coolers in and dockside grills were being cleaned for the day.  There was a whole other ‘feeling’ in the air. It was like we weren’t in a big city anymore. We were in a beachside or island community.  The only thing missing was the clangy sound of steel drums.

These regular boaters are out here every weekend, enjoying the Chicago summer days, some never even taking their boat out, but just hanging out all day in a couple beach chairs on the dock.

A Perfect Day for Sailing in Chicago

The day could not have been more perfect.  We took the boat out. Got a semi-crash lesson in sailing by Bill. Cooled off (it was a very hot day) by jumping in the 77-degree lake (warm for us!) not far out from Foster Avenue beach. Enjoyed a tasty vegan lunch of quinoa salad, hummus, veggies, fruit, chips, homemade guacamole, and some cold beers of course (I am not vegan, but have been eating less meat and love all this stuff).

 

Then we spent the rest of the day sailing around, chatting, and just soaking up the sun (a little too much sun).

Just another perfect summer day in Chicago and another reason to love this city.

 

Rent A Sailboat in Chicago

If you don’t have a friend with a sail boat like I do, you can still go sailing in Chicago! Go for a sail from Belmont Harbor with Windy City Sailing. They have charters for fun, romantic, or even educational experiences for up to ten people. Rates start at $200/hour.