Chicago is better by boat

One of the best ways to experience Lake Michigan is to actually be on the water. Even if your family doesn’t own a boat, it’s possible to rent charter boats for large groups (up to 18 people) or small intimate family outings.

Last summer, my family spent a sunny morning on a 32-foot Cobalt 323 that included swimming and tubing on the lake. Capt. Al Skalecke, owner of Captain Al’s Charters, says it is possible to do a number of trips with children, including fishing trips.

“Once the kids see dad (catch a fish), they want to get one,” says Skalecke. Other trip ideas can include fireworks, sightseeing, swimming and tubing. Capt. Al offers packages that include a dockside bed and breakfast that can handle up to four people.

I prepared a bag for our day trip that included towels and sunblock, plus sunglasses to protect our eyes from the glare of the water.

Our captain, Bob, drove us out around the lighthouse that is visible from Lake Shore Drive near the DuSable Harbor at 111 N. Lake Shore Drive. After a short run going north around Navy Pier, our captain headed directly for the best tubing spot.

Capt. Bob has been on many different bodies of water around the country but he says that Lake Michigan is his favorite because you can be on the water right away. Other ports have watercrafts go through a shipping lane that might take 20-30 minutes before hitting open water, he says.

To find a local boat charter service start here. Take the time to ask questions about different packages and services that are offered as well as which harbor the charter uses, suggests Dana Fennewald, public relations manager at the National Marine Manufacturers Association. Harbors are located from Waukegan all the way down to Hammond, Ind. If your family includes smaller children, make sure to explain that so the captain can be aware before you arrive at the dock.

Finally, your captain will let you know if weather will be an issue on the day of your trip.

“Some storms you can see coming 10 hours away to a specific area, other times you may not know what weather is going to do even an hour before it hits,” says Fennewald. “If (bad) weather is a possibility, the captain should periodically check in on the weather and keep you updated.”

A simple rain may not deter a fishing trip but electrical storms and high winds that cause high waves will.

“I do not want people to have a bad experience,” says Capt. Al. “I want them to come back after having a (wonderful and) memorable day.”

- Advertisement -

LATEST STORIES

New Illinois laws impacting families in 2026

New Illinois laws in 2025 include school safety updates, vaping restrictions, trauma training and required relaxation activities for students.

5 foods to eat when you have the flu, and 3 foods to avoid

When the flu hits, your body needs more than just rest. Proper nutrition plays a crucial role in helping your immune system fight off...

A parent’s guide to Chicago Bears game day with kids

At 5:30 p.m. CST Sunday, Jan. 18, 2026, the Chicago Bears take the field at Soldier Field, and for many families, game day is...

These glow-in-the-dark indoor mini golf spots are perfect for Chicagoland families

These indoor mini spots in Chicago and the suburbs make the game so much more fun with glow-in-the-dark experiences, fun themes and more.
- Advertisement -


- Advertisement -