Chicago, Illinois Fishing Charters - 2025

Fishing Charter Reviews in Chicago

1. 

   Sharon

   Private Tours on 27' Baja Boss Speedboat in Chicago with Captain Bob

   Captain Bob was friendly, professional, and made sure my husband and I had the best time. We enjoyed seeing the spectacular Chicago Skyline and Navy Pier Fireworks from a prime spot on the lake. Captain Bob’s experience also made us feel at ease, especially being on the lake at night. Highly recommend Captain Bob!

2. DH

   Danielle

   SeaRay 320 Sundancer Yacht - 31st Street Harbor Beach Playpen Chicago

   From start to finish, I had a 5 star experience. Kat made booking easy, was extremely accommodating, and responsive! The vessel was clean, and just as photoed. Captain Derek was personable, professional and a good time. If you find yourself in Chicago, book with “Owner”, they rock!

3. KK

   Katherine

   SeaRay 320 Sundancer Yacht - 31st Street Harbor Beach Playpen Chicago

   Every box checked from fun to safety. Great communication from booking to docking back on the deck. So excited to be able to keep you in mind for all boat adventures. Great super clean boat (even the bathroom), expert and experienced captain, the best sound system, and plenty of space for twelve of us to not be on top of each other.

4. KF

   Khari

   Luxurious 47' Sea Ray Sun Yacht - Explore Lake Michigan the Ultimate Experience

   We had an amazing time out on the water thanks to boat owner Breanna and Captain Mike! From the moment we arrived, everything was handled professionally and with such a warm, welcoming attitude. Breanna made the booking process smooth and stress-free, and Captain Mike was outstanding—friendly, knowledgeable, and clearly experienced. What stood out the most was how safe we felt the entire time. Captain Mike explained all the safety protocols before we left the dock, and throughout the trip, he stayed attentive and in control. It allowed us to fully relax and enjoy the experience, knowing we were in great hands. The boat was clean, comfortable, and well-equipped. Whether you’re looking to cruise, swim, or just soak up the sun, this is the trip to book. We highly recommend Breanna and Captain Mike to anyone looking for a safe and unforgettable boating experience. We’ll definitely be back!

5. 

   Husein

   20' Lund Bass Boat for 3 in Chicago, Illinois

   I honestly didn’t expect to walk away from this trip with a whole new hobby, but here I am—hooked for life. Guy has this way of making the entire experience feel effortless and exciting, whether you’re a total beginner or someone who’s been at it for years. From teaching the basics with real patience to creating an atmosphere that’s both laid-back and full of energy, he made it easy to fall in love with fishing. The way he explained the gear, read the water, and shared his stories made every moment out there on the water feel like something special. You can tell he truly loves what he does, and that kind of passion is contagious. I went in thinking this was just a one-time adventure, but now I’m already planning my next trip—and buying my own gear. Can’t thank Guy enough for turning what was supposed to be a relaxing weekend into the start of a lifelong obsession. If you’ve ever been on the fence about trying fishing, let Guy be the reason you dive in—you won’t regret it.

6. AS

   Alexa

   Private Tours on 27' Baja Boss Speedboat in Chicago with Captain Bob

   Had an amazing day on the water during the Air and Boat Show with Captain Bob as our guide. He's helpful in giving instructions to the dock, helps set up music and ensures a comfortable and safe experience. Due to his background in the CFD, he knew exactly where to anchor the boat so we could see great views of the air show. It was a worthwhile and memorable experience to share with friends and family!