Experience the best Shoreline Cruises in Chicago

Our tour guide was very knowledgeable and entertaining. It was just the right amount of time. Everyone was helpful and friendly. Thank you!

We loved our cruise. Richard was our docent and was wonderful. He was funny and engaging and very knowledgeable. Highly recommend.

Liam did an amazing job and truly did a great job of providing the details of the buildings and keeping us thoroughly entertained! Memories for a lifetime!

Taking my mother from India on the Chicago Architecture Cruise was one of the sweetest memories we made during her visit. We booked the cruise through an amazing Headout offer, and we’re so grateful for the opportunity. A special thank you to Headout for making this experience so accessible and worthwhile, and to Shoreline Sightseeing for such a wonderful cruise. Our tour guide, Eric, was absolutely fantastic! He explained Chicago’s architecture and history with so much passion and made everyone feel comfortable, welcomed, and engaged. His storytelling made the buildings come alive, and seeing my mother amazed by the beautiful Chicago skyline made the experience even more emotional and special. This was more than just a tour—it became a beautiful memory I’ll always cherish with my mom. Thank you, Headout, Shoreline, and Eric!

The 45-minute Lake Michigan sunset cruise was amazing!! The views of the Chicago skyline at sunset were beautiful, and the whole cruise was very relaxing and enjoyable. Shoreline organized everything really well, and the staff were friendly and welcoming. Definitely a great way to experience Chicago from the water!