Discover the best things to do in Chicago

My experience on the Chicago River Cruise was nothing short of AMAZING!! I learned a lot from the presenter, he was very knowledgeable about the information he provided and spoke very fluently. The people on board were very friendly, the workers were very professional and polite. It was very clean, the ride was very smooth. I rate this experience two thumbs up and 100 stars.

My 45‑minute Wendella architecture cruise turned out to be one of the best things I did in Chicago. From the moment the boat pulled away from the dock, I felt like I was seeing the city from a completely new angle. The river-level views made familiar buildings look monumental, and the guide’s storytelling brought the skyline to life with history, humor, and details I’d never noticed before. Even though the tour was short, the pace felt perfect—fast enough to stay engaging but never rushed. By the time we returned, I had a deeper appreciation for Chicago’s architecture and a camera full of riverfront shots. I genuinely would recommend this very affordable tour to anyone visiting the city or even locals who want to see Chicago from a fresh perspective.

This experience was amazing it was our first time using it and it is the best option to check out the city of chicago with out the hustle of the traffic my family and I enjoyed every second of it and is easy-to-use once you download the app you can see where the next bus is so you dont wait long time on the bus stop we are most definitely going back.

Our evening on the Odyssey Chicago River Architecture Dinner Cruise was unforgettable. The views of Chicago’s iconic skyline and historic buildings were breathtaking, and the narration made the city’s architecture come alive. The staff was genuinely warm and attentive, the meal was delicious, and the atmosphere on board felt both elegant and relaxed. Watching the city lights reflect on the river while enjoying dinner with friends was a perfect experience. I would gladly recommend this cruise to anyone looking for a memorable way to experience Chicago.

The guide was amazing! He was very funny while being so informative and never crass. The sunset tour was beautiful and I thought it was very smart to offer sweatshirts in the lovely cabin. The bar staff was slammed but still so nice! Would definitely recommend to Chicago natives and out of towners!

I really enjoyed this tour. I can't speak on the day time cruise but the night cruise was EVERYTHING. Seeing the darkness fall over the water and the beautiful lighting on the buildings is the only way I wanna see it.

I had a great experience booking with Headout. The tickets were delivered instantly, the entry process at Six Flags Great America was fast, and everything worked exactly as expected. The park had incredible rides, friendly staff, and a fun atmosphere. Overall, it was a smooth experience from booking to the end of the day, and I would definitely book through Headout again.

Fantastic introduction to the architecturally marvelous city of Chicago. Our volunteer guide was friendly and knowledgeable. Highly recommended this tour for anyone visiting Chicago for the first time.