Chicago Jazz CruisesLive jazz on the water.
Cruise Guides

Sunset vs. Night Cruises: Which Sailing Is Right for You?

Two departures, two very different evenings. A quick guide to choosing between golden hour and the city after dark.

The Chicago skyline from the river at dusk

We run two departures most evenings in season, and the question we are asked most often is which one to pick. Both have the same band and the same route. The difference is the light.

The sunset sailing

Leaving about ninety minutes before sunset, this cruise moves through the river while the buildings are still lit from the west, then reaches the lake just as the sun drops behind the skyline. It is the photographer’s cruise and the one we recommend for first visits and anniversaries. The music is gentler and the mood is unhurried.

The night sailing

The later departure boards after dark. The river becomes a corridor of reflected light, the lake goes black and the whole skyline glows. The band plays harder and the bar is busier. This is the cruise for groups, birthdays and anyone who wants the evening to feel like a club night that happens to have a view.

Our honest advice

If you can only do one, take the sunset sailing in May, June and September, and the night sailing in July and August when the days are long and the city stays warm late. And if you cannot decide, the crew will tell you that the second cruise is cheaper and the first is prettier, which is usually enough to settle it.

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