Chicago Cruises: Book Tickets Now

The Chicago River is lined with some of the most photographed buildings in the world, and a guided cruise is the easiest way to take them all in at once. You'll pass under dozens of bridges, float past the Wrigley Building, the Merchandise Mart and Marina City, and have a knowledgeable guide explain the stories behind what you're seeing.

Most architecture cruises run from around March through November, with multiple departures each day during the summer months.

Heading out onto Lake Michigan puts you far enough from shore to see the entire downtown skyline in one frame. On a clear day that view is hard to beat, whether you're on a speedboat doing 40 miles an hour or a slower vessel with a drink in hand.

Brunch and lunch cruises on the lake are a popular option for groups and families who want a relaxed couple of hours on the water without rushing back to the dock.

Navy Pier runs fireworks every Wednesday and Saturday evening from late May through late August, and watching them from a boat on the lake is something else entirely. You get an unobstructed view of the explosions over the water, with the lit-up skyline behind them.

These cruises tend to sell out well in advance, so it's worth booking as soon as you know your dates.

Chicago at night from the river or the lake is a different city. The skyscrapers light up, the bridges reflect off the water, and the crowds that fill the Riverwalk during the day have thinned out.

Night sightseeing cruises cover much of the same ground as daytime tours but with a completely different mood, and they're a good option if your days are already packed with other plans.