Photographing Chicago from the river

Get a seat on the open upper deck

Cabin windows add glare and the odd smear, so the open upper deck is where good river photos come from. On Wendella's boats the deck seats go first come, first served. Arrive about 30 minutes early and get through the bag search, so you are near the front when boarding opens about 15 minutes before departure. First Lady's Architecture Center cruise from ~$57 guarantees seating on its open-air upper decks, which takes the race out of boarding. Chicago Line's boats on the architecture tour with drinks from ~$42 are open-air throughout, with some covered areas.

A rail seat at the side gives a clean frame without heads in it, but only toward one bank. A seat in the middle of the deck lets you turn to both sides, at the cost of shooting over other passengers. The back of the deck shows the view behind the boat, handy after a bridge, though one Wendella reviewer found the guide hard to hear on the upper deck near the exhaust.

Which side of the boat

Every cruise on our list heads out and comes back over much of the same water, so both sides get their turn with the big buildings. Leaving the Michigan Avenue bridge westbound along the main branch, the north bank is on your right, with the Wrigley Building and Trump Tower, then Marina City and the Merchandise Mart. The south bank is lined by the Riverwalk, and at the bend near Wolf Point stands 333 Wacker Drive. On the South Branch, the Willis Tower and the Civic Opera House stand on the east bank, to your left heading south.

The guide usually calls out which side to look a few seconds before a building appears. Use those seconds to raise the phone and frame the shot, instead of starting once the building is already beside you. If you can only claim one side, the right side on the way out holds most of the main branch's famous facades. What you see from the river goes through the route branch by branch.

Glass canyons and bridges

Downtown towers rise straight from the banks, so the river runs through a canyon with bright sky above and shaded water below. Phones struggle with that range. Leave HDR on and tap the building you want, then drag the brightness down a little so the sky keeps its color. The ultrawide lens (0.5x on most phones) fits a tower from base to top when the boat is close, and the Willis Tower at 1,451 ft (442 m) needs it on the South Branch. Turn on the grid to keep the water line level, and accept that verticals will lean when you tilt up.

With 37–38 movable bridges on the river, Chicago has more than any other city in North America, and the CAC docent cruise passes under 13 bascule bridges on its route. Each one makes a frame. Shoot a bridge as you approach, with the towers beyond seen through the gap beneath it, then turn around after you pass under for the steel underside against the sky. Burst mode helps here, since a boat slides under a bridge faster than you expect.

Reflections on glass and water

The river's best reflection belongs to 333 Wacker Drive, whose curved green glass follows the bend of the river at Wolf Point. From the water the facade holds a picture of the river and the towers across it, and a slow pan as the boat rounds the bend shows the image sliding across the glass. Toward the lake, Aqua's balconies ripple across its facade, reaching out up to 12 ft (3.7 m), and a little zoom turns them into an abstract pattern. Use the phone's optical zoom lens if it has one, because digital zoom softens detail fast.

At dusk and after dark the water itself becomes a mirror for lit facades. Wakes from other boats break the reflection into streaks, so wait a few seconds after a passing boat before you shoot. A slight downward angle that takes in both the building and its reflection usually beats a shot of the tower alone.

Marina City and the Merchandise Mart

Bertrand Goldberg's Marina City gives the river one of its most photographed views. The two round towers rise 587 ft (179 m), with car parking on spiral ramps over the lower 19 floors and a marina at the water's edge. From a boat you look straight up past the moored boats to the cars on their curving ramps, an angle the street cannot give. Shoot vertical and start as the boat approaches, since alongside you can only fit one tower at a time.

The Merchandise Mart poses the opposite problem. When it opened in 1930 it was the largest building in the world, and from the river its Art Deco front runs so long that no lens takes it in from close up. Catch it from a distance as the boat comes up the main branch, or sweep a horizontal panorama with the phone held steady. After dark the Art on theMART projections light up its river facade, and an evening cruise that passes during a show makes a good short video.

Golden hour and night shots

Morning and late afternoon light warms the stone and turns glass towers gold, while midday sun leaves the floor of the canyon in hard shadow. A departure in the last hours before sunset is the one to aim for, so check the times for your date. On sunny days bring sunglasses and a sun hat, as First Lady advises, since an open deck offers little shade. The best time to go sets out how the light and the crowds change through the year.

Night is a different subject. The lit towers and their reflections make a strong picture, but a moving boat defeats long exposures, and phone night mode smears lights when it holds the shutter for seconds. Brace your elbows on the rail and keep the night-mode time short, accepting some grain. Video copes with motion better than stills. One reviewer of the 45-minute Wendella cruise called the city lit up at night beautiful, and a Shoreline guest found an 8:30 pm tour an excellent way to see the buildings after dark. Night cruises covers the evening departures, and the lake and river guide has the skyline from Lake Michigan at dusk.

Gear and deck manners

• A wrist strap. Phones dropped over the rail do not come back
• A lens cloth. Spray and light rain spot the lens
• A charged battery. Ninety minutes of video drains a phone
• No drone. Drones are not allowed on First Lady cruises
• No tripod. A crowded deck has no room for one, and the boat moves anyway

Stand to shoot when a building calls for it, then sit back down so the people behind you get their turn. Shoreline's architecture cruise from ~$39 includes a boarding photo, which is often the only picture of the whole group, since whoever holds the phone misses out on all the others. For a child with a phone of their own, our family guide suggests which cruise to pick, and the accessibility guide covers seats you can reach without stairs.