The Best Chicago Night Tours Compared: River, Lake, Streets or Air

The Chicago Night guided tours sold here split three ways: where you see the city from, who talks, and whether it is dark when you do. Most are cruises from two docks at the Michigan Avenue Bridge. One is a bus, one is a short flight, and one is a daytime museum ticket. This guide sets them side by side so you can choose in a few minutes.

Which Chicago night tour is best for a first visit?

For most first evenings, First Lady's By Night cruise. You get 90 minutes, a live guide, the river between the towers and then the lake, for $50 a person. It scores 4.7 from 1,240 reviews, and it sails after dark.

The same cruise is sold under a second title, Chicago By Night River and Lake Cruise, at the same fare. Book whichever has the date you want.

Here is every option in one place.

Fares are per person. Drinks on the boats and tips are extra everywhere.

River only or out on the lake?

This is the biggest difference between the cruises. The By Night cruise and the sunset cruise pass through the Chicago Harbor Lock onto Lake Michigan. From the lake you see the skyline as one long line of lit towers, which you cannot see from the river.

The 45-minute tour and the Creepy Cruise stay on the river. You sail between the towers rather than looking back at them, and you never wait at the lock. On a busy evening a lake cruise can wait its turn there, which eats into your time on the water. Our short read on the lock explains what happens inside it.

Sunset cruise or a cruise after dark?

Wendella's sunset cruise is timed so that you are on the lake as the sun goes down and the lights come on. You see the change happen. It has light narration from the crew, and it is not a guided tour.

The By Night cruise sails later, in the dark, with a live guide the whole way. Pick the sunset if the light is the point. Pick the night cruise if you want the city fully lit and the stories behind it.

With two evenings, you can do both. Take the sunset cruise on the first, for the view, and the By Night cruise on the second, when you want the stories. They leave from docks on opposite banks, so check which one your booking names.

Sunset moves a long way through the year: 8:27pm on 15 June, 7:00pm on 15 September and 4:20pm on 15 December. Check the dark times by month before you pick a sailing.

Is 45 minutes enough?

For a first look at the river, yes. Wendella's 45-minute tour costs $28, has a live guide, and passes the Merchandise Mart and Marina City. It is the best seller here, with 3,624 reviews.

It is not a night tour, though. It runs through the day, and only its last departures reach dusk and the lit towers. If the dark matters to you, book the last one of the day, or book a 90-minute cruise instead. It is also the cheapest seat on the river, which makes it an easy extra on another day.

Live guide or light narration: does it matter?

It matters if you want to know what you are looking at. On the By Night cruise and the 45-minute tour, a guide names the buildings, the bridges and the people who built them. On the Creepy Cruise a storyteller tells the city's dark history.

On the sunset cruise the crew gives light narration, and the time on the lake is for the view. That suits a couple who want to talk to each other rather than listen. It suits less well if this is your only cruise and you want the city explained.

Is the Creepy Cruise worth it?

If you have seen the skyline already, it is a different evening on the same river. A live storyteller covers the Eastland disaster, the Great Chicago Fire and H. H. Holmes. It sails on Fridays, Saturdays and select Thursdays and Sundays, and it stays on the river.

It is sold under two titles, rated 4.1 and 4.3, the lowest scores here. It mixes disaster and fire with crime, so gangster fans may prefer the bus. Our gangster and ghost tours set it against the crime bus.

Is the Night Crimes bus worth it?

For anyone who came for the Prohibition gangsters, yes. The Night Crimes bus scores 4.8, the highest here. It leaves 163 E. Pearson St at 7:30pm, runs two to two and a half hours, and lets you off at five stops, the Biograph Theater among them.

Two things to know. It is recommended for ages 10 and up, with steps into the bus and no lift. And a 7:30pm start is daylight in June, so its first hour is not a night tour until about September.

Is a seven-minute helicopter flight worth it?

It is the one view no boat or deck can give you: the whole grid of the city from above. The 10-mile flight costs $129.99 a seat and lasts about seven minutes, counting take-off and landing. It leaves from Vertiport Chicago, at 1339 S. Wood St, about two miles south-west of the Loop.

Fly Heli sells sunset and evening slots, and they fill fast. The listing prints no flight times, so pick your slot when you book. For the price of the flight, two people could take the By Night cruise with money to spare.

Which night tour suits children?

The cruises suit most ages. Under-4s ride free on both lines, strollers are allowed, and every boat has a restroom. The 45-minute tour is the easiest length for small children.

The crime bus is recommended for ages 10 and up, and it has no restroom break. The storytelling cruise has no age limit given, but its subject is disaster and murder, so judge it by your own children.

Which one on a cold or wet night?

The boats sail rain or shine. Each has an enclosed lounge below the open deck, and severe weather cancels a sailing with a new date or a refund. On the lake the wind picks up, so bring a jacket even in summer; our guide to what to wear goes month by month.

The bus is the warm option. You are indoors between stops, and each stop lasts 5 to 15 minutes.

Who should skip a night tour?

If you only want to see the lights, you may not need one. The Chicago Riverwalk is free and open until 11pm, and both cruise docks are on it. Walk it after dark, and add a deck or the projections on the Mart.

Skip a tour, too, if you are in town in June and want real darkness on an early evening. Sunset is after 8pm, so a 7pm departure is daylight. Our every way to see the city after dark compares the rest.

Frequently asked questions

Three different ways to see the city lit up

Chicago by Night River and Lake Cruise

Ninety minutes with a live guide from the stairs at Michigan and Wacker: the river, then through the lock onto the lake after dark. Bring your own snacks; the bar sells drinks.

From $50 per person

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Chicago Night Crimes Tour by Bus

Two to two and a half hours by bus from 163 E. Pearson St at 7:30pm, with a live guide and five stops off the bus. No restroom breaks; recommended for ages 10 and up.

From $55 per person

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Chicago: Downtown Chicago Skyline Helicopter Tour

About seven minutes over the skyline on the 10-mile flight, from the vertiport at 1339 S. Wood St; longer flights cost more. Fly Heli sells sunset and evening slots.

From $129 per person

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