What to Expect on a Chicago Night Tour

Here is the evening in order, from the dock to the lock and back. You will know when to arrive and where to sit, what the lock does, and what to wear. You will also know what the bar takes and what happens if you miss the boat. Booking Chicago Night tickets? This is what the listings leave out.

Arrive 30 minutes early: boarding starts 15 minutes out

1. Find your dock. First Lady boards on the Riverwalk, down the stairs at the northeast corner of Michigan & Wacker. Wendella boards at 400 N Michigan Ave, by the Wrigley Building, on the other bank.
2. Arrive 30 minutes before. Both operators ask for this. Boarding starts about 15 minutes before the sailing; First Lady's priority boarding opens at 20.
3. Pick your deck. Seats are first come, first served, and the top deck fills first.
4. Settle in. The boat leaves on time. First Lady does not refund or exchange a missed boat.

Leave your cases at your hotel. First Lady takes no luggage on board, and neither dock stores bags. The step-free way down to each dock is on the meeting-points map.

Two decks: open air on top, a heated lounge below

The top deck: Open seating in the air, with the best view of the towers and the bridges. It is where you want to be on the lake, and where the wind reaches you.

The lounge below: Enclosed and climate-controlled, with the bar and the restrooms. Wendella says its cabins are heated in fall, winter and spring.

Moving between them: You can go down to the bar during the cruise. On some Wendella boats a lift links the decks; ask when you book if you need it.

Through the Chicago Harbor Lock

Only the lake cruises do this part. First Lady's night cruise and Wendella's sunset cruise pass the lock at the river's mouth. The Creepy Cruise and the 45-minute tour stay on the river. Here is what happens.

1. The river: you cruise east along the main branch, under the lit bridges.
2. Into the lock: the boat enters the Chicago Harbor Lock, and the gates close behind it.
3. Level water: the water between river and lake is brought level. A typical cycle takes 12 to 15 minutes, for a difference of two to five feet.
4. The lake: the far gates open, and you are out on Lake Michigan with the whole skyline behind you.
5. Back again: the boat returns through the lock to the river and the dock.

The lock handles a lot of traffic, and on a busy evening your boat waits its turn. Travellers on the lake cruises report waits. On the night cruise, one 90-minute sailing ran 2 hours 20 minutes. On a sunset sailing in August 2026, the boat waited about an hour and never reached the lake.

The wind on Lake Michigan after dark

This is the most repeated warning in the reviews. On the lake, the wind picks up and the air cools as the sun goes down. Travellers who sailed in May, August and September all say to bring a jacket.

Wear layers you can add as you leave the river. A hat helps from October. If you feel the cold, sit on the top deck for the lock and the skyline, then go down to the lounge for the way back. The evening lows for each month are on the weather page.

Bars, snacks and cards-only payment

Drinks are not in any fare. Each boat has a bar, but how you pay and what you may bring differ.

On First Lady's night cruise you may bring your own snacks. No boat allows outside alcohol. Wendella's bar takes cards only, so bring one even if you carry cash. Tips are not in any fare. The crime bus suggests about $5 a person.

Rain, cancellations and missed boats

• Rain: the cruises run rain or shine. The lounge below is covered.
• Severe weather: the operator cancels, and you are offered a new date or a full refund.
• You cancel: every tour here refunds in full up to 24 hours before the start.
• You are late: First Lady does not refund or exchange a missed boat, and the crime bus leaves on time without you.
• The lock: a long wait at the lock is not a cancellation. Allow extra time after a lake cruise.

On the bus and at the heliport

The crime bus: Check in 15 minutes early outside 163 E. Pearson St. If you have not checked in 10 minutes before the start, call 312-888-6224. The bus has five steps and no lift, and no restroom. You step off at five stops of 5 to 15 minutes, including the Biograph Theater.

The heliport: Check in 10 to 15 minutes before your booked time at Vertiport Chicago. Fly Heli asks for photo ID that matches the booking and the card. The weight limit is 295 lbs a passenger. There is a safety briefing before you board.

On the bus, eating and drinking are not allowed, though you may drink soft drinks at the stops. The guide tells the stories of Al Capone, John Dillinger and Frank Nitti at the sites. Chicago Crime Tours recommends the evening for ages 10 and up.

Getting back after the tour

The cruises return to the dock you left from, on the Chicago Riverwalk. The Riverwalk stays open until 11pm, and the stairs lead back up to Michigan Avenue. The crime bus ends where it began, at Pearson St. The helicopter lands where it took off, so plan a ride back from South Wood Street.

Questions about the night itself

Where these facts come from

Boarding times, bars, access and terms come from the operators' own pages, checked 27 September 2026. What each fare includes is from the tour's own listing, captured on 27 September 2026. The lock's cycle is from its Wikipedia article. The waits at the lock are travellers' reviews from 2026.

• The night cruise through the lock (First Lady Cruises)
• Finding the dock and the step-free route (First Lady Cruises)
• Boarding, access and getting there (Wendella FAQ)
• The sunset cruise (Wendella)
• Check-in, steps and ages (Chicago Crime Tours FAQ)
• Downtown flights, sunset slots and the weight limit (Fly Heli)
• The lock at the river's mouth (Wikipedia)

Tours that fit a first evening on the water

Chicago by Night River and Lake Cruise

The river and then the lake after dark, with a live guide for the full 90 minutes. It boards at the stairs on Michigan and Wacker and can wait its turn at the lock.

From $50 per person

Check Availability

Lake Michigan Sunset Cruise in Chicago

Wendella's cruise timed to the sunset, from 400 N Michigan: the river, then the lake as the towers light up. The crew gives light narration; there is no guide.

From $45 per person

Check Availability

Chicago River Ghost & Dark History Night Cruise

Ghost stories and dark history from a live storyteller over 90 minutes. The boat stays on the river and never goes out to the lake.

From $46 per person

Check Availability