
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 AvailabilityTwo things decide what a Chicago night tour feels like: when it gets dark, and how cold the lake is after sunset. Sunset moves more than four hours through the year. The evening low moves from about 19°F to 68°F. Before you book chicago night time tours, check your month.
Sunset falls at 4:19pm on 7 December and at 8:30pm on 27 June. The Night Crimes bus leaves at 7:30pm all year. In June you set out in full daylight. In early December it has been dark for more than two and a half hours.
The lake adds its own weather. Out past the lock, the wind picks up as the sun goes down. Travellers who sailed in May, August and September all say to bring a jacket. The evening low is the temperature you sail in, not the day's high.
The season sets the rest. First Lady sails its 2026 season from 15 March to 22 November. Wendella publishes no season dates, so check the dates offered when you book. Rain alone rarely stops a cruise. Severe weather does, and then you are offered a new date or a refund.
Each month gives the average high and low at Chicago Midway, NOAA's 1991-2020 normals, and the sunset and dark times on the 15th from the U.S. Naval Observatory. Use the low for your evening.
The coldest month, with evenings near the average low of 19°F. It is dark by 5:15pm, so a 7:30pm start is more than two hours after dark. First Lady does not sail until mid-March. Dress for the wind at every stop off the bus.
Still cold, with an average low of 23°F and the least rain of the year, 1.46 inches. The sun sets at 5:24pm by mid-month. Anything you do in the evening is in full dark. The cruise season has not started yet.
The clocks go forward on 8 March, and sunset jumps an hour, to 6:57pm by mid-month. First Lady's 2026 season opened on 15 March. Lows average 32°F, so a cruise this month is a cold one. Sit in the heated lounge for the lake.
The night cruise's own season starts in April. Sunset is 7:32pm at mid-month and it is dark by 8:01pm, so pick a late sailing. Lows average 41°F, with 3.57 inches of rain. In 2026, Art on theMART returned on Thursdays to Sundays from 9 April.
Evenings warm to a low of about 52°F, but May is the wettest month, with 4.09 inches. The sun sets at 8:04pm by mid-month. A 7:30pm start is daylight, and the lights come on part-way through. Bring a jacket for the lake.
The longest evenings: sunset reaches 8:27pm at mid-month and 8:30pm on 27 June, the latest of the year. It is not dark until 9:02pm. Only the latest sailings reach the night, so book the last one on offer. Evening lows average 62°F, mild enough for the top deck.
The warmest month, with an average high of 85°F and evenings near 68°F. The sun sets at 8:24pm by mid-month. The top deck is at its best now, and the lake breeze is welcome. In 2026, Navy Pier's summer fireworks ran on Wednesdays and Saturdays.
Warm and humid, with lows near 66°F and 3.99 inches of rain. Sunset is 7:50pm by mid-month and it is fully dark by 8:20pm. A 7:30pm bus starts in daylight. Travellers still say to bring a jacket on the lake.
Evenings cool to about 59°F. Sunset moves from 7:00pm at mid-month to 6:32pm on 1 October. In 2026, Art on theMART moved to 7:30pm on 10 September. By the end of the month, most evening sailings start at dusk or later.
Lows fall to about 46°F, and it is dark by 6:37pm at mid-month. A 7:30pm start is now in full dark, and so is any evening cruise. The wind on the lake is sharp. Bring a hat and a warm layer.
The clocks go back on 1 November, and sunset drops to 4:30pm by mid-month. Lows average 35°F. First Lady's 2026 season ends on 22 November. Any late-afternoon sailing is already a night cruise this month, and it is fully dark by 5:00pm. Wear gloves on the lake.
The earliest dark of the year: sunset at 4:19pm on 7 December. Lows average 25°F. The First Lady boats are docked for the winter, so check what else sails. In 2026, Art on theMART plays at 7:30pm until 27 December, free from the Riverwalk.
Here are the twelve months side by side. "Fully dark" is the end of civil twilight, when the skyline is lit against a black sky. Times are for 2026; other years fall within a minute or two.
| Month | Sunset (15th) | Fully dark | Avg high °F | Avg low °F | Rain, inches |
|---|---|---|---|---|---|
| January | 4:45pm | 5:15pm | 32.7 | 19.4 | 1.48 |
| February | 5:24pm | 5:52pm | 36.8 | 22.6 | 1.46 |
| March | 6:57pm | 7:25pm | 47.6 | 31.7 | 1.88 |
| April | 7:32pm | 8:01pm | 59.9 | 41.4 | 3.57 |
| May | 8:04pm | 8:36pm | 71.1 | 52.0 | 4.09 |
| June | 8:27pm | 9:02pm | 80.9 | 62.3 | 4.01 |
| July | 8:24pm | 8:57pm | 85.0 | 67.7 | 3.55 |
| August | 7:50pm | 8:20pm | 82.7 | 66.4 | 3.99 |
| September | 7:00pm | 7:28pm | 76.3 | 58.8 | 2.77 |
| October | 6:09pm | 6:37pm | 63.4 | 46.5 | 3.48 |
| November | 4:30pm | 5:00pm | 49.1 | 35.0 | 2.35 |
| December | 4:20pm | 4:52pm | 37.6 | 25.0 | 1.79 |
See the top night tours, then pick a sailing that leaves after the dark time for your date.
For a cruise in full dark with mild air, come in September or October. Sunset falls between about 7pm and 6pm, evening lows are about 47°F to 59°F, and an evening sailing starts at dusk or later.
For warm nights on the top deck, come from June to August. The catch is the light: the sun sets after 8pm, so only the latest sailings reach the dark. Summer is also when Navy Pier runs its fireworks.
From late November to mid-March, First Lady is docked, and the evenings are near or below freezing. The Night Crimes bus and the city's own lights are your evening then. Skydeck Chicago and 360 Chicago stay open, and 360 Chicago opens until 11pm.
If you can choose, start about half an hour before the dark time for your month. You see the last light over the lake, then the skyline switches on around you. In June that means a sailing after 8:30pm, not at 7pm.
On a lake cruise, allow for the lock. The wait can add half an hour or more, so a sailing that leaves at sunset may reach the lake after dark. Plan the end of the evening too: the Chicago Riverwalk closes at 11pm.
Temperatures and rain are NOAA's 1991-2020 normals for Chicago Midway Airport. Sunset and dark times are the U.S. Naval Observatory's for 2026, at the Michigan Avenue Bridge. Season dates are the operators' own, checked 27 September 2026.

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
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A seat on a bus from 163 E. Pearson St at 7:30pm, a live guide, and short stops on foot where the crimes happened. Two to two and a half hours; no restroom breaks.
From $55 per person
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A timed daytime entry to the science museum in Hyde Park, open 9:30am to 4pm: a covered plan for a wet afternoon before a cruise. The U-505 and the Coal Mine cost extra.
From $25 per person
Check AvailabilityNext: read what to expect on the night, choose a tour on the night tour options, or compare every tour on Chicago Night Tours.