What to Wear on the Water on a Chicago Night, Month by Month

Evening temperatures, month by month

These are the NOAA 1991 to 2020 normals at Chicago Midway: the average daily high and the average daily low. An evening on the water sits between the two, and nearer the low once the sun is down. Wind on the open lake makes it feel colder still.

Only the sailing months are shown. The full year, with rain and the dark times, is on Chicago weather at night.

Why the lake is colder than the street

On the river you sit between towers that block most of the wind. Once the boat is through the lock and out on Lake Michigan, nothing stands between you and the open water. The air comes off a lake that stays cold well into summer, and the boat's own speed adds to it.

Travellers keep coming back to the same advice. A September passenger on the 6pm boat wrote that it was warm by day and cold by night, so bring a jumper. An August one said to wrap up because the wind off the water makes it feel colder. Another wrote that the lake can be choppy at night. None of that is bad weather; it is just the lake after sunset.

Layers, not a big coat

• A windproof top layer. It matters more than thickness, because the wind is the cold part.
• Something for your head and hands from October. A traveller on an October night cruise said to bring gloves for the wind.
• Shoes with grip. The First Lady dock is down stairs, two levels below Michigan Avenue, and decks can be wet.
• A small bag only. Neither dock stores luggage, and bags are screened at Wendella.
• Nothing for the rain but a hood. The boats sail rain or shine, and Wendella sells ponchos on board.

The lounge below deck

Both operators give you somewhere warm to retreat to. First Lady's boats have an open upper deck and an enclosed, climate-controlled salon below with large windows. Most Wendella boats have an enclosed, climate-controlled lounge on the lower deck, with the bar and the restrooms. On a cold night the bar on the Creepy Cruise has served hot chocolate.

The trade-off is the view and the sound. On the 45-minute tour, one traveller who arrived too late for the top deck found the view below still good but the guide hard to hear. So sit up top for the skyline, and go below to warm up between the best stretches. The two docks, and the way down to each, are on the meeting-point map.

On the bus, and in the air

If you would rather not be out in the wind at all, the Night Crimes bus keeps you indoors between five short stops. One traveller called it a good first night because it was warm on the bus instead of out in the cold. You still step off at each stop for five to fifteen minutes, so a coat is still worth it in autumn.

The skyline flight lasts about seven minutes, take-off and landing included. Dress for the check-in and the walk to it. Every way to see the city after dark is compared on the night tour options page.

Month by month, in a sentence

• May: an average low of 52°F. Wear a jacket and a warm layer under it.
• June to August: lows of 62 to 68°F. You will be warm on the river and glad of a light jacket on the lake.
• September: a low of 59°F. You will want a proper jacket by the time the boat turns for home.
• October: a low of 46°F. Wear a coat, and add gloves and a hat for the lake.
• November: a low of 35°F. Dress as for winter; First Lady's season ends on 22 November.

Children feel the cold on deck sooner than you do, and they are harder to keep still below. Bring one more layer for them than you think they need. On First Lady boats, pushchairs are folded and stored in the salon, so a small blanket in your bag is worth more than a pushchair cover.

If it rains

The cruises sail rain or shine, so a wet forecast is not a reason to cancel. You sit in the salon or the lounge below, which has large windows, and go up top when it eases. May is the wettest sailing month at Midway, with about 4.1 inches on average. If severe weather calls a sailing off, you are offered a new date or a full refund. And if you cancel yourself at least 24 hours ahead, you get your money back.

A quick packing list

For a 90-minute cruise from May to September: a light jacket or a jumper, comfortable shoes, a phone for photographs and a card for the bar. From October add gloves and a hat. For the night cruise onto the lake, you may bring your own snacks; the bar sells drinks. For the stories on the river, the Creepy Cruise stays between the towers, where the wind is gentler. The FAQ answers the rest.

Evenings dressed for the wind

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

Check Availability

Chicago River Ghost & Dark History Night Cruise

Ninety minutes of ghost stories and dark history told by a live storyteller, from the dock at Michigan and Wacker. It stays on the river, with a bar on board.

From $46 per person

Check Availability

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

Check Availability