Canadian, Great Lakes and New York cities · November to March

Packing list for Toronto, Montreal, Chicago and New York in winter

The Great Lakes, the St. Lawrence and New York from November to March: 5°F (-59°F (15°C)) with the wind, salt on every boot, underground cities that let you skip whole blocks, and buildings heated to 72°F that have you taking layers off and putting them back on all day.

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On a phone with Waystop installed, the button adds the list to your trip as a bag you can tick off. Otherwise copy it and paste it into Waystop’s Chat with “add this to my packing list”.

Checked October 10, 2026.

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What the weather is like

January highs sit around 30°F (-1°C) in Toronto, 32°F (0°C) in Chicago and 23°F (-5°C) in Montreal, with lows of 19°F (-7°C), 21°F (-6°C) and 9°F (-13°C); wind off the lakes takes the felt temperature to 5°F (-15°C) and below on most clear days. Montreal averages about 50 cm of snow in January alone, Chicago about 90 cm over the winter. Indoors it is 70 to 73°F (21 to 23°C) everywhere. New York runs a January high of about 39°F (4°C) and a low of 28°F (-2°C), with about 75 cm of snow a year.

Leave at home

Leather dress shoesSalt lines will mark them in a day, and boots to dinner are normal.
A wool overcoat as your only coatIt is fine at 28°F (-2°C) but lets the wind through at Montreal's 9°F (-13°C) mornings. Bring an insulated coat instead.
A pile of US or Canadian cashCards and phones tap everywhere, and leftover US dollars are awkward to spend in Canada.

Buy when you land

A toqueSold on every corner for a few dollars, and a Canadian one is the souvenir you will actually wear.
Boot waterproofing sprayCanadian Tire, hardware stores and shoe shops sell it, and it keeps road salt from eating leather.
Slip-on ice cleatsHardware stores and outdoor shops sell them, and Chicago and Toronto sidewalks glaze over after freezing rain.

Worth knowing

Toronto's PATH runs about 30 km under the financial district and Montreal's RESO about 32 km; both are open while the metro runs, but some entrances and most shops close at weekends, so learn the route before Saturday.
It is dark by about 4:40 p.m. in Toronto and 4:20 p.m. in Chicago in December; put the CN Tower, the lookout at Mont Royal and the Riverwalk before 3:30 p.m. and save the lights, the galleries and dinner for after dark.
Tap-to-pay works at every café, tram and transit gate, including Presto in Toronto and Ventra in Chicago, so you can leave the mitts on; carry a little cash only for the odd market stall.

Trips to pack this for

In the app

Never leave the charger in the hotel again.

Waystop keeps a list for each bag and each person. On the morning you change hotels it walks you through a quick pack-up check, and Chat can suggest items to add when you ask what to bring.

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Packing list for Toronto, Montreal, Chicago and New York in winter

The outer layer
- A long insulated coat with a hood (A wool overcoat is for 28°F (-2°C); Montreal mornings sit at 9°F (-13°C) before the wind, and a hood beats a hat when it gusts off the lake)
- Insulated boots with a lugged sole (Pavements ice over by late afternoon and the city salts them; the salt eats suede and leather, so pick boots you do not mind staining)
- A toque and mitts, not gloves (Toque is the Canadian word for a knitted hat, and fingers kept together in mitts stay warm when gloved fingers go numb; a thin liner glove underneath works the phone)
- A scarf or neck gaiter that covers the chin (At a wind chill of -18°F (-28°C) exposed skin can freeze in about 30 minutes, and Chicago's streets channel the wind straight up from the river)
- Wool or thermal socks, one pair per day (Slush gets in at the curb and damp feet are the fastest way to a miserable afternoon)

The layers that come off
- A thin merino base layer (The formula is base layer, one mid layer, one coat; the coat and the mid layer come off indoors and the base layer carries you through a museum at 72°F (22°C))
- One fleece or light sweater, not three heavy ones (Offices, malls and the metro are hot; most of your day is spent inside with the coat over your arm)
- Pants that dry fast, with thermal tights or long johns for the coldest days (Jeans wick slush up the leg and stay wet for hours; a thermal under ordinary pants is the layer locals actually wear)
- A tote that folds into a pocket (Coat checks at the AGO, the Musée des beaux-arts and the Art Institute take the coat; the tote holds the toque, mitts and scarf so you do not lose one)

Skin and kit
- Lip balm and a rich moisturizer (Indoor heating pushes humidity to desert levels; lips and knuckles crack within two days)
- Hand and toe warmers (For the Nathan Phillips Square rink, the Old Port in Montreal and the Lincoln Park Zoo lights; one pair lasts a whole evening)
- Sunglasses (Fresh snow at midday is brighter than a summer beach)
- Power bank kept in an inside pocket (A phone at 14°F (-10°C) shuts down with 40% showing; body heat keeps it alive)
- A type A/B adapter if you are not from North America (Canada and the US run 120 V at 60 Hz on the flat two-pin plug; most phone and laptop chargers accept it, but check hair tools)

From https://waystop.app/packing/north-america-winter-cities

Packing list for Toronto, Montreal, Chicago and New York in winter

What the weather is like

Worth knowing

Trips to pack this for

3 days in Toronto

3 days in Montreal

3 days in Chicago

4 days in New York

Never leave the charger in the hotel again.