What to Wear on a Chicago Boat Tour in November and Winter

The classic outdoor-industry system, as REI explains it, is three layers: one that moves sweat off your skin, one that holds heat, and one that blocks wind and rain. The CDC's cold-weather guidance adds the key rule: cotton loses its insulation when it gets wet, while wool, silk and most synthetics keep insulating.

• Base layer. A snug long-sleeve top in merino wool or polyester, plus leggings or long underwear from December to February. Merino is soft and resists odor; synthetics dry fastest. Skip the cotton tee.
• Mid layer. A fleece, wool sweater or thin down or synthetic puffy. In November one is enough; in January you may want two.
• Outer shell. The most important item: a windproof, water-resistant jacket with a hood, ideally insulated from December to February. One long enough to cover your hips helps on cold metal benches.
• Legs. Jeans alone are a poor choice once they get wet. Add a base layer underneath, or wear insulated or fleece-lined pants.
• Head. A knit hat that covers your ears. A hood alone tends to blow back once the boat gets moving.
• Hands. Gloves you can use your phone with, or thin touchscreen liners under warmer mittens. Disposable hand warmers in your pockets are a cheap upgrade.
• Neck. A scarf or fleece neck gaiter seals the biggest gap in most jackets, and you can pull it over your nose on deck.
• Feet. Waterproof boots with real tread and wool-blend socks. Docks, gangways and stairs get wet, and Wendella's own guidance warns that decks can get slick. Its Michigan Avenue dock is 62 steps down from street level, and the First Lady dock is also reached by stairs.

• CAC River Cruise aboard First Lady: an open-air upper deck, where outdoor seating is guaranteed for every guest, plus an enclosed, climate-controlled lower salon with large windows. The docent's narration plays throughout the boat over a PA system, so you can warm up downstairs without missing the commentary. The 2026 season ends on November 22.
• Wendella: every boat except the Ouilmette has a heated, air-conditioned lower lounge, and Wendella says its cabins are heated through fall, winter and spring. Seating is first come, first served, so arrive early if you want a particular spot.
• Shoreline: most boats are double-deckers with a partly covered overhead, but four architecture boats are single-deck with no cover, and Shoreline says its open upper decks give no protection from the elements (there is a lightweight awning for rain). If you book Shoreline in November, dress as if you'll be outside the whole time.

Our approach: sit outside for the first stretch and the best landmarks, then duck inside to thaw for 10 minutes. For a fuller operator comparison, see CAC First Lady vs Wendella vs Shoreline in Late Fall.

Sun makes a bigger difference than you'd think. The NWS's "Understanding Wind Chill" page notes that bright sunshine can raise the effective wind chill by 10–18°F, which is why a sunny 1 p.m. sailing in November can feel pleasant while a 6 p.m. one feels like winter.

• Daytime: three layers, and you may unzip in the sun. Sunglasses help with low-angle glare off the glass towers.
• Sunset: after the clocks fall back on November 1, Chicago sunsets in 2026 run from about 4:46 p.m. on November 1 to 4:22 p.m. by the end of the month, according to timeofsunset.com's November 2026 table. A late-afternoon cruise starts in daylight and ends in the dark and cold, so pack one more layer than you think you need.
• Night: treat it as a winter outing even in November, with an insulated jacket, hat, gloves, scarf and warm boots.

Picking a departure? Our November sunset table suggests a time for each week of the month.

Apple's support article "If your iPhone or iPad gets too hot or too cold" says iPhones are designed for ambient temperatures between 32°F and 95°F. Below that, battery life can drop temporarily, the phone may shut off, and it may refuse to charge until it warms up. Most phones behave in a similar way.

• Keep your phone in an inside chest pocket between shots.
• Carry a small power bank, and keep it warm too.
• Use a wrist strap; wind and cold fingers are a bad combination at the rail.
• When you come back inside, let your camera warm up in a closed bag to limit fogging.

• ☐ Non-cotton base layer (top; add bottoms December to February)
• ☐ Fleece, wool or puffy mid layer
• ☐ Windproof, water-resistant hooded jacket
• ☐ Warm pants (no plain jeans in deep winter)
• ☐ Knit hat covering your ears
• ☐ Scarf or neck gaiter
• ☐ Touchscreen gloves (plus warmer mittens December to February)
• ☐ Hand warmers
• ☐ Waterproof boots with good tread
• ☐ Wool-blend socks (plus a spare pair for kids)
• ☐ Phone, charged, in an inside pocket
• ☐ Power bank and cable
• ☐ Credit or debit card (Wendella and Shoreline take cards only)
• ☐ Sunglasses for daytime glare
• ☐ Packable blanket or poncho (optional backup)
• ☐ Wrapped snacks (First Lady and Wendella only, not Shoreline)
• ☐ Tickets on your phone; arrive 30 minutes early

Keep planning

• Visiting over Thanksgiving weekend? Our Thanksgiving weekend itinerary covers the holiday dates, and our holiday boat tours guide covers the fireworks and Christmas sailings.
• Boats done for the season? See the architecture tours that run when the boats stop.