Chicago river cruises in winter
A winter cruise on the Chicago River is a smaller, quieter thing than the summer version. Fewer boats sail and the decks are cold. By late afternoon the light is going. In return you get the towers almost to yourself, and the boats that do run have heated cabins with big windows.
Who keeps sailing after November
From late November the river belongs mostly to Wendella. While other operators dock for the season, Wendella says it keeps cruising all year, and its 90-minute architecture cruise from ~$45 lists year-round sailings with a choice of the open deck or a climate-controlled interior. The company goes out in snow and wind unless the captain says otherwise, and it refunds the ticket if the captain calls a trip off.
What Wendella does not publish is a winter timetable. We could not confirm which of its three architecture tours run between December and February, or how often they leave, so check the times for your date before you build a day around one. Wendella also warns that schedules can shift with the season or the weather. The dock and even the boat may change too, so read your voucher on the morning of the cruise.
| Cruise | From | In the cold months |
|---|---|---|
| Wendella 90-minute river cruise | ~$45 | Listed as year-round, check your date |
| Wendella 45-minute family cruise | ~$28 | Check which tours run in midwinter |
| Wendella Lake and River cruise | ~$45 | Check your date |
| Shoreline architecture cruise | ~$39 | 60 minutes from November 1 to April 15 |
| Docent cruise on Chicago's First Lady | ~$57 | About mid-March to late November |
| Chicago Line tour with drinks | ~$42 | Roughly mid-March to late November |
| First Lady's Chicago by Night | ~$50 | April to November only |
Shoreline's shorter winter tour
Shoreline's architecture cruise from ~$39 normally lasts 75 minutes, but the listing says it runs 60 minutes from November 1 to April 15. The live guide speaks English or Spanish, and the barcoded ticket lets you skip the ticket office. Outside summer, Shoreline's own FAQ says the schedule depends heavily on the weather, so a departure is less certain than it would be in July.
Shoreline also notes that its boats may offer little shelter from wind or rain, and one reviewer's advice was to dress warm when it is windy and wet. If the forecast looks grim, rebooking on the tour day itself adds $10 to each ticket, so decide the evening before.
November, the last month for many boats
If architecture is the reason for your trip, November is the month to act. The docent cruise on Chicago's First Lady from ~$57 runs from about mid-March to late November, narrated by one of more than 100 volunteer docents trained by the Chicago Architecture Center. Seats on the open upper deck are guaranteed, and the enclosed salons below are climate-controlled. Drinks and snacks are sold on board. Our guide to the docent cruise explains what sets it apart.
Chicago Line keeps a similar calendar, and its boats are open-air with covered areas rather than enclosed, so a late-November trip on the Chicago Line tour from ~$42 calls for proper winter clothes. The free coffee and tea on that cruise help. First Lady's night cruise onto the lake runs only from April to November. Our night cruise guide covers the evening options that remain once it stops.
The Wendella boats in the cold
Wendella says its cabins are heated through the cold months, and every boat in its fleet except the Ouilmette has a heated lounge on the lower deck, next to the restrooms. The boats are cashless, so bring a card for the bar, which sells Garrett's Popcorn alongside local beer and spirits. You may bring your own food and non-alcoholic drinks, so a thermos of hot coffee is allowed on board. Bags are searched before boarding.
If the 45-minute family cruise from ~$28 is running on your date, it keeps the cold to three quarters of an hour, which suits small children. The 90-minute tour covers all three branches of the river and gives you more time to warm up inside between the highlights.
The cruise that sails all year, from ~$45
Wendella's 90-minute tour has a live guide and a heated cabin to retreat to. Free cancellation up to 24 hours before helps when the forecast turns.
Cabin window or open deck
On a cold day the sensible plan is to split the cruise. Sit by a cabin window for the long straight stretches, then climb to the open deck for the moments that need a wide view, such as Wolf Point, where the three branches meet. The bridges are a good reason to go up as well, since you pass right under them. Windows give you warmth but add reflections and sometimes fog, which spoils photos. On deck the wind channels between the towers and feels sharper than the forecast suggests.
Deck seats on Wendella go first come, first served, but with winter's thinner crowds you rarely have to fight for one. For photos through glass and from a moving boat, see our photography guide.
What to wear on a cold river
Dress as if you will stand still outside for an hour and a half, because on deck you will. Layers work better than one heavy coat, since you will move between a heated cabin and the wind several times.
- A warm hat that covers your ears
- Gloves that work with a phone screen
- A windproof outer layer with a hood
- Shoes with grip for wet stairs and decks
- A scarf or neck warmer for the open deck
- A spare battery, since cold drains phones fast
The stairs matter more than people think. Wendella's main dock by the Michigan Avenue bridge sits 62 steps below street level with no elevator, and the First Lady dock is two levels down from Wacker Drive. Our dock guide has the details, and the accessibility guide covers step-free routes.
Fewer people and an early dusk
The upside of cold-weather cruising is space. Summer weekends sell out, while a winter weekday may leave room at every rail. The trade is light. The sun sets before 4:30 pm in December, so a mid-afternoon departure ends in dusk with the office windows lit. You can plan it that way on purpose, catching the facades in the last daylight and the lit towers on the return. Our guide to timing compares the months, and the night cruise guide describes the river after dark.
When spring comes back
The river wakes up in stages. The docent cruise and Chicago Line return around the middle of March, and the river turns green for a day on the Saturday before St. Patrick's Day. April brings average highs of 59 °F (15 °C) but lows near 40 °F (5 °C), so an early spring cruise still calls for a hat. Per the listing, Shoreline returns to its 75-minute tour after April 15. First Lady's night cruise starts again in April.