When to take a Chicago river cruise
Chicago's architecture cruises sail for most of the year, but a windy April morning and a hot July evening show you two different cities. Summer brings long light and sold-out weekends. Spring and fall trade warmth for space on the deck, and the hour you choose matters as much as the month.
The cruising year at a glance
Wendella's boats sail all year, but most of the river's architecture cruises keep a shorter calendar. The docent cruise on Chicago's First Lady runs from about mid-March to late November, and Chicago Line keeps roughly the same months. Shoreline says its tours usually sail in summer. Its schedule in spring and fall depends heavily on the weather. The figures below are average highs and lows at O'Hare, which lies inland, so read them as a rough guide to how the river will feel.
| Month | Average high | Average low | On the river |
|---|---|---|---|
| April | 59 °F (15 °C) | 40 °F (5 °C) | Cool on deck. The docent cruise is back |
| May | 71 °F (21 °C) | 51 °F (10 °C) | Mild days on the upper deck |
| June | 80 °F (27 °C) | 61 °F (16 °C) | Long evenings and busy weekends |
| July | 85 °F (29 °C) | 66 °F (19 °C) | Hottest month, fullest boats |
| August | 83 °F (28 °C) | 65 °F (18 °C) | Warm nights, summer crowds |
| September | 76 °F (24 °C) | 57 °F (14 °C) | Warm days with more room at the rail |
| October | 63 °F (17 °C) | 45 °F (7 °C) | Crisp air and earlier sunsets |
| November to March | Cold | Often below freezing | Fewer boats, see the winter guide |
Summer brings long light and full boats
From June to August the river is at its busiest, and the sun stays up past 8 pm, so even a late afternoon departure comes home in daylight. The open upper deck is where everyone wants to sit, and only the docent cruise guarantees you a seat up there. On the Wendella boats deck seats go first come, first served, which makes arriving 20–30 minutes early the difference between the top deck and the cabin.
Summer is also when the listings start to warn you. Both 90-minute Wendella cruises say they are likely to sell out, and so do the docent cruise and Shoreline's tour. Weekends go first. If your trip is fixed, book the cruise once your dates are set rather than turning up at the dock hoping for a seat. Heat is the other summer issue. First Lady's listing tells guests to bring sunglasses and a sun hat, which is sound advice on any boat in July, and the climate-controlled cabins on the Wendella boats are a relief on a hot afternoon.
The Lake and River cruise from ~$45 has a summer quirk of its own. It passes through the Chicago Harbor Lock, where the river sits a few feet below Lake Michigan, and in high summer the lock gets busy enough that the listing warns the trip can run past 90 minutes. The passage alone takes about 10–15 minutes. Leave slack in your plans after this one. The lake and river guide covers the route.
A guaranteed deck seat, from ~$57
The docent cruise on Chicago's First Lady promises open-air seating on the upper deck, so a busy summer departure never leaves you stuck below. It runs from about mid-March to late November.
Spring and fall give you room at the rail
April and October share a feel. Average highs are 59 °F (15 °C) and 63 °F (17 °C), and the wind moving down the river between the towers makes the open deck feel colder than the number suggests. What you get in return is space. The boats are less full, the sun sits lower in the sky for more of the day, and the glass towers pick up color in a way that flat summer noon light never allows.
May and September, with highs of 71 °F (21 °C) and 76 °F (24 °C), are mild enough to stay on deck for a whole 90-minute cruise.
Early spring has one oddity. On the Saturday before St. Patrick's Day the river is dyed green, a tradition Plumbers Local 130 has kept almost every year since 1962. The docent cruise season starts around the middle of March, so check whether it is running that weekend. Wendella, which sails all year, is the safe bet. At the other end, late November is the last chance for the docent cruise until spring, which our winter guide covers along with what still runs in the cold.
Picking the hour
The time of day changes what the buildings look like more than most people expect. The main branch runs east to west, so the towers along its north bank face south and catch sun for most of the day, while the river fronts on the south bank sit in their own shade much of the time. Along the North and South branches, which run roughly north to south, east-facing walls light up in the morning and west-facing ones in the afternoon.
At midday in summer the sun stands high. The river glitters while the facades look flat, and the glass throws glare back at the deck. Late afternoon is the photographers' favorite. The light warms up and long shadows give the stone buildings depth. Our photography guide covers which side of the boat to sit on.
Sunset and the first hour of dark
A departure timed to leave shortly before sunset gives you both cities in one trip, the facades in daylight on the way out and the lit skyline on the way back. In Chicago the sun sets around 8:30 pm in late June but before 4:30 pm in December, so the same slot means very different things through the year. Check the times for your date and work back from sunset. A Wendella reviewer chose an early evening departure at sunset, and a Shoreline guest on an 8:30 pm tour called it an excellent way to see the buildings at night. Our night cruise guide covers the evening options, among them a First Lady cruise that heads onto the lake after dark.
When it rains on the river
Rain rarely cancels a cruise. Wendella says it sails through rain and snow alike unless the captain decides otherwise, and refunds you if the captain does cancel. First Lady's cruises depart rain or shine. One reviewer described a docent who kept talking on the top deck from under an umbrella. Shoreline's captains may delay or cancel for weather, with a refund when they do.
On a wet day the covered seating matters. Wendella and First Lady both have climate-controlled cabins below the open deck. Chicago Line's boats are open-air but have covered areas. One Wendella guest cruised through light rain and the tour carried on as normal.
Booking ahead for a weekend
For a Saturday in July, book days ahead rather than hours. Our pick, Wendella's 90-minute cruise from ~$45, offers free cancellation up to 24 hours before and lets you reserve now and pay later, which takes the risk out of booking early. Shoreline charges a $10 fee per ticket for date or time changes made on the day of the tour, so settle your plans the night before.
Plan to reach the dock 15–30 minutes before departure, since Wendella searches every bag and Shoreline starts boarding 15 minutes ahead. Our dock guide shows where each boat leaves from.
Matching the cruise to the season
- High summer with lake views. The Lake and River cruise, booked early, with time to spare for the lock
- A hot afternoon. Any Wendella cruise, for the cool cabin below deck
- Architecture first, March to November. The docent cruise while its season lasts
- A chilly spring or fall day. A boat with an indoor cabin to retreat to
- Small children. The 45-minute family cruise from ~$28, see our family guide
- Not sure which boat. Which cruise to choose sorts them by priority