Chicago Holiday Boat Tours 2026

Wendella Holiday Fireworks Cruise (Sat Nov 21, 2026)

This is the headline holiday sailing: one night only, 90 minutes on the Chicago River, with hot apple cider, hot cocoa and holiday sweets included and seasonal music throughout. Fares are $50 for ages 13 and over, $25 for kids 4–12, and free under 4. The boats have an open upper deck and a heated lower deck with restrooms and a cashless bar. Wendella says plainly that the parade itself isn't part of the cruise: you're on the water for the fireworks, not on Michigan Avenue for the floats. It's sold on Wendella's own website, not through GetYourGuide.

About the timing. Wendella hasn't published a departure time. Its fireworks guide says the boat anchors "near Navy Pier" for fireworks "at around 9:00 PM", but that line appears to be carried over from its summer cruises. The Magnificent Mile Association's 2026 announcement puts the Lights Festival fireworks at approximately 7:15 p.m. over the Chicago River at Michigan Avenue, while Choose Chicago's Lights Festival guide gives 7:30 p.m. Expect an evening departure timed to the river show, and check the time on your ticket.

Shoreline Sightseeing: hot chocolate sailings and the Holiday Express

Shoreline's Skyline Lake Tour leaves from Navy Pier on the lake side, so it isn't affected by the Chicago Harbor Lock closure (Nov 16 through mid-April) that ends river-to-lake tours. Shoreline's own tour page says that in December the 5, 6 and 7 p.m. departures add holiday music and complimentary hot chocolate. In 2025 Navy Pier marketed these as "Hot Chocolate Cruises" running Friday to Sunday, Dec 5–28, with tickets sold in person at Navy Pier and at 401 N. Michigan Ave. The 2026 dates haven't been announced yet.

The standard fare is $34 for adults, $13 for kids 3–12, and free for 2 and under. The tour is 45 minutes in the regular season, but GetYourGuide's listing says it runs 30 minutes from Nov 1 to Apr 15, and Shoreline's ticket store describes the Hot Chocolate Cruise as a 30-minute sailing on Lake Michigan. That GetYourGuide lake listing showed no December dates when the site checked, so buy the holiday sailings from Shoreline directly. Sunset in early December comes at about 4:20 p.m., so all three departures are fully after dark, with the skyline lit.

Shoreline also ran a Holiday Express Water Taxi on weekends in December 2025 (noon to 6 p.m., Michigan Avenue ↔ Navy Pier). It's the cheapest way onto the water for the holidays; the last published fares (2024) were $6 adult and $3 child for that hop.

City Cruises (Odyssey, Spirit of Chicago, Seadog) at Navy Pier

City Cruises' parent, Hornblower Group, announced its 2026 holiday lineup in an Oct 15, 2026 PR Newswire release. It covers Christmas Eve and Christmas Day brunch and dinner cruises "with freshly prepared meals, holiday music, dancing and games," New Year's Eve dining cruises with fireworks views on select sailings, and New Year's Day brunch. It gives no Chicago times or prices, so check City Cruises' calendar for each of these:

• Christmas Eve Premier Dinner Cruise: 2.5 hours aboard Odyssey from Navy Pier, with a three-course plated dinner and a DJ. It's the one holiday dinner on GetYourGuide (from $198), and it's newly listed, with 4.3/5 from only 15 reviews, so read the recent ones before you book.
• Christmas Day Premier Dinner Cruise: the same format, sold by City Cruises directly.
• Holiday fireworks dinner cruises: in past seasons these sailed on December Saturdays. In 2026 Navy Pier's Winter Fireworks are Saturdays at 8 p.m. on Nov 28 and Dec 5, 12, 19 and 26, so look for sailings on those dates.
• New Year's Eve: lake and river dinner cruises plus a daytime brunch.

These are dress-up dinners more than kids' outings, though families do book Christmas Day. Holiday sailings bought from City Cruises are non-refundable, non-transferable final sale, and its Ticket Assurance add-on isn't available for them. On an ordinary December night, City Cruises' regular sailings cover the same boats: the Brunch, Lunch or Dinner River Cruise on the Odyssey Chicago River (4.5/5 from 257 reviews, from $74), the Lake Michigan Lunch or Dinner Cruise on the Spirit of Chicago (4.4/5 from 370 reviews, from $63) and the Premier Lunch or Dinner Cruise on the Odyssey Lake Michigan (4.2/5 from 519 reviews, from $82). Our Chicago dinner cruises guide compares them.

Hot tub boats (Chicago Electric Boat Co.)

This one is quirky: a self-driven, heated hot-tub boat for up to six people, for 90 minutes on the downtown river. The operator's listing shows separate holiday pricing per boat for weekdays and weekends and says to check back in November 2026 for the new season, so check its calendar for this year's rates. Passengers must be 13 or older, drinks are BYO and food isn't allowed. Sailings may be rescheduled when it gets down to about 20°F. It's fun for adults, but it isn't a guided holiday-lights tour.

What's not running

The Chicago Architecture Center's CAC River Cruise aboard First Lady ends its season on Nov 22, 2026 (4.7/5 from 672 reviews, from $57), and Tall Ship Windy has no holiday sailings listed. If you want a narrated architecture tour before the holiday rush, compare the options in CAC First Lady vs Wendella vs Shoreline in Late Fall. For December, Wendella's 90-minute architecture cruise (from $45) and the shorter 45-minute Wendella tour (4.7/5 from 2,965 reviews, from $28) are the river options. On land, the Secret Interiors Architecture Walking Tour (4.8/5 from 712 reviews) spends much of its time inside the Loop's landmark lobbies, out of the wind.

• Navy Pier: a free, 10-minute fireworks show at 11:59 p.m. on Thursday, Dec 31, 2026, synchronized to music.
• The river: for 2025–26 the city added a five-minute fireworks show launched from river bridges, with THE MART as the countdown backdrop, for ABC's New Year's Rockin' Eve. The river was closed to boats from Franklin to Columbus between 11:30 p.m. and 12:15 a.m. The city hasn't confirmed a repeat for 2026–27.
• Wendella NYE Fireworks Cruise: 90 minutes, anchoring on the river for the midnight show. Last season Wendella charged $50 for adults and kids alike; it hasn't posted the 2026 fare or departure time yet. The marketing mentions Champagne, but Wendella's FAQ says drinks aren't included, so plan to buy your toast at the bar. Like the fireworks cruise, it's sold on Wendella's own site.
• City Cruises: lake and river NYE dinner cruises plus a brunch sailing. 2026 times and prices weren't posted in October, so check City Cruises' calendar.

• The Magnificent Mile trees at the Michigan Avenue Bridge, best on and after Nov 21.
• The Wrigley Building and Tribune Tower, lit at the river's edge right above Wendella's dock.
• Art on theMART: Thursday to Sunday, 7:30–8:00 p.m., the Joffrey Ballet's Nutcracker is projected across THE MART's river facade from Nov 19 to Dec 27, 2026. The best views are from the Riverwalk around Wells and Franklin.
• Navy Pier and the skyline from the lake on Shoreline's evening sailings, plus the Centennial Wheel.

For timing your sailing around sunset, see Best Time of Day for a Winter Chicago River Cruise.

• Book the one-night sailings early. The Nov 21 and Dec 31 cruises each run on a single night, and reseller listings tag City Cruises' holiday dinners as "likely to sell out."
• Wendella: you can move your ticket to another time before departure, but after the scheduled departure it's non-refundable and non-transferable. Cruises run rain or shine, and if the captain cancels, you get a refund. Arrive 30 minutes early, since boarding starts 15 minutes before departure. In-person discounts don't apply on holidays.
• City Cruises: holiday cruises bought from City Cruises are final sale. Third-party sites sometimes advertise free cancellation, so read the cancellation terms on the specific listing before you pay.
• Shoreline hot chocolate sailings were sold in person in 2025. Buy at the Navy Pier window when you arrive.
• For winter cancellation rules by operator, see our guide to winter cancellations and refunds.