Wendella's Wine & Cheese Cruise is a two-hour, adults-only evening on the water — a curated wine tasting paired with hors d'oeuvres, served as you drift down the Chicago River and out onto Lake Michigan for full golden-hour skyline views. It's priced at $70 per person, it's strictly 21 and over, and it's built for the "pinkies up" crowd: date nights, foodie catch-ups, and any excuse to toast the city. Here's everything worth knowing before you book.
Quick Answer: The Wine & Cheese Cruise at a Glance
- Price: $70 per person
- Age: 21+ only — valid ID required
- Duration: 2 hours
- Route: Chicago River and Lake Michigan
- Included: Curated wine tasting and hors d'oeuvres, open-air seating, covered lower deck, restrooms onboard
- Narration: Light narration — relaxed, not a fully guided tour
- Departs: 400 N Michigan Avenue, by the Wrigley Building at the northwest corner of the DuSable Bridge
- Bar: Full-service bar onboard (cashless)
What Is the Wendella Wine & Cheese Cruise?
This is Wendella's most laid-back, grown-up cruise. Where the architecture tours are about lively, fully guided commentary, the Wine & Cheese Cruise is about slowing down. You get a curated lineup of wine and hors d'oeuvres, gentle music, and two unhurried hours to take in the city from the water. Think of it as a floating picnic, a little more luxe.
The route runs down the Chicago River for up-close views of the city's architectural gems, then glides onto Lake Michigan, where the skyline opens up in full golden-hour glory. Most guests settle in on the open-air deck for the views, but there's a climate-controlled lounge below if the breeze picks up — plus a full-service bar if you'd like to branch out from your wine flight.
What's Included
Every ticket comes with:
- A curated wine tasting and hors d'oeuvres, served throughout the two hours
- Open-air seating on the upper deck and a covered lower deck
- A friendly crew on hand to answer questions
- Iconic skyline views from the river and the lake
- Restrooms onboard
You won't leave hungry or thirsty, but if you'd like more, the onboard bar has snacks, soft drinks, beer, wine, hard seltzer, cider, and cocktails for purchase. The bar is cashless, so bring a card.
How Much Does It Cost?
The Wine & Cheese Cruise is $70 per person, and it's a 21-and-over experience — there's no children's pricing because kids aren't aboard this one. Everyone needs valid ID for entry.
Wendella does offer discounts, but only for in-person purchases at the ticket office (not online, and not on holidays): college students get 50% off on Tuesdays with a valid student ID, active-duty military and spouses get 50% off Monday through Thursday with military ID, and veterans and reservists get $10 off Monday through Thursday with valid ID.
The Route and What You'll See
The cruise starts at the Michigan Avenue dock, heads down the Chicago River past the city's architecture, then moves through the Chicago Lock onto Lake Michigan for the wide-open skyline view. Some of the landmarks you'll pass:
- Chicago Lock
- Navy Pier
- Oak Street Beach
- Museum Campus
- Buckingham Fountain
- Wolf Point
Depending on the locks, the weather, and the captain's call, the boat may head further into the river as well. All routes are subject to change without notice.
Is It Narrated?
Lightly. This cruise includes light narration — highlights and stories shared along the way — but it's far more relaxed than Wendella's fully guided architecture tours. If you'd rather just listen to the water and the music, that's the whole point. The crew is happy to answer questions if you're curious about what you're seeing, but no one's going to talk over your evening. If you want the full, deep-dive guided experience, that's what the architecture tours are for.
When Does It Run?
The Wine & Cheese Cruise runs on a seasonal evening schedule. Check the booking page for current dates and availability — these evening cruises are popular and can sell out during peak season, so booking ahead is the safe move.
Where It Departs and How to Get There
All cruises leave from Wendella's dock at 400 N Michigan Avenue, right by the historic Wrigley Building at the northwest corner of the DuSable (Michigan Avenue) Bridge. Arrive at least 30 minutes before your scheduled departure — boarding begins 15 minutes prior, and the boat doesn't wait.
For parking, there's the Interpark lot, the AMA Plaza Garage, and the Trump Tower Garage nearby, or you can use the SpotHero app to reserve a spot in advance. Full directions are in the Getting to the Dock guide.
What to Wear and Weather
The vibe is smart-casual — nice enough to feel like an occasion, comfortable enough for a boat. Layers are your friend, since evening breezes on the river and lake can be cool even in summer. Wendella cruises depart rain or shine; the boats are built for Chicago weather, with a climate-controlled lower deck if you need to duck out of the elements. If conditions turn genuinely unsafe and the captain cancels, you're covered. See the full weather and seasons guide for what to pack.
Good to Know Before You Board
- 21+ only — bring valid ID
- Cashless — bring a card for the bar
- Outside alcohol and weapons aren't allowed; all bags are screened
- Tickets are non-refundable and non-transferable after the scheduled departure time
- Wheelchair accessible from Wendella's West Dock, with a ramp to the upper deck and ADA-compliant restrooms — call (312) 337-1446 in advance so the crew can assist
Who It's For
The Wine & Cheese Cruise is a great fit if you're planning a date night, a foodie evening out, a birthday or anniversary, or trading the usual night out for something on the water. It's adults-only by design, so it's the cruise for when you've got a sitter lined up. If you're traveling with kids or a mixed-age group, Wendella's other tours and cruises welcome all ages — the Sunset Cruise is a good family-friendly evening alternative.
Frequently Asked Questions
How much is the Wendella Wine & Cheese Cruise?
The cruise is $70 per person. It's a 21-and-over experience, so everyone aboard needs valid ID. In-person ticket-office discounts are available for college students (50% off Tuesdays), active-duty military and spouses (50% off Monday–Thursday), and veterans and reservists ($10 off Monday–Thursday), but not online or on holidays.
What's included on the Wine & Cheese Cruise?
Each ticket includes a curated wine tasting and hors d'oeuvres served throughout the two-hour cruise, open-air upper-deck seating, a covered lower deck, and restrooms onboard. A full-service bar is available for additional drinks and snacks for purchase (cashless).
How long is the cruise?
Two hours, running along the Chicago River and out onto Lake Michigan.
Is the Wine & Cheese Cruise narrated?
It includes light narration — highlights and stories along the way — but it's more relaxed than Wendella's fully guided architecture tours. The crew is happy to answer questions, but the focus is on a laid-back evening rather than a deep-dive tour.
Can I bring my kids?
No. The Wine & Cheese Cruise is 21 and over only. For a family-friendly outing, Wendella has other tours and cruises that welcome kids aboard.
Where does the cruise depart from?
From Wendella's dock at 400 N Michigan Avenue, by the Wrigley Building at the northwest corner of the DuSable (Michigan Avenue) Bridge. Arrive 30 minutes before departure; boarding begins 15 minutes prior.
What happens if it rains?
Cruises depart rain or shine — the boats have a climate-controlled lower deck for cover. If the captain deems conditions genuinely unsafe and cancels, you're covered. Check the weather guide before you head out.
Related Reading
- Wendella Sunset Cruise Guide — another relaxed evening cruise, family-friendly
- Chicago Architecture Boat Tour Guide — for the fully guided, deep-dive experience
- Chicago Fireworks Cruise Guide — Wendella's five fireworks cruises
- Private Boat Events Guide — for booking the boat for a group
- Getting to the Dock — directions and parking
- Wendella FAQ — full policies
