Top Chicago Sunset Cruises

A sunset cruise in Chicago is hard to resist. Looking at ratings and reviews previously given by customers, these are the best sunset cruises available right now:

• Lake Michigan Sunset Cruise in Chicago
• Chicago Private Sunset Sail on Lake Michigan
• Chicago Architecture River Cruise
• Lake Michigan Skyline Cruise in Chicago
• Chicago By Night River and Lake Cruise

Yes, sunset cruises in Chicago are worth every penny. Reviewers say that even if you’ve been to the city before, a sunset cruise is a “must-do,” in part because it will give you a new perspective on Chicago during the golden hour. While cruise companies can’t guarantee perfect conditions, previous customers say the trip is usually worth it, even in cloudy or cold weather.

Chicago sunset cruises start at around US$50 per person, but you can pay upwards of US$125 for a cruise that includes dinner, drinks, or other extras. If you have a group, consider booking a private experience. These typically start at about US$475 for your whole crew.

Most sunset cruises in Chicago last between one and three hours. Obviously, the brilliant view of the sun going down doesn’t last for three hours—that’s closer to 30 minutes. But it’s well worth soaking up the views of Chicago’s iconic skyline as it lights up after dark, and longer tours often include a buffet-style dinner or a live DJ to round out the night.

Some of the best places to see the sunset in Chicago include the Skydeck (the observation deck at the top of the Willis Tower), as well as the Adler Planetarium and the Shedd Aquarium, both of which are poised on the Lake Michigan waterfront. You also can’t go wrong at Navy Pier—consider viewing the sunset from its Ferris wheel—or with a sunset cruise on the lake.

There are tons of fun tours and excursions in Chicago aside from sunset cruises. According to previous travelers, these are the best activities to book for your next trip:

• Bus Tours
• Architecture Tours
• Dinner Cruises
• Night Cruises
• Hop-On Hop-Off Buses

Chicago sunset cruise prices vary depending on duration and inclusions. If you’re looking for high-quality experiences on the lower end of the price range, these are the best tours to book now: 

• Chicago River 45-Minute Architecture Tour From Magnificent Mile
• Lake Michigan Skyline Cruise in Chicago
• Chicago River 90-Minute Architecture Tour
• Lake Michigan Sunset Cruise in Chicago
• Come Sailing with us at Navy Pier: Sunset Sail on Lake Michigan

Check the itinerary carefully before booking a Chicago sunset cruise: Some evening cruises are timed for sunset, while others operate throughout the late afternoon and evening. Also, consider whether you want to take a themed cruise or one with general commentary—some sunset cruises focus specifically on architecture, while others don’t have such a niche focus.

Bring warm clothing for your Chicago sunset cruise so you can comfortably sit outside and enjoy the best views from the outdoor decks—this is especially essential in the cooler months, when it can get very chilly after dark. Before boarding, check whether your vessel has a cash bar, as you may want to watch the sunset with a drink in hand.

No, Chicago sunset cruises do not typically include food and drinks, though some cruises do have on-board cash bars that sell refreshments. Alternatively, Chicago dinner cruises include food and drinks, and may be timed with the sunset. If you’d like to enjoy both, check what time the sun sets during your trip, and book a dinner cruise for then.

Departure points for Chicago sunset boat tours vary depending on the operator. Popular boarding areas include Navy Pier, as well as various spots along the Chicago River. Check your specific tour’s meeting point when booking, and leave extra time for parking or public transit before the scheduled departure. Boarding often commences early, so it’s best to be punctual.

Yes, booking ahead is recommended when scheduling a Chicago sunset cruise. Unlike architecture cruises, which are offered throughout the day, sunset cruises are innately time-limited. That means they can sell out early, particularly during the summer high season and on weekends. Many tours offer free cancellations up to 24 hours beforehand, so you can reserve early and adjust later if need be.

Chicago sunset cruises typically operate during the warmer months of the year. Because the timing of the sunset shifts seasonally, it’s best to check when it falls during your visit. Choose a cruise that boards early enough to catch the transition from daylight to golden hour—and which stays on the water afterwards, so you can admire views of the city lights.

You can, of course, expect to see views of the sun setting during a Chicago sunset tour (although on cloudy days, this may look more like a gradual dimming of the daylight than vibrant colors). No matter the weather, however, you can count on admiring luminous skyline views, plus vistas overlooking Lake Michigan or the Chicago River as the city glows at golden hour.

Yes, many Chicago sunset cruises are perfectly welcoming to families, and provide a fun pre- or post-dinner activity, depending on the time of year. However, note that some cruises—including dinner cruises, or those that include festive celebrations—may have their own age restrictions. In that case, consider a shorter river or lake cruise for younger children.