Top Chicago Sunset Cruises

A sunset cruise in Chicago is hard to resist, and they’re all fantastic options. But 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 Skyline Tall Ship Sightseeing Cruise (Skyline Sunset Sail option)
• Chicago Buffet Dinner Cruise on Lake Michigan
• Chicago Private Sunset Sail on Lake Michigan
• Chicago Architecture River 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.” Nonetheless, it will give you a new perspective on Chicago during the golden hour. While cruise companies can’t guarantee perfect conditions, previous customers say it was worth it even in cloudy, 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. They 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 behind the skyline doesn’t last three hours—that’s closer to 30 minutes. But longer tours often include a buffet-style dinner or a live DJ to round out the night with dancing.

Chicago sunset cruises provide a safe and memorable experience with stunning waterfront views. Some cruises include dinner, a DJ, and dancing; others are more history-focused, with a local expert guide giving live narration. Several cruises are long enough to see the city’s lights glow after sunset.

Skydeck—at the top of Willis Tower—the Adler Planetarium and Shedd Aquarium lawn are some of the best places to see the sunset in Chicago. You also can’t go wrong at Navy Pier—consider viewing it from the Ferris wheel—or with a sunset cruise on Lake Michigan.

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 essential in winter when it can get very cold 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. Some cruises have onboard cash bars that sell drinks and snacks, or you may be allowed to bring your own. However, Chicago dinner cruises include food and drinks, and may be timed so you can enjoy the sunset; if you’d like to combine a meal with watching the sun go down, check what time the sunsets during your trip and book a dinner cruise for then.