Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    1. Local experiences/
    2. Things to do in Chicago…/
    3. Specialty Tours/
    4. Sunrise and Sunset Tours/
    5. Chicago Sunset Cruise
    Why travelers choose Greetwell

    Curated by our team

    Every experience is hand selected and approved by Greetwell.

    Personal concierge

    Real humans available to help before, during, and after your booking.

    Intimate & authentic

    Including unique in-home experiences you won't find anywhere else.

    Easy booking & cancellation

    Reserve in minutes with free cancellation on most experiences.

    Greetwell

    Experiences that stay with you long after the trip

    Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

    About

    • Our Story
    • For Experience Providers
    • For Hospitality Partners
    • For Developers

    Concierge Support

    • Help Center
    [email protected]1-877-GREET-WELL

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Product image 1
    Gallery image

    Chicago Sunset Cruise

    Cruise about two miles offshore for wide-open Chicago sunset views

    5.0 stars• 54 reviews
    From$238incl. taxes and fees

    Duration

    1+ Hours

    Highlights

    Head out on open water and watch Chicago fade into silhouette as the sun drops toward the horizon. Cruise about two miles offshore for a clear view, with departure times that shift seasonally and are confirmed ahead of your charter.

    • Board at 2759 North Lake Shore Drive West in Chicago
    • Cruise offshore for wide-open horizon views
    • Watch the skyline turn into silhouette at sunset
    • Choose a one-hour or two-hour trip length
    • Look for the green flash if timing and luck align

    Cancellation Policy

    Total amount due upon agreement of boat ride. Refundable with five days notice. If scheduled service is less than five days there is a $150 cancellation fee.

    FAQs

    Plan to arrive at least 15 minutes early. The area is very congested, and building in extra time helps you leave on schedule.

    From the street, walk east through the Diversey Harbor parking lot to C-dock.

    Search for "Chicago Blue Water Charters" on Google Maps.

    Meeting details

    2759 North Lake Shore Drive West Chicago, IL US 60614

    Experience provided by Chicago Blue Water Charters
    Experience provided by Chicago Blue Water Charters

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text 1-877-GREET-WELL

    Report an issue

    Reference #GNATW2

    One Hour Trip

    $238.50

    0

    Two Hour Trip

    $477

    Most popular

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    5.0
    Excellent
    54 reviews•Google Maps
    53
    0
    1
    0
    0

    Captain Bob has earned a near-perfect reputation on Lake Michigan, and it's easy to see why. Reviewers consistently praise his deep knowledge of Chicago's waterways, his engaging storytelling, and the relaxed, welcoming atmosphere he creates on board. His boat is frequently described as spotless, comfortable, and impressively well-maintained, with one guest comparing it to "a Porsche on water." What stands out beyond the boat itself is how personally invested Captain Bob seems in every outing. He tailors experiences to his guests, whether that means finding the best spots for the Air and Water Show or navigating to scenic sunset views. He's praised for being safety-conscious and skilled on busy waters, which clearly puts first-timers at ease. Repeat bookings and "can't wait to go back" comments show up throughout the reviews, which is about as strong an endorsement as you can get.

    What people are saying

    Review 1 of 4
    5/5

    Captain Bob was happy to accommodate my group of 6 and our timing! Great sunset views on the lake.

    Photo of Olivia Kroeger

    Olivia Kroeger

    May 9, 2026

    Review 1 of 1
    5/5

    Captain Bob was happy to accommodate my group of 6 and our timing! Great sunset views on the lake.

    Photo of Olivia Kroeger

    Olivia Kroeger

    May 9, 2026

    Great for groups

    Thumbnail
    Boat Rentals2

    Explore the Chicago River on a 2-Hour E-Boat Rental

    From$211/ boat
    Thumbnail
    Boat RentalsUp to 6

    Drive an 18' Pontoon on the Chicago River

    $184.44
    Thumbnail
    Boat RentalsUp to 10

    Drive a 22' Pontoon Boat on the Chicago River

    $396.44

    Nearby activities

    Thumbnail
    Speed Boating

    Ride a Speedboat on Lake Michigan in Chicago

    From$238/ boat
    Thumbnail
    Boat Tours

    Watch Navy Pier Fireworks Cruise in Chicago

    From$265
    Thumbnail
    Food Tours

    Explore Chicago’s West Loop on a 3-Hour Food Tour

    From$136/ person
    Thumbnail
    Food Tours

    Taste Iconic Chicago Foods on a 3-Hour Tour

    From$90/ person
    Thumbnail
    Food Tours

    Explore Chicago Chinatown Food Tour With 5 Tastings

    From$104/ person
    Thumbnail
    Street Food Tours

    Tacos & Tequila Walking Tour in Chicago Pilsen

    From$111/ person