Processing your payment

Headout logo. Link to home.
Help

Dinner Cruises in Chicago

  • All
  • Sightseeing Cruises
  • Dinner Cruises
  • Lunch Cruises

    • Top experiences in Chicago

    5 experiences

    Free cancellation
    Guests dining on Odyssey Lake Michigan Dinner Cruise at sunset.
    Cruises
    Odyssey Lake Michigan Dinner Cruise
    from
    $136.68
    Odyssey Lake Michigan Dinner Cruise. Rated 4.6 out of 5 from 9 ratings.From $136.68
    Free cancellation
    Odyssey Chicago River boat cruising on the Chicago River with city skyline.
    Cruises
    Odyssey Chicago River Architecture Dinner Cruise
    from
    $184.52
    Odyssey Chicago River Architecture Dinner Cruise. Rated 4.7 out of 5 from 25 ratings.From $184.52
    Free cancellation
    Guests enjoying drinks on a Lake Michigan dinner cruise with Chicago skyline in the background.
    Cruises
    Lake Michigan Dinner Cruise
    from
    $121.65
    Lake Michigan Dinner Cruise. Rated 0 out of 5 from 0 ratings.From $121.65
    Free cancellation
    Tourists on Sea Dog Cruise on Lake Michigan with Chicago skyline in background.
    Cruises
    Sea Dog Cruise on Lake Michigan
    from
    $42.79
    Sea Dog Cruise on Lake Michigan. Rated 5 out of 5 from 1 ratings.From $42.79
    Free cancellation
    Dinner cruise boat on Chicago River with illuminated city skyline at night.
    Cruises
    Chicago Dinner Cruise
    from
    $121.65
    Chicago Dinner Cruise. Rated 4.6 out of 5 from 34 ratings.From $121.65

    How Headout makes choosing experiences effortless

    We curate the best ways to experience

    We research and organise all unique experiences - from tickets to tours to special combos - so you get all the choices without the clutter.

    We partner with the best

    Every supplier is vetted for quality, reliability, and value so you only get top rated experiences. No surprises, no disappointments.

    All the best options, in one place

    Each experience is thoughtfully organised to give you maximum availability, great value and an easy way to choose.

    Book with complete peace of mind

    Free cancellations, Flexible payments, and 24/7 support - thoughtfully designed for flexibility, assurance, and total peace of mind.

    1/4

    Slide 1 of 4
    We curate the best ways to experience
    We partner with the best
    All the best options, in one place
    Book with complete peace of mind
    Download app section background

    What our guests say

    Irma M

    Group
    Last week
    ‌
    ‌
    ‌

    +4 more

    I had the best experience ever ! Loved the courtesy of the personal, food was excellent! Drinks amazing, loved the view of the city of Chicago from the Oddyssey !!

    Odyssey Lake Michigan Dinner Cruise

    Destiny M

    United States
    Couple
    2 weeks ago
    ‌
    Views were incredible, food was good , vibes were there , wasn't a rocky ride would highly recommend for date night & quality time spent with your significant other

    Odyssey Chicago River Architecture Dinner Cruise

    Anthony B

    United States
    Couple
    5 days ago
    The customer service was amazing. Very polite knew what they were doing. Offered to take pictures of me and my girlfriend. Me and her had an amazing time definitely recommend going!!!

    Chicago Dinner Cruise

    Charlotte M

    United States
    Couple
    Mar 2026
    The atmosphere was amazing. My husband and I were on vacation for my birthday and this cruise was the highlight of my trip. The staff and captain were amazing and the food was delicious. There was nothing better than the views, they were breathtaking!

    Chicago Dinner Cruise

    We've served 49 million+ guests and we are here for you

    49 million+

    Happy customers across 10,000+ experiences

    In the media

    Featured and recommended by the best brands

    24 x 7 help center

    Have a question? Live chat with local experts anywhere, anytime