Cruising Season 2025 March 16–November 23

First Lady

Ideas for Labor Day and Beyond

Chicago Cruises Labor Day

Summer’s Not Over Yet!

Labor Day may mark the unofficial end of summer but that doesn’t mean it's the end of summer fun. Take advantage of your long labor day weekend and soak up the last days of summer with an endless array of city activities to choose from!

Chicago beach sun 900x450 choose

Hit The Beach

Kickstart your Labor Day weekend by the water with a beach day! Chicago holds about 24 beaches spreading out of lake Michigan and offers endless options. Oak Street Beach, Rainbow beach, and North Avenue Beach have many activities to offer such as volleyball tournaments, playgrounds, gyms, handball courts, bike, and kayak rentals. Check out a list of Chicago beaches right here!

Grebe0377 no bumpers

Take A Cruise… Win Prizes!

Our 2022 Cruise Chicago Photo Contest is happening RIGHT NOW! With the arrival of late summer comes slightly cooler temperatures, which makes for perfect cruising weather! Enjoy Chicago’s best views and tag your photos on social media with #cruisechi2022 for a chance to win a private cruise for 6 on our vintage yacht and more! Pro Tip: Take our Evening Cruise or our morning Capture Chicago Photography Cruise for the most dramatic light. For full rules and prize details, visit cruisechicago.com/photocontest.