Cruises From Chicago
Chicago has a waterfront and a cruise season, but no ocean ships. Here are the two honest ways to cruise from the Windy City.
Get Free Quotes From Your PortSearches for cruises from Chicago come from two kinds of traveler: people who want to sail the Great Lakes, and people who would simply like a cruise that does not involve a long trip to the coast. Both can be done. The first starts right on Lake Michigan; the second means a short flight, and there are ways to keep that flight from wiping out your savings.
Option 1: Great Lakes Cruises That Start or End in Chicago
Ships that sail the Great Lakes are small, because they must fit the locks of the Welland Canal, the Soo and the St. Lawrence Seaway. The regional promotion group Cruise the Great Lakes lists American Cruise Lines, Pearl Seas Cruises, Ponant, St. Lawrence Cruise Lines and Victory Cruise Lines among its participating lines, and features Chicago among its ports. Viking also sails the Lakes with its expedition ships, and announced 2026 voyages that bring a Viking ship to Chicago for the first time.
Typical routes link Chicago or Milwaukee with Georgian Bay, Mackinac Island, the Soo Locks, Lake Superior, Detroit, Niagara and Toronto. These are small-ship, destination-focused trips rather than resort ships with water slides, and they are priced accordingly. Our sister site US Riverboat Cruising goes lake by lake.
Option 2: Fly to an Ocean Homeport, Cleverly
For a Caribbean, Mexico, Alaska or Europe cruise, Chicago travelers fly. That is not a reason to give up on cruising for less; it means planning the air the way cruisers in coastal cities plan parking.
Pick a port with many flights
Chicago’s airports have frequent service to Miami, Fort Lauderdale, Orlando (for Port Canaveral), Tampa, Houston (for Galveston), New Orleans and Seattle. More flights mean more fare choices.
Fly in the day before
It costs a hotel night, but it protects a cruise you cannot afford to miss. Winter storms in the Midwest are the main risk.
Compare total cost
A slightly higher cruise fare from a port with cheap nonstop flights can beat a bargain fare from a port with expensive connections.
Ask about air programs
Some lines sell flights with the cruise. They are not always cheaper, but they can include help if a delay makes you miss the ship. Cruise Airfare explains the trade-offs.
A Drive-To Alternative for the Midwest
Some Midwesterners skip both flights and lakes and drive south. From Chicago it is a long day’s drive to the Gulf Coast ports, and a road trip to New Orleans, Mobile or Galveston can make sense for a family that wants to bring plenty of luggage and see a bit of the country on the way. Add fuel, a hotel night each way and parking to your comparison before choosing this route.
Whichever way you go, the Mister Cruise cruise-offers newsletter flags promotions on the homeports Chicagoans use most.
Chicago Cruise Questions
Are there ocean cruises from Chicago?
No. Chicago is on Lake Michigan, so the only ships that start there are small vessels built to fit the Great Lakes locks. For an ocean cruise, Chicagoans fly to a coastal homeport.
When do Great Lakes cruises sail?
The season is roughly late spring to fall, when the lakes and locks are open and the weather is mild. Popular sailings fill well ahead.
Can I do a cruise from Chicago to Mackinac Island?
Several Great Lakes itineraries include Mackinac Island, but they are multi-night cruises, not quick trips. Ask us which sailings call there in your month.
Plan a Cruise From Chicago
Tell us whether you want the Great Lakes or an ocean cruise. Our cruise advisors at Mister Cruise will match sailings to your dates and the flights that make sense from O’Hare or Midway.
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