Embark on a Chicago cruise today, and visit one of America's most iconic travel destinations, along the beautiful shores of Lake Michigan. Chicago is not only the most popular travel destination across the great lakes, but across all of America!
Chicago was founded as a town in 1833, but was settled by Native Americans hundreds of years before. Now, Chicago is the third largest city by population in the United States and features a mix of sophistication, outdoor adventures, and a gorgeous skyline. We invite you to experience these dynamic destinations and experience all it has to offer. Whether you're looking to indulge in top-tier shopping, explore the museums and learn the history, or experience a gourmet culinary meal, a Great Lakes cruise cruise to Chicago offers something to impress even the pickiest of travelers!
Chicago was founded as a town in 1833, but was settled by Native Americans hundreds of years before. Now, Chicago is the third largest city by population in the United States and features a mix of sophistication, outdoor adventures, and a gorgeous skyline. We invite you to experience these dynamic destinations and experience all it has to offer. Whether you're looking to indulge in top-tier shopping, explore the museums and learn the history, or experience a gourmet culinary meal, a Great Lakes cruise cruise to Chicago offers something to impress even the pickiest of travelers!
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Chicago Multi Day CruiseVictory Cruises has cruises that cruise to Chicago and cruise from Chicago. There are multiple options whether you want to Embark or Disembark in Chicago and we would love to help you choose the best Chicago cruise that fits your budget and expectations!
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Chicago Cruise Itineraries
All of the cruises to Chicago and the cruises from Chicago have itineraries that you won’t want to miss! They all of course include some days of just sailing on Lake Michigan and taking in all the beautiful sights that it has to offer. They also offer a chance to see and take in the sights of the other Great Lakes as well: Lake Superior, Lake Huron, Lake Erie, and Lake Ontario.
The cruises to and from Chicago also give you the opportunity to see some of the most beautiful sights of the world. One of the most beautiful stops is Niagara Falls. Being the oldest state park in the US known for its breathtaking waterfalls, it appears on many bucket lists! Many of our Detroit Cruises, Toronto Cruises, and Montreal Cruises also feature Niagara Falls as a stop too, and we are here to help you find the best fit and check off your bucket list.
You will also get to visit and see many other cities and beautiful sights around the great lakes, and each cruise we offer has different highlights!
The Great Lakes & St. Lawrence Seaway cruise is one of our Montreal Cruises and can be traveled from Chicago to Montreal or Montreal all to Chicago. One of the highlights on its itinerary is visiting Toronto. Toronto Cruises are pretty popular because you get to experience the diverse culture and get to see some iconic landmarks like the CN Tower.
The cruises to and from Chicago also give you the opportunity to see some of the most beautiful sights of the world. One of the most beautiful stops is Niagara Falls. Being the oldest state park in the US known for its breathtaking waterfalls, it appears on many bucket lists! Many of our Detroit Cruises, Toronto Cruises, and Montreal Cruises also feature Niagara Falls as a stop too, and we are here to help you find the best fit and check off your bucket list.
You will also get to visit and see many other cities and beautiful sights around the great lakes, and each cruise we offer has different highlights!
The Great Lakes & St. Lawrence Seaway cruise is one of our Montreal Cruises and can be traveled from Chicago to Montreal or Montreal all to Chicago. One of the highlights on its itinerary is visiting Toronto. Toronto Cruises are pretty popular because you get to experience the diverse culture and get to see some iconic landmarks like the CN Tower.
Most Popular Cruise Routes
Cruises to Chicago
The most popular cruise to Chicago is the Ultimate Great Lakes Cruise. This cruise is only 9 days long, but also includes a 1 night hotel stay. It goes from Toronto to Chicago and is also offered as a cruise from Chicago to Toronto. This cruise gains popularity because it visits all 5 of the Great Lakes, so you get a chance to see a little bit of everything.
Cruises from Chicago
The most popular Cruise that disembarks in Chicago is also one that also embarks from Chicago, the Chicago Roundtrip Cruise. It is also hosted by Victory Cruises. It is a 14-Day Cruise that focuses on Lakes Michigan and Superior. It really is one of only two itineraries by any cruise line that actually spends dedicated time exploring the beautiful nature of places on Lake Superior like the Apostle Islands and Thunder Bay.
Best Things to Do in Chicago, IL
360 CHICAGO OBSERVATION TOWER
For more information click here: Chicago Observation Tower
CHICAGO FIREBOAT TOURS
Just a short stroll north of Navy Pier, one of the top Chicago cruise attractions, finds the restored Fred A. Busse Fireboat docked and ready for its next exploration. Take a ride on an actual piece of Chicago history onboard the Freed A. Busse which was actively fighting fires from 1937 to 1981. After retirement the vessel was converted into an excursion boat that now cruises from Sturgeon Bay, Wisconsin to Chicago's lakefront. This veteran owned Chicago tour boat company conducts many tours including sunset cruises along the Chicago River and Lake Michigan.
For more information click here: Chicago Fire Boat Tours
CHICAGO'S GANGSTERS & GHOSTS TOURS
The best way to familiarize yourself with Chicago's legends of the past is to walk down haunted alleyways, reminiscing the gangster interactions during the 1920s and 1930s. Visit the Loop Vice District with the assistance of your tour guide
and learn about the mayhem that dominated the newspaper headlines and the locations that it all happened.
For more information click here: Gangsters & Ghost Tours
DRIEHAUS MUSEUM
The Richard H. Driehaus Museum is just a couple blocks from Chicago's Magnificent Mile. Explore the rare architecture of the Gilded Age along with its early design and art at the Nickerson Mansion.
For more information click here: Driehaus Museum
LOU MALNATI'S PIZZERIA
For over 40 years Lou's pizza is best known for its made from scratch, flaky, buttery deep dish pizza crust, specially grown roma tomatoes, and fresh Wisconsin cheese. Be sure to taste this secret family recipe for yourself when in Chicago. There are 57 locations in Chicago alone!
For more information click here: Lou Malnati's Pizzeria
MUSEUM OF CONTEMPORARY ART CHICAGO
The Museum of Contemporary Art features current day exhibits in a variety of mixed media platforms from both local and international artists.
For more information click here: Museum of Contemporary Art
NAVY PIER
The Navy Pier is Chicago's lakefront treasure, and one of the first things you'll see on cruises to Chicago. Millions of guests visit each year to enjoy the 50 acres of amazing attractions and experience the culture and art of this diverse area.
For more information click here: Navy Pier
SECOND CITY COMEDY CLUB
Second City is considered the world's premier comedy club, comedy theater, and school of improvisation. Featuring a lot of famous faces through the years with its ongoing improvisational theatre troop based in Chicago. The theatre hosts nightly live performances throughout the week.
For more information click here: Second City.
DRAKE HOTEL
Opened in 1920 on the LANDMARK Magnificent Mile. This upscale hotel features traditionally decorated rooms, lake views, elegant furnishings and luxurious Italian marble bathrooms. The hotel accommodates 30,o000 sq. ft. of meeting space, 3 restaurants that include their ornate dining room and afternoon tea service.
For more information click here: Drake Hotel.
For more information click here: Chicago Observation Tower
CHICAGO FIREBOAT TOURS
Just a short stroll north of Navy Pier, one of the top Chicago cruise attractions, finds the restored Fred A. Busse Fireboat docked and ready for its next exploration. Take a ride on an actual piece of Chicago history onboard the Freed A. Busse which was actively fighting fires from 1937 to 1981. After retirement the vessel was converted into an excursion boat that now cruises from Sturgeon Bay, Wisconsin to Chicago's lakefront. This veteran owned Chicago tour boat company conducts many tours including sunset cruises along the Chicago River and Lake Michigan.
For more information click here: Chicago Fire Boat Tours
CHICAGO'S GANGSTERS & GHOSTS TOURS
The best way to familiarize yourself with Chicago's legends of the past is to walk down haunted alleyways, reminiscing the gangster interactions during the 1920s and 1930s. Visit the Loop Vice District with the assistance of your tour guide
and learn about the mayhem that dominated the newspaper headlines and the locations that it all happened.
For more information click here: Gangsters & Ghost Tours
DRIEHAUS MUSEUM
The Richard H. Driehaus Museum is just a couple blocks from Chicago's Magnificent Mile. Explore the rare architecture of the Gilded Age along with its early design and art at the Nickerson Mansion.
For more information click here: Driehaus Museum
LOU MALNATI'S PIZZERIA
For over 40 years Lou's pizza is best known for its made from scratch, flaky, buttery deep dish pizza crust, specially grown roma tomatoes, and fresh Wisconsin cheese. Be sure to taste this secret family recipe for yourself when in Chicago. There are 57 locations in Chicago alone!
For more information click here: Lou Malnati's Pizzeria
MUSEUM OF CONTEMPORARY ART CHICAGO
The Museum of Contemporary Art features current day exhibits in a variety of mixed media platforms from both local and international artists.
For more information click here: Museum of Contemporary Art
NAVY PIER
The Navy Pier is Chicago's lakefront treasure, and one of the first things you'll see on cruises to Chicago. Millions of guests visit each year to enjoy the 50 acres of amazing attractions and experience the culture and art of this diverse area.
For more information click here: Navy Pier
SECOND CITY COMEDY CLUB
Second City is considered the world's premier comedy club, comedy theater, and school of improvisation. Featuring a lot of famous faces through the years with its ongoing improvisational theatre troop based in Chicago. The theatre hosts nightly live performances throughout the week.
For more information click here: Second City.
DRAKE HOTEL
Opened in 1920 on the LANDMARK Magnificent Mile. This upscale hotel features traditionally decorated rooms, lake views, elegant furnishings and luxurious Italian marble bathrooms. The hotel accommodates 30,o000 sq. ft. of meeting space, 3 restaurants that include their ornate dining room and afternoon tea service.
For more information click here: Drake Hotel.
More Honorary Mentions: Shedd Aquarium · Adler Planetarium · Art Institute of Chicago · Frank Lloyd Wright District
Learn More About the Port of Chicago
Find luxury shopping on Chicago's Magnificent Mile, home to historic landmarks such as the Chicago Water Tower, the Tribune Tower, and other breathtaking skyscrapers. Don’t forget to explore the Millennium Park, home to the famous Chicago Bean -- one of the city's most picture-worthy spots. While you’re in the city, stop by the Navy Pier, an iconic Chicago cruise attraction. The Navy Pier recently celebrated its 100th anniversary, and it features the newly added 200-foot-tall Centennial Wheel. Other Chicago attractions include world-class museums such as the Museum of Science and Industry, the Art Institute of Chicago, the Chicago Botanic Garden, and the Shedd Aquarium (located inside the Museum Campus). There is a museum for everyone.
Everyone loves to refresh and grab a bite. Chicago has an amazing variety of cuisines to try. Some of the most popular gastronomic hubs in the city are found in the local food halls. Eataly, Forum 55, Latinicity, and the Wellstreet Market offer hundreds of local restaurants you need to try. From a quick bite, to an elaborate dish, or a tasty dessert, the local food halls got you covered. Also, make sure you stop for some of Chicago’s classic Deep-Dish Pizza from Lou Malnati’s, and a Buttermilk Old-Fashioned Chicago Doughnut at Do-Rite Donut. These are a must-try according to several national publications, and have even been praised in some of the top food TV shows.
Regardless of what you choose to do while you are in Chicago, we know you will enjoy your time in Chicago and can not help to plan your dream trip! Reach out to our Experts and get your cruise booked before they are all booked up.
Everyone loves to refresh and grab a bite. Chicago has an amazing variety of cuisines to try. Some of the most popular gastronomic hubs in the city are found in the local food halls. Eataly, Forum 55, Latinicity, and the Wellstreet Market offer hundreds of local restaurants you need to try. From a quick bite, to an elaborate dish, or a tasty dessert, the local food halls got you covered. Also, make sure you stop for some of Chicago’s classic Deep-Dish Pizza from Lou Malnati’s, and a Buttermilk Old-Fashioned Chicago Doughnut at Do-Rite Donut. These are a must-try according to several national publications, and have even been praised in some of the top food TV shows.
Regardless of what you choose to do while you are in Chicago, we know you will enjoy your time in Chicago and can not help to plan your dream trip! Reach out to our Experts and get your cruise booked before they are all booked up.
Chicago Cruise FAQ’s
Which cruise lines sail out of Chicago?
Victory Cruises have multiple itineraries that leave from Chicago! Contact us and we can help you choose which one fits you best!
Do cruise ships go to Chicago?
Yes! For example Victory Cruises have 2 different cruise itinerary options that cruise to Chicago, one from Montreal and the other from Toronto.
Are there cruises from Chicago?
Yes! Victory Cruises has options to sail from Chicago!
Does Chicago have a cruise port?
Yes, it is called the Port of Chicago.
Do cruise ships go on Lake Michigan?
Yes! There are multiple Cruises that occur on Lake Michigan including those that include Chicago as a destination or as a starting point.
Updated 01/22/25 - RC
