• TRAVEL NOTICE: Learn more about COVID-19
  • Newsletter
  • Write a Review
  • Boards
  • Find a Cruise
  • Reviews
  • Cruise Tips
  • News
  • Deals

Cruises to Chicago

Chicago (Photo:marchello74/Shutterstock)

About Chicago

Chicago often is called the Second City, a self-mocking nickname that places it runner-up to New York, but although the popular comedy troupe embraces the moniker, there's nothing second rate about this jewel of the Midwest.

Known as the birthplace of the skyscraper, Chicago's home to some of the nation's top chefs, best sports teams, and most prized cultural treasures. Its iconic skyline overlooks Lake Michigan, one of the five Great Lakes of North America and the only one located entirely in the United States. Known as the Windy City, both for its frigid temperatures and blustery politicians, the third-largest city in the U.S. is the heart of America's Heartland, from the bustling downtown business district known as the Loop to the leafy and luxurious Lincoln Park neighborhood.

Chicagoans take pride in being a hardy, hard-working bunch. The city was once the country's meatpacking capital, and poet Carl Sandburg described it as the "city of big shoulders, hog butcher for the world." This tough town survived the massive fire of 1871 to rebuild one of the world's most recognizable skylines. Culturally, it has one of the world's best collections of impressionist art at the Art Institute of Chicago.

Chicagoans are also fanatical sports enthusiasts. Every major sport is represented, ensuring that any time of year, a game is being played somewhere. The NFL's Chicago Bears play in the modernist marvel Soldier Field, while Michael Jordan's statue stands guard in front of the United Center where the NBA's Chicago Bulls play, as well as the 2010 and 2013 NHL Stanley Cup winners, the Chicago Blackhawks. Although Chicago's home to two Major League Baseball teams, it's the historic ivy-covered walls of Wrigley Field and the Chicago Cubs that hit a home run with tourists.

Chicago's winters are downright frightful, which means that when spring finally arrives, Chicagoans celebrate like giddy school children. That's when the Windy City, also known as the city of neighborhoods, also becomes the city of festivals. From May through September, block parties, street festivals, music fests or art fairs are in swing. Blues Fest, Jazz Fest, Taste of Chicago, Lollapalooza and just about every type of ethnic festival you can imagine are celebrated in what's been called the quintessential American city.

Another hot spot in the summer is the beach. Architect and urban planner Daniel Burnham is credited with protecting the Lake Michigan shoreline, known in the Midwest as America's Third Coast, as public space for all to enjoy. One-hundred years after he proclaimed "The lakefront by right belongs to the people," the 18 miles of continuously connected public waterfront remain one of the best things about Chicago.

While the Windy City is far from being a cruise hub, those lucky enough to spend time here as they embark or disembark on a Great Lakes cruise, will find the city of broad shoulders gives no one the cold shoulder, just a friendly Midwestern welcome.

  • Why go to Chicago?

  • Chicago Cruise Port Facilities?


We're sorry no itineraries matched your search. Please update your search criteria and try again.

Why go to Chicago?


Navy Pier, where you're docked, is the most popular tourist destination in the Midwest


The only cruises that dock in Chicago are a small selection of ships on Great Lakes itineraries

Bottom Line:

Home to top art museums, sports stadiums and restaurants, Chicago is a world-class city

Chicago Cruise Port Facilities?

Navy Pier has an amusement park feel, with the iconic 150-foot replica of the 1893 Columbian Exposition Ferris wheel as a main attraction. The half-mile-long pier also hosts a carousel, outdoor stage, IMAX theater, beer hall, and plenty of shops and chain restaurants. Strolling performers and family-friendly entertainment add to the fun atmosphere.

The Chicago Children's Museum and highly respected Chicago Shakespeare Theater are also housed there, as well as the not-to-be-missed Smith Museum of Stained Glass Windows, which is free. Throughout the summer, Navy Pier has fireworks displays at 9:30 p.m. Wednesdays and 10:15 p.m. Saturdays.

Good to Know?

Chicago is famous for its incredible architectural, culinary and cultural treasures. However, it's also famous for a dark history of crime, from the days of mobster Al Capone to present-day high crime rates. Tourist areas, including the Loop, Michigan Avenue and Lincoln Park are generally safe. Although non-touristy neighborhoods on the outskirts of the city are reachable via the El, make certain you're going to a safe area, or have a cab take you directly to your destination.

Getting Around?

To the Pier: It's about a 30-minute, $40 cab ride from either of Chicago's international airports, Midway or O'Hare, to Navy Pier. You can also take Chicago's elevated subway, known as the El or the L, from either Midway or O'Hare to the Red Line's Grand/State Station. From there, you can take the free Navy Pier trolley one mile east to Navy Pier. The trolley runs every 20 to 30 minutes from May 23 to September 1. If you drive instead, parking is available for $21 for 24 hours at Navy Pier.

At Navy Pier:

On Foot: The pier is in a central downtown location, making it a breeze to access the museums, restaurants and tourist sites of the Windy City, even if you only have a few hours. It's a scenic one-mile walk along the Chicago River, from Navy Pier to the high-end shops of Michigan Avenue. Go in the other direction, and it's a 1.5-mile walk along the lakefront to Chicago's jewel, Millennium Park.

Taxis: Line up at the front entrance to the pier to get a licensed driver.

Free Trolley: Navy Pier offers a complimentary trolley that takes visitors to the shopping hub, Michigan Avenue. It leaves every 20 to 30 minutes from the front doors at Navy Pier.

Tourist Bus: If you want the "Chicago in a nutshell" tour, hop on Chicago's Big Red Double Decker bus (773-648-5000), which takes you to the major tourist attractions and allows you to hop off and on at your leisure. Buses leave about every 15 minutes from the front entrance to Navy Pier. Look for the folks with red vests standing at the front doors.

Pedicab: Chicago's version of rickshaws carry up to two people and are available at the front entrance to the pier.

Bicycle: Wondering who all those cheerful people zipping by on blue bikes are? Chicago has a very easy-to-use bike-share program called Divvy. Grab a 24-hour pass for $7 at any one of the hundreds of stations and enjoy the ride south along the lakefront to Chicago's Museum Campus, or north along the lake to the Lincoln Park Zoo or Wrigley Field.

Water Taxi: Another fun option is to take the shoreline water taxi (312-222-9328) from Navy Pier to the Museum Campus, home to the Shedd Aquarium, the Field Museum of Natural History and the Adler Planetarium. Frequent departures from 10 a.m. to 6:30 p.m. daily, Memorial Day through Labor Day; more limited departures in May and September; $8 for adult tickets.

Currency & Best Way to Get Money?

U.S. dollars are used, and ATMs are readily available.


English is primarily spoken in Chicago, but it's also home to a large Spanish-speaking population, as well as a large Polish population.

Where You're Docked?

Chicago's Navy Pier is much more than a pier, it's a destination itself. Not only is it Chicago's most visited site, attracting about nine million visitors a year, but it's also the most popular tourist destination in the Midwest.

Related Cruises

Cruises to Guadeloupe
Cruises to Rome (Civitavecchia)
Cruises to King's Wharf
Cruises to Hiroshima
Cruises to Budapest
Cruises to Punta Arenas
Cruises to Bari
Cruises to Honfleur
Cruises to Napier
Cruises to Bilbao
Cruises to Hobart
Cruises to Kobe
Cruises to Sydney (Nova Scotia)
Cruises to Cobh (Cork)
Cruises to Catania
Cruises to Alicante
Cruises to Olden
Cruises to Toulon
Cruises to Vernon
Cruises to Argostoli (Kefalonia)
Want to cruise smarter?
Get expert advice, insider tips and more.
By proceeding, you agree to Cruise Critic’s Privacy and Cookies Statement and Terms of Use.