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Chicago (Photo:marchello74/Shutterstock)
Chicago (Photo:marchello74/Shutterstock)
5.0 / 5.0
Cruise Critic Editor Rating

Andrea Guthmann
Cruise Critic Contributor

Port of 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.

Shore Excursions

About 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

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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.

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.

Food and Drink

Celebrity chefs like Charlie Trotter and Rick Bayless put the Second City on the map as a first-rate dining destination. Although Chicago's avant-garde culinary scene has a world-class reputation, plenty of moderately priced fare is available to satisfy anyone's appetite. Three must-try items are deep dish pizza, the messy Italian beef sandwich and the Chicago-style hot dog, loaded with everything except ketchup.


Deep dish pizza is why some people come to Chicago. Pizzeria Uno (29 E. Ohio Street; 312-321-1000; open 11 a.m. to 1 a.m. Monday to Friday, 11 a.m. to 2 a.m. Saturday and 11 a.m. to 11 p.m. Sunday) claims they created the deep dish pizza. Lou Malnati's (439 N Wells Street; 312-828-9800 and 1120 N. State Street; 312-725-7777; open 11 a.m. to 11 p.m. Sunday to Thursday and 11 a.m. to midnight Friday to Saturday) would surely disagree. Either pizzeria is a great choice and has a number of locations, including just off the Magnificent Mile.

If you really want a taste for a messy Chicago favorite, make the trip to Al's Italian Beef's original location in the city's Little Italy neighborhood. Order an Italian beef sandwich with hot peppers and ask for it dipped. (1079 W. Taylor Street; 312-226-4017; open 9 a.m. to 11 p.m. Monday to Friday, 10 a.m. to 11 p.m. Saturday and closed Sunday) There's also a location at 169 W. Ontario Street in the River North neighborhood, closer to the bustling Magnificent Mile and Navy Pier.

Everything in the garden, from pickles to tomatoes to peppers, even cucumbers, can go on a Chicago dog. There's just one rule: No ketchup! Not to worry though. Being Midwesterners, they're pretty accommodating. If you insist, Wiener Circle, a popular hot dog joint about a mile south of Wrigley Field, will give you your ketchup. (2622 N. Clark Street; 773-477-7444; open 10:30 a.m. to 4 a.m. Sunday to Thursday, 10: 30 a.m. to 5 a.m. Friday to Saturday)

Stand in line for your corned beef or half and half (half corned beef, half pastrami) piled high on rye at Manny's Coffee Shop and Deli, a Chicago tradition for more than 50 years. Take a look at the photos on the walls of this humble cafeteria and you'll see it's been a required stop on the campaign trail for decades. Famous for its corned beef and potato pancakes, Manny's customers come from all over the country to dine at this family owned delicatessen. (1141 S. Jefferson Street; 312-939-2855; open 6 a.m. to 8 p.m. Monday to Saturday, closed Sundays)

Lao Sze Chuan is a Chinatown favorite, located in the southwest corner of Chinatown Square. It takes reservations only for parties of six or more. Leave your name as soon as you arrive, and instead of standing around waiting, check out the surrounding gift shops, selling everything from Chinese toys and trinkets to exotic herbs and teas. (2172 S. Archer Avenue; 312-326-5040; open 11 a.m. to midnight daily)

With a view:

Galileo's Cafe, the outdoor patio of the Adler Planetarium, offers a jaw-dropping view of the Chicago skyline, and the telescopes are a fun way to check out the details of the skyscrapers lining the lake. A tip: You don't need to pay museum admission to enjoy an alfresco lunch there. You just can't bring your own food. (1300 S. Lake Shore Drive; 312-922-7827; open 10 a.m. to 2:30 p.m. daily)

The base of the iconic Tribune Tower, home to the Chicago Tribune newspaper, is the perfect spot for an alfresco lunch. Drink in the view of Michigan Avenue and the landmark Wrigley Building, along with your choice from hundreds of beers at Howells and Hood. The restaurant's named after the Tribune Tower's architects and serves classic American fare with a fun twist. A "Blues Brunch" with live music is offered Sundays. (435 N. Michigan Avenue; 312-262-5310; open 11 a.m. to 10 p.m. Monday to Thursday, 11 a.m. to 11 p.m. Friday to Saturday and 10 a.m. to 10 p.m. Sunday)


If it's not raining or cloudy, get a bird's-eye view of the skyline from the 95th floor of the John Hancock Tower at the Signature Room at the 95th, a great place to celebrate something special. You can also just have a drink in the Signature Lounge on the 96th floor. (875 N. Michigan Ave; 312-787-9596; open 11 a.m. to 2:30 p.m. for lunch and 5 p.m. to 9:30 p.m. for dinner daily)

Generations have dined in style just off the Mag Mile, inside the historic 1890s McCormick Mansion at Lawry's The Prime Rib. Meals in this ornate dining room are wheeled to your table on silver carts. Don't feel like wearing a suit and tie? Adjacent to the formal dining room is the more casual, and hipper, SideDoor. (100 E. Ontario Street; 312-787-5000; open 5 p.m. to 9 p.m. daily)

Located on the 16th floor of the Trump Hotel Chicago, Sixteen serves breakfast, lunch and dinner in an elegant setting with million-dollar views. Not surprisingly, those exclusive views from the floor-to-ceiling windows come at a high price. During the warmer months Sixteen opens its doors to the outdoors. There may be nowhere better to dine on a starry summer night in Chicago than the Terrace at Trump, overlooking the twinkling lights of downtown. (401 N. Wabash Avenue; 312-588-8030; open 5:30 p.m. to 9 p.m. daily)

Consistently ranked as one of the best restaurants in North America and the only one in Chicago with Michelin's coveted three star rating, is Lincoln Park's Alinea. Reserve a table far in advance to experience Chef Grant Achatz's innovative modernist fare. (1723 N. Halsted Street; 312-867-0110; open 5 p.m. to 9:30 p.m. Wednesday to Sunday, closed Monday to Tuesday)


Chicago's a big sports town, so a jersey or hat representing one of its professional teams is a hit with sports fans. Sports-themed stores are located along Michigan Avenue and at Navy Pier.

Architecture and history enthusiasts will enjoy a unique gift from the Chicago Architecture Foundation's Gift shop (224 S. Michigan Avenue). Choose from Chicago themed jewelry, scarves and T-shirts. You'll also find plenty of architectural toys, games and gifts, including Frank Lloyd Wright-inspired stained glass.