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Port City: Chicago, Illinois


Whether arriving early or extending the adventure, Chicago offers many activities for cruisers who embark from the city. Brian Said, vice president of global development at Choose Chicago, gave managing editor David Hoekman the scoop.

Brian Said Chicago

Photo: Choose Chicago Brian Said

Q. What makes Chicago an appealing port city?

A: Whether you are on a pre, post or day excursion in Chicago you will be spoilt for choice. As the third-largest city in the USA, the options are endless — from amazing architecture, parks and shopping to festivals, music, arts and world-class museums. Chicago offers attractions that are of interest to every age group.

Q. What attractions do you recommend cruisers visit?

A: Chicago’s location along Lake Michigan makes it ideal for outdoor recreation. Enjoy Chicago’s treasured lakefront, whether by bike, running, Segway or walking. Spend some time at Museum Campus — home to the Field Museum, Shedd Aquarium and Adler Planetarium — which is also along the lakefront. Or, venture over to one of the many other cultural institutions in the city’s downtown area and neighborhoods, including the Art Institute of Chicago, the new American Writers Museum, the Museum of Contemporary Art, the Museum of Science and Industry, the DuSable Museum or the Peggy Notebaert Nature Museum. Many of these attractions are either in or near a beautiful Chicago park, too. The two iconic green spaces in Chicago, Millennium Park and Grant Park, also play host to a number of free music, food and entertainment festivals.

Beyond that, guests have the option to shop along the Magnificent Mile, dine their way through some of the city’s great restaurants, catch a sports game that’s in season, see a performance in the Theatre District or a neighborhood theater, or check out a jazz or blues performance. Truly, there is something in Chicago for every traveler.

Q. What advice do you have for first-time visitors?

A: A visit to Chicago is not complete without a visit to an observation deck to view the impressive skyline and the city from high above, an architectural river cruise, a visit to Millennium Park and a stroll along famed Michigan Avenue. Grab an official visitors guide or check for more details and ideas. Chances are you will want to come back to discover more of this wonderful destination. 

Choose Chicago


Sail the Great Lakes on Pearl Seas Cruises

Pearl Mist

Photo: Pearl Seas Cruise Pearl Mist

Pearl Mist
Aug. 17–24, 2019

Day one: Chicago, Ill.
Day two: Muskegon / Holland, Mich.
Day three: Mackinac Island, Mich.
Day four: Sault Ste. Marie, Ontario
Day five: Little Current, Ontario
Day six: Parry Sound, Ontario
Day seven: Midland, Ontario
Day eight: Toronto, Ontario

Eleven-night cruises from Chicago to Toronto also are available.

Pearl Seas Cruises

Disembark on Mackinac Island
•Take a horse-drawn carriage tour to get a closer look at the island and learn its history.
•Taste the island’s famous fudge — its most popular souvenir.
•Discover Fort Mackinac, classic Victorian architecture and the unforgettable Grand Hotel.


About Author

David Hoekman, Managing Editor

David Hoekman is a former newspaperman on a quest to tell the stories of the world’s various places and cultures in compelling ways. He especially enjoys learning and writing about the business of group travel. His favorite destination is wherever he is going next and his travel tip is to always pack an emergency granola bar or two.

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