The most popular spot in Chicago during the summer — and really, anytime — is Navy Pier #2, drawing over 8 million people annually. (Opening photo — Dinner cruiser Odyssey, leaving Navy Pier for a Skyline Cruise.)

Be a kid again at Navy Pier.

Originally there was to be a second pier (#1) constructed back in 1916, but it never materialized.  Today, Navy Pier is jam packed with entertainment, recreation, and sailing and dinner cruise ships. The original round brick ballroom at the very end of the pier is one of the largest in the world, and the pier often serves as a conference and trade show site.

The master plan for the pier was designed in 1909 by Daniel Burnham, and the 1.5 mile pier was commissioned for completion near the mouth of the Chicago River . Construction finally began in 1914 and it was completed in 1916 at a cost of $4.5 million. When it opened it was the only pier that combined the business of shipping with public entertainment. During the U.S. entrance to World War I the pier housed regiments of soldiers, Red Cross, and Home Defense units, and as a barracks for the recruits. After the war the Pier added its own street car line, theater, restaurants, and an emergency hospital.

In the early 1920s Chicago Mayor William H. Thompson created a 15 day Pageants of Progress that drew nearly one million visitors.  In 1926 WCFL labor radio station was added to the north tower, and in 1927 the pier was officially renamed Navy Pier in honor of the World War I vets.

During the Great Depression business on the pier dropped drastically. During the World War II years over 15,000 pilots were trained and qualified for their war duty — even George Bush, Sr. trained here. Many pilots practiced take offs and landings from a flattop aircraft carrier anchored near the ballroom, and to this day over 200 WWII planes rest at the bottom of Lake Michigan due to accidents during training. The Pier was no longer needed after the War and from 1946 to 1965 it served as a University of Illinois campus with the largest reading room library in Illinois, housed in the Navy’s main mess hall.

With the post war boom in business the pier was once again back in business with trade shows, exhibits, and social events and shipping. Then with the McCormick Place opening for trade shows in 1960, the Pier reverted back to a more demure use.  The Pier’s peak shipping handling peaked in the mid-sixties at about 250 vessels annually; soon after the pier was widened by 100 feet on the South Dock. 1960 also saw the city’s first Holiday Folk Fest with products from around the world. Then the pier was pressed back into service as a trade show and convention site when McCormick Place is destroyed by fire in 1967. This is short lived when the huge McCormick Convention center is rebuilt, and the pier falls into disuse until 1975.

Then the city fathers wake up to the importance of the inland pier and the Grand Ballroom is renovated for the Country’s Bicentennial Celebration in 1976.

Navy Pier is designated a Chicago Historical Landmark.  For a few years it hosts ChicagoFest, drawing millions of visitors with music, food, and entertainment.  After the Metropolitan Pier and Exposition Authority is created by the state legislature to manage and operate both McCormick Place and Navy Pier, a redesign of the pier is ordered, and five years later and $150 million later the pier opens with much fanfare, including the addition of the 1,500 seat Skyline Stage, year around entertainment, shops, restaurants, attractions, and exhibitions.

In years to follow officials welcome the Shakespeare Repertory Theater, which is modeled after London's Swan Theatre, featuring an intimate 525-seat courtyard-style theater with unequaled views of the lakefront, an English-style pub, a studio theater, a bookstore, a Teacher's Resource Center, and an English Garden.  Then the pier acts as the host of the city’s first Tall Ships festival, and the latest addition is the Smith Museum of Stained Glass Windows, dedicated solely to stained glass windows.

The Windy I unfurls daily from Navy Pier.

Windy II offers special week-long
summer adventure sailings

I am lucky enough to visit the Navy Pier in 2005, on its 10th anniversary of the renovations, and I celebrate with some great sailing and dinner cruising on Lake Michigan. The city is hot and humid, so the pier is packed with citizens partaking of the cool breezes blowing in.

As a tall ship aficionado, I was awed by the rigging and sails that fluffed full on Lake Michigan as I peered out from the Pier in jealousy.  The next day I am sailing on the 148 foot, 4-masted gaff topsail schooner, Windy, a sister ship to Windy II (both class B tall ships), both dock for day sails at the Pier.

Wendy looks older than her 1990s birth, but she is a replica of a traditional old trading schooner and training ship, but with modern navigation and equipment. Guests assist either Captains George Lisner or Bob and Janine Marthal and their crew in raising the sails or with a hitch at the wheel; I sit back and enjoy the 90-minute Skyline Cruise on Lake Michigan , the shallowest of the Great Lakes . Both ships sail regularly throughout the day, with the firework sailings at sunset the most popular trips, when Navy Pier lights up with sparkles and bangs and bangles. Parties and marriages have been performed on board the ships, and the aft cabin often serves as a dining area. Both ships offer educational programs for students, scouts, or schools so that young sailors can get a wisp of the wind and a spray of the salt, creating new burning adventurous desires on a tall ship.

Touristy crew on the Windy I.

The Windys are a member of the American Sail Training Association.  The top sail Barquentine, Windy II, often embarks on longer working and educational voyages on the Great Lakes that can last up to 12 days, with chances to learn modern seamanship. 

For more information on both ships visit for schedules and departure dates, or call 312/595-5555.  Tickets can also be purchased (fro day sails) on the day of the sail from the ticket booth located on the Pier. Advance reservations are required for the lengthier sailings on Wendy II.

The Navy Pier is a place where adults can be kids again, and after I hook up with Cynthia, Public Relations Manager of Premier Yacht Cruises, operator of the Odyssey, we first have to prep ourselves as big kids at the 3D Funhouse Maze before embarking on a luxury dinner cruise on the Odyssey. Don’t eat any hot dogs or too much cotton candy at the Pier, because the Odyssey’s Executive Chef and galley staff prepare a distinctive menu of appetizers, entrées and desserts on board daily, complemented with an extensive  comprehensive wine list.

I have to laugh at Cynthia because she orders a complete tasting menu of the Odyssey's entire menu, and other guests on board gasp at us in disbelief at our order as the 145 foot yacht silently cruises away from the Pier and out into calm, but deeper waters.  The linen is crisply folded and the dinnerware sparkles as we toast to the towering skyline. This is no brash Vegas-style buffet, and Kim, our kindly waitress, keeps the wine flowing. We were on the Lunch Cruise, which is more informal than the nightly dinner cruises that requires appropriate dinner attire.

Gourmet cuisine while
viewing Chicago's skyline.

During the Lunch Cruise, the Amethyst, Sapphire, and Topaz Decks herald three piece bands with vocalists offering a broad repertoire. Cynthia and I are dining on the Amethyst deck, featuring the piano and vocal stylings of Steve Carson, performing classical, jazz, show tunes, and pop selections in a relaxed atmosphere.

During the Sunday Brunch, the three decks feature recorded, upbeat jazz background music. Weather permitting, guests will enjoy the sounds of the Mike Frost Group on the outside deck playing a wide range of jazz from artists such as John Coltrane, Miles Davis, and Branford Marsalis. At midnight, all cruises feature live jazz entertainment.

The largest dinner cruiser in the USA!

The Odyssey is a fantastic ship, and after visiting the bridge and joking around with the captain and first mate, I feel that I could even captain this smooth running vessel because only a joy stick controls all the onboard navigation computers.  I think the captain is having the most fun of all, another adult, acting like a kid, on Navy Pier.

Book a special event with Odyssey.

Add an extra flair to your Odyssey cruising event with the Special Occasion Package. It includes a keepsake Odyssey logo photo frame (5x7 photo included) and a box of four delicious chocolate truffles in an Odyssey logo gift bag that will be waiting for you at your private table. Plus, your party will receive an elegant special dessert presentation that will highlight your special occasion. Call the Odyssey reservation agents at 888/741.0281 (Groups of 30-700, call 888/741.0282 for additional Group Cuisine & Menu options) or add the Special Occasion Package to your online reservation at

Fine dining Sunset Cruise on the Odyssey.

I didn’t have to act like a kid any more because I am one when Cynthia orders every conceivable dessert onboard, and I must admit, I had to shy away from the some of the mountainous tempting treats. Later I collect my souvenir photo taken with Cynthia that was snapped upon boarding — and no I didn't turn into a rail bird after all the choco desserts!

Lake Michigan Seadogs!

Something Completely Different

I thought this Navy Pier adventure was over, but nope, I was going to turn into a real Sea Dog on the speedboat — The Sea Dog, which is also operated by the same company as the Odyssey. The Sea Dogs (there is four Seadog speed boats) are also berthed at Navy Pier, and it is the antithesis of the stately and sedate and smooth cruise of the Odyssey.  Yeah, the hair is blown back, the spray washes your face, and the roar of the powerful 2000 HP turbo-charged engines scream only loader than the passengers as we hit a top speed of 30 knots. We cruise along the lake shore to Chicago's Museum Campus where we will pause to hear about Chicago's interesting lakefront landmarks, architecture, and history. Seadog then races North past Navy Pier to cruise the Magnificent Mile shoreline with unique views of the Sears Tower, Buckingham Fountain, and Grant Park along the way.

The historic Architectural Tour
on the Chicago River with
a Seadog cruise.

Discover why over 150,000 people annually ride Seadog! And your dog rides free!! Hah — Fido will even get a kick, but bring goggles! Become a Seadog at

The Premier Yachts also offer dinner cruises in Boston, and a very unique dinner barge in Washginton, D.C., plus the more informal Mystic Blue dinner cruise from Navy Pier. Fopr more info on these cruises visit

The Odyssey is the largest dinner cruise boat in the U.S.! Here are a few of its menu samples:


Port Glazed Duck Confit — Slow Roasted Duck with Natural Juices, Bay Leaves and Port Wine served atop a pillow of Sweet Corn Polenta with Currants and Apricots;

Classic Caesar Salad — Crisp Romaine Lettuce tossed with Parmesan Cheese and Croutons served with a Classic Caesar Dressing;

Crab and Corn Chowder — Sweet Blue Crab and Tender Corn simmered with Potatoes and Peppers in a Rich Sherry Cream;

Main Courses

Maple-Glazed Roasted Chicken — Chicken Breast roasted with Maple Syrup and served with Garlic and Herb Gnocchi, Butternut Squash and a Brown Sugar and Soy Drizzle;

Maine Lobster Ravioli — Lobster Stuffed Ravioli finished with a Brandy-Lobster Reduction and Grilled Asparaus Tips;

Center-Cut Sirloin — Slow Braised Beef Sirloin served with Cheddar Mashed Potatoes and Roasted Root Vegetables;

Asian Salmon Salad — Sesame-Crusted Salmon marinated with Soy and Ginger served with Romaine Greens tossed in a Cilantro-Rice Wine Vinaigrette;

Spinach and Portabella Wellington — Fresh Spinach, Roasted Red Peppers and Grilled Portabella Mushrooms wrapped in a Golden Brown Puff-Pastry served on a bed of Marinara with Grilled Asparagus and Carrots,

The Chef can prepare a vegetarian option for the main entree
should you prefer one. Simply notify your server or give notice before boarding the Odyssey. There is also wide selection of seasonal desserts, mostly chocolate laced!

Sure Navy Pier offers a rollarcoaster and ferris wheel and there is sidewalk dining with free jazz and the Chicago free trolley makes a stop at the Pier, plus there is lots more to do, so check out for details. I guarantee you will feel like a kid again. The largest cruise ship on the Great Lakes also docks at Navy Pier during the summer. Please read my feature about The German flagged C. Columbus, entitled: "Great Lakes Sonnig Cruise".

By Kriss Hammond, Editor, Jetsetters Magazine.