Chicago, Illinois

Carve out a few extra days on your Great Loop adventure to explore Lake Michigan’s Windy City.

Cruisers who complete the Great Loop—the waterway route enabling circumnavigation of the eastern half of the U.S.—build in extra days for unplanned delays but also to explore specific areas on their more than 5,000-mile journey. Some seek out the seclusion of picturesque bays, while others prefer the excitement of cities they’ve never explored. If your Great Loop excursion plans take the traditional counterclockwise route, you’ll exit the Great Lakes region via Lake Michigan to the Chicago River through Chicago, Illinois. Build in several days and even up to a week to explore the “Windy City”. Its appeal may surprise you and even whet your appetite for a return trip though likely not in the winter months.

As you approach the southwest end of Lake Michigan, even from a distance, Chicago’s downtown skyline is striking. The Willis Tower—formerly named but still frequently referred to as the Sears Tower—is the second tallest building in the western hemisphere and easy to spot. The surrounding architecture encompasses a lively urban landscape with the city’s financial district and juxtaposes the many museums, parks and fountains lining the lakefront. Moored at Monroe Harbor, sailboat masts accentuate the view like exclamation points on a cityscape, while colorful sails catch the currents off Lake Michigan; take care as you approach the Windy City for sailing regattas in process. Just north of the mouth of the Chicago River, a Chicago landmark juts out into the lake; Navy Pier was built in 1916 to service freighters on Lake Michigan. Converted in 1941 for military training prior to World War II, Navy Pier was renovated in the early 90s for its current purpose as a recreation center and remains one of the most popular tourist attractions in the Midwest. The ferris wheel was dismantled in 2015, but there are plenty of other attractions for young and old, including a spectacular July 4th fireworks display and summertime music events, many of which are also accompanied by fireworks.


For the most part, where you dock is determined by how close you want to be to your favorite activities. The Chicago Harbor System has 10 unique harbors, some of which are along Chicago’s lakeshore and each with its own distinct attributes. All offer transient dockage; several offer boat ramps and trailer parking for those traveling with boats on trailers. Be sure to review the System’s website and make your reservations well in advance, especially for holiday weekends that attract Midwest cruisers from 100 miles away or farther ( An alternative to the large lakeside marinas is Marina City on the Chicago River in the heart of the city’s action. Again, make reservations well in advance for the few transient slips located under the famed steakhouse Smith & Wollensky. This is also a great location to get off the boat for a few nights since the Marina City complex houses Hotel Chicago (an Autograph Collection Hotel). Request a room on one of the upper floors to enjoy a spectacular nighttime view of the city.

Repeat “Loopers” and local cruisers alike are familiar with the wide variety of Chicago’s offerings. Art and history buffs have their pick of museums, many of which are within walking distance from lakefront harbors. Even the most finicky eater will be hard-pressed to find something to complain about when introduced to a Chicago-style deep-dish pizza or a hotdog from a street vendor. They pile dogs high with Chicago-style fixings, sans the ketchup—a faux pas here. For the fashionistas on board, a full day of shopping on “The Magnificent Mile” awaits on a one-mile stretch of Michigan Avenue. If you’re as comfortable with heights as you are on the water, take the elevator ride to the skydeck on the 103rd floor of Willis Tower, but go late in the day to escape the crowds and take advantage of the sunset view (

Sports venues are varied and frequent. For baseball fans, Wrigley Field is a cab-ride away. For football fans or music lovers, Soldier Field ( is the home field and stadium for the Chicago Bears, hosts many summertime concerts and is conveniently situated close to Burnham Harbor. From Lake Michigan, the marina entrance is at the south end of Northerly Island, with channels and shallow areas well marked. Burnham Harbor’s location also provides walking distance access to the Field Museum, Shedd Aquarium—a family favorite—and the Adler Planetarium. All three are worthy of at least a half- or full-day visit, so plan your time accordingly since there’s so much more to see, including the Chicago Water Tower, one of the few buildings to remain after the Great Chicago Fire of 1871.

In addition to choosing which of the city’s attractions to see, deciding where to eat will likely be your biggest challenge with so many options. Limited space prevents offering a comprehensive list, but seafood lovers won’t want to miss Catch 35 on the south shore of the Chicago River near Trump Tower. Steak lovers must dine at Gene and Georgetti’s, but bring your autograph book and camera. Celebrities and politicians alike have been dining there alongside locals since 1941.


—Dockage and Fuel—
Belmont Harbor
3600 Recreation Drive
(312) 742-7673 •
* Family favorite

Burnham Harbor
1559 S. Lake Shore Drive • (312) 747-7009
* Close to Shedd Aquarium, museums and Soldier Field

DuSable Harbor
111 N. Lake Shore Drive
(312) 742-3577 •
* Lakeside, just south of the Chicago River

Marina City
300 N. State Street
(866) 490-5297 x161 •
* Downtown river location

Hotel Chicago (Autograph Collection)
333 N. Dearborn Street
(312) 245-0333

—Eateries & Attractions—
Catch 35 Seafood & Premium Steaks
35 W. Wacker Drive • (312) 346-3500

Gene and Georgetti’s
500 N. Franklin Street • (312) 527-3718

Harry Caray’s Restaurant Group
8 locations • 

By Liz Pasch, Southern Boating Magazine August 2016