The Windy City, Chi-Town, Second City, City by the Lake. Whatever you call it, there’s no place quite like Chicago, Illinois, and we loved every minute! October 6 – 14, 2019 🌬🌬🌬🌬🌬🌬🌬🌬🌬🌬🌬🌬🌬🌬

Heading south on Lake Michigan, Chicago, here we come!!

We again had a beautiful (and rare!) day to boat on crazy Lake Michigan for our 62 mile trip down to Chicago.  It was sunny and clear, and while it was only 51 degrees when we left shortly after 8 am, it warmed up to 70 later in the day.  Although the winds were blowing at 12 mph, they were coming out of the west, so we had only gentle rollers on the Lake.  We felt so fortunate to be able to calmly experience this beautiful lake.

Just north of the city, the sprawling campus of Northwestern University and it’s unique buildings line the Lake shore.

Beautiful Northwestern University

It’s always a thrill to approach a big city from the water, and Chicago is no exception.  The harbor was busy with various kinds of pleasure craft, as it was a Sunday, almost always the busiest day on the water anywhere!

Entering the Harbor in Chicago

We were settled into our slip at 2:30, which left us plenty of time to get on our bikes and start exploring! The park, bike paths and the river walk were jammed, so we headed back to the boat and relaxed enjoying our spectacular view of both the skyline and the Navy Pier. The last time we were in Chicago together was shortly after our wedding 40 years ago, when we drove across country to live in San Diego for a few years. It’s clearly been a while, so we were super excited to spend time here again.

Views from the bike path and the boat

We loved staying in DuSable Marina, as we were in the heart of the city…convenient to everything!  We took great advantage of our location, particularly having the bike paths so close, as we biked everywhere!  There was always something going on, and you can’t beat the views!

Lots of air traffic on the day of the Chicago Marathon

Night time views of Chicago from beautiful…love this city!

Our first stop the next morning was the Art Institute of Chicago.  The museum has changed a lot since we were last here 40 years ago.  This is an amazing museum, with extensive collections of European painting and sculpture (including a remarkable Impressionist collection), Modern, Ancient and Byzantine, African, American, Japanese art, and so much more.


Degas, Chagall, Van Gogh, Rodin, Cezanne, Renoir, Cassat, Homer, O’Keefe, Ancient Greek and Roman…Spectacular! Love this incredible museum.

This is one of the most breathtaking collections of Monets in the world, and Nancy was in heaven to see it again!

Ahhh…Monet ❤️

One of the best known pieces in the Institutes’ Impressionist collection is Georges Seurat’s “A Sunday on La Grande Jatte”, painted in 1884. It is Seurat’s best known and largest work, and was revolutionary for its time, as he painted this by applying dabs of unmixed pigments to the canvas so they would come together when viewed from a distance.


“Sunday in the Park with George”

We continued to explore Millennium Park, enjoying the beautiful gardens, fountains and paths throughout. We especially enjoyed  Pritzker Pavillion, Frank Gehry’s beautiful band shell, and the paths and bridges leading to it.

Frank Gehry’s Pritzker Pavillion, bridges and paths

pic 15

Millenium Park, Centennial Fountain, and of course, “The Bean”, officially titled “Cloud Gate” by artist Anish Kapoor

We decided that we wanted to enjoy a nice steak dinner in Chicago, but try to do it without breaking the bank! After soliciting suggestions from friends and former colleagues of Nancy’s, we settled on Kinzie Chophouse. The restaurant is beautiful, and the food was fabulous, but unfortunately, our service was pretty awful. Regardless, we thoroughly enjoyed this delicious meal.

Delicious steak dinner at Kinzie Chophouse

The next morning we were off to take the Chicago Architecture Center Boat Tour.  Everyone we know who lives in or has visited Chicago has recommended taking this tour of the River that runs through downtown Chicago, with docents who are professional architects. Their insight was priceless, the buildings spectacular, and it was fascinating!

Chicago River Architecture Tour

After the boat tour, you can visit the Architecture Center’s exhibit that features models of the world’s tallest buildings, a great model of the city, and the gift shop has some reasonably priced, unique gift items.

Chicago Architecture Center

After finishing our tour, we were starving, so we went on a hunt for Pizzeria Uno, home of Chicago’s famous deep dish pizza. It was amazing, and well worth both the walk and the 25 minute wait for the pizza to cook!!

The Original Pizzeria Uno…delicious!

No visit to Chicago would be complete without a visit to the top of Willis Tower, known as Sears Tower until 2009. Since we last visited 40 years ago, they have added crazy glass extensions that you can step out into for a full view above, around and below you.  We opted not to wait on the very long line to get freaked out!

Willis Tower views

One of the really great things abouChicago is you can wander endlessly, and constantly stumble on something to enjoy, from murals and sculptures, to beautiful old hotels, parks, and gorgeous old buildings with all of their stunning accents!


We had read that the Chicago Cultural Center was a must see, with it’s beautiful Tiffany stained-glass dome (one of two in the building) and tile work, along with the incredible building itself.  Dating back to 1897, this landmark building was Chicago’s first public library and free cultural center, and still offers a wide variety of cultural activities to the general public. Each wing of the building has coffered ceilings, grand staircases of marble and mosaics, and it’s own stained glass dome (the Tiffany being one of them).

The Chicago Cultural Center

The Palmer House Hotel was built by Potter Palmer, a Chicago business magnate, in 1871 as a wedding gift for his wife Bertha. Unfortunately, only 13 days after its grand opening, the Palmer House was destroyed by the great Chicago fire. Potter rebuilt the hotel, and it reopened on November 8, 1873. Now owned by Hilton, the hotel recently underwent a $179 million renovation.  It’s worth a walk through…just spectacular!

The beautiful Palmer House Hotel

After our wanderings, we stopped into Luke’s for a famous Chicago Hot Dog and beef sandwiches.  Yum!

We were super excited to see Hamilton while we were in Chicago. We have been wanting to see the show for quite a while, but tickets in NYC are silly expensive. Fortunately, tickets here were far more reasonable! If you haven’t seen it, figure out a way to go, as it is an incredible show! Probably the best, and definitely the smartest production we’ve ever seen!

Chicago’s Navy Pier was a short bike ride from the marina, and we had a great time exploring the area, riding the ferris wheel, and Nancy had a blast on the swings! The entire pier was decked out with fun fall decorations, including incredible carved pumpkins, skeletons, mums, corn stalks and more.


Pumpkin Fest at the Navy Pier

The Ferris Wheel


Nancy on the swings…she had them all to herself!! ❤️

Nancy had a great time reuniting with her Prevention Magazine friends/colleagues Lorna Phillips and Clarisse Challgren…it was as if no time had passed!


Clarisse, Lorna and Nancy

There are so many amazing museums in Chicago, and we tried to hit as many as possible.  We enjoyed the huge and varied exhibits at the Museum of Science and Industry, including a great Imax film on the oceans, a rebuilt coal mine, an amazing display of model trains and much more.

Museum of Science and Industry

We tried several dates and times for dinner reservations at Girl and the Goat without success, but had read through our boater forum that they welcome early walk-ins. After a disastrous Uber ride (our driver got hopelessly lost), we finally made it to the restaurant at 4:45 (I know, nerdy old people!). We were seated immediately in the main dining room with the caveat that we finish our meal by 6:30. No problem! It also helped that the service was outstanding…along with the food!  Absolutely one of the best restaurants of our entire Loop!

The Girl and the Goat..a truly remarkable meal!

The Shedd Aquarium was another great stop, with extensive exhibits on various fresh and salt water habitats, dolphins, sharks and some very cool jelly fish!

Some of the residents at Shedd Aquarium

After a fabulous week in Chicago, it was time for us to head down to Hammond Marina in Hammond, Indiana, where we would be meeting a group of fellow Loopers to stage our progression down the rivers and through the locks. We left Chicago on the morning of October 14th, under warm, sunny skies and calm seas, to get ourselves provisioned and coordinated for the trip.

Three of the locks south of Chicago were closed for maintenance from September 21 – October 6 . There were nearly 100 Looper boats who did not rush to get through the locks before their closure.  Additionally, there was a big back up of commercial vessels, along with other (non-Looper) pleasure craft, all working together to coordinate traffic and ease congestion.  We were so fortunate to have AGLCA, Waterway Guide, and the Lock system working together along with the boaters to ensure an easy passage. Misty was set to join Group #3, along with No Schedule, Domino, Yots of Fun, Drifters, Thunderbolt, Kissed Some Frogs, Velsignet, Pura Vida and Long Way Home.


Carol, Malachi, and Ken/No Schedule greeting us upon arrival at Hammond Marina

So, good-bye for now Chicago, we loved every minute!

   Send article as PDF   

Leave a Reply