Chicago Summer Weekend

For years, I traveled to Chicago for business, but those trips left little time for exploring the city. After one such trip, we finally stayed for a long weekend and discovered just how much Chicago has to offer—great food, endless activities, and a walkable downtown that made a car unnecessary. We were eager to return.

When the chance to visit again came up, we jumped at it. Our first stop? Pizza, of course! Not the deep-dish Chicago is known for, but enjoying a slice by the river on a sunny day was the perfect welcome. While Chicago offers far more than we can cover, here are a few highlights to consider for your own trip.

Chicago has a Riverwalk, along the Chicago river. There are tons of open air restaurants along the walk. There are also beautiful town homes and high rise condos, that I am sure are where you pay for the view.

You can rent any kind of water vessel along this river. From Kayaks to Luxury Yachts and everything in between we saw tons of activity on the water. This was actually about 7:30 on a beautiful summer evening. It seemed everyone was out.

Millennium Park

Our hotel was a little over a mile from the Riverwalk area. After a delicious Italian dinner we walked back. We stopped at the famous Cloud Gate Sculpture. This stainless steel sculpture was added to the park in 2006. It’s called the “bean” sculpture by the locals.

But of course, everyone, including us, had to get a picture in front of the Cloud Gate Sculpture. The bright stainless piece is meant to reflect the Chicago skyline. (And everyone’s backsides in their pictures!)

Next, we came across Crown Fountain. A pair of 50 foot glass sculptures with lifelike images bookending a pool of water. Right at dusk it was beautiful to see against the Chicago skyline. Of course, in the warm weather, kids were splashing in the pool. A great end to the evening!

The next morning we woke up and got out early, ready for more adventure. We could see this fountain from our hotel room, so we went to check it out. It’s Buckingham Fountain, famously in many TV shows and movies, namely the opening to “Married, with Children.”

Historic Hotel

The brown with beige top building was our hotel. The hotel was opened in 1927 as the Stevens Hotel. At the time of opening, the over 1,500 rooms made it the largest hotel in the world.

It was purchased by Hilton in the early 1980’s and renovated. Inside, it still has a lot of art deco architecture and décor. We were lucky to have a lake view.

We walked back to the Riverwalk and hopped on an architectural tour boat. If you go to Chicago for the first time, this tour should be the #1 stop. There are several tour companies. We booked our tour online before venturing out in the morning and were able to jump on the boat at noon.

So many historic buildings to see. There is a guide on every boat that takes you through the various architectural styles. Too many for me to name! Below is the Wrigley building (as in gum), built in 1924, once the headquarters to the company.

Front Row Seats

We had great seats right on the top deck, right up front. But, as our luck goes, the one hour it rained all day was the latter part of our tour. So we hustled down and took shelter on the bottom deck for the remainder of the tour.

Willis Tower, once home to Sears, was the tallest building in the world for a long time. The locals still call it the “Sears Tower” as it stands above all else in Chicago at 110 stories and almost 1,500 ft.

The interesting thing abut the river is it runs backwards, coming from Lake Michigan out. This was an attempt to keep Lake Michigan clean as it is drinking water to the area.

Staying dry below deck.

The tour was fantastic and the rain cleared up just as we were finishing up.

Overall a great day in Chicago!

After a great evening, we woke up to a hazy day. We had decided to rent e-bikes again to ride along Lakeshore Drive. The path along the lake is 18 miles.

Great Bike Riding

I’m not a confident bike rider in street traffic. The paths here, were specific to bikes, out of traffic, as well as mostly out of the way of pedestrians.

Hazy Chicago Skyline

It did not rain again but the haze remained.

We loved riding along the parks, marina, beaches and restaurants on the path.

We went a total of 22 miles!

We were in Chicago to see one of our favorite bands play in our first concert in two years. So we had an early dinner at 4:30. Easier to get a reservation at a One Star Michelin restaurant called Tzuco. It is the only Mexican chef in Chicago to have earned a Michelin star. The prices were reasonable for an outstanding meal in a very well designed space. We ate on the patio. Would definitely be back to Tzuco!

After a great night at the concert, we wanted to escape the heat and humidity. We went to the Art Institute of Chicago. Again, if you only visit once, this museum is definitely one to consider.

We were lucky, there was a special exhibit of the official portraits of Barack and Michelle Obama. They are on loan from the Smithsonian.

This museum is huge, with a surprising amount of very notable work. The architecture of the building itself was beautiful.

There was everything from Warhol to Renoir to Renaissance. For me, it’s all about the Impressionism art. The Art Institute had a significant collection, that was impressive. We only spent about 3 hours overall in the museum. You could easily spend all day!

Monet is my absolute favorite classic artist. We try to see his work wherever we visit. There are about 2,500 Monet paintings in the world. The Art Institute has 6 of the nearly 2 dozen of the famous “Wheat Stack” series. Magnificent to see for sure!

A recent acquisition for the museum is the Hartwell Memorial Window. This was commissioned in Rhode Island over 100 years ago, by the Tiffany Studios, for a church. In 2018 it was gifted to the museum. It’s made up of 48 unique panels of different glass types. It was beautiful and you can see how large it is.

A great afternoon in an beautiful (and air conditioned) museum!

As our time in Chicago came to an end, we were so grateful we were able to return. This is an interesting and lively city, well worth visiting. We hope to come back someday again!