ILLINOIS

YEAR VISITED: 2009, 2016, 2018, 2020, and 2025.

FAVORITE CITIES AND EXPERIENCES: Chicago is a world class city and the 3rd largest in the United States. Located on the shores of Lake Michigan it consistently ranks as one of the prettiest cities in the world. It is certainly one of our favorite big cities to visit. I have been there three times and each visit has begun at Navy Pier. It jets out over 3,000 feet into Lake Michigan and is a perfect mix of shopping, restaurants, and activities – a perfect place to spend an afternoon.

We bought tickets for the Centennial Wheel, a Ferris wheel that reaches heights of 200 feet, and were impressed with the awesome 360 degree views of the lake and city skyline.

Following the ride we headed to Harry Caray’s Tavern on the pier. By my count, there are now seven different Harry Caray sports bar locations around Chicago. Besides this one, I have been to two other locations (7th Inning Stretch and Harry Caray’s Shortstop).

All are decorated with pictures of legendary sports figures and celebrate the late Cubs announcer. In 2009 Jill and I purchased an observation ticket to the Willis Tower.

This towering skyscraper stands at 1,450 feet tall, which is the 2nd tallest in North America, and the 12th tallest building in the world. From the 103rd floor, four states are visible on a clear day; Illinois, Indiana, Wisconsin, and Michigan. While I didn’t trust it, Jill loved walking out on the Skydeck (a section of the observation deck made of all glass that jets out from the building four feet).

In 2018 Jill and Bailey also visited the tower and both walked out on the Skydeck as well. Maddie and I, who don’t love heights, decided to stay on the ground and elected to go swimming. We walked north from Navy Pier and ran into the Ohio Street Beach. Not only was the beach sandy, we had beautiful skyline views of the city as well.

Both parties enjoyed our afternoon. When in Chicago you need to make a point to have Chicago style deep-dish pizza. Many establishments serve deep dish, but in my opinion the best is Lou Malnati’s. I have eaten at Lou’s multiple times at different locations, I have never been disappointed.

Another true Chicago establishment is the Billy Goat Tavern. While I believe there are seven or eight total locations, Jill and I visited the original tavern on lower Michigan Avenue and the entire family ate at the Navy Pier location. The Tavern became famous when owner, William Sianis, cursed the Cubs.

As the legend goes, William bought a ticket for himself and his goat to attend the Cubs World Series game in 1945. The stadium attendants, enforcing the no pet rule, didn’t allow William’s goat inside. After arguing futilely, Sianis issued his infamous curse “The Cubs ain’t gonna win no more. The Cubs will never win a world series so long as the goat is not allowed in Wrigley Field.” Was this an honest to goodness actual curse, or simply an angry reaction to being turned away from the big game? This question has been debated about in Chicago for decades. What isn’t debatable is that the Cubs lost the World Series to the Tigers in 1945 and didn’t go onto to break the Billy Goat curse for another 70+ years when they finally defeated the Cleveland Indians in the 2016 World Series. The tavern has a couple framed newspaper articles commemorating the Curse as well as neon signs reading “cheezborger, cheezborger, cheezeborger” in reference to the SNL skit filmed there in 1978.

This is a great spot to drop in, admire the unique decor, and order a cheeseburger and a Pepsi! Outside of Wrigley Field, one of the coolest experiences in Chicago is a boat tour. While there are many different companies, all offering somewhat of a unique experience, your two main choices are whether you would like a River or a Lake tour. We selected the Lake Michigan Skyline Sightseeing Tour and it was one of our favorite experiences of our trip.

The temperature was perfect, the sun was setting, and for approximately an hour and a half we had a perfect view of Chicago’s beautiful skyline.

When we return we look forward to selecting a river cruise as we have heard great things about that tour as well.

STADIUMS AND/OR SPORTING EVENTS: As far back as I can remember I have always loved baseball. In college I grew to be quite the history buff and caught the travel bug as well. Somewhere along the line my love of baseball and history morphed into a infatuation with MLB teams with long and storied traditions. As a result, outside of my hometown Seattle Mariners, the Chicago Cubs are one of my favorite MLB franchises as they have over one hundred years of history.

In 2009 Jill and I were able to travel to Chicago and attend a Cubs game. As we explored historic Wrigley Field and watched the game, I had to pinch myself. I had grown up watching the Cubs on WGN, followed their lovable history over the years, and now I was finally in this baseball cathedral; it was surreal to say the least. In 2018 I took the family there but with the Cubs out of town we just walked around the outside of the stadium and explored Wrigleyville.

Jill and I purchased a stadium tour ticket where we were able to take a guided tour through Wrigley Field.

We explored the press box, dugout, field, and walked around sections of the empty stadium.

This trip made such an impression on me that in 2016 when the Cubs made their historic run to the World Series, first time since 1945, I felt compelled to go. On a whim, a couple buddy’s and I flew to Chicago, I bought an extremely expensive ticket, and I attended Game #3 of the World Series in Wrigley Field.

While the Cubs lost that game, they went onto win the World Series and end their 108 year title drought. In some weird way I feel like I was a part of, or at least a witness to, baseball history.

Saturday I watched Game #4 from outside the stadium where it was reported an estimated 500,000 people showed up just to witness history. It was one of the coolest experiences I have ever been a part of and Wrigley Field and Wrigleyville holds a special place in my heart.

The Chicago White Sox have over a hundred and thirty years of history. Comiskey Park served as the home of the White Sox from 1910-1990. 1991 was the first year of the new stadium, which has had multiple sponsorship names over the years. While my preference would have been for the White Sox to continue playing at Comiskey Park, they did a nice job of preserving home plate of the historic stadium.

I attended a game with my dad in 1991 (the first year of the new stadium) and another game in 2025. My most recent trip game on the back end of a week long baseball trip, it was a Sunday day game, and I attended the game by myself. I purchased a club level ticket down the right field line and had a great day. My ticket came with a menu and a waiter.

The organization has a fairly storied past and they have done a good job of preserving their history.

There are statues of White Sox greats in the outfield and multiple plaques and pictures around the stadium celebrating historic moments.

An added bonus was getting to see the 2005 World Series trophy that was on display for the weekend.

ADVENTURE(S): I consider President Abraham Lincoln to be my favorite President. Therefore, in both 2009 and 2020 I made a point to drive the roughly three hours from Chicago to Springfield in order to explore the hometown of the 16th President of the United States.

Jill and I started our adventure at the Lincoln Presidential Museum.

If you have never been, I can’t recommend presidential museum’s enough. In my opinion, they are the perfect blend of interactive exhibits combined with real artifacts to make it a one of a kind experience. I have visited seven presidential museum’s and Lincoln’s is my favorite – the introductory video was unlike any I have ever seen. Following the museum we strolled through downtown. Highlights for us were the law offices of Lincoln-Herndon as well as the Old State Capital building.

The Capital building is where Lincoln delivered his “House Divided Speech” as well as where he lay in state following his assassination in 1865.

As I toured the historic building I could almost hear Lincoln deliver his now immortal words, “a house divided against itself cannot stand…”.

Our last stop in town was the Abraham Lincoln Home. We reserved a ticket and took a guided tour through the two story house. This was the only home that Abraham and Mary Todd ever owned.

It is also where three of their children were born and sadly where one child died. Today the home, and a three or four block radius, is well preserved. I remember walking the historical streets feeling as if I had gone back in time.

Following the Lincoln home tour we got back into the car and drove the 50 minutes to Oak Ridge Cemetery.

This is where President Lincoln, and eventually his wife and three of his four children were all laid to rest.

Behind the Arlington National Cemetery in Washington DC, this is the most visited cemetery in the United States.

NOTABLE DESTIANTIONS & STOPS: In 2020 we stayed a night in Joliet. Among other things, Joliet is the home of the Illinois State Penitentiary and the prison from the fictional movie Blues Brothers.

Seeing as I was a big fan of the 1980’s movie, I was excited to check out the sites made famous by John Belushi and Dan Akyrod.

That night I read up on specifics and discovered you could take a tour of the prison, and or walk around the grounds on your own, as the prison was no longer a working prison. The next morning I got the family up early and decided to drive to the prison, just like I read about, to take pictures of where the movie was filmed. We pulled into the parking lot adjacent to the prison as I was telling the girls all about the movie from my childhood, and I started taking pictures of the prison (I thought was no longer in commission) made famous from the movie Blues Brothers. Within thirty seconds a white truck pulled up behind us and a uniformed prison officer got out and asked if we were okay. I’ll never forget his exact words, “Are you under duress in anyway? Is there anything I can help you with?” While I stammered, “No, I am just a movie buff and we wanted to see where the movie Blues Brothers took place” somehow as the words were coming out of my mouth I knew I had somehow messed up and this was a working prison. He informed me exactly that and while he wasn’t going to pursue anything, he could prosecute me for taking pictures of a working prison. Then he escorted us off the premises. As I drove a couple miles down the road, I was understandably shaken and wondering how I had gotten this so wrong, which is about the time I somehow stumbled upon the former Illinois State Penitentiary which is what I was looking for all along.

This is the site you can take a tour of and or walk around taking pictures.

Please don’t make the same mistake I did… you want the former Illinois State Penn. While we laugh now, we were all a little shaken that morning. The beauty of road trips is that you win some and lose some but you just keep on truck’n with a smile on your face. Besides, everything turns into a story at a later date. Both times Jill has been to Chicago she has made a point to go to Six Flags Great America located in Gurnee. The first time she took me and the second time she took Bailey. Bailey and Jill love roller coasters equally; the bigger the better.

They had a blast riding the 10+ thrill ride coasters over and over again. When I went with Jill I spent more time taking pictures with characters and ultimately holding her purse while she rode the large roller coasters.