As the school year came to a close in 2024, my wife and eldest daughter went on a service trip to Nicaragua, starting on Memorial Day weekend and lasting for 8 days. To keep the wander lust as bay, Clara, JR and I decided to take a short jaunt to Chicago and catch a White Sox home game.
If you are asking why in the world did we choose the White Sox, the answer is pretty straightforward. For one, it is a direct flight from NOLA to Chicago, which made traveling with a three year old a lot easier. Two, we had never been, and I would like to see a ball game in home stadium of every team. Counting the ChiSox, I am up to fourteen.
We were in Chicago for less than 24 hours total, but we had a great time. There’s so much to do there, that we could go back again and have a completely different experience.
What We Did
Stax Cafe: We arrived quite early, and the game didn’t start until 1:10 pm, so our first stop was at Stax for pancakes. There are at least two of these in Chicago, and I was very impressed. They have a very diverse menu for breakfast and for lunch, and have several options for kids. All three of us got pancakes, and while JR, who is a bit of a pancake snob, said they weren’t the best he’s ever had, they were definitely above average. We were all very satisfied.
Maggie Daley Park: This is a great public play area right off the water in downtown Chicago. It has a lot to offer, and while we didn’t have a ton of time, we managed to get in 18 holes of mini golf and about 45 minutes on the playgrounds. There’s a lot more to do in this area, and it has great options for kids. We probably could have spent the whole day there. The only drawback is that parking is kind of confusing and kind of expensive.
White Sox Game: If you were too suggest that the White Sox stadium has the worst name in baseball, I wouldn’t disagree. That said, the stadium itself is quite impressive. While it isn’t in the best part of the city, the area immediately surrounding the stadium is great. There is ample parking, and since the team is pretty mediocre at the moment, we were able to park less than five minutes away.
There is a large Kids’ Zone in the outfield, but we actually didn’t take advantage of it. JR said the pretzel was a 6 out of 10, which is much higher than Philadelphia, and Clara easily took care of a hot dog. My only complaint about the food is that they didn’t have any candy (as far as we could tell), which helps to get a three year old through 3 hours of ball.
My favorite things about the White Sox experience are the batters eye and City Connect jerseys. Centerfield is lovely copse of green trees and bushes that creates a much more esthetic batters’ eye than does a simple green wall. While they weren’t wearing their City Connect jersey’s that day, I think the White Sox’ is one of the best. I see little reason to ever go back the Guaranteed Rate, but I would definitely recommend it.
Lou Malnati’s: We closed the night with deep dish pizza and spaghetti at Lou Malnati’s. I am not expert in Chicago-style pizza; frankly, it’s not my favorite. That said, the food was good, the beer was cold and the people were friendly, so what could there be to complain about?
We had a great, brief experience in Chicago, and while the Sox field certainly doesn’t compare to Wrigley, it certainly isn’t at the bottom of the list of stadiums that we’ve visited. It probably doesn’t make the list of must-do things in Chicago, but for the MLB fans hoping to visit every stadium, Guaranteed Rate is more than just a box to check, it was a very pleasant experience. We spent the night at a Holiday Inn Express (which was not very nice) near the airport and caught the early flight home.
Next up, we’ve got an RV trip through the Dakotas, so stay tuned to see if I hit another Dairy Queen.
I have said many times that the planning of a trip creates almost as much joy as does the vacation itself, and I stand by that statement. In the case of the Igoe’s recent vacation to Chicago, the planning was a multi-year process.
In early 2020, we decided to take a vacation over the Easter holiday to Chicago. As I am sure everyone is aware, only a few weeks after we planned everything out, the world went crazy and everything was shut down due to COVID.
This year, as Easter approached, we very closely watched the news, and the numbers, and all the information from the various departments of health, and when the time came, we were able to pull the trigger and take the vacation that we had been planning since 2019.
On Good Thursday, we landed at Midway Airport and drove straight to Lou Malnati’s. This is a deep dish restaurant chain that makes a great, almost stereotypical Chicago-style pizza. For those of you who have never had deep dish pizza in Chicago, it is very different than what is considered deep dish elsewhere. For one, the crust is actually not very think, but is much more like what you would see in an actual pie. The next layer on our pizza was cheese, followed by a pizza-sized patty of sausage. To clarify, I do not mean multiple chunks of sausage, but one large disc. On top of this was poured the sauce, so to most us, this is basically an upside down pizza. While I will not say that Lou’s is the best pizza I have ever had, it was a great way to wade into the deep dish pizza waters.
From there, we headed down town to stay a Hampton Inn in the Majestic building. The year prior, we had reservations at the Palmer House, but due to capacity limitations, could not get a room. While there was nothing all that special about the Hampton Inn, it was inside the loop, walking distance to plenty of attractions and more than adequate in terms of accommodations.
The next morning, we all awoke when the baby started making noise, loaded up the rental car and headed for Indiana. On the way, we stopped at Firecakes Donuts. Evidently, Chicago has become a mecca for artisan style donuts, and Firecakes was the first of the three we tried. At all three, I got a classic old fashioned, and while Firecakes was not the best of the three, it was nonetheless fantastic. More on the donuts to come…
About an hour east of Chicago is Indiana Dunes National Park. Indiana Dunes is one of the country’s newest National Parks, previously designated a National Lakeshore, to the point that they have not yet installed a permanent National Park sign. When we arrived, the kids got their passport books stamped, and we picked up three junior ranger packets. We headed into the park, straight for the Three Dune Challenge. This is a relatively strenuous hike that goes up and down three separate sand dunes. It is not easy to explain how difficult a dune can be to ascend if you have never hiked one before, but walking up hill in the sand is quite cumbersome (especially with an 18 pound butterball strapped to your stomach). The payoff was worth it though, as the views of Lake Michigan from atop each peak are nothing short of spectacular.
Indiana Dunes is far more popular in the summer time, when you can camp out on the beach and play in the water, but there is plenty to do and see, no matter what time of year you visit. It is definitely a park that you could spend three or four days exploring, but it is also one that can be adequately experienced if you only have a few free hours. Even though this was our first excursion of the trip, I think it was my favorite experience overall. If you get the chance, I strongly recommend visiting this really unique park to take in a landscape that can be found in very few other places across the country.
On our way back to Chicago, since we had our passport books, we decided to stop at the Pullman National Monument. This site memorializes a really interesting moment in Chicago history when George Pullman created a planned community in which his factory workers could live. He was attempting to keep the families of his employees from having to live in slums, but at the same time, forced them to rent from him. It was quite controversial and eventually led to significant strife.
This site was only designated a part of the NPS in 2015 and is still in development. It is really interesting, but there is not a whole lot to do as of yet. If we ever get back to Chicago, I hope to visit the monument again.
From there, we got drove to the hotel, parked the Hyundai and walked up to the Chicago River, where we got on-board a Wendella tour. There several companies that offer architectural river tours, and the one recommended to us by several friends was Wendella. At certain times of the year, they actually go into Lake Michigan as well, but for this time of year, that was not available.
Following the Great Fire of 1871, Chicago developed a very interesting and unique architectural style. Multiple skyscrapers, luxury apartments and stone buildings have gone up along the river, and this 90 minute cruise gives tourists a chance to take it all in and learn a lot about the history of the city. I should warn you that the cruise does get a bit chilly, so dress appropriately and do not hesitate to take advantage of the bar and warm yourself up with a cocktail. I believe this was Alyson’s favorite part of our trip and in terms of bang for your buck, this is a can’t miss tourist attraction.
That night, we ate at Harry Caray’s Italian Steakhouse. As it was a Friday in Lent, I was a little disappointed not to get to try the steak (as was the waiter), but the pasta dishes we all got were amazing. This is one of the most impressive restaurants that I have ever been in. It is basically a high-end version of a sports bar, with pictures and quotes and memorabilia everywhere. And it is not just a bunch of Cubs non-sense; the entire baseball community is represented in one form or another. We were actually lucky enough to meet one of Ernie Banks’ sons during our meal. I was quite skeptical at first, but he very quickly proved that he was, in fact, the child of Mr. Cub.
The next morning, Clara woke us up early again, and we headed for the Donut Vault. Another of Chicago’s boutique bakeries, the Vault offers the classics as well as several unique options. I got the old fashioned again, and again it was great, but it was not the best one I had over the weekend. My son got a pair of enormous donut holes that he claims were the best thing he ate all trip.
That morning we went to Field Museum, one of the city’s most diverse attractions. I visited once as a child and remember it being primarily dinosaur bones. Whether or not that is just a child’s memory or things have changed, this museum has evolved into one of the greatest natural history attractions in the country, rivaling the Smithsonian.
In addition to really impressive dinosaur skeletons, like the T. Rex Sue, the museum has amazing exhibits on the history of the planet, on the history of human beings, an impressive collection of gem stones, and then about six more hours worth of things to see for which we did not have time. They even have several virtual reality simulators that helped to keep the kids engaged throughout. I think this was Eileen’s favorite part of our Chicago adventure.
It was recommended to us that we eat at the Billy Goat Tavern. Those of you that are older might recall a classic SNL sketch based on this restaurant. It is a classic, tucked underneath the city streets that can be hard to find if you come from the wrong direction. There are a few options, but 95% of the food served are thin, grilled burgers. The food is good, but the atmosphere is what makes it worthwhile. If you have never been there before, it is important to keep in mind that even though the menu only has singles and doubles, you can order as many patties as you like. I got a triple, which ended up being the appropriate meat-to-bun ratio, but in my hungrier youth, I could easily have put down a quadruple or quintuple.
The next stop on our tour was the 360 Chicago Observation Deck in the John Hancock building. I have heard that the views from the Willis (Sears) Tower are actually better, but it was closed due to COVID, so beggars can’t be choosers. I am forced to confess that this was my least favorite part of our trip. We purchased 2 pm tickets and arrived at 1:40. When we got there, we were told it would be about an hour and fifteen minute wait. When I asked an associate what was the point of having 2 o’clock tickets if it didn’t mean we got to go at 2 o’clock, she told me that they do not guarantee anything, but that our tickets were good for a year.
As unhelpful as that was, we decided to stick it out, and made it to the 94th floor at around 2:45. Once I got over my impatience, I did enjoy the views and would recommend it, just be aware that the numbers on your tickets are basically meaningless. You step off the elevator into a room with panoramic overlooks of the city. For a little extra, you can try the tilt, where you stand against the glass and are slowly tilted out beyond the edge of the building. It is actually scarier to watch than it is to do, and it definitely makes the wait a bit more worthwhile. There is also a bar that serves drinks and gelato, so at least that is something.
As a result of the unexpected wait, we had to hurry through a bit, got back to the car and headed north to Milwaukee. I am aware that I have billed this as a Chicago trip, and that to this point, as much time will have been spent outside of Chicago as in, but due to the circumstances, we had to broaden our horizons.
It just so happens that we have all grown up as big baseball fans; the kids and I of the Cardinals, and Alyson of the Astros. While neither of those teams happened to be in Chicago or Milwaukee, both of those teams were playing at home, so on Saturday night, we drove to American Family Field (formerly Miller Park), and watched the Brewers lose to the Twins.
American Family is a nice, clean park, but it is not super unique. I suppose it was heavily limited by COVID, but it felt like we could have been watching a ball game anywhere. Even so, we all had a great time. Capacity was maxed at 25%, so we had plenty of room to spread out and there was not a bad seat in the house. The game itself was actually quite entertaining as well, for the more committed baseball fan. Both teams threw perfect games into the 5th, and the Twins pitching staff completed a really impressive one-hitter for a 2-0 victory. If you are the type of person who wants to see the greatest sporting venues this country has to offer, Milwaukee probably shouldn’t be on your list, but if you want to enjoy baseball in a nice, comfortable stadium, American Family Field will do the trick.
The next day was Easter, and since our church reservations were not until 10, and Clara woke us up at 7, we decided to go out for breakfast. Instead of donuts, we went to a restaurant called Yolk on the Chicago River. This is just simple, straightforward breakfast food with some interesting twists. My daughter got Oreo pancakes while my son got s’mores-based pancakes. Eileen loved hers but when my son started scraping off all the graham cracker and marshmallow fluff, we came to the decision that he is no longer allowed to order specialty pancakes. No matter how good they sound, all he ever wants is plain.
For Easter, we went to church at Holy Names Cathedral. A beautiful building, the service was performed by Cardinal Cupich, so it was a unique experience. When we do attend church in larger cities whilst on vacation, we always try to go the cathedral, if the city has one. These buildings are usually a sight worth seeing in and of themselves, and it helps to deepen the experience one gets in a different town.
Afterwards, we jumped on the L-train (which evidently is the same thing as the subway), and headed for Wrigley Field. The Cubs opened the 2021 season again division rivals, the Pittsburgh Pirates, and we were lucky enough to get four of the 10,000+ tickets available, due to capacity limitations.
If you are a baseball fan, and have never been to Wrigley, this is a must visit. Contrasting it to American Family the night before, it is easy to understand how the Cubs ballpark has become one of the most iconic sports venues in the country. Wrigley is tucked into a residential neighborhood and could easily be missed if it weren’t for the throngs of fans. Every seat, including those on the roof tops across the street, is amazing, and the atmosphere is electric, even at 25%.
Having grown up a Cardinals’ fan, I refuse to say it is the best baseball stadium I have ever visited, but it is certainly up there. I will also note the while the fan base is committed, the fans in the bleachers perhaps take it too far at times, in several not particularly family friendly ways. On Easter Sunday, the Cubs beat Pirates 4-2, and while I was certainly pulling for visitors, I have to admit that I had an amazing time.
After the game, we took the L-train back to the loop, and once again, walked to the Chicago River. We decided that we could not visit Chicago without experiencing one of the almost countless Chicago steakhouses. For the meat eaters out there, this is something that everyone should do at least once. That said, be prepared to pay. We ate at Chicago Cut, and it was fantastic, but the price for four of us was well over $200, and that included two steaks, two sides and a few drinks.
The reason these meals get so expensive is that the entrees usually start at around $60. Since both Jonathan and Eileen enjoy steak, we ordered two, along with two sides, and shared everything. I am glad we did it, and if we go back to Chicago, I could see doing it again, but this type of meal is obviously geared toward tourists and business folk, not the every day Chicago resident.
The next day, Monday, was our last day in Illinois, and we had few concrete plans, other than to get a donut. On Monday morning, we hit up Stan’s, and I got my third and final old fashioned. I am glad that we stuck with it, because this was my favorite donut of the weekend. Funny enough, it was my wife’s least favorite. Of the three donut places we hit, she enjoyed Firecake’s the most, and JR and Eileen preferred the Donut Vault. It just goes to show that there are different strokes for different folks, and that the Chicago donut scene, evidently, is blowing up.
We spent the rest of the day driving around different parts of Chicago. We went to the Lincoln Park area to see the Sacred Heart school and Loyola Marymount. This is a really scenic location, and a place that I could see my daughter going for college. We also ate at Pequod’s Pizza, a great neighborhood restaurant and bar. While Lou Malnati’s is certainly more well-known, the whole family agreed that the pizza at Pequod’s was far superior.
We flew home on Southwest that afternoon, and all crashed hard. It is extraordinarily satisfying to get to a experience a new city, mostly on foot. We love trying new restaurants, seeing new parks, and who could pass on finally getting to go back to a baseball game in person. One of the great things about this trip is that while we all enjoyed every activity, we all had different favorites. I enjoyed the Indiana Dunes the most, Alyson loved the river tour, JR’s favorite part was both baseball games, and Eileen loved the Field Museum. Oh, and Clara liked laughing at inappropriate moments during the Cardinal’s homily on Easter.
Chicago is a great and unique American city, and it has plenty of family friendly activities for all ages. It is also a city that offers so much, that it cannot all be done in one trip. If you have any questions, please reach out; our family would love to help yours enjoy Chicago as much as we did.
