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The city of Chicago vs. Houston: A tale of the tape

Most pundits believe Houston will surpass Chicago as the third largest city in America by 2020. I had not been there since…well, sometime before 2007. The Falconer (a.k.a. the wife) is there for an extended time for work training, so I visited for the weekend and took in as much of the culture as possible.

After spending a weekend there, I decided it was worth comparing the two in some key metrics to see which was the better city. (And have an excuse to share some cool photos). Keep in mind, these are things that are important to me. Some of you might have other things you feel are critical — pesky little things like school, health care, etc. — so you can adjust the rankings accordingly for that. But these are my standards, so take it for what it is.


Do we even need to discuss this? Even Chicago’s “other” baseball team has won a World Series (Astros fans remember that well). The Bears are down but are still an iconic franchise that boasts perhaps the best team ever. The Bulls vs. Rockets? Not even close. On top of that, Chicago has the Blackhawks, the NHL equivalent of the Patriots. Houston could not even keep a minor league hockey team. Better teams, better fans, better all around. If we were scoring this by points, we’re talking 10-2 Chicago. As it is, they just get one checkmark.



At first blush, you might see this as a negative. I see it as intriguing. Chicago had Al Capone. Frank Nitti. John Dillinger. (Yes, I went on a crime tour while I was there and it was all kinds of awesome). I even saw the Walgreens where the Tylenol scare started. Houston has a mafia, too, but nobody is making movies about it. They even have a serial killer who whacked over 200 people that no one has ever heard of. That’s strong. What do we have? Robert Durst. Woo hoo. We have to share him with New Orleans and Galveston. Another landslide.


unnamed (6)BEER

Our beer scene gets better by the day. But let’s face it, they had a huge head start. Getting closer, but another point for Chicago.



Yet another that is not even close. Chicago’s downtown is filled with amazing structures and go-to tourist places. It has a lake. It has rivers through the city. Millennium Park makes Memorial look like a dog park. Downtown is simply amazing. And it is huge. You can walk from one side of downtown Houston to the other in 15 minutes. Chicago has a real downtown; it’s huge, with massive buildings and several cool areas. And it would take forever to walk from one end to the other. There are also all kinds of cool structures like this…

unnamed (2)And especially this…

unnamed (5)

Houston has newer sports facilities, but that’s the only thing where it is even close. Yes, Chicago has much more history and has a big head start on us, but still…not close.



Interestingly enough, there were 10,000 speakeasys during prohibition. There are 2400 bars now. Unlike most downtowns, you can walk 20 minutes and not find a decent bar. They are all in one area of downtown in Chicago, and after that there really is not much. Houston has bars every five feet, and in several areas of concentration. Congratulations H Town, we are on the board.



I separated this, because pizza is the nectar of the gods. No one ever talks about Houston-style pizza. That’s because Houston style would be laughed off the shelf anyplace else. The worst pizza I had there would destroy anything in Houston. And Lou Malnati’s? The best. Period. If you visit, go there. The wait is worth it.



So even if you throw in the pizza difference, Houston has Chicago beat. More variety, more quality, pretty much better at everything else across the board. I suggest going there and eating nothing but pizza.



Of course I was not really looking, because I was with the wife, and she would have castrated me on the spot. But for research purposes only, I did some general scouting for the people for this piece. From my prior trips, I would have said Houston and it is not close. Maybe it was because I was in the tourist area and they were all imports, but Chicago’s female game was strong. The men are all fit, too. (Sorry Houston, I blame myself for that. Working on it). And maybe it was because there were so many redheads, and my appreciation of that particular flavor is a matter of lore. But a mild upset here. (As an aside, props to Southwest Airlines for upping their flight attendant game, at least on the Hobby to Midway run).



Maybe it’s because every time I have been there the weather sucks. It rained all weekend. It rained the last time I was there. One time it snowed. Another it was ridiculously hot. Houston weather sucks, too. During the summer here, you can be disintegrated by the heat if you stay out too long. You begin with a humidity sweat, and suddenly you disappear, never to be heard from again. But there? The infernal wind. It never stops. It is strong enough to pick you up and carry you to Wisconsin. No one wants to go to Wisconsin. Not a strong suit for either, but…



There’s a reason so many people move here. A six-figure salary in H Town goes a long way. In Chicago? Not so much. Beer costs more. Food costs more. Alcohol costs more. Cigarettes. Weed is decriminalized in Houston; big edge.


So even though they are close in population, Chicago has a 6-4 edge, and a much bigger advantage in some key areas. I’ll stick with H Town, but if you have never visited Chicago, you owe it to yourself to try it out. As a tourist destination, it has a huge advantage.

4 Comments on The city of Chicago vs. Houston: A tale of the tape

  1. What a fun read! Glad you had some time to get a “taste” of my hometown. Pricey yes, but great food, passionate sports fans and plenty of places to check out makes it my favorite place in the states to be!


  2. Donald Burrell // March 27, 2017 at 11:27 pm // Reply

    Fred, really? Houston women are the most beautiful in the world. Write a review about the women at an Astros game in July, Chicago doesn’t come cloze.


  3. Hey-I’m glad you had a great trip (and without being castrated, yay for you!) but I take issue with your analysis… you can’t give them points for pizza without giving Houston points for Tex mex. And since no one looks really good in fluffy winter down coats and they spend 6months bundled from head to toe- I think Houston hotties (male and female) in short shorts or skirts, or wranglers and cowboy boots win this one easily, despite the lucky weather you glimpsed. Finally- rodeo. No need to say more…Points and win big – Houston. (IMHO)


  4. Houston third ward vs Chicago south side

    I’ll take third ward any day


2 Trackbacks / Pingbacks

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