I've lived in both Chicago and Houston. I currently live in Houston.
I would have to say that Houston win's the war here.
But I'll break it down for you in these categories:
Skyline: Chicago (Winner, 3rd best AND tallest skyline in the world) Houston (3rd HIGHEST skyline in the country, 5th tallest in the country, 14th tallest in the world- according to Emporis)
Food: Pretty much the same except these things.
Chicago: You have Chicago style pizza that can't be replicated here, but Houston does have great pizza as well.
Houston: You have Tex-Mex food (Not to be confused with Mexican food) that can't be replicated in Chicago.
Underground food tunnel in Houston's downtown houses roughly 3,750 restaurants, and street level on downtown houses 730. As well as other areas of Houston having tens and thousands of more restaurants. The cypress area by itself has 6,000 restaurants.
So the quality and quantity of restaurants in both cities should be about the same. I put more emphasis on Houston because you haven't been here yet, so I have to display it.
As for jobs:
Chicago: Very big hub for companies, the capital of the midwest (Economically), largest inner city port in the world. Home to 9 Fortune 500 companies. Also home to nearly 26,000 businesses in the area.
Houston: Very big hub for companies as well, and the capital of the South AND South West (Economically), home to 27 Fortune 500 campanies, 3X more than Chicago. (Most Fortune 500 companies than any other city in USA besides NYC) Also in top 5 cities in the world for Fortune Global 500 campanies. (placed at 3rd place in the world) The energy capital of the world, and the oil capital of the USA, and a major IT sector and telecommunications hub. Port of Houston, second busiest and largest port in the USA *Behind Miami) and 12th in the world for importing/exporting and revenues and total tonnage.
Fortune 500 2009: Cities with most companies - FORTUNE on CNNMoney.com
Chicago: Naperville is ranked as 2nd best place to live in the USA as far as suburbs go, (Right behind Fort Collins, Colarado suburb of Denver, and right infront of Sugar Land, Texas suburb of Houston) Plus the places downtown that are very nice, great view of the city and the lake, and extremely nice nightlife.
Houston: Sugar Land is ranked as 3rd best place to live in the USA as far as suburbs go, (Right behind Naperville suburb of Chicago) With many great places to live in downtown as well, although the view isn't as nice as downtown Chicago's view. There are great places as well in Midtown, West Chase district, Rice Village, and where former president George H.W Bush resides Uptown (Galleria Area)
MONEY Magazine: Best places to live 2006: 10 Best Big Cities
^^^ (The list of cities in the middle of the page)
Theater and Arts:
Chicago: Very vibrant and world glass theater and arts, surpassing that of Houston's. 3rd in the country, right behind NYC, and Pittsburgh.
Houston: Best arts district and theater district in Texas and 7th in the country.
Chicago: 6 Flags Great America
Houston: 6 Flags AstroWorld (Demolished), Earth Quest Adventures (Groundbreaking and construction started, Schlitterbahn at Galveston.
Chicago and Houston both have many historical and great parks in the city and suburban areas. Both have good parks in downtown.
Chicago: The zoo is slightly better than Houston's
Houston: One of the best zoo's in the country but falls behind Chicago's
Chicago: Has a very efficient medical center for it's population
Houston: Medical District has it's own skyline, and is the NUMBER ONE medical center in the world for cancer treatment, and in the top 3 for heart problems. Ranked number one medical center in the country.
Source- New worldbook online
Chicago: University of Chicago - 13th best overall, Northwestern University 19th best overall, Layola University, University of Illinois at Chicago, North Park University, Saint Xaviers University, and many more...
Houston: Rice University 15th best overall and tied with Duke, University of Houston, St. Edwards University, Houston Baptist University, Texas Southern University, and Texas A&M Prairie View University, and Texas A&M University (50 minutes away from downtown Houston)
Transportation by Air
- Midway International Airport (2nd busiest in metro equivalent to Hobby for Houston)
- Chicago/Gary International Airport
- Chicago/Rockford International Airport
- O'HARE INTERNATIONAL AIRPORT (2nd busiest in USA after Atlanta and 4th in the world)
- William P. Hobby Airport (2nd busiest in metro equivalent of Midway for Chicago)
- Galveston International Airport
- Bryan/College Station International Airport
- George W. Bush International Airport (2nd busiest in Texas and 7th in USA, 32 in world)
Transportation by rail:
Chicago: Chicago has had rail service for a century, and it is one of the busiest in the nation, getting 1,607,000 people daily.
Houston: METRO rail was established and operational in 2004, and currently only has 8.6 miles, with expansions up to 38.4 miles by 2012. Receives 307,000 people daily.
Transportation by road
Chicago: Also known as city with most Interstate's in the country!!
- Interstate 90
- Interstate 94
- Interstate 57
- Interstate 190
- Interstate 355
- Interstate 55
- Interstate 88
- Interstate 290
Houston: Has the average amount in USA cities
- Interstate 10
- Interstate 45
- Interstate 610
- Interstate 69 (currently 59, soon to be renamed)
Chicago: Has many variations of crime and corruption, and has many gangs and scums, but is still safer than majority of American cities like DC, Baltimore, New Orleans, St. Louis, Philadelphia, Detroit, Grand Rapids, Cleveland, Los Angelas and Cincinnati.
Houston: Although gangs do exist, there aren't many crime involvements with gangs and civilians. Safe city amongst other American cities like those listed above.
World City Status:
Chicago: Alpha World City (NYC, LA, Chicago are the only Alpha world cities in USA)
Houston: Beta World City (Houston, San Francisco, DC, Seattle, Detroit, Philadelphia are Beta world cities)
Houston thing's I forgot:
I forgot to include that Houston's Uptown skyline is the size of downtown LA, Denver, and Dallas, where as Houston's downtown is double the size of it's uptown and it's skyline is double the size of it's uptown skyline. The city has 7 different and separate skylines. (Downtown, Uptown, Midtown, West Chase, Medical Center, Fairbanks, and North Houston) The city/metro is home to 42,000 businesses. That's all the information I left out earlier about Houston.
I think you'll love the move to Houston, and in many ways both cities are similar but they are unique in their own ways.