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my biggest cities...

Cincinatti, OH.
Below is a list of the biggest cities and metropolitan areas I have ever seen. Not much, but I'm not a business traveler. Updated 3/7/2007. Cities in italics added in last year. Population statistics from www.infoplease.com.
My biggest 40 cities by population...
New York, NY 8.21 million
Chicago, IL 2.86 million
Toronto, ON 2.48 million
Montreal, QC 1.62 million
Philadelphia, PA 1.47 million
San Jose, CA 904k
Detroit, MI 901k
Indianapolis, IN 784k
Jacksonville, FL 783k
San Francisco, CA 744k
Memphis, TN 672k
Charlotte, NC 630k
Mississauga, ON 613k
Boston, MA 591k
Milwaukee, WI 584k
Seattle,.WA 571k
Louisville, KY 556k
Washington, DC 554k
Nashville, TN 546k
Okla. City, OK 528k
Hamilton, ON 490k
Atlanta, GA 471k
Cleveland, OH 459k
Kansas City, MO 447k
San Juan, PR 442k
Virginia Beach, VA 438k
Oakland, CA 398k
Miami, FL 386k
Tulsa, OK 384k
Minneapolis, MN 374k
Colorado Springs, CO 369k
London, ON 337k
Tampa, FL 329k
Pittsburgh, PA 316k
Cincinnati, OH 314k
Toledo, OH 298k
Buffalo, NY 283k
St. Paul, MN 277k
Lexington, KY 266k
St. Petersburg, FL 249k
  My biggest 25 metro areas by population...
New York 18.8 million
Chicagoland 9.5 million
Washington-Baltimore 8.0 million
San Francisco Bay 7.0 million
Philadelphia 6.4 million
Toronto-Hamilton 6.0 million
Detroit-Windsor 5.9 million
Miami-Ft. Lauderdale 5.5 million
Atlanta 4.9 million
Boston 4.4 million
Pudget Sound 3.7 million
Greater Montreal 3.6 million
Twin Cities, MN 3.1 million
Cleveland 2.9 million
Denver-Aurora 2.6 million
Tampa Bay 2.6 million
St. Louis 2.6 million
San Juan 2.5 million
Pittsburgh 2.3 million
Cincinnati 2.0 million
Kansas City 1.8 million
Milwaukee 1.7 million
Indianapolis 1.7 million
Las Vegas 1.7 million
Norfolk-VA Beach 1.6 million

6 most impressive skylines...

Chicago, IL - an architectural mecca- Hancock, Sears, and Smurfitt-Stone buildings make this a perfect skyline
Toronto, ON - a very well balanced skyline, looks good at night, punctuated by CN Tower
San Francisco, CA - hills and bridges accentuate features like the Coit Tower and the Transamerica Pyramid
St. Louis, MO - wouldn't be much without the Gateway Arch
Philadelphia, PA - a group of tall buildings reaching into the sky
Atlantic City, NJ - long and colorful seaside skyline
Seattle, WA - Space Needle and Smith Building, classic
Twin Cities, MN - together make an impressive sight


Top to Bottom: Seattle, Washington, St. Louis, Cleveland, Pittsburgh, Montreal