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Cities I have been to:

Rank Urbanized Area (over 500,000) Population Square Miles Population Density
1 New York--Newark, NY--NJ--CT 17,799,861 3,353 5,309
2 Los Angeles--Long Beach--Santa Ana, CA 11,789,487 1,668 7,068
3 Chicago, IL--IN 8,307,904 2,123 3,914
4 Philadelphia, PA--NJ--DE--MD 5,149,079 1,799 2,861
5 Miami, FL 4,919,036 1,116 4,407
6 Dallas--Fort Worth--Arlington, TX 4,145,659 1,407 2,946
7 Boston, MA--NH--RI 4,032,484 1,736 2,323
8 Washington, DC--VA--MD 3,933,920 1,157 3,401
9 Detroit, MI 3,903,377 1,261 3,094
10 Houston, TX 3,822,509 1,295 2,951
11 Atlanta, GA 3,499,840 1,963 1,783
12 San Francisco--Oakland, CA 2,995,769 428 7,004
13 Phoenix--Mesa, AZ 2,907,049 799 3,638
14 Seattle, WA 2,712,205 954 2,844
15 San Diego, CA 2,674,436 782 3,419
16 Minneapolis--St. Paul, MN 2,388,593 894 2,671
17 St. Louis, MO--IL 2,077,662 829 2,506
18 Baltimore, MD 2,076,354 683 3,041
19 Tampa--St. Petersburg, FL 2,062,339 802 2,571
20 Denver--Aurora, CO 1,984,887 499 3,979
21 Cleveland, OH 1,786,647 647 2,761
22 Pittsburgh, PA 1,753,136 852 2,057
23 Portland, OR--WA 1,583,138 474 3,340
24 San Jose, CA 1,538,312 260 5,914
25 Riverside--San Bernardino, CA 1,506,816 439 3,434
26 Cincinnati, OH--KY--IN 1,503,262 672 2,238
27 Virginia Beach, VA 1,394,439 527 2,647
28 Sacramento, CA 1,393,498 369 3,776
29 Kansas City, MO--KS 1,361,744 584 2,330
30 San Antonio, TX 1,327,554 408 3,257
31 Las Vegas, NV 1,314,357 286 4,597
32 Milwaukee, WI 1,308,913 487 2,688
33 Indianapolis, IN 1,218,919 553 2,205
34 Providence, RI--MA 1,174,548 504 2,332
35 Orlando, FL 1,157,431 453 2,554
36 Columbus, OH 1,133,193 398 2,849
37 New Orleans, LA 1,009,283 198 5,102
38 Buffalo, NY 976,703 367 2,664
39 Memphis, TN--MS--AR 972,091 400 2,431
40 Austin, TX 901,920 318 2,835
41 Bridgeport--Stamford, CT--NY 888,890 465 1,910
42 Salt Lake City, UT 887,650 231 3,847
43 Jacksonville, FL 882,295 411 2,149
44 Louisville, KY--IN 863,582 391 2,207
45 Hartford, CT 851,535 469 1,814
46 Richmond, VA 818,836 437 1,875
47 Charlotte, NC--SC 758,927 435 1,745
48 Nashville-Davidson, TN 749,935 431 1,741
49 Oklahoma City, OK 747,003 322 2,317
50 Tucson, AZ 720,425 291 2,473
51 Honolulu, HI 718,182 154 4,660
52 Dayton, OH 703,444 324 2,174
53 Rochester, NY 694,396 295 2,353
54 El Paso, TX--NM 674,801 219 3,080
55 Birmingham, AL 663,615 392 1,693
56 Omaha, NE--IA 626,623 226 2,768
57 Albuquerque, NM 598,191 224 2,671
58 Allentown--Bethlehem, PA--NJ 576,408 289 1,991
59 Springfield, MA--CT 573,610 309 1,857
60 Akron, OH 570,215 308 1,853
61 Sarasota--Bradenton, FL 559,229 270 2,068
62 Albany, NY 558,947 284 1,966
63 Tulsa, OK 558,329 261 2,136
64 Fresno, CA 554,923 139 4,003
65 Concord, CA 552,624 176 3,132
66 Raleigh, NC 541,527 320 1,694
67 Grand Rapids, MI 539,080 257 2,095
68 Mission Viejo, CA 533,015 137 3,894
69 New Haven, CT 531,314 285 1,862
70 McAllen, TX 523,144 314 1,667
71 Toledo, OH--MI 503,008 202 2,486
  Total 140,022,057 44,013 3,181