I think that Chicago is very similar to Milwaukee and the things that people hate about either can be found in both cities. On the whole, Chicago has a more extensive public transportation system, however, expensive cross-town cabrides are sometimes necessary and always maddening. We both have Lake Michigan. An art museum. Pro teams in all sports. So there are many similarities, but the biggest difference in my opinion, and the only reason I'd choose Chicago over Milwaukee, is the abundance of quality music venues that Chicago has to offer. The Pabst, Turner and Riverside are all nice and bring top-notch acts in to town routinely, but Chicago has the types of venues (of all sizes) to ensure that no notable act will ever bypass the city on their tour schedule. Milwaukee unfortunately gets skipped which causes me to travel to Chicago. Also, at a football game at Soldier Field several years back i was pelted with a hunk of cheese as I stood to celebrate a packers touchdown, but I cannot hold one drunken person's actions against an entire city. Come to think of it, I doubt said person was drunk because the cheese hit me squarely in the back of the head which would be tough to do if one were drinking heavily.

 

Size Matters! Chicago is also the 3rd largest city in the country! We;'re 34th. So, a lot of this has to do with size people. As far as comparing the two cities - Chicago doesn't even think of us as "little bro." XRT radio in Chicago ran a billboard campaign: "What would Chicago be without XRT? Milwaukee" Enough said.

 

Milwaukee is the Hampton's of Chicago. Okkayyyyy.

 

Milwaukee is the 22nd largest city in the country. Oh Keribus, check your facts son.