Boystown, Chicago, IL

The first officially recognized gay village in the United States, this southern enclave of Lakeview is undeniably the end of the rainbow for the Midwest's LGBT community, though Boystown’s myriad dining and entertainment options welcome unprejudiced partiers of every persuasion to join the fun.

The main thoroughfare on North Halsted – easy to spot given the nearly two dozen twenty-foot, rainbow-ringed pylons lining the street – bursts with shops, eateries, and the largest LGBT community center in the Midwest.

Daytime crowds of happy same-sex couples and inquisitive groups of friends peruse the gay-themed stores – but if the sex toys and bathhouses are a bit much for some, a bevy of fine dining, neighborhood bars, and relaxed bistros are also readily available.

The Boystown nightlife tends to be wild, with LGBT residents and young artsy types taking full advantage of the 5am bars and dance clubs, though nearby live theaters and comedy clubs also bring in older professionals and families just looking for a low-key evening.

Regardless of age, race, or gender identity, the annual Chicago Pride Parade at the end of June is only one of the countless reasons to check out the proud neighborhood-within-a-neighborhood of Boystown.