Another guest post from the inimitable and mysterious Lynn. Thanks!
Keep in mind that I haven’t lived in this area since it was affordable (so that would be the 1960s) so my latter-day experience is as a tourist, though a local one!
First, a little history: http://en.wikipedia.org/wiki/Old_Town,_Chicago
They say that if you can hear the bells of St. Michaels, you are in Old Town. It’s one of the few churches that survived the Great Fire: http://en.wikipedia.org/wiki/St._Michael’s_Church,_Old_Town,_Chicago
Anyway, lots of neat old quirky homes around Old Town. We used to live on Burton Place, a block-long street between Wells and LaSalle, and I still think the places there are cool. Some fun boutique shopping on Wells Street and on Armitage Avenue (Armitage Ave shopping is west of Halsted).
Late-night bar Burton Place is ok. Gold Coast Dogs on Clark has great Chicago-stle hot dogs http://www.goldcoastdogs.net.
Restaurants I like are Old Jerusalem and Nookies (which I think is more morning fare) Kamehachi (sushi) Salpicon (Mexican). Twin Anchors on Sedgwick is known for its ribs and beer and is usually crowded, but people like it. Geja’s (on Armitage) is known for fondue (I think that’s all they serve?) and they have flamenco on the weekend. Lots of other places, I know, but those are the ones I know. Fireplace Inn has been in Old Town forever.
Things to see:
Second City is in Old Town: http://www.secondcity.com
Chicago History Museum, recently remodeled small museum. Chic Chicago is a nice exhibit if you like fashion: http://chicagohistory.org
Lincoln Park, which is technically not Old Town, but it’s right next door! Zoo http://www.lpzoo.org, swan boats, Nature Museum, Shakespeare Gardens (which is a garden around the statue of Shakespeare directly across from…) Lincoln Park Conservatory http://en.wikipedia.org/wiki/Lincoln_Park_Conservatory, North Avenue Beach and its boat-shaped beach house with a decent restaurant. I think there is even a health club along the beach. Midwest Buddhist Temple and the area around it is wonderful: http://www.midwestbuddhisttemple.org.