As for Burlington, there is little to see outside of downtown (unless you want to go to my parents' house), but while there, you could check out the following:

Church Street is the pedestrian shopping district with lots of boutiquey shops, restaurants and bars, as well as city hall, and the Firehouse Gallery, a city-run art space right next door to city hall. If you are there on a Saturday, there is a great farmers market in City Hall Park, which also includes an artists' fair featuring some great local artists and craftspeople. There are also many nightlife options on Church St. with a lot of the bars and restaurants setting up outdoor seating after dark.

A block down College St. from Church, there are 2 great eateries, each of which brews their own beer. American Flatbread is a wood-fired oven pizzeria, and VT Pub & Brewery has great pub fare. On the topic of beer, there is also a great brewery tour at the Magic Hat Brewery in South Burlington.

The Burlington Waterfront extends from Battery Park in the north down to Perkin's Pier to the South, a distance that can be easily walked in 10-15 minutes. Beansie's bus sells tasty fries and burgers out of the park, and along the way, you can check out the Burlington Boathouse and The Echo Lake Aquarium and Science Center, which is targeted at kids, but is a lot of fun for those of us who refuse to grow up (If you like the Exploritorium…).

at niagra falls, ride “maid of the mist.” goes right into the bottom of the waterfall. just a little bit of cheesey, a whole lot of thrilling and you get to keep the flimsy poncho as a great keepsake.

in VT, if possible, break away from the 12 hours jokers (or convince them to tag along) and go to waterbury to tour the ben and jerry's factory. tasty and fun.

in chicago eat at lou malnati's pizza. it will make you re-think the way you view pizza (and possibly casserole).

in boston, have clam chowder at the fairmont copley plaza … they serve the same chowder at the bar that they do in the restaurant — you can just eat it in there and save an over-priced and otherwise lackluster meal.

toronto island park will be ideal in shoulder season. it's easy to mass transit/ferry there.