If you're not familiar with The Second City, almost every comedian you've ever enjoyed has been in this company at some point in time in their career. Tickets are very limited for this so we'd suggest buying them early if you're going to be in town and want to check them out. Their mainstage performances are at 8pm and 11pm, with a variety of matinee performances on weekends.
We plan to go to Maggie Daley Park at about Noon on Sunday. Skate rentals are cheap ($10-15), and the "ribbon" is a really unique alternative to a traditional skating rink. We are planning on being here til about 2:30 pm.
After ice skating we will likely be hungry and cold, so beer and a snack is in order. The Game Room is on the second floor of the renovated Chicago Athletic Association hotel, just across the street from Maggie Daley park. They've got a bunch of pool/foosball/shuffleboard tables as well as a bocce court, along with great food and drinks. We are planning on being here from 3pm to 5pm or so on Sunday.
If you're looking for a great pizza (NOT that deep dish nonsense) during your stay, this place is a can't-miss.
This is one of our absolute favorite restaurants -- it's a really inventive menu in an unpretentious setting at reasonable prices. It's a little small, so a big group is going to be tough here.
This is good Italian food.
Aire is a take on a Roman bath, with a top-notch massage staff and a really relaxing environment. We may find time to go in the run-up to the wedding, but if you're looking for a little relaxation you could do a lot worse than a massage here and a warm-up in the pools.
This is probably our favorite bar in Chicago, certainly our favorite Irish bar. They have a Sunday night traditional Irish music session that is legendary, which begins at 8 pm. Seating is limited, so you may end up standing, but the atmosphere is amazing (and the food's not bad either).