What are some fun, adventurous things to do in Chicago besides Navy Pier?

Totally depends on you. If you want 5 star stuff - Alinea is a world class restaurant, Topolobampo and Charlie Trotter's are great as well. But then again - Italian beef sandwiches from Johhny's are excellent and so are hot dogs from Hot Doug's. Beers at the Map Room are a good choice. Or maybe you are into tea at the Drake. Go see a Cubs game or get a little more adventurous and see the Sox. Shopping on Damen in Bucktown/Wicker Park is good and more diverse then Mag Mile stuff. Bike ride up the Lakefront is good too. Shows at Martyrs, Vic, Metro, Aragon, HOB, Chicago Theater. As far as hotels go, I'm not sure since I never had to stay in one but I would think that anything on the river is good. Places near the south loop are probably too far for your liking so stick with stuff in the River North area orStreeterville. Sheraton or Peninsula or the Allerton for vintage. Art Institute can't miss. Aquarium good too. Navy Pier is not Adventurous

There's very little parasailing here and the only jet skiing I've seen are a few guys at the Montrose Beach boat launch. As far as kayaking, there are a few rental places that take you down the Chicago river. One even lets you kayak down the river near Navy Pier to see the fireworks from the river. As far as restaurants, etc. check out Time Out Chicago magazine (http://www.timeout.com/chicago/

The Aquarium is cool...as is the art museum. Also, just outside of town is Hausermann's Orchids. They grow and sell Cattleya Orchids and to see them all blooming under like 3 acres of glass is awesome and a joy to the nose! They do tours. Shopping on The Magnificent Mile! Also, take a boat trip up the Chicago River through downtown. Have a cocktail at the bar at the top of Hancock Tower at sunset. Chicago also has a great Greek Town with great restuarants...Try Athena Restaurant! Italian Restaurants are everywhere...and Pizzaria Due is the best! Michael Jordan's restaurant, One Sixty Blue is also a hot spot....very contemporary..... Stay at the boutique hotel, The Tremont. Centrally located.... Have fun!

There are plenty of great things to do. Shopping, visiting the museums, hanging at the beach, seeing plays and ballets, etc. Sometimes the best thing is to just wander around and get 'lost' then grab a cab back to where you want to be. You will usually find some unusual things. :)